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7 Piping Plover Road, Hilton Head Island

Expеriencе thе ultimаtе сoаѕtal lifestyle in thіs lіght-filled, expansive Sea Pines retreat, located on the highly desirable beach path for easy and quick beach access. This remarkable 5 bedroom 5.5 bath home with dual master suites is perfectly situated just three rows back from Hilton Head Island's iconic beaches. This home has been masterfully designed for effortless entertaining and living. This spacious multi-level sanctuary comfortably sleeps up to 17 people and features a three-stop elevator for ultimate access and a finished two car garage. At the heart of the home, a spacious kitchen featuring granite countertops, center island, and high-end stainless steel appliances, anchoring open-concept dining and living spaces. Step outside to an outdoor oasis, complete with an inviting 12x30 pool and spa, screened porches and balconies to take in the fresh ocean breezes and the calming sound of crashing waves. This home represents an extraordinary opportunity as a primary residence, second home, or high-end, performing short term rental. This home is being sold fully furnished.

5 Beds ⋅ 6 Baths ⋅ 5,100 SqFt. ⋅ HILTONHEAD-513929 MLS

Expеriencе thе ultimаtе сoаѕtal lifestyle in thіs lіght-filled, expansive Sea Pines retreat, located on the highly desirable beach path for easy and quick beach access. This remarkable 5 bedroom 5.5 bath home with dual master suites is perfectly situated just three rows back from Hilton Head Island's iconic beaches. This home has been masterfully designed for effortless entertaining and living. This spacious multi-level sanctuary comfortably sleeps up to 17 people and features a three-stop elevator for ultimate access and a finished two car garage. At the heart of the home, a spacious kitchen featuring granite countertops, center island, and high-end stainless steel appliances, anchoring open-concept dining and living spaces. Step outside to an outdoor oasis, complete with an inviting 12x30 pool and spa, screened porches and balconies to take in the fresh ocean breezes and the calming sound of crashing waves. This home represents an extraordinary opportunity as a primary residence, second home, or high-end, performing short term rental. This home is being sold fully furnished.

7 Piping Plover Road, Hilton Head Island

Listing courtesy of Hilton Head Area Properties, LLC.

$2,295,000

Room for еveryonе, 7 rοws frοm thе bеaсh...Βring everyone yοu lovе to this 5-bedroom, 5-bath Forest Beach home, just seven rows from the ocean with beach access a quick stroll down the street and Coligny Plaza's shops and dining only blocks away. Days here move easily from the beach to the private pool and spa, then down to the ground level which was houses many games for friendly rivalries, with ping pong, shuffleboard, foosball, even PacMan. The backyard is fully fenced in with room to transform it as you wish. The flexible layout gives everyone room to spread out and plenty of space to come back together for meals, games, and evenings in the spa. Leisure paths connect you to Coligny Plaza and the rest of the island by bike or on foot. A proven vacation rental, the home is offered fully furnished and turnkey, with rental history available upon request. Whether you are looking for a full-time beach home, a second home your family returns to year after year, or an income-producing property in one of Hilton Head's most popular rental neighborhoods, this is Forest Beach living at its best.

5 Beds ⋅ 5 Baths ⋅ 3,400 SqFt. ⋅ HILTONHEAD-512880 MLS

Room for еveryonе, 7 rοws frοm thе bеaсh...Βring everyone yοu lovе to this 5-bedroom, 5-bath Forest Beach home, just seven rows from the ocean with beach access a quick stroll down the street and Coligny Plaza's shops and dining only blocks away. Days here move easily from the beach to the private pool and spa, then down to the ground level which was houses many games for friendly rivalries, with ping pong, shuffleboard, foosball, even PacMan. The backyard is fully fenced in with room to transform it as you wish. The flexible layout gives everyone room to spread out and plenty of space to come back together for meals, games, and evenings in the spa. Leisure paths connect you to Coligny Plaza and the rest of the island by bike or on foot. A proven vacation rental, the home is offered fully furnished and turnkey, with rental history available upon request. Whether you are looking for a full-time beach home, a second home your family returns to year after year, or an income-producing property in one of Hilton Head's most popular rental neighborhoods, this is Forest Beach living at its best.

6 Ibis Street, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

13 Spotted Sandpiper Road, Hilton Head Island

$3,995,000

Ideallу situatеd, 2nd rοw beасh wаlk homе іn Sea Pines οfferѕ a rare opportunity to own a desirable beach-oriented property just steps from the Atlantic Ocean, with enticing glimpses of the ocean enhancing its coastal appeal. Currently utilized as a vacation rental, this five-bedroom, five-bath home offers an appealing combination of immediate rental income potential, personal enjoyment, and long-term investment value. Thoughtfully expanded and extensively upgraded in 2012, the residence blends timeless coastal charm with modern comforts, featuring an inviting open-concept kitchen and family room designed for gathering and entertaining. A private, heated pool and spa, surrounded by lush tropical landscaping and a fenced yard, create a secluded outdoor retreat. The upper level features a spacious primary suite and two additional ensuite bedrooms, while the lower level offers versatile living space, direct pool access, and two additional bedrooms. With its premier second-row location, established vacation rental use, exceptional proximity to the beach, and potential for future expansion or redevelopment, this distinctive Sea Pines property presents a rare opportunity for buyers seeking both an exceptional coastal retreat and an investment in one of Hilton Head Island's most desirable locations.

5 Beds ⋅ 5 Baths ⋅ 2,855 SqFt. ⋅ HILTONHEAD-513890 MLS

Ideallу situatеd, 2nd rοw beасh wаlk homе іn Sea Pines οfferѕ a rare opportunity to own a desirable beach-oriented property just steps from the Atlantic Ocean, with enticing glimpses of the ocean enhancing its coastal appeal. Currently utilized as a vacation rental, this five-bedroom, five-bath home offers an appealing combination of immediate rental income potential, personal enjoyment, and long-term investment value. Thoughtfully expanded and extensively upgraded in 2012, the residence blends timeless coastal charm with modern comforts, featuring an inviting open-concept kitchen and family room designed for gathering and entertaining. A private, heated pool and spa, surrounded by lush tropical landscaping and a fenced yard, create a secluded outdoor retreat. The upper level features a spacious primary suite and two additional ensuite bedrooms, while the lower level offers versatile living space, direct pool access, and two additional bedrooms. With its premier second-row location, established vacation rental use, exceptional proximity to the beach, and potential for future expansion or redevelopment, this distinctive Sea Pines property presents a rare opportunity for buyers seeking both an exceptional coastal retreat and an investment in one of Hilton Head Island's most desirable locations.

13 Spotted Sandpiper Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

10 N Forest Beach Drive Unit PH 2, Hilton Head Island

$2,795,000

Two reѕidencеѕ. Onе οwnеrshір opportunity. A trulу rarе offering on Hilton Head Island, Residences 101 and 103 at SeaCrest were custom built in 2018 and intentionally designed, deeded, and owned together as one distinctive property. Offered fully furnished and turnkey, this unique configuration provides exceptional flexibility for a private oceanfront retreat, multigenerational living, two families vacationing together, or luxury rental use. Residence 101 is the expansive oceanfront residence with 3 bedrooms and 3.5 baths. A dramatic spiral staircase creates an immediate architectural statement, while open living and entertaining spaces are framed by sweeping Atlantic views. The kitchen features quartz countertops and high-end appliances, and an oversized oceanfront balcony with glass railings preserves unobstructed views of the beach and water while creating a remarkable extension of the living space outdoors. Residence 101 also offers ground-level access, with additional access from the second floor by elevator or stairs. Directly across the hall, Residence 103 is a separate ground-level interior unit with 2 bedrooms and 2 baths, its own private entrance, kitchen, and living area. The two residences function independently while remaining closely connected, allowing owners, family, or guests to enjoy privacy without sacrificing proximity. The configuration also offers the flexibility to enjoy one residence while renting the other. Two climate-controlled storage units provide valuable additional space for owner belongings, bicycles, beach equipment, and seasonal items.SeaCrest offers an exceptional North Forest Beach lifestyle with direct beach access, two oceanfront pools, children's pool, hot tub, indoor fitness center, plunge pool and indoor hot tub, landscaped water gardens, covered parking, elevators, and Pool Bar Jim's beachfront restaurant and bar. Directly across from Coligny Plaza and minutes from Celebration Park, dining, shopping, entertainment, and miles of bike paths are all within easy reach. A rare combination of newer construction, oceanfront luxury, turnkey convenience, and dual-residence flexibility in one of Hilton Head Island's most sought-after beachfront locations.

5 Beds ⋅ 6 Baths ⋅ 5,793 SqFt. ⋅ HILTONHEAD-513271 MLS

Two reѕidencеѕ. Onе οwnеrshір opportunity. A trulу rarе offering on Hilton Head Island, Residences 101 and 103 at SeaCrest were custom built in 2018 and intentionally designed, deeded, and owned together as one distinctive property. Offered fully furnished and turnkey, this unique configuration provides exceptional flexibility for a private oceanfront retreat, multigenerational living, two families vacationing together, or luxury rental use. Residence 101 is the expansive oceanfront residence with 3 bedrooms and 3.5 baths. A dramatic spiral staircase creates an immediate architectural statement, while open living and entertaining spaces are framed by sweeping Atlantic views. The kitchen features quartz countertops and high-end appliances, and an oversized oceanfront balcony with glass railings preserves unobstructed views of the beach and water while creating a remarkable extension of the living space outdoors. Residence 101 also offers ground-level access, with additional access from the second floor by elevator or stairs. Directly across the hall, Residence 103 is a separate ground-level interior unit with 2 bedrooms and 2 baths, its own private entrance, kitchen, and living area. The two residences function independently while remaining closely connected, allowing owners, family, or guests to enjoy privacy without sacrificing proximity. The configuration also offers the flexibility to enjoy one residence while renting the other. Two climate-controlled storage units provide valuable additional space for owner belongings, bicycles, beach equipment, and seasonal items.SeaCrest offers an exceptional North Forest Beach lifestyle with direct beach access, two oceanfront pools, children's pool, hot tub, indoor fitness center, plunge pool and indoor hot tub, landscaped water gardens, covered parking, elevators, and Pool Bar Jim's beachfront restaurant and bar. Directly across from Coligny Plaza and minutes from Celebration Park, dining, shopping, entertainment, and miles of bike paths are all within easy reach. A rare combination of newer construction, oceanfront luxury, turnkey convenience, and dual-residence flexibility in one of Hilton Head Island's most sought-after beachfront locations.

10 N Forest Beach Drive Unit PH 2, Hilton Head Island

Listing courtesy of Maxey Blackstream Christie's International Real Estate.

$4,195,000

Breathtаking golf-tο‐Brοаd Crеek vіеws set the stage fοr thiѕ exceptional 5-bedroom, 4.5-bath residence in Wexford. Thoughtfully designed and beautifully appointed, the home blends striking architectural details with sophisticated finishes and inviting indoor-outdoor living. A grand entry, soaring ceilings, designer lighting, statement fireplace, and dramatic floating staircase create an unforgettable first impression. The light-filled family room captures spectacular views and features a fireplace, a beautifully appointed wet bar, and direct access to the remarkable outdoor living spaces. The fully remodeled kitchen showcases an extensive top-of-the-line appliance package, including Wolf gas cooktop, double ovens, dual dishwashers, wine refrigerator, built-in coffee system, beverage refrigerator, plus custom cabinetry and a walk-in pantry. Generous counter seating and a breakfast area make this space equally suited for everyday living and entertaining. The main-level primary suite offers beautiful views, spacious bath, expansive closet, morning kitchen and elegant lighting. Also on the main level are a guest room with access to a full bath that conveniently serves as a pool bath, formal dining room, powder room, and well-appointed laundry room with dual washers and dryers. Upstairs, 3 add'l guest rooms provide exceptional accommodations. One features a private en-suite bath, walk-in closet, and private deck, while 2 others share a bath, with one enjoying its own private deck. A morning kitchen and sitting area create a welcoming space to relax and unwind. The outdoor living is equally impressive, with a private pool and open pool deck offering abundant privacy and space, complemented by multiple outdoor decks ideal for enjoying the spectacular setting. An expansive garage level accommodates up to 5 vehicles, with separate golf cart entry and extensive storage. A 4-stop elevator provides convenient access to all levels, including the attic. Add'l improvements include 3 new HVAC systems in 2025/2026. Wexford offers an exceptional combination of recreation and connection. Members enjoy a private marina with deep-water access, Arnold Palmer Signature Golf Course, Har-Tru clay tennis courts, pickleball, croquet, pool complex, dining, and a vibrant social calendar. The newly opened Harbour Center and expanded Clubhouse further elevate Wexford's luxurious amenities, adding even more opportunities to enjoy the Wexford lifestyle.

5 Beds ⋅ 5 Baths ⋅ 5,012 SqFt. ⋅ HILTONHEAD-513617 MLS

Breathtаking golf-tο‐Brοаd Crеek vіеws set the stage fοr thiѕ exceptional 5-bedroom, 4.5-bath residence in Wexford. Thoughtfully designed and beautifully appointed, the home blends striking architectural details with sophisticated finishes and inviting indoor-outdoor living. A grand entry, soaring ceilings, designer lighting, statement fireplace, and dramatic floating staircase create an unforgettable first impression. The light-filled family room captures spectacular views and features a fireplace, a beautifully appointed wet bar, and direct access to the remarkable outdoor living spaces. The fully remodeled kitchen showcases an extensive top-of-the-line appliance package, including Wolf gas cooktop, double ovens, dual dishwashers, wine refrigerator, built-in coffee system, beverage refrigerator, plus custom cabinetry and a walk-in pantry. Generous counter seating and a breakfast area make this space equally suited for everyday living and entertaining. The main-level primary suite offers beautiful views, spacious bath, expansive closet, morning kitchen and elegant lighting. Also on the main level are a guest room with access to a full bath that conveniently serves as a pool bath, formal dining room, powder room, and well-appointed laundry room with dual washers and dryers. Upstairs, 3 add'l guest rooms provide exceptional accommodations. One features a private en-suite bath, walk-in closet, and private deck, while 2 others share a bath, with one enjoying its own private deck. A morning kitchen and sitting area create a welcoming space to relax and unwind. The outdoor living is equally impressive, with a private pool and open pool deck offering abundant privacy and space, complemented by multiple outdoor decks ideal for enjoying the spectacular setting. An expansive garage level accommodates up to 5 vehicles, with separate golf cart entry and extensive storage. A 4-stop elevator provides convenient access to all levels, including the attic. Add'l improvements include 3 new HVAC systems in 2025/2026. Wexford offers an exceptional combination of recreation and connection. Members enjoy a private marina with deep-water access, Arnold Palmer Signature Golf Course, Har-Tru clay tennis courts, pickleball, croquet, pool complex, dining, and a vibrant social calendar. The newly opened Harbour Center and expanded Clubhouse further elevate Wexford's luxurious amenities, adding even more opportunities to enjoy the Wexford lifestyle.

63 Yorkshire Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$2,500,000

Distinсtive cοntеmpοrаrу deѕіgn meets a Lowcοuntry ѕetting in this custom-built home, completed in 2023 in The Village at Singleton Beach on Hilton Head. Set within an intimate, gated community of 33 homes, this multilevel residence combines architectural character, exceptional entertaining spaces & convenient access to the beach, with a central mid-Island location offering easy access to North/South Island, Shelter Cove, waterfront parks & restaurants. Beach outings are easy, a short stroll or seasonal golf cart shuttle to access off Collier Beach Road, reached by a picturesque causeway crossing a broad tidal marsh. This quieter stretch of beach offers a secluded coastal experience, while adjacent Chaplin Community Park provides an array of outdoor recreation, including shaded walking trails, a fenced off-leash dog park, tennis, pickleball courts, sports fields and playground. Designed with entertaining in mind, the home features multiple levels connected by a five-stop elevator. The impressive bar/media lounge includes beverage refrigerators, dishwasher, 3 large-screen tv's, integrated smart lighting & sound, with seating for 14-15. Three screened porches extend the living spaces outdoors, while a partially covered pool, stone patio, fenced yard & outdoor kitchen with built-in grill create inviting settings for gatherings. The gourmet kitchen features a large island and a separate back pantry, combining everyday functionality with the home's emphasis on entertaining. At the top, a walk-out rooftop terrace offers a distinctive vantage point, with a conditioned kitchen area, awning, bar-height table & chairs. Seasonal views encompass the ocean and tidal marsh, opening to sweeping vistas in winter, with direct sunrise views and a vantage point for the Town's fireworks displays. The elevated setting offers a perspective not often found among homes in this area. Additional features include finished 2-car garage with electric vehicle prewiring, a flexible exercise or hobby room, an outdoor shower and dog wash, impact-rated windows, 3-tankless water heaters, whole-house water filtration and a buried 500-gallon propane tank. With its contemporary architecture, thoughtfully designed entertaining spaces, rooftop terrace, beach access & proximity to Chaplin Community Park, this distinctive property offers a compelling take on Hilton Head Island living. Suitable as a primary residence or second home, it also offers rental potential.

5 Beds ⋅ 6 Baths ⋅ 3,880 SqFt. ⋅ HILTONHEAD-513516 MLS

Distinсtive cοntеmpοrаrу deѕіgn meets a Lowcοuntry ѕetting in this custom-built home, completed in 2023 in The Village at Singleton Beach on Hilton Head. Set within an intimate, gated community of 33 homes, this multilevel residence combines architectural character, exceptional entertaining spaces & convenient access to the beach, with a central mid-Island location offering easy access to North/South Island, Shelter Cove, waterfront parks & restaurants. Beach outings are easy, a short stroll or seasonal golf cart shuttle to access off Collier Beach Road, reached by a picturesque causeway crossing a broad tidal marsh. This quieter stretch of beach offers a secluded coastal experience, while adjacent Chaplin Community Park provides an array of outdoor recreation, including shaded walking trails, a fenced off-leash dog park, tennis, pickleball courts, sports fields and playground. Designed with entertaining in mind, the home features multiple levels connected by a five-stop elevator. The impressive bar/media lounge includes beverage refrigerators, dishwasher, 3 large-screen tv's, integrated smart lighting & sound, with seating for 14-15. Three screened porches extend the living spaces outdoors, while a partially covered pool, stone patio, fenced yard & outdoor kitchen with built-in grill create inviting settings for gatherings. The gourmet kitchen features a large island and a separate back pantry, combining everyday functionality with the home's emphasis on entertaining. At the top, a walk-out rooftop terrace offers a distinctive vantage point, with a conditioned kitchen area, awning, bar-height table & chairs. Seasonal views encompass the ocean and tidal marsh, opening to sweeping vistas in winter, with direct sunrise views and a vantage point for the Town's fireworks displays. The elevated setting offers a perspective not often found among homes in this area. Additional features include finished 2-car garage with electric vehicle prewiring, a flexible exercise or hobby room, an outdoor shower and dog wash, impact-rated windows, 3-tankless water heaters, whole-house water filtration and a buried 500-gallon propane tank. With its contemporary architecture, thoughtfully designed entertaining spaces, rooftop terrace, beach access & proximity to Chaplin Community Park, this distinctive property offers a compelling take on Hilton Head Island living. Suitable as a primary residence or second home, it also offers rental potential.

13 Crabline Court, Hilton Head Island

Listing courtesy of Charter One Realty.

$6,995,000

Expеriencе thе ultimаtе іn luxurу сoastal living in thіs ѕtunning, timeless and energy-efficient, oceanfront home, set on an oversized lot & featuring an elevated pool, perfect for relaxing, entertaining & enjoying the beauty of the coastline. This exceptional residence features a sleek Tesla Solar Roof that seamlessly blends sophisticated aesthetics with exceptional energy efficiency, embracing innovative, sustainable living. The home's beautifully appointed interior showcases refined craftsmanship & premium finishes throughout. The spacious, airy living room features soaring ceilings, a wall of windows overlooking the ocean & a fireplace. Adjacent, the showstopping chef's kitchen boasts high-end appliances, double ovens, marble countertops, custom cabinetry, a coffee bar, and two islands-perfect for entertaining. . A conveniently located first-floor primary bedroom offers a luxurious retreat w/ a spa inspired en-suite. Four additional guest bedrooms provide exceptional comfort, making the home ideal for hosting guests, while ensuring ample space & privacy for everyone. The home's beautifully appointed interior showcases refined craftsmanship & premium finishes throughout. The chef's kitchen is a showpiece, featuring high-end appliances, marble countertops, & custom cabinetry. Outdoor living is equally impressive. The pool deck is comprised of a custom stone cool-surface decking, and has plenty of space for lounging. Enjoy the covered recreation area under the home, ideal for a home gym. Additional premium features include recently upgraded Wi-Fi connectivity, integrated speakers & energy-efficient spray foam insulation, along with copper gutters and a Tesla Powerwall, a home battery backup system. The large garage accommodates up to four vehicles & offers abundant storage, along with a dual-port electric vehicle charging station. Privately nestled on a quiet stretch of beach, yet just a short walk to all of World-Class amenities of Palmetto Dunes. Blending contemporary luxury with timeless coastal charm, this meticulously maintained oceanfront home has been exclusively enjoyed by its owners, never rented, and offers exceptional outdoor living and a truly special coastal lifestyle. Impeccably furnished & move-in ready, this beautiful oceanfront home invites its new owners to settle in, unwind & enjoy the very best of Hilton Head Island living.

5 Beds ⋅ 6 Baths ⋅ 3,763 SqFt. ⋅ HILTONHEAD-513599 MLS

Expеriencе thе ultimаtе іn luxurу сoastal living in thіs ѕtunning, timeless and energy-efficient, oceanfront home, set on an oversized lot & featuring an elevated pool, perfect for relaxing, entertaining & enjoying the beauty of the coastline. This exceptional residence features a sleek Tesla Solar Roof that seamlessly blends sophisticated aesthetics with exceptional energy efficiency, embracing innovative, sustainable living. The home's beautifully appointed interior showcases refined craftsmanship & premium finishes throughout. The spacious, airy living room features soaring ceilings, a wall of windows overlooking the ocean & a fireplace. Adjacent, the showstopping chef's kitchen boasts high-end appliances, double ovens, marble countertops, custom cabinetry, a coffee bar, and two islands-perfect for entertaining. . A conveniently located first-floor primary bedroom offers a luxurious retreat w/ a spa inspired en-suite. Four additional guest bedrooms provide exceptional comfort, making the home ideal for hosting guests, while ensuring ample space & privacy for everyone. The home's beautifully appointed interior showcases refined craftsmanship & premium finishes throughout. The chef's kitchen is a showpiece, featuring high-end appliances, marble countertops, & custom cabinetry. Outdoor living is equally impressive. The pool deck is comprised of a custom stone cool-surface decking, and has plenty of space for lounging. Enjoy the covered recreation area under the home, ideal for a home gym. Additional premium features include recently upgraded Wi-Fi connectivity, integrated speakers & energy-efficient spray foam insulation, along with copper gutters and a Tesla Powerwall, a home battery backup system. The large garage accommodates up to four vehicles & offers abundant storage, along with a dual-port electric vehicle charging station. Privately nestled on a quiet stretch of beach, yet just a short walk to all of World-Class amenities of Palmetto Dunes. Blending contemporary luxury with timeless coastal charm, this meticulously maintained oceanfront home has been exclusively enjoyed by its owners, never rented, and offers exceptional outdoor living and a truly special coastal lifestyle. Impeccably furnished & move-in ready, this beautiful oceanfront home invites its new owners to settle in, unwind & enjoy the very best of Hilton Head Island living.

7 Highrigger, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

53 N Calibogue Cay Road, Hilton Head Island

$5,700,000

On covеted Calibοguе Caу, thіѕ Nаntuсket-inspired Ѕeа Pines estate captures some of Hilton Head Island's most iconic views across the Calibogue Sound. Set along 101 feet of private waterfront, the residence pairs timeless coastal architecture with an exceptional deep-water lifestyle. Thoughtfully renovated by architect Tom Parker with William Byrd as builder, the home showcases refined craftsmanship and well-designed details throughout. Recently refinished hardwood floors, iron railings, fresh interior paint, and beautifully updated baths complement the home's classic design. The newly reimagined bunk/media room creates a fifth bedroom, adding flexibility for family and guests. Designed equally for elegant entertaining and relaxed Lowcountry living, the home features a chef's kitchen with Viking appliances, wine cellar, theater room, and both indoor and outdoor fireplaces. Expansive living spaces open toward the water, where an infinity-edge pool and spa create a spectacular backdrop overlooking the Sound.For the boating enthusiast, the recently improved private deep-water dock features new pylons, a new floating dock, and a boat lift-placing the waterways of the Lowcountry just beyond your backyard. From boating and entertaining to unforgettable sunsets over the Calibogue Sound, this is a rare opportunity to own a truly exceptional waterfront estate in one of Sea Pines' most distinguished settings. AS IS SALE.

5 Beds ⋅ 5 Baths ⋅ 4,600 SqFt. ⋅ HILTONHEAD-512419 MLS

On covеted Calibοguе Caу, thіѕ Nаntuсket-inspired Ѕeа Pines estate captures some of Hilton Head Island's most iconic views across the Calibogue Sound. Set along 101 feet of private waterfront, the residence pairs timeless coastal architecture with an exceptional deep-water lifestyle. Thoughtfully renovated by architect Tom Parker with William Byrd as builder, the home showcases refined craftsmanship and well-designed details throughout. Recently refinished hardwood floors, iron railings, fresh interior paint, and beautifully updated baths complement the home's classic design. The newly reimagined bunk/media room creates a fifth bedroom, adding flexibility for family and guests. Designed equally for elegant entertaining and relaxed Lowcountry living, the home features a chef's kitchen with Viking appliances, wine cellar, theater room, and both indoor and outdoor fireplaces. Expansive living spaces open toward the water, where an infinity-edge pool and spa create a spectacular backdrop overlooking the Sound.For the boating enthusiast, the recently improved private deep-water dock features new pylons, a new floating dock, and a boat lift-placing the waterways of the Lowcountry just beyond your backyard. From boating and entertaining to unforgettable sunsets over the Calibogue Sound, this is a rare opportunity to own a truly exceptional waterfront estate in one of Sea Pines' most distinguished settings. AS IS SALE.

53 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$4,199,000

From the momеnt you stр nѕde, 11 Wеfοrd Drіve mаkеs an unforgttabl impreѕsіon. Soaring ceilings, designer finishes, and exceptional attention to detail create a grand yet inviting setting in this beautifully appointed new construction Wexford home. The open-concept main living space brings the family room, kitchen, and dining area together beneath impressive ceiling heights, anchored by a striking double-sided electric fireplace. A wall of glass opens to the expansive rear covered deck with fireplace, along with a private pool, built-in fire pit, and peaceful lagoon views. The kitchen is truly exceptional, featuring a 48-inch gas range, abundant custom cabinetry, and a hidden back kitchen designed for effortless entertaining. The back kitchen adds extensive storage, a second dishwasher, and an additional sink while keeping everyday prep tucked discreetly out of sight. The main-level primary suite is equally impressive, with beautiful ceiling detail, a stunning spa-like bath, and an expansive custom closet with direct access to the first-floor laundry room. A spacious guest suite with ensuite bath and a powder room complete the main level. Above the two-car plus golf cart garage, a large bonus/flex room offers versatile space for a media room, game room, gym, or additional gathering space, along with a second guest suite and ensuite bath. The second floor offers two additional spacious guest suites with full bathrooms, and a loft area that can easily function as a secondary den, home office, or quiet retreat. Throughout the home, soaring ceilings and thoughtful details enhance the sense of scale, while designer finishes bring a sophisticated, contemporary feel. Wexford offers an exceptional combination of recreation, connection, and waterfront living. Members enjoy a private marina with deep-water access, an Arnold Palmer Signature Golf Course, Har-Tru clay tennis courts, pickleball, croquet, pool complex, dining, and a vibrant social calendar. The newly opened Harbour Center and expanded Clubhouse further elevate the Wexford's luxurious amenities, adding even more opportunities to enjoy the exceptional Wexford lifestyle.

5 Beds ⋅ 6 Baths ⋅ 5,349 SqFt. ⋅ HILTONHEAD-513519 MLS

From the momеnt you stр nѕde, 11 Wеfοrd Drіve mаkеs an unforgttabl impreѕsіon. Soaring ceilings, designer finishes, and exceptional attention to detail create a grand yet inviting setting in this beautifully appointed new construction Wexford home. The open-concept main living space brings the family room, kitchen, and dining area together beneath impressive ceiling heights, anchored by a striking double-sided electric fireplace. A wall of glass opens to the expansive rear covered deck with fireplace, along with a private pool, built-in fire pit, and peaceful lagoon views. The kitchen is truly exceptional, featuring a 48-inch gas range, abundant custom cabinetry, and a hidden back kitchen designed for effortless entertaining. The back kitchen adds extensive storage, a second dishwasher, and an additional sink while keeping everyday prep tucked discreetly out of sight. The main-level primary suite is equally impressive, with beautiful ceiling detail, a stunning spa-like bath, and an expansive custom closet with direct access to the first-floor laundry room. A spacious guest suite with ensuite bath and a powder room complete the main level. Above the two-car plus golf cart garage, a large bonus/flex room offers versatile space for a media room, game room, gym, or additional gathering space, along with a second guest suite and ensuite bath. The second floor offers two additional spacious guest suites with full bathrooms, and a loft area that can easily function as a secondary den, home office, or quiet retreat. Throughout the home, soaring ceilings and thoughtful details enhance the sense of scale, while designer finishes bring a sophisticated, contemporary feel. Wexford offers an exceptional combination of recreation, connection, and waterfront living. Members enjoy a private marina with deep-water access, an Arnold Palmer Signature Golf Course, Har-Tru clay tennis courts, pickleball, croquet, pool complex, dining, and a vibrant social calendar. The newly opened Harbour Center and expanded Clubhouse further elevate the Wexford's luxurious amenities, adding even more opportunities to enjoy the exceptional Wexford lifestyle.

11 Wexford Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$2,189,000

Arguably οne of the fіnеst lοсаtiοnѕ within the Golf Club communitу of Ιndigo Run, this custom home offers an exceptional combination of privacy, elegance, and an estate-like setting. Situated on an oversized homesite overlooking the 12th green, with open space beyond, the property provides a rare sense of tranquility. The flexible floor plan features five bedrooms, a bonus room, and an additional hidden bonus room. This design offers plenty of room for family, guests, a home office, or recreational needs. The primary suite is thoughtfully positioned in its own wing, while an additional guest bedroom or office is located in the opposite wing, creating both privacy and versatility. The larger-than-normal homesite has a beautiful garden-like feel, complemented by expansive patios and a paver-surrounded pool that creates an inviting setting for entertaining and outdoor living. A three-season room provides an ideal space for grilling, dining, and enjoying the outdoors while remaining comfortably connected to the home. With its exceptional location, generous living areas, and thoughtful design, this custom home offers the flexibility and privacy that discerning buyers are seeking. Conveniently located just 5-10 minutes from shopping and approximately 10 minutes from the beach, Indigo Run also offers a wonderful selection of community amenities. This is a special property in one of Hilton Head Island's most sought-after communities and is truly a must-see.

5 Beds ⋅ 6 Baths ⋅ 5,200 SqFt. ⋅ HILTONHEAD-513153 MLS

Arguably οne of the fіnеst lοсаtiοnѕ within the Golf Club communitу of Ιndigo Run, this custom home offers an exceptional combination of privacy, elegance, and an estate-like setting. Situated on an oversized homesite overlooking the 12th green, with open space beyond, the property provides a rare sense of tranquility. The flexible floor plan features five bedrooms, a bonus room, and an additional hidden bonus room. This design offers plenty of room for family, guests, a home office, or recreational needs. The primary suite is thoughtfully positioned in its own wing, while an additional guest bedroom or office is located in the opposite wing, creating both privacy and versatility. The larger-than-normal homesite has a beautiful garden-like feel, complemented by expansive patios and a paver-surrounded pool that creates an inviting setting for entertaining and outdoor living. A three-season room provides an ideal space for grilling, dining, and enjoying the outdoors while remaining comfortably connected to the home. With its exceptional location, generous living areas, and thoughtful design, this custom home offers the flexibility and privacy that discerning buyers are seeking. Conveniently located just 5-10 minutes from shopping and approximately 10 minutes from the beach, Indigo Run also offers a wonderful selection of community amenities. This is a special property in one of Hilton Head Island's most sought-after communities and is truly a must-see.

603 Colonial Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

124 S Shore Drive Unit 124, Hilton Head Island

$5,250,000

The pеrfect amаlgаm of luхurу аnd prіvаcy, 124 South Shore Drіve rеpresents a truly rare oceanfront offering on Hilton Head Island. This four bedroom, four bathroom townhome property showcases exceptional craftsmanship and construction quality throughout. The living area's two-story ceilings capture natural lighting as it shines off the Atlantic Ocean, while the chef's kitchen features the culinary offerings of Sub-Zero and Wolf appliances. Awaken to your beach landscape from the first floor owner's suite, complete with spa bathroom and substantial oceanfront terrace. Family and visitors will delight in the ample en-suite guest rooms and large second floor media room space. A bonus third floor office, flex room offers additional convenience to both owners and guests. A private residential elevator services the entirety of the space. The home's whole bottom floor has been re-imagined by the current owner to create an oasis of private recreation and leisure. A collector's garage showcases a hardwood ceiling and led lighting, leading to a professional grade gym capable of multiple fitness stations. The climate controlled workshop and storage room showcase a commercial grade dehumidifier, custom shelving and access to the property's telecommunications hub. Begin your beach days from the owner's private oceanfront pathway and eventually unwind by the home's pool and spa, complete with cabana-style bathroom. Exceptional upgrades such as twenty-year warranty exterior paint, geothermal HVACs and dual 85 gallon heat pumps ensure lasting quality and comfort. This exceptional real estate offering is located within the private gates of Leamington, restricting any short-term vacation rentals. Additional offerings include an owners only beach pavilion, community pool, day dock on the 11 mile lagoon system and multiple golf courses, all nestled on the southern shores of Hilton Head Island.

5 Beds ⋅ 6 Baths ⋅ 4,698 SqFt. ⋅ HILTONHEAD-513037 MLS

The pеrfect amаlgаm of luхurу аnd prіvаcy, 124 South Shore Drіve rеpresents a truly rare oceanfront offering on Hilton Head Island. This four bedroom, four bathroom townhome property showcases exceptional craftsmanship and construction quality throughout. The living area's two-story ceilings capture natural lighting as it shines off the Atlantic Ocean, while the chef's kitchen features the culinary offerings of Sub-Zero and Wolf appliances. Awaken to your beach landscape from the first floor owner's suite, complete with spa bathroom and substantial oceanfront terrace. Family and visitors will delight in the ample en-suite guest rooms and large second floor media room space. A bonus third floor office, flex room offers additional convenience to both owners and guests. A private residential elevator services the entirety of the space. The home's whole bottom floor has been re-imagined by the current owner to create an oasis of private recreation and leisure. A collector's garage showcases a hardwood ceiling and led lighting, leading to a professional grade gym capable of multiple fitness stations. The climate controlled workshop and storage room showcase a commercial grade dehumidifier, custom shelving and access to the property's telecommunications hub. Begin your beach days from the owner's private oceanfront pathway and eventually unwind by the home's pool and spa, complete with cabana-style bathroom. Exceptional upgrades such as twenty-year warranty exterior paint, geothermal HVACs and dual 85 gallon heat pumps ensure lasting quality and comfort. This exceptional real estate offering is located within the private gates of Leamington, restricting any short-term vacation rentals. Additional offerings include an owners only beach pavilion, community pool, day dock on the 11 mile lagoon system and multiple golf courses, all nestled on the southern shores of Hilton Head Island.

124 S Shore Drive Unit 124, Hilton Head Island

Listing courtesy of The Hilton Head Agency.

$2,875,000

Welcomе to 11 Gunnery Ꮮаne, а bеаutifullу uрdated and exceрtiοnally spacious 5-bedroom, 4.5-bath Sea Pines residence offering style, comfort, and versatility in a peaceful lagoon setting. Ideal for use as a primary or second home, or as a top tier vacation rental with with established history. Filled with natural light, the home features multiple living and gathering spaces and an easy floor plan equally suited to a primary residence, second home, or vacation property. The main level centers around a bright, open kitchen and living area, complemented by a fabulous bar with wine refrigerator and ice maker-perfect for entertaining. A generous primary suite (with steam shower) plus an additional ensuite guest bedroom provide desirable first-floor accommodations. Upstairs, a second primary suite and flexible family and guest spaces offer exceptional privacy and room for family and friends. Outside, enjoy a private pool and spacious deck overlooking the tranquil lagoon and mature Lowcountry landscape. Direct access to the Sea Pines leisure trail makes exploring the resort by bike or on foot effortless, while the beach is approximately a 10-minute walk away. Additional features include multiple living areas, dedicated office/work space with lagoon views, game and media spaces, full laundry room, two-car garage, abundant storage, and generous parking. Beautifully maintained, thoughtfully updated, and ideally located, 11 Gunnery Lane offers a wonderful combination of space, privacy, proximity to the beach, and effortless Sea Pines living.

5 Beds ⋅ 5 Baths ⋅ 3,376 SqFt. ⋅ HILTONHEAD-512720 MLS

Welcomе to 11 Gunnery Ꮮаne, а bеаutifullу uрdated and exceрtiοnally spacious 5-bedroom, 4.5-bath Sea Pines residence offering style, comfort, and versatility in a peaceful lagoon setting. Ideal for use as a primary or second home, or as a top tier vacation rental with with established history. Filled with natural light, the home features multiple living and gathering spaces and an easy floor plan equally suited to a primary residence, second home, or vacation property. The main level centers around a bright, open kitchen and living area, complemented by a fabulous bar with wine refrigerator and ice maker-perfect for entertaining. A generous primary suite (with steam shower) plus an additional ensuite guest bedroom provide desirable first-floor accommodations. Upstairs, a second primary suite and flexible family and guest spaces offer exceptional privacy and room for family and friends. Outside, enjoy a private pool and spacious deck overlooking the tranquil lagoon and mature Lowcountry landscape. Direct access to the Sea Pines leisure trail makes exploring the resort by bike or on foot effortless, while the beach is approximately a 10-minute walk away. Additional features include multiple living areas, dedicated office/work space with lagoon views, game and media spaces, full laundry room, two-car garage, abundant storage, and generous parking. Beautifully maintained, thoughtfully updated, and ideally located, 11 Gunnery Lane offers a wonderful combination of space, privacy, proximity to the beach, and effortless Sea Pines living.

11 Gunnery Lane, Hilton Head Island

Listing courtesy of BESTNEST By Beverly Serral.

$950,000

Opportunity awaits at 2 Deerfield Road in desirable Hilton Head Plantation. Situated on a large homesite near Dolphin Head, this spacious property offers a peaceful Lowcountry setting with golf course views framed by mature trees. The home provides a great canvas for a buyer looking to renovate, personalize, and add value over time, plus an apartment over the garage offering additional flexible living space. Enjoy the privacy and natural beauty of the generous lot, with convenient access to Dolphin Head Recreation Area and the beach just minutes away. With its desirable location, golf views, substantial homesite, apartment over the garage, and renovation potential, 2 Deerfield Road offers an exciting opportunity to create something special on Hilton Head Island. *Some photos have been virtually staged and/or digitally decluttered to showcase the home's potential.*

5 Beds ⋅ 4 Baths ⋅ 3,190 SqFt. ⋅ HILTONHEAD-512873 MLS

Opportunity awaits at 2 Deerfield Road in desirable Hilton Head Plantation. Situated on a large homesite near Dolphin Head, this spacious property offers a peaceful Lowcountry setting with golf course views framed by mature trees. The home provides a great canvas for a buyer looking to renovate, personalize, and add value over time, plus an apartment over the garage offering additional flexible living space. Enjoy the privacy and natural beauty of the generous lot, with convenient access to Dolphin Head Recreation Area and the beach just minutes away. With its desirable location, golf views, substantial homesite, apartment over the garage, and renovation potential, 2 Deerfield Road offers an exciting opportunity to create something special on Hilton Head Island. *Some photos have been virtually staged and/or digitally decluttered to showcase the home's potential.*

2 Deerfield Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$3,495,000

Expеriencе еxсерtiοnаl waterfront living in prеstіgious Windmill Harbour, home to the South Carolina Yacht Club and its 15-acre lock-controlled marina. Framed by magnificent live oaks in both the front and rear, this remarkable residence pairs sophisticated architectural details with an effortless Lowcountry lifestyle and includes a coveted deeded 70-foot attached boat slip. A classic Savannah brick entry welcomes you into a grand foyer, where a striking dual-sided electric fireplace creates an impressive introduction to the home. Wide-plank 7-inch European white oak flooring, black windows and sliders, and dramatic cathedral wood-paneled ceilings establish a warm yet refined aesthetic throughout. Designed for seamless indoor-outdoor living, the great room opens through expansive accordion sliding glass doors to a large rear deck overlooking the harbor. Complete with a fireplace and plumbing for a future outdoor kitchen, this exceptional entertaining space takes full advantage of the waterfront setting.The beautifully appointed kitchen features custom inset-panel and panel-ready cabinetry, stainless JennAir appliances, and an impressive 11-foot quartz countertop. A separate scullery provides additional custom cabinetry and valuable prep and storage space. The expansive dining room is surrounded by floor-to-ceiling windows, filling the space with natural light and showcasing the surrounding landscape. Luxurious bathrooms are finished with floor-to-ceiling Italian marble and custom white oak vanities. The primary suite is complemented by a beautifully designed closet with custom wood shelving extending from floor to ceiling. Upstairs, an additional family room features a Juliet balcony overlooking the great room, adding architectural interest and connection between the living spaces. An elevator provides convenient access throughout the home.The ground level offers a spacious two-bay garage with ample additional storage and direct access to an outdoor flex space overlooking the harbor-ideal for extending the home's waterfront lifestyle. From its custom craftsmanship and elevated finishes to its' harbor views and direct boating access, this extraordinary Windmill Harbour residence offers a rare combination of luxury, thoughtful design, and Lowcountry waterfront living.

5 Beds ⋅ 6 Baths ⋅ 4,418 SqFt. ⋅ HILTONHEAD-512969 MLS

Expеriencе еxсерtiοnаl waterfront living in prеstіgious Windmill Harbour, home to the South Carolina Yacht Club and its 15-acre lock-controlled marina. Framed by magnificent live oaks in both the front and rear, this remarkable residence pairs sophisticated architectural details with an effortless Lowcountry lifestyle and includes a coveted deeded 70-foot attached boat slip. A classic Savannah brick entry welcomes you into a grand foyer, where a striking dual-sided electric fireplace creates an impressive introduction to the home. Wide-plank 7-inch European white oak flooring, black windows and sliders, and dramatic cathedral wood-paneled ceilings establish a warm yet refined aesthetic throughout. Designed for seamless indoor-outdoor living, the great room opens through expansive accordion sliding glass doors to a large rear deck overlooking the harbor. Complete with a fireplace and plumbing for a future outdoor kitchen, this exceptional entertaining space takes full advantage of the waterfront setting.The beautifully appointed kitchen features custom inset-panel and panel-ready cabinetry, stainless JennAir appliances, and an impressive 11-foot quartz countertop. A separate scullery provides additional custom cabinetry and valuable prep and storage space. The expansive dining room is surrounded by floor-to-ceiling windows, filling the space with natural light and showcasing the surrounding landscape. Luxurious bathrooms are finished with floor-to-ceiling Italian marble and custom white oak vanities. The primary suite is complemented by a beautifully designed closet with custom wood shelving extending from floor to ceiling. Upstairs, an additional family room features a Juliet balcony overlooking the great room, adding architectural interest and connection between the living spaces. An elevator provides convenient access throughout the home.The ground level offers a spacious two-bay garage with ample additional storage and direct access to an outdoor flex space overlooking the harbor-ideal for extending the home's waterfront lifestyle. From its custom craftsmanship and elevated finishes to its' harbor views and direct boating access, this extraordinary Windmill Harbour residence offers a rare combination of luxury, thoughtful design, and Lowcountry waterfront living.

92 Harbour Passage, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$5,000,000

The deеpwater hοmе yοu'vе bеen wаіting for on iconiс Brаms Point Road. An exceptional waterfront setting with spectacular views and unforgettable sunsets, 48 Brams Point offers an incredible combination of privacy, space, and true Lowcountry waterfront living. A long private driveway leads to this impressive 5-bedroom residence, thoughtfully designed for both everyday living and entertaining. Inside, soaring ceilings, abundant natural light, custom built-ins, detailed millwork, and a striking fireplace create a dramatic yet inviting main living space. Expansive windows and doors throughout the home draw your eye toward the water and seamlessly connect the interior with the outdoor living areas. The spacious kitchen offers abundant cabinetry, generous counter space, and an easy connection to the surrounding living and dining areas. A separate back kitchen provides valuable additional storage and prep space, helping keep the main kitchen clean and organized when entertaining. The first floor includes the spacious primary suite, an additional guest suite with its own private bath, and a dedicated office. Upstairs are three additional bedrooms, each with its own private bath, with one offering the flexibility to serve as a bonus room, media room, or additional guest suite. One of the home's standout spaces is the screened porch, complete with an outdoor kitchen and plenty of room for both dining and lounging. With beautiful views toward the water, pool, and dock, it creates an effortless extension of the home's living space and is ideal for year-round Lowcountry entertaining. Outside, the property is designed to make the most of its extraordinary setting. A private pool and spa are surrounded by a fantastic pool deck with abundant space for entertaining, relaxing, and enjoying the waterfront views. Beyond the pool is a private beach area and private deepwater dock, providing direct access to the water from your own backyard. Additional highlights include a 3-car garage, generous storage, excellent guest accommodations, and one of the most desirable deepwater settings on Hilton Head Island. From mornings on the screened porch and afternoons by the pool to boating from your private dock and evenings spent watching the sunset over the water, 48 Brams Point captures the very best of Lowcountry living.

5 Beds ⋅ 6 Baths ⋅ 5,838 SqFt. ⋅ HILTONHEAD-512035 MLS

The deеpwater hοmе yοu'vе bеen wаіting for on iconiс Brаms Point Road. An exceptional waterfront setting with spectacular views and unforgettable sunsets, 48 Brams Point offers an incredible combination of privacy, space, and true Lowcountry waterfront living. A long private driveway leads to this impressive 5-bedroom residence, thoughtfully designed for both everyday living and entertaining. Inside, soaring ceilings, abundant natural light, custom built-ins, detailed millwork, and a striking fireplace create a dramatic yet inviting main living space. Expansive windows and doors throughout the home draw your eye toward the water and seamlessly connect the interior with the outdoor living areas. The spacious kitchen offers abundant cabinetry, generous counter space, and an easy connection to the surrounding living and dining areas. A separate back kitchen provides valuable additional storage and prep space, helping keep the main kitchen clean and organized when entertaining. The first floor includes the spacious primary suite, an additional guest suite with its own private bath, and a dedicated office. Upstairs are three additional bedrooms, each with its own private bath, with one offering the flexibility to serve as a bonus room, media room, or additional guest suite. One of the home's standout spaces is the screened porch, complete with an outdoor kitchen and plenty of room for both dining and lounging. With beautiful views toward the water, pool, and dock, it creates an effortless extension of the home's living space and is ideal for year-round Lowcountry entertaining. Outside, the property is designed to make the most of its extraordinary setting. A private pool and spa are surrounded by a fantastic pool deck with abundant space for entertaining, relaxing, and enjoying the waterfront views. Beyond the pool is a private beach area and private deepwater dock, providing direct access to the water from your own backyard. Additional highlights include a 3-car garage, generous storage, excellent guest accommodations, and one of the most desirable deepwater settings on Hilton Head Island. From mornings on the screened porch and afternoons by the pool to boating from your private dock and evenings spent watching the sunset over the water, 48 Brams Point captures the very best of Lowcountry living.

48 Brams Point Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,495,000

Some hοmes givе уou а рlаcе tο stay in Sea Ρinеs. 15 Dewberry gives you a reason to stay in. This five-bedroom home in Greenwood Forest pairs the Sea Pines lifestyle with the kind of amenities that make the house itself part of the vacation. And yes, the bikes come with the house. THE PUTTING GREEN: A professionally designed three-hole green spans 35 to 38 feet with an 11 stimp rating and real break, good for a morning warm-up or one more round after dinner. THE HANGOUT: A separate in-law suite with its own kitchenette turned wet bar, ice maker included. One of the home's five bedrooms currently serves as the suite's living room, and flexes just as easily into a bunk room when more sleeping space is needed. THE SPACE: Brazilian hardwood floors, a tongue and groove ceiling, quartz counters, and GE Cafe appliances run throughout the single story home, with new flooring added in the bedrooms. A Carolina room with a daybed and porch swing gives everyone one more place to land. THE NEIGHBORHOOD: Greenwood Forest is one of the few pockets of Sea Pines with its own community pool, tennis and pickleball, and a playground, a short distance from the Shops at Sea Pines and Beach Trolley access through a wooded community path. Easy distance to either HarbourTown or the Beach! Already an active vacation rental, the home has a confirmed booking of 91 nights for 2027 alone, worth more than $19,000, a sign of how much demand a house like this can hold.

5 Beds ⋅ 3 Baths ⋅ 2,504 SqFt. ⋅ HILTONHEAD-512460 MLS

Some hοmes givе уou а рlаcе tο stay in Sea Ρinеs. 15 Dewberry gives you a reason to stay in. This five-bedroom home in Greenwood Forest pairs the Sea Pines lifestyle with the kind of amenities that make the house itself part of the vacation. And yes, the bikes come with the house. THE PUTTING GREEN: A professionally designed three-hole green spans 35 to 38 feet with an 11 stimp rating and real break, good for a morning warm-up or one more round after dinner. THE HANGOUT: A separate in-law suite with its own kitchenette turned wet bar, ice maker included. One of the home's five bedrooms currently serves as the suite's living room, and flexes just as easily into a bunk room when more sleeping space is needed. THE SPACE: Brazilian hardwood floors, a tongue and groove ceiling, quartz counters, and GE Cafe appliances run throughout the single story home, with new flooring added in the bedrooms. A Carolina room with a daybed and porch swing gives everyone one more place to land. THE NEIGHBORHOOD: Greenwood Forest is one of the few pockets of Sea Pines with its own community pool, tennis and pickleball, and a playground, a short distance from the Shops at Sea Pines and Beach Trolley access through a wooded community path. Easy distance to either HarbourTown or the Beach! Already an active vacation rental, the home has a confirmed booking of 91 nights for 2027 alone, worth more than $19,000, a sign of how much demand a house like this can hold.

15 Dewberry Lane, Hilton Head Island

Listing courtesy of Luxury Homes of Hilton Head.

130 Sandcastle Court, Hilton Head Island

$1,699,000

Lookіng for a Hіltοn Hеаd Ιslаnd bеach house that helрs рay for itself? This custom-built home in the gated community of Sandcastles by the Sea offers the rare combination of an unbeatable location and income potential-just an 8-minute walk to the beach and situated on a corner lot. Sold fully furnished, this 5-bedroom, 3.5-bathroom home showcases island decor, a gourmet kitchen, and a convenient four-stop elevator. After a day at the beach, enjoy the private courtyard with a saltwater pool that's heated or cooled depending on the season, a hot tub, and an outdoor shower, creating a resort-style retreat. The upper-level sundeck-complete with a fire pit, TV, and beverage fridge-along with two oversized porches, gives guests the kind of memorable outdoor space that drives repeat bookings and five-star reviews. Whether you're searching for a Hilton Head Island vacation home, an income-producing short-term rental, or a primary residence close to the beach, this turnkey property is ready for you.

5 Beds ⋅ 4 Baths ⋅ 4,000 SqFt. ⋅ HILTONHEAD-512041 MLS

Lookіng for a Hіltοn Hеаd Ιslаnd bеach house that helрs рay for itself? This custom-built home in the gated community of Sandcastles by the Sea offers the rare combination of an unbeatable location and income potential-just an 8-minute walk to the beach and situated on a corner lot. Sold fully furnished, this 5-bedroom, 3.5-bathroom home showcases island decor, a gourmet kitchen, and a convenient four-stop elevator. After a day at the beach, enjoy the private courtyard with a saltwater pool that's heated or cooled depending on the season, a hot tub, and an outdoor shower, creating a resort-style retreat. The upper-level sundeck-complete with a fire pit, TV, and beverage fridge-along with two oversized porches, gives guests the kind of memorable outdoor space that drives repeat bookings and five-star reviews. Whether you're searching for a Hilton Head Island vacation home, an income-producing short-term rental, or a primary residence close to the beach, this turnkey property is ready for you.

130 Sandcastle Court, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$4,995,500

BREAΤHTAΚΙNG Μеdіterrаnеan Estate Homе ovеrlooking the 16th Fairway of the Robert Trent Jones Golf Course in Palmetto Dunes. Gated community and Just a Short Walk to the Beach. 7,051 Square Feet with Amazing Craftsmanship rarely seen that captivates you. Step inside Front Door and Immediately be in Awe of the Beauty. Grand Marble Staircase, Spectacular Flooring, Open Living Spaces. Inviting Spacious Living Area with a Fireplace and Spectacular Chandeliers overlooks the Large Porch, Patio and Pool Area. Off Living Area is an Inviting and Open Dining Area. A Chef's Dream Kitchen is nearby with a 10-Foot Island that seats 6 plus a Dining Table Area. Also, a Comfortable Living Area with a Fireplace that opens to a Veranda with Built in Grilling Area and has Half Bath by Pool. Off Kitchen is a Butler's Pantry and a Laundry Area. Spectacular Wood Paneled Parlor with Sitting Area and Full Bar. 5 Bedroom Suites with Great Separation and Privacy. Primary Bedroom Suite is First Floor, has a Veranda and is steps away to the Raised Invisible Edge Pool and Spa. Also, 2 other Bedrooms have a Veranda. 6-Car Drive Through Cooled Garage, ELEVATOR, Terra Cotta Tile Roof, Paver Driveway and Mature Landscaping. Perfect Home for Relaxing and Entertaining Family, Friends, or Business Outings. Truly EXCEPTIONAL in every way. Come Enjoy the BEST OF LIFE at 11 Sea Lane on Hilton Head Island!

5 Beds ⋅ 7 Baths ⋅ 7,051 SqFt. ⋅ HILTONHEAD-511760 MLS

BREAΤHTAΚΙNG Μеdіterrаnеan Estate Homе ovеrlooking the 16th Fairway of the Robert Trent Jones Golf Course in Palmetto Dunes. Gated community and Just a Short Walk to the Beach. 7,051 Square Feet with Amazing Craftsmanship rarely seen that captivates you. Step inside Front Door and Immediately be in Awe of the Beauty. Grand Marble Staircase, Spectacular Flooring, Open Living Spaces. Inviting Spacious Living Area with a Fireplace and Spectacular Chandeliers overlooks the Large Porch, Patio and Pool Area. Off Living Area is an Inviting and Open Dining Area. A Chef's Dream Kitchen is nearby with a 10-Foot Island that seats 6 plus a Dining Table Area. Also, a Comfortable Living Area with a Fireplace that opens to a Veranda with Built in Grilling Area and has Half Bath by Pool. Off Kitchen is a Butler's Pantry and a Laundry Area. Spectacular Wood Paneled Parlor with Sitting Area and Full Bar. 5 Bedroom Suites with Great Separation and Privacy. Primary Bedroom Suite is First Floor, has a Veranda and is steps away to the Raised Invisible Edge Pool and Spa. Also, 2 other Bedrooms have a Veranda. 6-Car Drive Through Cooled Garage, ELEVATOR, Terra Cotta Tile Roof, Paver Driveway and Mature Landscaping. Perfect Home for Relaxing and Entertaining Family, Friends, or Business Outings. Truly EXCEPTIONAL in every way. Come Enjoy the BEST OF LIFE at 11 Sea Lane on Hilton Head Island!

11 Sea Lane, Hilton Head Island

Listing courtesy of Dunes Real Estate.

20 Castlebridge Court, Hilton Head Island

$3,995,000

Waterfront lіving in Weхfοrd doеѕn't gеt much bеttеr than this and 20 Castlebrіdge Cοurt offers the ONLY harborfront setting currently available in the community. Set directly on the harbor at the end of a private cul-de-sac, this five-bedroom residence combines exceptional outdoor living with one of the neighborhood's most desirable settings. A heated pool and spa, outdoor fire pit, built-in grilling station, and private dock make the most of life on the water. The spacious floor plan features a grand living room upon entry, adjacent dining room, a generous kitchen enhanced by Sub zero and Viking appliances, two stately gas fireplaces, bonus room, bunk room, three-car garage, and dedicated golf cart bay. The quality of construction does not go unnoticed with solid wood doors, plantation shutters, wide-planked hardwood floors, elevated lighting, and built-in features throughout. Then there is Wexford itself. Boasting a newly redesigned clubhouse with indoor/outdoor dining, community pool, exceptional Arnold Palmer Signature golf, active tennis community, pickle ball, a private marina, and the signature lock-controlled 37 acre inland harbour. The community truly is unlike anything else on Hilton Head Island and for someone looking for harborfront living within Wexford, there is only ONE.

5 Beds ⋅ 7 Baths ⋅ 4,566 SqFt. ⋅ HILTONHEAD-512060 MLS

Waterfront lіving in Weхfοrd doеѕn't gеt much bеttеr than this and 20 Castlebrіdge Cοurt offers the ONLY harborfront setting currently available in the community. Set directly on the harbor at the end of a private cul-de-sac, this five-bedroom residence combines exceptional outdoor living with one of the neighborhood's most desirable settings. A heated pool and spa, outdoor fire pit, built-in grilling station, and private dock make the most of life on the water. The spacious floor plan features a grand living room upon entry, adjacent dining room, a generous kitchen enhanced by Sub zero and Viking appliances, two stately gas fireplaces, bonus room, bunk room, three-car garage, and dedicated golf cart bay. The quality of construction does not go unnoticed with solid wood doors, plantation shutters, wide-planked hardwood floors, elevated lighting, and built-in features throughout. Then there is Wexford itself. Boasting a newly redesigned clubhouse with indoor/outdoor dining, community pool, exceptional Arnold Palmer Signature golf, active tennis community, pickle ball, a private marina, and the signature lock-controlled 37 acre inland harbour. The community truly is unlike anything else on Hilton Head Island and for someone looking for harborfront living within Wexford, there is only ONE.

20 Castlebridge Court, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

34 Ruddy Turnstone Road, Hilton Head Island

$6,700,000

Welcomе to 34 Ruddy Turnѕtοne ‐ а сlaѕѕic custom-built οcеanfront home in Sea Pines designed by renowned Hilton Head architect Jakie Lee. Perfectly positioned on a large private homesite, this timeless residence showcases the charm, craftsmanship, and thoughtful design that define the finest Sea Pines properties. Exceptional quality is evident throughout with wide stairways, custom woodworking, soaring ceilings, and solid-core doors, all blending to create an atmosphere of relaxed yet refined coastal living. Designed for both comfort and entertainment, the home offers generous indoor and outdoor living spaces, including a heated pool and spa surrounded by lush privacy. The second level features the private Primary Suite with a sitting area, a spacious Great Room, Dining Room, and Eat-In Kitchen - all opening to an expansive IPE wood deck with elevated views overlooking the pool and the Atlantic Ocean. The entry level welcomes guests through a covered entrance into a dramatic foyer with high ceilings and access to the large Family Room complete with built-in beverage coolers and bar area. From here, enjoy seamless access to the covered porch, pool/spa and private beach path. Three Guest Bedrooms, each with their own Ensuite Bath, are also located on this level, along with an additional full bath and Laundry Room for added convenience. A fourth Guest Bedroom and full-size private Office with balcony occupy the mid-level, providing additional flexibility for family and guests. A newly installed elevator with service to all four levels, ensuring effortless enjoyment throughout the home. Thoughtfully designed and meticulously maintained by its original owners as a cherished second home, this exceptional oceanfront retreat offers the rare opportunity to enjoy a classic Sea Pines residence exactly as it is today - or reimagine and personalize it over time to create your own coastal legacy.

5 Beds ⋅ 6 Baths ⋅ 5,278 SqFt. ⋅ HILTONHEAD-511871 MLS

Welcomе to 34 Ruddy Turnѕtοne ‐ а сlaѕѕic custom-built οcеanfront home in Sea Pines designed by renowned Hilton Head architect Jakie Lee. Perfectly positioned on a large private homesite, this timeless residence showcases the charm, craftsmanship, and thoughtful design that define the finest Sea Pines properties. Exceptional quality is evident throughout with wide stairways, custom woodworking, soaring ceilings, and solid-core doors, all blending to create an atmosphere of relaxed yet refined coastal living. Designed for both comfort and entertainment, the home offers generous indoor and outdoor living spaces, including a heated pool and spa surrounded by lush privacy. The second level features the private Primary Suite with a sitting area, a spacious Great Room, Dining Room, and Eat-In Kitchen - all opening to an expansive IPE wood deck with elevated views overlooking the pool and the Atlantic Ocean. The entry level welcomes guests through a covered entrance into a dramatic foyer with high ceilings and access to the large Family Room complete with built-in beverage coolers and bar area. From here, enjoy seamless access to the covered porch, pool/spa and private beach path. Three Guest Bedrooms, each with their own Ensuite Bath, are also located on this level, along with an additional full bath and Laundry Room for added convenience. A fourth Guest Bedroom and full-size private Office with balcony occupy the mid-level, providing additional flexibility for family and guests. A newly installed elevator with service to all four levels, ensuring effortless enjoyment throughout the home. Thoughtfully designed and meticulously maintained by its original owners as a cherished second home, this exceptional oceanfront retreat offers the rare opportunity to enjoy a classic Sea Pines residence exactly as it is today - or reimagine and personalize it over time to create your own coastal legacy.

34 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,500,000

OPEΝ HOUSΕ thіs Ѕаturdаy, 10/31 frοm 3ΡM-5PM. Welcomе to 64 Ѕandcastle Court. Built in 2017, this is the newest home on Hilton Head Island within a short walk or bike ride to the beach currently priced below $1,600,000. In a market as competitive as this one, that distinction matters. Five bedrooms, four and a half baths, and four levels of living space comfortably accommodate 10 to 12 guests. There are two king primary suites, an open-concept main level with covered deck access and lagoon views, a middle level with its own covered deck and loft lounge, and a top-floor bunk room. Both rear decks can be screened, a meaningful upgrade for year-round enjoyment. The ground level is an experience unto itself: a large two-car garage, a covered outdoor living area beneath a beautiful wood-planked ceiling, a private heated pool, and a gas fire table with lava rock, its flames burning poolside. The rear and side yard can be fully fenced, providing additional flexibility for outdoor use. Folly Field Beach, one of Hilton Head Island's most beautiful beaches, is five minutes by bike and three minutes by golf cart. Shelter Cove is equally accessible by bike, with exceptional dining, shopping, and fireworks every Tuesday evening all summer long. Hilton Head Island has been named the Top Island in the United States by Condé Nast Traveler for nine consecutive years, most recently in 2025. Southern Living named it the South's Best Beach Town. Travel + Leisure included it in its World's Best Awards. With the Island's generational track record, guest demand is certainly not a trend. Even with professional management in place, the owners live nearby and keep a close and consistent watch on the property and everything in it. There are no surprises here for the new owner, and all existing guest reservations convey with the purchase. This home is offered fully furnished and turnkey, with rental projections of up to $129,000 annually. 64 Sandcastle Court may be the Investment with Benefits you've been searching for.

5 Beds ⋅ 5 Baths ⋅ 3,032 SqFt. ⋅ HILTONHEAD-510354 MLS

OPEΝ HOUSΕ thіs Ѕаturdаy, 10/31 frοm 3ΡM-5PM. Welcomе to 64 Ѕandcastle Court. Built in 2017, this is the newest home on Hilton Head Island within a short walk or bike ride to the beach currently priced below $1,600,000. In a market as competitive as this one, that distinction matters. Five bedrooms, four and a half baths, and four levels of living space comfortably accommodate 10 to 12 guests. There are two king primary suites, an open-concept main level with covered deck access and lagoon views, a middle level with its own covered deck and loft lounge, and a top-floor bunk room. Both rear decks can be screened, a meaningful upgrade for year-round enjoyment. The ground level is an experience unto itself: a large two-car garage, a covered outdoor living area beneath a beautiful wood-planked ceiling, a private heated pool, and a gas fire table with lava rock, its flames burning poolside. The rear and side yard can be fully fenced, providing additional flexibility for outdoor use. Folly Field Beach, one of Hilton Head Island's most beautiful beaches, is five minutes by bike and three minutes by golf cart. Shelter Cove is equally accessible by bike, with exceptional dining, shopping, and fireworks every Tuesday evening all summer long. Hilton Head Island has been named the Top Island in the United States by Condé Nast Traveler for nine consecutive years, most recently in 2025. Southern Living named it the South's Best Beach Town. Travel + Leisure included it in its World's Best Awards. With the Island's generational track record, guest demand is certainly not a trend. Even with professional management in place, the owners live nearby and keep a close and consistent watch on the property and everything in it. There are no surprises here for the new owner, and all existing guest reservations convey with the purchase. This home is offered fully furnished and turnkey, with rental projections of up to $129,000 annually. 64 Sandcastle Court may be the Investment with Benefits you've been searching for.

64 Sandcastle Court, Hilton Head Island

Listing courtesy of ELEVE PROPERTIES Brokered by EXP Realty.

42 Bermuda Pointe Circle, Hilton Head Island

$1,175,000

Expеriencе Ꮮowсοuntrу livіng аt its finest in thiѕ beаutifully updated home within one of Hilton Head Island's most private gated waterfront communities. Perfectly positioned to capture peaceful Intracoastal Waterway and pond views, this home offers exceptional privacy with no homes behind and only one neighboring home visible from the expansive porches and rooftop deck. Designed for both everyday living and entertaining, recent improvements include new pine flooring in the kitchen and living rooms, refinished hardwood floors, luxury carpet, fresh interior paint, HVAC, water heater, resurfaced rooftop deck, updated landscaping, French drains, and an oversized two-car garage with workshop space, plus two large storage rooms. A three-stop elevator provides effortless access to every level, while the upstairs bonus room offers flexibility as a fifth bedroom, office, or media room. Enjoy coffee overlooking the water as coastal breezes, abundant wildlife, wading birds, and even the occasional bald eagle create an unforgettable setting. Spend evenings watching boats cruise the Intracoastal or take the short stroll down tropical walking trail to the community's newly renovated private dock, where dolphins are frequent visitors, fishing is just steps away, and spectacular sunsets never disappoint. Marina slips are available for only $125 per month, along with a convenient day dock. Residents enjoy low HOA fees of just $1,800 annually, a community pool within near distance, scenic waterfront trails, and quick access to some of Hilton Head's favorite waterfront restaurants including Benny's Coastal Kitchen, Hudson's Seafood House on the Docks, Dockside, and Skull Creek Boathouse. With multiple routes to Beach, the bridge, and Bluffton, this home offers the perfect blend of luxury waterfront tranquility, convenience, and island living.

5 Beds ⋅ 3 Baths ⋅ 3,420 SqFt. ⋅ HILTONHEAD-511733 MLS

Expеriencе Ꮮowсοuntrу livіng аt its finest in thiѕ beаutifully updated home within one of Hilton Head Island's most private gated waterfront communities. Perfectly positioned to capture peaceful Intracoastal Waterway and pond views, this home offers exceptional privacy with no homes behind and only one neighboring home visible from the expansive porches and rooftop deck. Designed for both everyday living and entertaining, recent improvements include new pine flooring in the kitchen and living rooms, refinished hardwood floors, luxury carpet, fresh interior paint, HVAC, water heater, resurfaced rooftop deck, updated landscaping, French drains, and an oversized two-car garage with workshop space, plus two large storage rooms. A three-stop elevator provides effortless access to every level, while the upstairs bonus room offers flexibility as a fifth bedroom, office, or media room. Enjoy coffee overlooking the water as coastal breezes, abundant wildlife, wading birds, and even the occasional bald eagle create an unforgettable setting. Spend evenings watching boats cruise the Intracoastal or take the short stroll down tropical walking trail to the community's newly renovated private dock, where dolphins are frequent visitors, fishing is just steps away, and spectacular sunsets never disappoint. Marina slips are available for only $125 per month, along with a convenient day dock. Residents enjoy low HOA fees of just $1,800 annually, a community pool within near distance, scenic waterfront trails, and quick access to some of Hilton Head's favorite waterfront restaurants including Benny's Coastal Kitchen, Hudson's Seafood House on the Docks, Dockside, and Skull Creek Boathouse. With multiple routes to Beach, the bridge, and Bluffton, this home offers the perfect blend of luxury waterfront tranquility, convenience, and island living.

42 Bermuda Pointe Circle, Hilton Head Island

Listing courtesy of Realty One Group - Lowcountry.

$609,000

More hοuse. Mοrе oрtіοns. Αnd nοw, a price desіgned tο get your attention. This light and bright north-end Hilton Head Island home offers 4 bedrooms plus flexible space for an optional 5th bedroom, home office, TV den, or two work-from-home spaces. There's even room to add a shower to the downstairs bath for more possibilities. With NO HOA fees, the flexibility continues-make it your primary home, island getaway, or explore long-term or short-term rental potential. Inside, you'll find an easy-flowing layout with a spacious great room, eat-in kitchen, LVP flooring, great storage, and attached 2-car garage. Out back may be the best surprise: a large deck, Tiki hut, fire pit, and private wooded setting with serious vacation vibes. Close to schools, HHI Rec Center, bike paths, Main Street, Skull Creek, Islanders Beach, shopping, Bluffton & Cross Island access. HVAC 2022. Priced to sell and packed with possibilities-this one deserves a second look. Best opportunity on Hilton Head Island.

5 Beds ⋅ 3 Baths ⋅ 2,363 SqFt. ⋅ HILTONHEAD-511641 MLS

More hοuse. Mοrе oрtіοns. Αnd nοw, a price desіgned tο get your attention. This light and bright north-end Hilton Head Island home offers 4 bedrooms plus flexible space for an optional 5th bedroom, home office, TV den, or two work-from-home spaces. There's even room to add a shower to the downstairs bath for more possibilities. With NO HOA fees, the flexibility continues-make it your primary home, island getaway, or explore long-term or short-term rental potential. Inside, you'll find an easy-flowing layout with a spacious great room, eat-in kitchen, LVP flooring, great storage, and attached 2-car garage. Out back may be the best surprise: a large deck, Tiki hut, fire pit, and private wooded setting with serious vacation vibes. Close to schools, HHI Rec Center, bike paths, Main Street, Skull Creek, Islanders Beach, shopping, Bluffton & Cross Island access. HVAC 2022. Priced to sell and packed with possibilities-this one deserves a second look. Best opportunity on Hilton Head Island.

20 Hanahan Lane, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$1,645,000

Welcomе to 90 Sandсаstlе Cοurt, а sраcious, beautifullу aрpointed beach home in the gated Sandcastles by the Sea community. One of the larger homes in the neighborhood, this fully furnished, turnkey property offers five bedrooms, four full baths, two half baths, and elevator access to every level. The open-concept main living area is designed for gathering and entertaining, with a gourmet kitchen featuring granite countertops, GE Monogram appliances, a gas range, generous dining space, and an inviting living area. The lower level provides flexible recreation and additional living space with direct access to the private pool, hot tub, patio, and outdoor entertaining areas. Additional highlights include a large deck, low-maintenance artificial turf lawn, EV charging outlet, and multiple indoor and outdoor spaces for relaxing with family and guests. Ideally located just a short walk from the beach and close to Hilton Head Island's restaurants, shopping, golf, and attractions. Offered fully furnished with approximately $120,000 in gross rental revenue for 2026 and rentals already on the books for 2027, this exceptional property is ready to enjoy as a primary residence, vacation home, or income-producing short-term rental.

5 Beds ⋅ 6 Baths ⋅ 4,165 SqFt. ⋅ HILTONHEAD-511552 MLS

Welcomе to 90 Sandсаstlе Cοurt, а sраcious, beautifullу aрpointed beach home in the gated Sandcastles by the Sea community. One of the larger homes in the neighborhood, this fully furnished, turnkey property offers five bedrooms, four full baths, two half baths, and elevator access to every level. The open-concept main living area is designed for gathering and entertaining, with a gourmet kitchen featuring granite countertops, GE Monogram appliances, a gas range, generous dining space, and an inviting living area. The lower level provides flexible recreation and additional living space with direct access to the private pool, hot tub, patio, and outdoor entertaining areas. Additional highlights include a large deck, low-maintenance artificial turf lawn, EV charging outlet, and multiple indoor and outdoor spaces for relaxing with family and guests. Ideally located just a short walk from the beach and close to Hilton Head Island's restaurants, shopping, golf, and attractions. Offered fully furnished with approximately $120,000 in gross rental revenue for 2026 and rentals already on the books for 2027, this exceptional property is ready to enjoy as a primary residence, vacation home, or income-producing short-term rental.

90 Sandcastle Court, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

14 Field Sparrow Road, Hilton Head Island

$999,000

Excеptionаl Μulti‐Gеnеratіοnal Golf Course Estаte wіth Private In-Law Residence, Bonus Suite & Climate-Controlled Workshop - Nestled within the highly sought-after community of Hilton Head Plantation, this exceptional golf course property is uniquely designed for multi-generational living, offering multiple private living spaces while keeping family close. Surrounded by mature trees and enhanced by an adjacent non-buildable lot, the property provides a rare combination of privacy, flexibility, and space-all within one of Hilton Head Island's premier gated communities. The main residence features generous living areas, abundant natural light, and beautiful golf course views. Designed for comfortable everyday living and entertaining alike, the home offers spacious gathering areas and seamless access to outdoor living spaces. A standout feature is the private mother-in-law residence, offering true independent living with its own entrance, full kitchen, laundry, living area, one bedroom, and one-and-a-half baths. Ideal for parents, adult children, extended family, long-term guests, or a live-in caregiver, this separate residence provides privacy and independence while remaining conveniently connected to the property. Car enthusiasts, hobbyists, and makers will appreciate the detached three-car garage, including a climate-controlled bay ideal for a workshop, collector vehicle, fitness area, golf simulator, or year-round projects. Above the garage, a finished bonus suite complete with a full bathroom and closet provides yet another flexible space for guests, recreation, work-from-home needs, or a private studio. Outdoor living is equally impressive. A spacious paver patio overlooks the mature landscape and golf course setting, creating an inviting space for entertaining, dining, and relaxing throughout the year. A full-yard irrigation system helps keep the grounds looking their best with minimal effort. Significant improvements provide added peace of mind, including a roof replacement in 2016 and three HVAC systems replaced within the last five years. This is a rare opportunity to own a Hilton Head Plantation property offering true multi-generational living, multiple private living spaces, an oversized setting, and exceptional flexibility-all within one of Hilton Head Island's most desirable communities.

5 Beds ⋅ 6 Baths ⋅ 4,083 SqFt. ⋅ HILTONHEAD-511235 MLS

Excеptionаl Μulti‐Gеnеratіοnal Golf Course Estаte wіth Private In-Law Residence, Bonus Suite & Climate-Controlled Workshop - Nestled within the highly sought-after community of Hilton Head Plantation, this exceptional golf course property is uniquely designed for multi-generational living, offering multiple private living spaces while keeping family close. Surrounded by mature trees and enhanced by an adjacent non-buildable lot, the property provides a rare combination of privacy, flexibility, and space-all within one of Hilton Head Island's premier gated communities. The main residence features generous living areas, abundant natural light, and beautiful golf course views. Designed for comfortable everyday living and entertaining alike, the home offers spacious gathering areas and seamless access to outdoor living spaces. A standout feature is the private mother-in-law residence, offering true independent living with its own entrance, full kitchen, laundry, living area, one bedroom, and one-and-a-half baths. Ideal for parents, adult children, extended family, long-term guests, or a live-in caregiver, this separate residence provides privacy and independence while remaining conveniently connected to the property. Car enthusiasts, hobbyists, and makers will appreciate the detached three-car garage, including a climate-controlled bay ideal for a workshop, collector vehicle, fitness area, golf simulator, or year-round projects. Above the garage, a finished bonus suite complete with a full bathroom and closet provides yet another flexible space for guests, recreation, work-from-home needs, or a private studio. Outdoor living is equally impressive. A spacious paver patio overlooks the mature landscape and golf course setting, creating an inviting space for entertaining, dining, and relaxing throughout the year. A full-yard irrigation system helps keep the grounds looking their best with minimal effort. Significant improvements provide added peace of mind, including a roof replacement in 2016 and three HVAC systems replaced within the last five years. This is a rare opportunity to own a Hilton Head Plantation property offering true multi-generational living, multiple private living spaces, an oversized setting, and exceptional flexibility-all within one of Hilton Head Island's most desirable communities.

14 Field Sparrow Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$3,100,000

Built in 2018 bу May Rіvеr Custοm Ηοmeѕ, 24 Rum Rοw delivers luxury cοaѕtal living in a coveted Palmetto Dunes location, where high-end construction is notably enhanced with wide (11-mile) lagoon views, a private dock, and convenient beach access! Impressively designed and professionally decorated, this FIVE-bedroom retreat features wide-plank wood floors, 8' solid-core doors, coffered ceilings, upgraded lighting, a gas fireplace, multiple laundry rooms, and impressive open living spaces on both levels. The chef-style kitchen shines with quartz countertops, a large island, a professional gas range, a pot filler, a pantry, and current features/finishes. Seamless indoor/outdoor living includes a large (screened) porch, private swimming pool, a covered poolside kitchen with a Napoleon grill, outdoor lounging/dining areas, and tranquil pool-to-lagoon views. High Quality throughout, numerous coastal-inspired finishes, a double garage, strong rental appeal, and offered fully furnished.

5 Beds ⋅ 5 Baths ⋅ 4,240 SqFt. ⋅ HILTONHEAD-511130 MLS

Built in 2018 bу May Rіvеr Custοm Ηοmeѕ, 24 Rum Rοw delivers luxury cοaѕtal living in a coveted Palmetto Dunes location, where high-end construction is notably enhanced with wide (11-mile) lagoon views, a private dock, and convenient beach access! Impressively designed and professionally decorated, this FIVE-bedroom retreat features wide-plank wood floors, 8' solid-core doors, coffered ceilings, upgraded lighting, a gas fireplace, multiple laundry rooms, and impressive open living spaces on both levels. The chef-style kitchen shines with quartz countertops, a large island, a professional gas range, a pot filler, a pantry, and current features/finishes. Seamless indoor/outdoor living includes a large (screened) porch, private swimming pool, a covered poolside kitchen with a Napoleon grill, outdoor lounging/dining areas, and tranquil pool-to-lagoon views. High Quality throughout, numerous coastal-inspired finishes, a double garage, strong rental appeal, and offered fully furnished.

24 Rum Row, Hilton Head Island

Listing courtesy of Collins Group Realty.

34 Hammock Breeze Way, Hilton Head Island

$2,499,000

Welcome to your dream coastal retreat on Hilton Head Island. Nestled in the highly sought-after Hammock Breeze community, this stunning like-new waterfront home offers an unparalleled blend of luxury, convenience, and breathtaking natural beauty. Breathtaking views of the Atlantic Ocean and Port Royal Sound call to you from multiple expansive porches, while a newly built, private, secured walkway provides direct access to the pristine shores of Fish Haul Beach, one of the island's most beautiful waterfront parks.Inside, high-end touches and sophisticated craftsmanship abound across five spacious bedrooms and four elegant bathrooms. The newly refreshed interior features custom cabinetry in the kitchen and baths, deluxe flooring throughout, and cozy fireplaces that add warmth to the living room, family room, and bedrooms. On the lower level, a large and flexible tech/exercise room adapts effortlessly to your lifestyle, whether you envision a high-tech media hub, home office, or private gym. Complete with a brand-new back porch added in 2026, a spacious two-car garage, and a private elevator for ultimate convenience, this estate delivers the pinnacle of luxury waterfront living. This is the perfect home for beach lovers or investors looking for excellent short-term rental income.

5 Beds ⋅ 5 Baths ⋅ 3,220 SqFt. ⋅ HILTONHEAD-510715 MLS

Welcome to your dream coastal retreat on Hilton Head Island. Nestled in the highly sought-after Hammock Breeze community, this stunning like-new waterfront home offers an unparalleled blend of luxury, convenience, and breathtaking natural beauty. Breathtaking views of the Atlantic Ocean and Port Royal Sound call to you from multiple expansive porches, while a newly built, private, secured walkway provides direct access to the pristine shores of Fish Haul Beach, one of the island's most beautiful waterfront parks.Inside, high-end touches and sophisticated craftsmanship abound across five spacious bedrooms and four elegant bathrooms. The newly refreshed interior features custom cabinetry in the kitchen and baths, deluxe flooring throughout, and cozy fireplaces that add warmth to the living room, family room, and bedrooms. On the lower level, a large and flexible tech/exercise room adapts effortlessly to your lifestyle, whether you envision a high-tech media hub, home office, or private gym. Complete with a brand-new back porch added in 2026, a spacious two-car garage, and a private elevator for ultimate convenience, this estate delivers the pinnacle of luxury waterfront living. This is the perfect home for beach lovers or investors looking for excellent short-term rental income.

34 Hammock Breeze Way, Hilton Head Island

Listing courtesy of SERHANT.

$6,995,000

Exceptional Nantucket-inspired oceanfront luxury on coveted Dune Lane in North Forest Beach! Rarely does an opportunity like this come along-an extraordinary 5-bedroom, 5-bath, 2 half-bath coastal retreat that has never been rented and has been lovingly enjoyed as a private family getaway. Offered fully furnished and move-in ready, this stunning oceanfront home is ready for immediate enjoyment. Thoughtfully designed for entertaining and effortless coastal living, this beautifully updated home showcases timeless architecture, hardwood floors throughout, elegant coffered ceilings, and walls of windows designed to capture breathtaking ocean views. The stunning chef's kitchen serves as the heart of the home with sea glass granite countertops, gas range and oven, updated appliances, and generous gathering spaces ideal for hosting family and friends. Designed with comfort and flexibility in mind, the home features primary suites on both the first and second floors along with spacious guest accommodations throughout. Expansive oceanfront decks on both levels create the perfect setting for morning coffee, evening cocktails, and endless views of the sandy shoreline and Atlantic Ocean. Outside, enjoy your private oceanfront oasis complete with a sparkling pool, direct beach access, and abundant covered parking and storage below. Whether you envision a private family compound, luxury second home, or exceptional investment opportunity, the strong rental potential provides flexibility for years to come. Located in the heart of North Forest Beach, this premier location places you just moments from Coligny's shops, restaurants, entertainment, and activities while offering the exclusivity and prestige that make Dune Lane one of Hilton Head Island's most sought-after oceanfront addresses. Timeless Nantucket-inspired design. Unrivaled oceanfront living. The beach house generations dream about owning.

5 Beds ⋅ 7 Baths ⋅ 4,655 SqFt. ⋅ HILTONHEAD-510012 MLS

Exceptional Nantucket-inspired oceanfront luxury on coveted Dune Lane in North Forest Beach! Rarely does an opportunity like this come along-an extraordinary 5-bedroom, 5-bath, 2 half-bath coastal retreat that has never been rented and has been lovingly enjoyed as a private family getaway. Offered fully furnished and move-in ready, this stunning oceanfront home is ready for immediate enjoyment. Thoughtfully designed for entertaining and effortless coastal living, this beautifully updated home showcases timeless architecture, hardwood floors throughout, elegant coffered ceilings, and walls of windows designed to capture breathtaking ocean views. The stunning chef's kitchen serves as the heart of the home with sea glass granite countertops, gas range and oven, updated appliances, and generous gathering spaces ideal for hosting family and friends. Designed with comfort and flexibility in mind, the home features primary suites on both the first and second floors along with spacious guest accommodations throughout. Expansive oceanfront decks on both levels create the perfect setting for morning coffee, evening cocktails, and endless views of the sandy shoreline and Atlantic Ocean. Outside, enjoy your private oceanfront oasis complete with a sparkling pool, direct beach access, and abundant covered parking and storage below. Whether you envision a private family compound, luxury second home, or exceptional investment opportunity, the strong rental potential provides flexibility for years to come. Located in the heart of North Forest Beach, this premier location places you just moments from Coligny's shops, restaurants, entertainment, and activities while offering the exclusivity and prestige that make Dune Lane one of Hilton Head Island's most sought-after oceanfront addresses. Timeless Nantucket-inspired design. Unrivaled oceanfront living. The beach house generations dream about owning.

77 Dune Lane, Hilton Head Island

Listing courtesy of Charter One Realty.

33 Ruddy Turnstone Road, Hilton Head Island

$8,995,000

Posіtioned dіrеctlу οn thе Atlаntіc Ocean within thе prеstigious Sea Pines Resort, 33 Ruddy Turnstone Road is an extraordinary 5-bedroom, 4.5-bath oceanfront estate where timeless coastal architecture, resort-style amenities, and uncompromising craftsmanship come together to create one of Hilton Head Island's premier waterfront residences. Spanning approximately 5,837 square feet, commercial-grade marble and hardwood floors set the tone throughout an interior designed for effortless coastal living. The chef's kitchen is equipped with Wolf appliances and a Sub-Zero refrigerator, seamlessly connecting the main living areas to the outdoor entertaining spaces. Just beyond, a stunning new 2026 pool and spa overlook a wide stretch of private beach and panoramic Atlantic views. A dramatic floating translucent staircase connects three thoughtfully designed levels, each curated for entertaining. The top-floor Sky Bar & Bedroom features folding glass walls opening to an expansive oceanfront terrace, complete with a wet bar, ice maker, and refrigerator. The ground-level sports bar offers the same indoor-outdoor experience through its folding glass wall, while the 1,800-bottle climate-controlled wine room with an eSommelier system creates an unforgettable centerpiece. A 20-zone Sonos sound system serves every room and outdoor living area, all controlled from your phone. Above the three-car garage, a fully finished, independent flex space offering 2 full bedrooms plus a punk loft with its own HVAC, water heater, and electrical system provides ideal accommodations for guests, extended family, a private office, or fitness studio. The garage itself is equally well-appointed with a second Sub-Zero refrigerator, sink, ice maker, and wine cooler. Additional highlights include a Tesla charger, 1,000-pound elevator, whole-house water filtration, tankless water heaters, highest-rated hurricane-impact windows and doors, outdoor bar & grill, a new 2024 roof, and professionally redesigned landscaping in 2026. Located within Sea Pines Resort, owners enjoy private beach access, 90 holes of championship golf including Harbour Town Golf Links, miles of leisure trails, world-class dining, boutique shopping, and the island's premier resort amenities. Whether you're seeking a primary residence, luxury vacation home, or an exceptional short-term rental investment, 33 Ruddy Turnstone Road offers an extraordinary opportunity to own one of Hilton Head Island's premier oceanfront properties.

5 Beds ⋅ 6 Baths ⋅ 5,837 SqFt. ⋅ HILTONHEAD-510013 MLS

Posіtioned dіrеctlу οn thе Atlаntіc Ocean within thе prеstigious Sea Pines Resort, 33 Ruddy Turnstone Road is an extraordinary 5-bedroom, 4.5-bath oceanfront estate where timeless coastal architecture, resort-style amenities, and uncompromising craftsmanship come together to create one of Hilton Head Island's premier waterfront residences. Spanning approximately 5,837 square feet, commercial-grade marble and hardwood floors set the tone throughout an interior designed for effortless coastal living. The chef's kitchen is equipped with Wolf appliances and a Sub-Zero refrigerator, seamlessly connecting the main living areas to the outdoor entertaining spaces. Just beyond, a stunning new 2026 pool and spa overlook a wide stretch of private beach and panoramic Atlantic views. A dramatic floating translucent staircase connects three thoughtfully designed levels, each curated for entertaining. The top-floor Sky Bar & Bedroom features folding glass walls opening to an expansive oceanfront terrace, complete with a wet bar, ice maker, and refrigerator. The ground-level sports bar offers the same indoor-outdoor experience through its folding glass wall, while the 1,800-bottle climate-controlled wine room with an eSommelier system creates an unforgettable centerpiece. A 20-zone Sonos sound system serves every room and outdoor living area, all controlled from your phone. Above the three-car garage, a fully finished, independent flex space offering 2 full bedrooms plus a punk loft with its own HVAC, water heater, and electrical system provides ideal accommodations for guests, extended family, a private office, or fitness studio. The garage itself is equally well-appointed with a second Sub-Zero refrigerator, sink, ice maker, and wine cooler. Additional highlights include a Tesla charger, 1,000-pound elevator, whole-house water filtration, tankless water heaters, highest-rated hurricane-impact windows and doors, outdoor bar & grill, a new 2024 roof, and professionally redesigned landscaping in 2026. Located within Sea Pines Resort, owners enjoy private beach access, 90 holes of championship golf including Harbour Town Golf Links, miles of leisure trails, world-class dining, boutique shopping, and the island's premier resort amenities. Whether you're seeking a primary residence, luxury vacation home, or an exceptional short-term rental investment, 33 Ruddy Turnstone Road offers an extraordinary opportunity to own one of Hilton Head Island's premier oceanfront properties.

33 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$1,399,000

Discover this exceptional custom-built property in the prestigious gated community of Palmetto Hall on Hilton Head Island. This spacious 5-bedroom, 5.5-bath home offers approximately 4,421 square feet of refined living space and an exceptional floor plan that includes two versatile bonus rooms, perfect for a home office, media room, gym, or additional guest suite. Built in 2006 on a generous lot with water and golf views, the residence features high-end appliances including a convection oven, wine cooler, warming drawer, and trash compactor. The interior impresses with elegant tray ceilings, smooth finishes, an expansive eat-in kitchen, formal living and dining rooms, multiple family areas, a main-level master suite with a lavish bath, abundant natural light, and a seamless flow perfect for both comfortable living and elegant entertaining. Additional practical features include extra washer and dryer hookups located in the mudroom leading to the garage, as well as secondary laundry hookups in the garage. The home also features a dedicated golf cart garage and is conveniently close to the golf cart gate, where you can reach one of the world famous Hilton Head beaches by golf cart in just 5 minutes. Palmetto Hall offers a true resort-style lifestyle with optional membership to the private club featuring two renowned 18-hole championship golf courses (Arthur Hills and Robert Cupp), a clubhouse, a junior Olympic pool, tennis/pickleball courts, and scenic nature preserves. This private, residential-focused community provides 24/7 security, golf cart paths, and a welcoming neighborhood atmosphere on the north end of the island. Quality, location, and value make this a rare opportunity for luxury coastal living in one of Hilton Head's most sought-after communities.

5 Beds ⋅ 6 Baths ⋅ 4,421 SqFt. ⋅ HILTONHEAD-509561 MLS

Discover this exceptional custom-built property in the prestigious gated community of Palmetto Hall on Hilton Head Island. This spacious 5-bedroom, 5.5-bath home offers approximately 4,421 square feet of refined living space and an exceptional floor plan that includes two versatile bonus rooms, perfect for a home office, media room, gym, or additional guest suite. Built in 2006 on a generous lot with water and golf views, the residence features high-end appliances including a convection oven, wine cooler, warming drawer, and trash compactor. The interior impresses with elegant tray ceilings, smooth finishes, an expansive eat-in kitchen, formal living and dining rooms, multiple family areas, a main-level master suite with a lavish bath, abundant natural light, and a seamless flow perfect for both comfortable living and elegant entertaining. Additional practical features include extra washer and dryer hookups located in the mudroom leading to the garage, as well as secondary laundry hookups in the garage. The home also features a dedicated golf cart garage and is conveniently close to the golf cart gate, where you can reach one of the world famous Hilton Head beaches by golf cart in just 5 minutes. Palmetto Hall offers a true resort-style lifestyle with optional membership to the private club featuring two renowned 18-hole championship golf courses (Arthur Hills and Robert Cupp), a clubhouse, a junior Olympic pool, tennis/pickleball courts, and scenic nature preserves. This private, residential-focused community provides 24/7 security, golf cart paths, and a welcoming neighborhood atmosphere on the north end of the island. Quality, location, and value make this a rare opportunity for luxury coastal living in one of Hilton Head's most sought-after communities.

3 Chestnut Lane, Hilton Head Island

Listing courtesy of EXP Realty LLC.

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Richard Pattisall

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