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$1,495,000
5 Beds 3 Baths 2,504 SqFt. HILTONHEAD-512460 MLS
Some homes give you a place to stay in Sea Pines. 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.

$1,450,000
4 Beds 3 Baths 2,002 SqFt. HILTONHEAD-512678 MLS
Sparkling fresh and move-in-ready! This four-bedroom, three-bath home is ideally located in Greenwood Forest. Just minutes from the beach and walking distance to the shopping, dining and amenities of Sea Pines Center, this inviting property offers the perfect combination of comfort, convenience and potential. Designed for easy island living, with lots of light pouring in from windows and skylights, this home provides tons of space for family and guests. Rare four bedrooms with garage would perfectly serve as a primary residence, second home or income-producing vacation property. 2 large bedroom suites have their own bath, one with private entrance, and two living spaces are ideal for multi-generation living and vacations. Wet bar and wood burning fireplace are perfect for entertaining with access to outdoor dining on the large deck accessible from the primary bedroom as well. There is a large dining area indoors as well as an oversized kitchen island with stools and kitchen sitting area. The garage space has ample storage and access. Enjoy the added appeal of neighborhood amenities, including a community pool, tennis and basketball-perfect for relaxing, staying active and making the most of the Sea Pines lifestyle .With an excellent rental history and strong rental projections, 19 Dewberry Lane presents an outstanding opportunity for buyers seeking both a personal island retreat and an incredible investment. Whether you're looking for a easy getaway close to the beach, a full-time Hilton Head home or a property with attractive rental income potential, this home checks all the boxes. Come experience the convenience, amenities and coastal charm that make this area one of Hilton Head Island's most desirable destinations and this home is a must see.

19 Dewberry Lane, Hilton Head Island

Listing courtesy of BESTNEST By Beverly Serral.

$2,349,000
5 Beds 4 Baths 3,424 SqFt. HILTONHEAD-512304 MLS
One of the finest homes in Greenwood Forest, 19 Wisteria Lane offers a rare combination of newer construction, exceptional updates, and generous living space in the heart of Sea Pines. Built in 2008, this beautifully maintained 5-bedroom home has been cherished as a second home and has never been on the rental market. Beautiful hardwood floors flow throughout the main living areas and were refinished in 2023, complemented by tray and coffered ceilings, crown molding, designer lighting, updated hardware, and coordinated finishes throughout. The spacious kitchen was thoughtfully remodeled in 2023 and features custom heart pine cabinetry, new appliances, a large center island with a quartz countertop, abundant storage, and plenty of room for gathering and entertaining. The living area is anchored by a gas fireplace, while the sun-filled Carolina room provides an inviting additional living space and takes full advantage of the home's peaceful and private setting. Step outside to an oversized back deck overlooking a private wooded vista with plenty of room for a pool. Surrounded by mature Lowcountry landscaping, the setting feels tucked away and immersed in nature while still offering the convenience and lifestyle of Sea Pines. The first floor includes a primary suite providing convenient main-level living plus two guest bedrooms, and two additional bedrooms upstairs joined by a separate living area, offering excellent space for family and guests. Additional features include a side-entry two-car garage and numerous upgrades throughout. Centrally located in Sea Pines, Greenwood Forest residents enjoy a recently updated private community pool, tennis courts, and playground, along with access to all that Sea Pines has to offer, including miles of beaches and leisure trails, world-class golf and tennis, Harbour Town, South Beach Marina Village, dining, shopping, and more. An attractively updated and exceptionally cared-for home in one of Sea Pines' most desirable residential neighborhoods.

19 Wisteria Lane, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,875,000
4 Beds 4 Baths 2,632 SqFt. HILTONHEAD-511374 MLS
You must see this recently updated home in Greenwood Forest, built in 1996 and only ever owner occupied. It has 4 bedrooms, 4 baths and a den. Additionally, there is an oversized 2 car garage (24' by 35') with workshop, covered side porch, and large rear deck. Privacy abounds as permanent open space is on one side and across the street, while the rear deck offers a wooded view. Adjoining a sunny Carolina room is a completely renovated kitchen with white, Shaker style, soft-close cabinetry, spacious quartz countertops (peninsula & island), extra-large pantry cabinets, and newer stainless steel appliances - Bosch dishwasher, GE Profile oven/microwave combo, GE Profile refrigerator and GE 36" glass cooktop. Bathrooms have been strikingly renovated with new porcelain tile showers, vanities, lights and fixtures. The home has smooth, 10' ceilings with crown moulding while a soaring cathedral ceiling brings an elegance to the great room and dining room area. The great room shows off with a realistic electric fireplace and mantle where you can conveniently place a large, flat screen television. The entire house has been recently professionally painted and new cellular shades, window blinds, ceiling fans and designer LVP flooring have been upgraded throughout. Within the Greenwood Forest neighborhood there is a community pool, playground, tennis/pickleball court, and basketball court. This home is centrally located to the Atlantic beaches, Harbor Town, championship golf courses, Lawton Stables, and the South Beach Marina. Everything that makes Sea Pines great! This is an excellent opportunity for a relaxing permanent home, a carefree second home, or a very attractive vacation rental property.

11 Forest Drive, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry. Selling Office: COAST PROFESSIONALS Brokered by EXP Realty.

$1,449,000
4 Beds 3 Baths 2,500 SqFt. HILTONHEAD-510645 MLS
Experience the ease of the Sea Pines lifestyle in this beautifully updated Greenwood Forest retreat, where soaring ceilings, walls of glass, and a private wooded setting create a home that feels both spacious and serene. Tucked away on a quiet cul-de-sac, this light-filled 4-bedroom, 3-bath home offers exceptional indoor-outdoor living in one of Sea Pines' most convenient locations. Multiple gathering spaces flow seamlessly together, creating a layout equally suited for everyday living and entertaining. The heart of the home is the stunning kitchen, completely renovated in April 2026. Thoughtfully designed with expansive quartz countertops, abundant cabinetry, a large center island, stainless steel appliances, beverage cooler, and generous workspace, it balances style and function beautifully. Whether hosting friends or enjoying a quiet morning before a day at the beach, this is a space designed to bring people together. Just beyond, the spectacular sunroom serves as the home's signature gathering space. Framed by dramatic windows and vaulted ceilings, it captures peaceful views of the private backyard while flooding the interior with natural light. Morning coffee, afternoon reading, evening conversations-this is the space you'll find yourself drawn to again and again. Outdoor living is equally inviting. An expansive deck, hot tub, mature landscaping, and private wooded backdrop create a setting that feels worlds away while remaining remarkably convenient to everything Sea Pines has to offer. Greenwood Forest's central location is one of its greatest advantages. Residents enjoy access to the private community pool, miles of leisure trails, and a dedicated pathway to Sea Pines Center for coffee, lunch, shopping, and everyday conveniences. Harbour Town, golf, tennis, dining, and the beach are all just a short bike ride away. Whether you're searching for a primary residence, second home, or investment property, this thoughtfully updated home delivers the privacy, convenience, and lifestyle that make Sea Pines one of Hilton Head Island's most sought-after communities.

8 Pine Court, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$1,505,000
3 Beds 3 Baths 1,817 SqFt. HILTONHEAD-510269 MLS
This stunning single-level 3-bedroom, 3-bath home is located on Hilton Head Island, in the most private cul-de-sac of Greenwood Forest in Sea Pines Resort. Floor-to-ceiling windows overlook a lush, forested backyard that feels like your own private oasis. Enjoy a fenced in yard, sparkling pool, hot tub, outdoor kitchen, and an air-conditioned pool house that doubles as an office. The kitchen and bathrooms have been beautifully updated, so it's truly move-in ready. Just a quick bike ride to the beach or Harbour Town's restaurants and shops, you're right in the heart of it all. Greenwood Forest also offers its own tennis courts, playground, and community pool.

18 Forest Drive, Hilton Head Island

Listing courtesy of Dunes Real Estate. Selling Office: Sea Pines Real Estate South Beach.

$1,370,000
3 Beds 2 Baths 1,736 SqFt. HILTONHEAD-508432 MLS
Discover the effortless ease of the Sea Pines lifestyle in this beautifully updated coastal retreat, where thoughtful renovations, seamless indoor-outdoor living, and world-class amenities come together in one of Hilton Head Island's most coveted communities. This light-filled 3-bedroom, 2-bath home strikes the perfect balance of comfort and sophistication, showcasing smooth ceilings, rich travertine flooring, a cozy wood-burning fireplace in the main living area, and a fully updated kitchen built for everyday living and elevated entertaining. New windows in both the kitchen and sunroom flood the home with natural light and frame the lush surroundings, while the open, flowing layout extends into a stunning sunroom addition - a year-round haven equally suited to quiet morning coffee, sunset cocktails, or unwinding after a day at the pool or beach. At the heart of the home, the remodeled kitchen impresses with premium finishes, generous prep space, and an open connection to the living and dining areas that reinforces the home's relaxed coastal sensibility. Generously sized bedrooms offer comfort and flexibility for owners and guests alike, with the primary suite opening directly to the pool area for a true resort-style retreat. Step outside to your own private oasis, where a sparkling pool with attached spa anchors an expansive paver deck framed by a lush, wooded backdrop - the perfect setting for entertaining or quiet relaxation. A convenient storage area just off the pool deck adds everyday functionality, while the lot's serene positioning backing to community open space ensures lasting privacy and a peaceful natural buffer. Beyond your gate, enjoy easy access to community pools, championship golf, tennis, scenic bike trails, fine dining, Harbour Town, and world-class beaches just about a mile away. Whether you're seeking a primary residence, a second home, or a high-performing short-term rental investment, this property delivers rare versatility, tasteful updates, and the timeless coastal charm today's buyers are after on Hilton Head Island.

7 Wildwood Court, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: Charter One Realty.

$1,040,000
3 Beds 3 Baths 2,400 SqFt. HILTONHEAD-505701 MLS
Fabulous opportunity to own in Sea Pines just a short bike ride to the beach or HarbourTown. Desirable Greenwood Forest has private community pool, tennis and playground. Walk to the heritage golf tournament in minutes. This very special home has been loved dearly. There have been many gatherings over the years in this open floorplan. Added sq. footage includes: master bath added in the rear and side deck redesigned as a Carolina room. Garage addition, too. Vaulted ceiling, fireplace & wet bar in LR. Lots of light. Open space behind the home affords much privacy. Kitchen counters updated and one car garage added. Corner lot is convenient to the community pool which is a short walk down the street. Don't miss this one. Make your memories here.

2 Sweet Gum Lane, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty. Selling Office: Southern Lifestyle Properties of SC LLC.

$1,425,000
4 Beds 3 Baths 2,564 SqFt. HILTONHEAD-505577 MLS
Tucked within the Greenwood Forest enclave of Sea Pines, this bright and inviting 4-bedroom, 3-bath home offers vaulted ceilings, abundant natural light, and a flexible floor plan ideal as a primary residence, second home, or vacation retreat. The main living area features soaring ceilings and a fireplace, creating a warm gathering space that flows easily into the dining area and the updated kitchen, which has granite countertops and stainless steel appliances. The game room is perfect as a media room, playroom, or relaxed hangout for family and guests making the first floor space ideal for entertaining family and friends. The thoughtfully designed layout offers excellent bedroom separation, with three bedrooms on the first floor providing convenience and privacy for family and guests. Upstairs, a spacious private suite with walk-in closet and full bath offers a quiet retreat with room for a sitting area or additional sleeping space. Outdoor living is equally inviting with two private decks surrounded by the natural beauty of Sea Pines, ideal for morning coffee or relaxing after a day at the beach. The beach is less than a mile away, with easy access to the Sea Pines Beach Club, Harbour Town Marina, and South Beach. Greenwood Forest owners also enjoy a community pool and tennis courts, along with a convenient back path leading to Sea Pines Center for coffee, dining, and shopping. Whether you're searching for a primary home, second home, or Sea Pines vacation property, this Greenwood Forest retreat offers space, flexibility, and easy access to the very best of Hilton Head Island living.

11 Hollyberry Lane, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: The Hilton Head Agency.

$1,745,000
4 Beds 4 Baths 2,869 SqFt. HILTONHEAD-504130 MLS
Set on a nearly 1/3-acre private lot, this updated 4BR/4BA Greenwood Forest home offers exceptional outdoor living in the heart of Sea Pines-just a short bike ride to the beach. Enjoy a fenced backyard with a heated and cooled swimming pool, plus a two-car garage and flexible bonus room addition. Inside, the open floor plan has been refreshed with major recent improvements, including a full gut kitchen renovation with all-new soft-close cabinetry and upgraded appliances, new family room doors, fresh interior paint, and upgrades to two bathrooms. Outdoor enhancements include a new slate patio in the backyard and just off the kitchen, perfect for entertaining. Currently a rental property with forward bookings, this turnkey property also lives beautifully as a full-time residence, second home, or investment opportunity in one of Sea Pines' most desirable locations. Sold furnished.

67 Forest Drive, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club. Selling Office: RE/MAX Island Realty.

$2,080,000
3 Beds 3 Baths 2,293 SqFt. HILTONHEAD-502119 MLS
This exceptional 3-bedroom, 3-bath coastal retreat offers panoramic golf views of Harbour Town's famed #6 and #7 fairways and the #2 and #3 greens. Filled with natural light, the open floor plan features soaring ceilings, rich hardwood floors, and a seamless flow between living, dining, and kitchen areas. The newly renovated (2024) kitchen is stunning-complete with quartz countertops, soft-close cabinetry, decorative ceiling beams, and Wolf & Bosch appliances. The inviting great room includes a gas fireplace, while the flexible den can serve as a 4th bedroom or home office, both enjoying incredible golf vistas. The spacious owner's suite offers privacy, beautiful views, and a spa-like bath. Two guest suites provide comfort for family and friends. A new Trex deck overlooks the course, offering the perfect setting for outdoor relaxation and a front-row seat to the RBC Heritage Golf Tournament. Located in the heart of Sea Pines between Harbour Town and the Atlantic Ocean, residents enjoy community amenities including pool, tennis, playground, and basketball-plus easy access to beaches, shopping, and dining. Whether a primary residence, vacation home, or investment property, 13 Fern Court perfectly captures the best of coastal Lowcountry living.

13 Fern Court, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: BESTNEST By Beverly Serral.

$1,010,000
3 Beds 2 Baths 1,598 SqFt. HILTONHEAD-453366 MLS
Sea Pines beauty! Do not miss this exquisite fully furnished home in Greenwood Forest - move right in, just bring your suitcase! Beautifully decorated with high end furnishings. Complete remodel in 2018. Freshly painted exterior. HVAC 2022, water heater 2023, refrigerator & washer/dryer 2024. Centrally located between the beach, the Salty Dog, South Beach & Harbour Town. Cul-de-sac street. Walk to dining and shopping at Sea Pines Center. Greenwood Forest offers a community pool & playground. Perfect location for a primary or secondary residence or vacation rental. Open floorplan with large rear deck for indoor or outdoor entertaining.

25 Wildwood Road, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty. Selling Office: Real Life Brokered By EXP Realty LLC.

$1,375,000
3 Beds 3 Baths 2,300 SqFt. HILTONHEAD-444899 MLS
Lovely home located in Greenwood Forest. Renovated and meticulously maintained by the current owners with a Coastal Chic decor and an established rental history. Situated on one of the few lots that has a Harbourtown Golf Course and lagoon view. Interior features include LVP flooring, all-white kitchen design with recessed lighting, stainless appliances, quartz countertops, and subway tiled backsplash. The open living room offers great natural light and a shiplapped focal point fireplace. The primary bedroom offers great space with a his/hers walk-in closet. The all season heated/cooled Carolina Room has natural sunlight and beautiful views.

4 Wisteria Lane, Hilton Head Island

Listing courtesy of Hilton Head Area Properties, LLC. Selling Office: Southern Lifestyle Properties of SC LLC.

$1,250,000
3 Beds 2 Baths 2,291 SqFt. HILTONHEAD-442451 MLS
The slice of paradise you've been searching for! Centrally located in the world-famous Sea Pines Resort and within walking/biking distance to America's #1 Beach, Harbor Town, Sea Pines Center, and South Beach! This home is professionally decorated and boasts high-end finishes throughout. Complete with 3BRs w/ a Loft in the primary BR, 2BAs, 3 living spaces, a fireplace, and more! Gaze past the magnificent centuries-old Live Oak, into the wooded open space that provides extra privacy off a large deck built for entertaining. The community pool and tennis court are exclusive to Greenwood Forest owners & Guests. X-Zone, No Flood Insurance Needed!

12 Dewberry Lane, Hilton Head Island

Listing courtesy of Real Life Brokered By EXP Realty LLC. Selling Office: Charter One Realty.

$1,135,000
5 Beds 3 Baths 2,504 SqFt. HILTONHEAD-439928 MLS
Best Buy in SP, this charming 5 BR/3 BA renovated home includes an In-Law suite. Game room in in-law suite could be a bunk room & the Carolina Room with a daybed porch swing could be 6th BR! The Great Rm has a vaulted tongue & groove ceiling and Brazilian Hardwood floors. Other features include an all-new kitchen with S/S GE Café appliances, quartz countertops and new cabinets, updated baths, new furnishings, new LVP and tile flooring, a sprawling “paver” patio perfect for entertaining + new driveway. Located on a quiet culdesac. Could be primary, 2nd or rental. Amenities include community swimming pool, playground & tennis/pickleball court.

15 Dewberry Lane, Hilton Head Island

Listing courtesy of RE/MAX Island Realty. Selling Office: Luxury Homes of Hilton Head.

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