Overlook Homes For Sale

4 Beds ⋅ 5 Baths ⋅ 4,075 SqFt. ⋅ HILTONHEAD-512097 MLS

Welcome to a truly special island retreat in prestigious Port Royal on Hilton Head Island. This 4-bedroom, 3-full-bath, 2-half-bath West Indies-inspired home captures the essence of relaxed coastal luxury, with timeless architecture and an effortless sense of place. Just steps away from private beach access, it offers the perfect setting for barefoot mornings, sunset gatherings, and unforgettable days by the sea. A rare opportunity to experience the beauty, privacy, and laid-back elegance of Hilton Head Island at its finest.

6 Drayton Place, Hilton Head Island

Listing courtesy of Engel & Volkers.

$7,800,000

6 Beds ⋅ 8 Baths ⋅ 6,208 SqFt. ⋅ HILTONHEAD-510819 MLS

Experience unparalleled oceanfront luxury in the exclusive, private community of Port Royal on Hilton Head Island. This 6,208-square-foot, two-story coastal home features six bedrooms, five full baths, and three half baths, offering an exceptional blend of timeless architecture. Meticulously enhanced with extensive modern updates, the home welcomes you with a grand foyer, soaring ceilings, and open, light-filled living spaces. Stunning 2-story glass frames sweeping panoramic Atlantic vistas and the maritime landscape from nearly every room. The newly remodeled chef's kitchen is complete with leather-stamped quartz countertops, a premium Sub-Zero refrigerator, a gas Bertazzoni Range, 2 stainless steel sinks, a farmer sink and a customized bar area. A generous island designed for effortless entertaining seats six. Throughout the interior, earth toned tile, stone and wood flooring complement the home's design. The primary suite serves as a serene sanctuary with stunning ocean views and a spa-inspired bathroom while each guest suite ensures ultimate comfort with private en-suites. Notably, three of the six bedrooms boast breathtaking direct ocean views.The luxury extends outdoors to a private beachfront oasis designed for relaxation and entertainment. Expansive patios, second-story veranda balcony, and an oceanside salt water pool offer front-row seats to legendary sunrises, cool sea breezes, and the tranquil lapping of the waves. Enjoy direct, private access to Hilton Head's pristine shoreline right from your backyard. Thoughtfully updated, the property features a durable metal roof, a classic stucco exterior, a spacious three-car garage, newly paved driveway plus paver pathways and refreshed landscaping. Situated on one of Port Royal's private, winding, oak-tree-lined cul-de-sac streets, this gated-community oceanfront residence offers a rare combination of luxury, privacy, and coastal living at its best.

10 Drayton Place, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$4,250,000

3 Beds ⋅ 3 Baths ⋅ 2,733 SqFt. ⋅ HILTONHEAD-511980 MLS

Reimagine oceanfront living on one of Hilton Head Island's most exceptional beachfront properties. Set beneath magnificent live oaks and surrounded by mature natural landscaping, this private retreat offers sweeping ocean views, ample room for expansion, and the rare opportunity to renovate, enhance, or create a new coastal estate tailored to your vision. Ideally positioned in the most coveted section of Port Royal Plantation, the property enjoys a peaceful setting away from the island's resort corridor while remaining minutes from renowned dining, golf, shopping, and amenities. The expansive rear deck is perfectly suited for entertaining, oyster roasts, or simply enjoying the ocean breeze and breathtaking coastal views. The existing residence offers 3 bedrooms and 2.5 baths, with the half bath easily converted back to its original full-bath configuration. Wide-plank pine floors, a beautifully renovated chef's kitchen, and walls of glass create warm, inviting interiors that connect seamlessly with the surrounding landscape. Adding to the property's distinction is its remarkable architectural history. Designed by internationally acclaimed architect Dean Winesett, whose work has appeared in *Architectural Digest* and *Southern Living*, the home was also featured in *Southern Living* and reflects his signature Lowcountry style and craftsmanship. Port Royal Plantation prohibits short-term rentals, preserving the privacy, tranquility, and exceptional quality of life that define this exclusive oceanfront community. Private amenities reserved for property owners and their guests include an oceanfront Beach House and swimming pool overlooking the Atlantic, tennis and pickleball courts, community gardens, leisure trails, and an array of recreational and social offerings. An irreplaceable beachfront setting, celebrated architectural legacy, exceptional private amenities, and endless possibilities combine to create one of the most compelling oceanfront opportunities currently available on Hilton Head Island.

4 Middleton Place, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS III brokered eXp Realty.

$2,990,000

5 Beds ⋅ 7 Baths ⋅ 4,417 SqFt. ⋅ HILTONHEAD-502592 MLS

Custom-built to the highest standards by Steve Dill Builders, this luxurious ocean home in Port Royal defines refined coastal living on Hilton Head Island. Every element was curated for craftsmanship and comfort - from the Andersen impact windows and cement board exterior to interior finishes of oil-rubbed European oak floors, marble and granite surfaces, and artisan woodwork throughout-groove ceilings, poplar shiplap walls, Chicago brick, Italian tile, and a custom-commissioned chandelier create a timeless, coastal-modern aesthetic. The open living plan blends natural light and seamless flow, anchored by a chef's kitchen featuring an induction cooktop, double ovens, wine cooler, and Sub-Zero refrigeration. Each bedroom offers an en-suite bath, while multiple outdoor spaces invite year-round entertaining - including a private bocce court and sunlit terraces framed by lush landscaping. Just three homes back from the ocean, this residence pairs enduring architecture with the serenity of Hilton Head's most private beachfront community - where design, detail, and setting come together in perfect coastal harmony.

4 Heyward Place, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty. Selling Office: Keller Williams Realty.

$7,050,000

6 Beds ⋅ 9 Baths ⋅ 7,789 SqFt. ⋅ HILTONHEAD-453976 MLS

Unobstructed ocean views define this 1.16-acre Hilton Head Island estate cocooned in the privacy of a double lot. Designed for both quiet comfort and large-scale entertaining, noteworthy features include a temperature-controlled wine cellar for 1,000 bottles, an outdoor sports area with basketball, bocce, and shuffleboard, a beachfront putting green, a resort-style pool, and an outdoor kitchen. High ceilings and boundless windows allow for serene ocean vistas from the home's grand interiors, while coffered ceilings add to its timeless luxury. Complete with a temperature-controlled four-bay garage - this is the home for a true collector.

6 Overlook Pl, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Keller Williams Realty.

$1,625,000

3 Beds ⋅ 3 Baths ⋅ 2,530 SqFt. ⋅ HILTONHEAD-453684 MLS

Just steps from the beach, this beautifully maintained 3-bedroom, 2.5-bath second-row home is a rare find in Port Royal. Tucked into a quiet cul-de-sac with its own private beach walk. Bright updated kitchen with adjacent dining & living areas flow seamlessly. The primary suite boasts a spa-like bathroom with dual vanities & walk-in shower. Out back, enjoy a private oasis with a sparkling pool and lush landscaping. Other features include a 2-car garage with ample storage. Located in Hilton Head Island’s only private oceanside community, enjoy access to exclusive oceanfront Beach House, community pool, tennis, golf, and more.

12 N Port Royal Drive, Hilton Head Island

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

$2,380,000

4 Beds ⋅ 4 Baths ⋅ 5,220 SqFt. ⋅ HILTONHEAD-446523 MLS

3rd Row Gem! Lovingly Restored & Maintained! An Entertainer's Dream! Light & Bright w/ Walls of Windows! Main KIT & Prep Kit! Thermador dbl ovens, Wolf, Sub Zero, Miele warming drawer! A combination of honed and polished granite! Bar w/ loads of storage, glass doors, wine/bev fridge! 2nd flr Owner's Suite w/ peek a boo views, Carerra marble bath, walk in closet, 2 balconies! 4 bedrooms! Very unique, enclosed yard perfect for entertaining, with brick pavers, a large swimming pool, 2 pool sheds! This home sits on the beach path and is moments from the beach! OSCREA. Port Royal is a private, beach community. Golf Club memberships available.

32 N Port Royal Drive, Hilton Head Island

Listing courtesy of Engel & Volkers. Selling Office: RE/MAX Island Realty.

$2,000,000

5 Beds ⋅ 4 Baths ⋅ 3,654 SqFt. ⋅ HILTONHEAD-441087 MLS

Located adjacent to the beach path, this beautifully renovated 4th row house has a completely open floor plan with a 3-car garage, a very large loft overlooking the living area, a large screened-in porch overlooking a large picturesque pool landscaped for privacy. There are 5 bedrooms, one of which will easily double as an office or den opening to the pool, family room & dining area. The Primary Bedroom opens to the pool and includes sitting area and an oversized closet. Having no steps into the main living area is a plus. This move-in ready home is built for entertaining and is ideal as a primary or second home.

40 N Port Royal Drive, Hilton Head Island

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

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