housesonhiltonheadisland.com Search Results

$3,300,000

Ideally situated just four rows from the Atlantic Ocean in prestigious Palmetto Dunes, 99 Mooring Buoy is a masterfully designed six-bedroom, six-and-a-half-bath coastal retreat offering refined living across three spacious levels. Positioned directly across from the beach path and moments from the Robert Trent Jones Oceanfront Golf Course, this residence presents an exceptional lifestyle of luxury, leisure, and location.From the moment you step inside, natural light pours through oversized windows, illuminating a warm, coastal-inspired interior. The main living room welcomes you with plush seating, a 77" flat-screen TV, and a relaxed yet elegant gathering space. Entertain with ease in the formal dining room with seating for ten or host intimate meals at the adjacent breakfast nook.At the heart of the home, a chefs kitchen impresses with top-tier appliances, custom cabinetry, and abundant prep space, tailor-made for everything from quiet breakfasts to holiday hosting.With six beautifully appointed bedrooms, each with its own private en suite, this home was built with families, guests, and multi-generational living in mind. Two luxurious primary suites, located on separate levels, provide privacy and indulgence, featuring spa-like baths with soaking tubs, walk-in showers, and double vanities.The upper-level lounge offers a second living area complete with a 65" TV, sleeper sofa, wet bar, and mini fridge, perfect for movie nights, kids' hangouts, or casual entertaining. Outdoors, your private sanctuary awaits. A sparkling pool, lush landscaping, multiple dining areas, and a covered lounge invite you to relax, recharge, and enjoy the Lowcountry breeze.From sunrise walks on the sand to sunset soirees by the pool, this home captures the spirit of Hilton Head Island living, luxurious, effortless, and timeless.

6 Beds ⋅ 7 Baths ⋅ 5,300 SqFt. ⋅ HILTONHEAD-454917 MLS

Ideally situated just four rows from the Atlantic Ocean in prestigious Palmetto Dunes, 99 Mooring Buoy is a masterfully designed six-bedroom, six-and-a-half-bath coastal retreat offering refined living across three spacious levels. Positioned directly across from the beach path and moments from the Robert Trent Jones Oceanfront Golf Course, this residence presents an exceptional lifestyle of luxury, leisure, and location.From the moment you step inside, natural light pours through oversized windows, illuminating a warm, coastal-inspired interior. The main living room welcomes you with plush seating, a 77" flat-screen TV, and a relaxed yet elegant gathering space. Entertain with ease in the formal dining room with seating for ten or host intimate meals at the adjacent breakfast nook.At the heart of the home, a chefs kitchen impresses with top-tier appliances, custom cabinetry, and abundant prep space, tailor-made for everything from quiet breakfasts to holiday hosting.With six beautifully appointed bedrooms, each with its own private en suite, this home was built with families, guests, and multi-generational living in mind. Two luxurious primary suites, located on separate levels, provide privacy and indulgence, featuring spa-like baths with soaking tubs, walk-in showers, and double vanities.The upper-level lounge offers a second living area complete with a 65" TV, sleeper sofa, wet bar, and mini fridge, perfect for movie nights, kids' hangouts, or casual entertaining. Outdoors, your private sanctuary awaits. A sparkling pool, lush landscaping, multiple dining areas, and a covered lounge invite you to relax, recharge, and enjoy the Lowcountry breeze.From sunrise walks on the sand to sunset soirees by the pool, this home captures the spirit of Hilton Head Island living, luxurious, effortless, and timeless.

99 Mooring Buoy, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate. Selling Office: Southern Coast Realty LLC.

$5,800,000

Stunning estate for those who love deeply, live fully & entertain effortlessly. Set on one of Wexford’s best harbour front/golf view parcels. Custom built like a castle yet welcoming & fun for gathering indoors & out—all year round.6,013 sf of timeless craftsmanship:Chef’s kitchen & Luxe finishes. 4 ensuite BRs, office/wine room, leisure room w/ wet bar & pool table, 3-stop elevator, pull-thru garage for 5 cars. Private dock for 70-ft yacht-no bridges, easy lock access. Pool/spa, screen porch w/fireplace & grill. Curved doors, stone columns, French Oak & Stone floors, Hebel block construction.The kind of home where holidays are unforgettable & every day feels like one.

4 Beds ⋅ 7 Baths ⋅ 6,013 SqFt. ⋅ HILTONHEAD-454507 MLS

Stunning estate for those who love deeply, live fully & entertain effortlessly. Set on one of Wexford’s best harbour front/golf view parcels. Custom built like a castle yet welcoming & fun for gathering indoors & out—all year round.6,013 sf of timeless craftsmanship:Chef’s kitchen & Luxe finishes. 4 ensuite BRs, office/wine room, leisure room w/ wet bar & pool table, 3-stop elevator, pull-thru garage for 5 cars. Private dock for 70-ft yacht-no bridges, easy lock access. Pool/spa, screen porch w/fireplace & grill. Curved doors, stone columns, French Oak & Stone floors, Hebel block construction.The kind of home where holidays are unforgettable & every day feels like one.

56 Wexford Club Drive, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: William Raveis - Carolina LLC.

$4,150,000

A distinguished residence set on a rare estate-sized lot showcases exceptional craftsmanship. The home features impressive ceiling heights on both levels, complemented by transom windows and wide plank flooring. Striking impact windows frame majestic oak trees, providing elegant shade, with the lush greenery of Heron Point visible in the distance. The kitchen is designed for both form and function, enhanced by a butler's pantry for added convenience. 4 spacious bedroom suites, with multiple options for a fifth bedroom, ensure comfort for all. Conveniently close to Harbour Town, beaches, tennis, restaurants, shops, and the forest preserve.

4 Beds ⋅ 6 Baths ⋅ 6,084 SqFt. ⋅ HILTONHEAD-454296 MLS

A distinguished residence set on a rare estate-sized lot showcases exceptional craftsmanship. The home features impressive ceiling heights on both levels, complemented by transom windows and wide plank flooring. Striking impact windows frame majestic oak trees, providing elegant shade, with the lush greenery of Heron Point visible in the distance. The kitchen is designed for both form and function, enhanced by a butler's pantry for added convenience. 4 spacious bedroom suites, with multiple options for a fifth bedroom, ensure comfort for all. Conveniently close to Harbour Town, beaches, tennis, restaurants, shops, and the forest preserve.

5 Twin Pines Road, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: Sea Pines Real Estate - Beach Club.

$1,850,000

One of the best lots in The Golf Club w/ views of 16th green from front & LONG range 15th green views beyond your luxury stone SPOOL and grassy backyard. Live fencing surrounds this palatial property w/ balcony views. Making meals and memories in your gourmet kitchen or relaxing in your media room loft gives everyone ample space to enjoy. Create storied nights w/friends in your luxurious living areas and later retire in the bonus room above 3 car garage which houses all of your toys! The master suite w/ dedicated office space on primary opens to your outdoor playground with large covered veranda to take advantage of our lowcountry lifestyle.

4 Beds ⋅ 5 Baths ⋅ 5,264 SqFt. ⋅ HILTONHEAD-454015 MLS

One of the best lots in The Golf Club w/ views of 16th green from front & LONG range 15th green views beyond your luxury stone SPOOL and grassy backyard. Live fencing surrounds this palatial property w/ balcony views. Making meals and memories in your gourmet kitchen or relaxing in your media room loft gives everyone ample space to enjoy. Create storied nights w/friends in your luxurious living areas and later retire in the bonus room above 3 car garage which houses all of your toys! The master suite w/ dedicated office space on primary opens to your outdoor playground with large covered veranda to take advantage of our lowcountry lifestyle.

27 Heather Lane, Hilton Head Island

Listing courtesy of RE/MAX Island Realty. Selling Office: Charter One Realty.

$1,800,000

Tucked away on a private, oversized lot in Shipyard, this classic Lowcountry home offers timeless charm and coastal comfort. Heart pine flooring adds warmth, while a wide wraparound porch welcomes you, and the screened-in rear porch and spacious deck invite outdoor living. Inside, large bedrooms, elevator access and ample living space provide flexibility and comfort. The garage apartment is ideal for guests. New roof installed in 2026! Surrounded by lush landscaping on a quiet street and just moments from the beach, golf, and bike trails, this well-maintained home is the perfect second home or short term rental property, in one of Hilton Head's most beloved communities.

6 Beds ⋅ 6 Baths ⋅ 5,163 SqFt. ⋅ HILTONHEAD-454293 MLS

Tucked away on a private, oversized lot in Shipyard, this classic Lowcountry home offers timeless charm and coastal comfort. Heart pine flooring adds warmth, while a wide wraparound porch welcomes you, and the screened-in rear porch and spacious deck invite outdoor living. Inside, large bedrooms, elevator access and ample living space provide flexibility and comfort. The garage apartment is ideal for guests. New roof installed in 2026! Surrounded by lush landscaping on a quiet street and just moments from the beach, golf, and bike trails, this well-maintained home is the perfect second home or short term rental property, in one of Hilton Head's most beloved communities.

4 Saint Johns Place, Hilton Head Island

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

$7,050,000

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 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.

$7,010,000

Oceanfront luxury meets island lifestyle in this 6BR/6.5BA stunner on the quiet end of Armada in Palmetto Dunes. Enjoy panoramic views, private beach access, and a resort-style pool + spa—all just steps from the sand. This upside-down floorplan features dual primary suites, a chef’s kitchen, multiple living spaces, balconies on both levels, elevator, and 3-car garage. Located in Palmetto Dunes Resort with 3 golf courses, world-class tennis & pickleball, 11 miles of lagoons, bike trails, and beachfront dining. Turnkey, timeless, and a proven rental machine. Toes-in-the-sand ready.

6 Beds ⋅ 7 Baths ⋅ 5,736 SqFt. ⋅ HILTONHEAD-453883 MLS

Oceanfront luxury meets island lifestyle in this 6BR/6.5BA stunner on the quiet end of Armada in Palmetto Dunes. Enjoy panoramic views, private beach access, and a resort-style pool + spa—all just steps from the sand. This upside-down floorplan features dual primary suites, a chef’s kitchen, multiple living spaces, balconies on both levels, elevator, and 3-car garage. Located in Palmetto Dunes Resort with 3 golf courses, world-class tennis & pickleball, 11 miles of lagoons, bike trails, and beachfront dining. Turnkey, timeless, and a proven rental machine. Toes-in-the-sand ready.

11 Armada Street, Hilton Head Island

Listing courtesy of Dunes Real Estate. Selling Office: Dunes Real Estate.

$4,300,000

Your Dream Awaits with a 4-minute walk to the beach, inside this stunning, renovated, luxury masterpiece nestled in an exclusive beachside gated community. This Goliath-sized, breathtaking home is a place to live, a lifestyle, and a lucrative STR investment. Enjoy a very short walk to the beach, one of your many private terraces overlooking your private heated pool or the golf course, and evenings spent entertaining in exquisite designer spaces. Modern amenities, Expansive floor plan, peaceful, private & gated, & a proven rental revenue stream. Your chance has arrived to own a slice of heaven that could pay for itself. Community/home video available.

6 Beds ⋅ 7 Baths ⋅ 7,320 SqFt. ⋅ HILTONHEAD-453824 MLS

Your Dream Awaits with a 4-minute walk to the beach, inside this stunning, renovated, luxury masterpiece nestled in an exclusive beachside gated community. This Goliath-sized, breathtaking home is a place to live, a lifestyle, and a lucrative STR investment. Enjoy a very short walk to the beach, one of your many private terraces overlooking your private heated pool or the golf course, and evenings spent entertaining in exquisite designer spaces. Modern amenities, Expansive floor plan, peaceful, private & gated, & a proven rental revenue stream. Your chance has arrived to own a slice of heaven that could pay for itself. Community/home video available.

12 Port Tack, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$5,050,000

Live the ultimate Hilton Head lifestyle in this elegant lagoon-front estate, just minutes from the beach. Crafted for relaxed luxury, this home invites you to unwind, entertain, and savor every moment—whether dining al fresco, lounging by the pool or fireplaces, or enjoying tranquil water views from your screened living areas or private dock. Highest quality finishes and furnishings throughout offer coastal comfort with inviting spaces curated for connection and calm. Every detail, from the chef’s kitchen to the serene primary suite, enhances the experience of effortless island living. Offered fully furnished with designer touches throughout.

5 Beds ⋅ 7 Baths ⋅ 5,560 SqFt. ⋅ HILTONHEAD-453496 MLS

Live the ultimate Hilton Head lifestyle in this elegant lagoon-front estate, just minutes from the beach. Crafted for relaxed luxury, this home invites you to unwind, entertain, and savor every moment—whether dining al fresco, lounging by the pool or fireplaces, or enjoying tranquil water views from your screened living areas or private dock. Highest quality finishes and furnishings throughout offer coastal comfort with inviting spaces curated for connection and calm. Every detail, from the chef’s kitchen to the serene primary suite, enhances the experience of effortless island living. Offered fully furnished with designer touches throughout.

3 Port Tack, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: Alliance Group Realty/Howard Hanna Tate.

$1,950,000

Great opportunity to own a fantastic well-built and maintained 4BR/4.5BA home with many unique features in a very desirable area of Hilton Head Plantation. This house has over 5000 sqft of heated living space. The master bedroom suite is on the 1st floor. The other three bedrooms (new carpet) with en-suite baths are upstairs (accessed by stairs or power lift/elevator) along with separate game and craft rooms. The home has a 4-car oversized garage with additional work areas and storage. The backyard covered patio and saltwater pool overlook the Country Club of Hilton Head's 4th green.

4 Beds ⋅ 5 Baths ⋅ 5,066 SqFt. ⋅ HILTONHEAD-453088 MLS

Great opportunity to own a fantastic well-built and maintained 4BR/4.5BA home with many unique features in a very desirable area of Hilton Head Plantation. This house has over 5000 sqft of heated living space. The master bedroom suite is on the 1st floor. The other three bedrooms (new carpet) with en-suite baths are upstairs (accessed by stairs or power lift/elevator) along with separate game and craft rooms. The home has a 4-car oversized garage with additional work areas and storage. The backyard covered patio and saltwater pool overlook the Country Club of Hilton Head's 4th green.

3 Annabella Lane, Hilton Head Island

Listing courtesy of Alliance Group Realty/Howard Hanna Tate. Selling Office: RE/MAX Island Realty.

$2,600,000

Castle by the Sea! Income-generating 7BR home with 6 ensuite baths, custom closets, and multiple living spaces in a solid concrete build. Includes a 8th non-conforming bedroom as an owner’s lockout. Fully remodeled with newer geothermal systems, fresh paint, updated kitchen and baths, furnishings, and a pool heater. 12 foot ceilings throughout, heated and cooled floors with wood inlays, custom cabinetry and huge playroom. Four garages for multiple vehicles. Southern-facing views of the 11-mile lagoon. Private beach access close by. Located in Palmetto Dunes—Hilton Head’s top resort with 3 golf courses, pickleball, marina, dining, and shops.

7 Beds ⋅ 7 Baths ⋅ 6,180 SqFt. ⋅ HILTONHEAD-453048 MLS

Castle by the Sea! Income-generating 7BR home with 6 ensuite baths, custom closets, and multiple living spaces in a solid concrete build. Includes a 8th non-conforming bedroom as an owner’s lockout. Fully remodeled with newer geothermal systems, fresh paint, updated kitchen and baths, furnishings, and a pool heater. 12 foot ceilings throughout, heated and cooled floors with wood inlays, custom cabinetry and huge playroom. Four garages for multiple vehicles. Southern-facing views of the 11-mile lagoon. Private beach access close by. Located in Palmetto Dunes—Hilton Head’s top resort with 3 golf courses, pickleball, marina, dining, and shops.

25 Starboard Tack, Hilton Head Island

Listing courtesy of Hilton Head Properties. Selling Office: Coldwell Banker Access Realty.

$7,377,000

This architectural masterpiece spans two waterfront lots and features a primary residence and guest home. The estate offers eight bedrooms, eleven full baths, and four half baths. Exceptional amenities include a grand foyer, a great room with coffered ceilings, a gourmet kitchen, a movie theater, a bowling alley, a media room, and a wine cellar. Additional highlights include an elevator, extensive millwork, an outdoor kitchen, pool, hot tub, Koi pond, piers, five fireplaces, a seven-car garage, and a spa area. This one-of-a-kind property does not exist anywhere else! Enjoy all that Wexford has to offer along with the luxury of 80 Bridgetown!

8 Beds ⋅ 15 Baths ⋅ 18,056 SqFt. ⋅ HILTONHEAD-452855 MLS

This architectural masterpiece spans two waterfront lots and features a primary residence and guest home. The estate offers eight bedrooms, eleven full baths, and four half baths. Exceptional amenities include a grand foyer, a great room with coffered ceilings, a gourmet kitchen, a movie theater, a bowling alley, a media room, and a wine cellar. Additional highlights include an elevator, extensive millwork, an outdoor kitchen, pool, hot tub, Koi pond, piers, five fireplaces, a seven-car garage, and a spa area. This one-of-a-kind property does not exist anywhere else! Enjoy all that Wexford has to offer along with the luxury of 80 Bridgetown!

80 Bridgetown Ln, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Charter One Realty.

$5,500,000

Stately, Sound front home with Ocean views. 199 ft of Waterfront. Water views from every room to include Ocean, Sound, Lagoon and #6 Oyster Reef Golf green. The home boasts man-made and natural elements that make it Dazzle. Designed for Cooking and Entertaining with large open concept spaces surrounded by glass. Well designed Chefs Kitchen to include Sub zero refrigerators, Wolf cooktop and Miele appliances. Formal living spaces include Cypress ceilings, Rosewood inlays, White Oak flooring, Teak inlays and 2-story Stone and Copper clad Fireplace. Expansive Resort style Pool with Spa, Wading area, new decking and Pool House. 4 Car Garage with quiet lift door mechanisms. Glass door Elevator, Wine Room, Den, Game & Theater rooms.

5 Beds ⋅ 7 Baths ⋅ 9,287 SqFt. ⋅ HILTONHEAD-452750 MLS

Stately, Sound front home with Ocean views. 199 ft of Waterfront. Water views from every room to include Ocean, Sound, Lagoon and #6 Oyster Reef Golf green. The home boasts man-made and natural elements that make it Dazzle. Designed for Cooking and Entertaining with large open concept spaces surrounded by glass. Well designed Chefs Kitchen to include Sub zero refrigerators, Wolf cooktop and Miele appliances. Formal living spaces include Cypress ceilings, Rosewood inlays, White Oak flooring, Teak inlays and 2-story Stone and Copper clad Fireplace. Expansive Resort style Pool with Spa, Wading area, new decking and Pool House. 4 Car Garage with quiet lift door mechanisms. Glass door Elevator, Wine Room, Den, Game & Theater rooms.

16 Oyster Shell Lane, Hilton Head Island

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

$7,300,000

Own this architecturally custom-crafted 5BD/6.5BA, 1st row, oceanfront masterpiece in the world-class Sea Pines community on Hilton Head Island. Dramatic ocean views, substantial woodwork, custom beams, solid 8’ doors & skylights that bathe the space in natural light & beauty. Large gathering spaces including expansive great room, screened porch, multiple outdoor decks, study, oversized bdrms & massive bonus/rec room. Private walkway to beach + pool. Primary, vacation home, or a coveted short-term rental. The home is set back on a large lot w/ pines, live oaks & a natural landscape yet the ocean waves & sandy beach still take center stage.

5 Beds ⋅ 7 Baths ⋅ 5,386 SqFt. ⋅ HILTONHEAD-452596 MLS

Own this architecturally custom-crafted 5BD/6.5BA, 1st row, oceanfront masterpiece in the world-class Sea Pines community on Hilton Head Island. Dramatic ocean views, substantial woodwork, custom beams, solid 8’ doors & skylights that bathe the space in natural light & beauty. Large gathering spaces including expansive great room, screened porch, multiple outdoor decks, study, oversized bdrms & massive bonus/rec room. Private walkway to beach + pool. Primary, vacation home, or a coveted short-term rental. The home is set back on a large lot w/ pines, live oaks & a natural landscape yet the ocean waves & sandy beach still take center stage.

36 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: Sea Pines Real Estate - Beach Club.

$2,565,000

Truly unique and one of a kind architectural splendor in this highly designed home featuring 4 bedrooms and 6 full and 1 half baths. Gourmet custom kitchen as well as an outdoor kitchen with motorized screens overlooking pool and hot tub. Open concept design, 3 fireplaces, office, studio, wine room, 3 car garage, gym, sauna, built in 2024. 3 stop elevator from garage. Seller is interior designer. Once in a lifetime opportunity to own this stunning home. Must see to appreciate! Furniture negotiable.

4 Beds ⋅ 7 Baths ⋅ 5,950 SqFt. ⋅ HILTONHEAD-452566 MLS

Truly unique and one of a kind architectural splendor in this highly designed home featuring 4 bedrooms and 6 full and 1 half baths. Gourmet custom kitchen as well as an outdoor kitchen with motorized screens overlooking pool and hot tub. Open concept design, 3 fireplaces, office, studio, wine room, 3 car garage, gym, sauna, built in 2024. 3 stop elevator from garage. Seller is interior designer. Once in a lifetime opportunity to own this stunning home. Must see to appreciate! Furniture negotiable.

2 Delta Lane, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club. Selling Office: BESTNEST By Beverly Serral.

$10,995,000

An oceanfront masterpiece designed for elevated coastal living and exceptional entertaining. The open great room - anchored by a coffered ceiling and fireplace-flows seamlessly into an expansive chef's kitchen with a generous center island and an ocean-view dining area. On the main level, the primary suite enjoys serene pool-to-ocean vistas, while a private study with sleeper sofa and adjacent full bath offers flexible accommodations. Upstairs, four guest suites capture sweeping ocean views, complemented by two bunk rooms-each with its own full bath-creating an ideal retreat for multi-generational gatherings. Outdoors, a resort-caliber setting awaits: a large private pool with heated spa and separate children's pool, plus an exclusive boardwalk leading directly to the beach. A covered patio with outdoor kitchen, spacious dining area, and TV lounge completes the experience-perfect from sunrise coffee to evening cocktails. Solar panels support efficient heating and cooling. Proven rental performance exceeds $500,000 in 2024 and 2025. For the discerning oceanfront buyer, this is a must-see.

7 Beds ⋅ 9 Baths ⋅ 6,200 SqFt. ⋅ HILTONHEAD-452384 MLS

An oceanfront masterpiece designed for elevated coastal living and exceptional entertaining. The open great room - anchored by a coffered ceiling and fireplace-flows seamlessly into an expansive chef's kitchen with a generous center island and an ocean-view dining area. On the main level, the primary suite enjoys serene pool-to-ocean vistas, while a private study with sleeper sofa and adjacent full bath offers flexible accommodations. Upstairs, four guest suites capture sweeping ocean views, complemented by two bunk rooms-each with its own full bath-creating an ideal retreat for multi-generational gatherings. Outdoors, a resort-caliber setting awaits: a large private pool with heated spa and separate children's pool, plus an exclusive boardwalk leading directly to the beach. A covered patio with outdoor kitchen, spacious dining area, and TV lounge completes the experience-perfect from sunrise coffee to evening cocktails. Solar panels support efficient heating and cooling. Proven rental performance exceeds $500,000 in 2024 and 2025. For the discerning oceanfront buyer, this is a must-see.

15 Grey Widgeon Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach (505).

$6,750,000

Absolutely stunning Spanish Wells deep waterfront estate situated perfectly on a 1.5 acre gorgeously landscaped property. Custom designed and exquisitely built for current owners inspired by their previous Richmond, VA home. 6 bedrooms & 6 baths plus 2 half baths, perfect in-law suite with full kitchen, majestic entry foyer with grand staircase, walnut paneled den/office, open & well-appointed kitchen to warm and inviting family room, first floor master suite all with amazing sunset views out to the dock on the Calibogue sound. Don't miss the incredible climate-controlled wine room, full home generator, elevator and so much more. Interior 7037SF + 1339 SF of additional covered space and a 550 SF Garage. One of the finest custom homes on Hilton Head!!

6 Beds ⋅ 8 Baths ⋅ 7,037 SqFt. ⋅ HILTONHEAD-452018 MLS

Absolutely stunning Spanish Wells deep waterfront estate situated perfectly on a 1.5 acre gorgeously landscaped property. Custom designed and exquisitely built for current owners inspired by their previous Richmond, VA home. 6 bedrooms & 6 baths plus 2 half baths, perfect in-law suite with full kitchen, majestic entry foyer with grand staircase, walnut paneled den/office, open & well-appointed kitchen to warm and inviting family room, first floor master suite all with amazing sunset views out to the dock on the Calibogue sound. Don't miss the incredible climate-controlled wine room, full home generator, elevator and so much more. Interior 7037SF + 1339 SF of additional covered space and a 550 SF Garage. One of the finest custom homes on Hilton Head!!

34 Brams Point Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club. Selling Office: Sea Pines Real Estate - Beach Club.

$3,700,000

This stunning home offers unparalleled, unobstructed views of the sound w/ the ocean in the backdrop & beautifully designed backyard. Spanning nearly 6,000 sq ft, this exceptional residence w/impressive curb appeal features 5 spacious ensuite BR, plus powder room. The 2nd floor office area has sweeping views of both the sound & backyard pool. Along with a brand-new designer kitchen the home offers the perfect space for entertaining & relaxation. Recent additions include a new whole home generator. Located in sought after amenity rich Hilton Head Plantation this property offers access to world-class golf facilities & picturesque nature trails.

5 Beds ⋅ 6 Baths ⋅ 5,722 SqFt. ⋅ HILTONHEAD-451501 MLS

This stunning home offers unparalleled, unobstructed views of the sound w/ the ocean in the backdrop & beautifully designed backyard. Spanning nearly 6,000 sq ft, this exceptional residence w/impressive curb appeal features 5 spacious ensuite BR, plus powder room. The 2nd floor office area has sweeping views of both the sound & backyard pool. Along with a brand-new designer kitchen the home offers the perfect space for entertaining & relaxation. Recent additions include a new whole home generator. Located in sought after amenity rich Hilton Head Plantation this property offers access to world-class golf facilities & picturesque nature trails.

14 Herring Gull Lane, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry. Selling Office: Howard Hanna Allen Tate Lowcountry.

$2,800,000

This rarely available large luxury property is located in the heart of the Sea Pines Resort on a highly desired quiet street. Located just off the Calibogue Sound and Harbour Town Golf Links, this home is large enough for annual gatherings or attractive for an investor looking for an investment rental property. With six bedrooms and baths, open floor plan and in-law suite, totally remodeled kitchen, pool, lush landscaping and lagoon view, this immaculately cared for home is being offered furnished ( a few personal items excluded) and won't be available for long.

6 Beds ⋅ 6 Baths ⋅ 5,000 SqFt. ⋅ HILTONHEAD-452187 MLS

This rarely available large luxury property is located in the heart of the Sea Pines Resort on a highly desired quiet street. Located just off the Calibogue Sound and Harbour Town Golf Links, this home is large enough for annual gatherings or attractive for an investor looking for an investment rental property. With six bedrooms and baths, open floor plan and in-law suite, totally remodeled kitchen, pool, lush landscaping and lagoon view, this immaculately cared for home is being offered furnished ( a few personal items excluded) and won't be available for long.

6 Marsh Drive, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club. Selling Office: Sea Pines Real Estate - The Cottage Group, LLC.

$3,250,000

This is a one-of-a-kind property nestled on a private peninsula offering breathtaking views of the 13th and 14th holes of the Harbour Town Golf Course. Situated on over half an acre with spectacular water & golf views, this luxurious coastal retreat blends relaxed luxury with timeless design Featuring a dream kitchen, stunning great room, soaring ceilings, designer lighting, 2 owner suites, spacious guest ensuites, and 2 fireplaces, this home is filled with natural light and offers seamless indoor-outdoor living. Truly an amazing property for easy living and entertaining with incredible privacy surrounded by natural beauty.

5 Beds ⋅ 6 Baths ⋅ 6,158 SqFt. ⋅ HILTONHEAD-451650 MLS

This is a one-of-a-kind property nestled on a private peninsula offering breathtaking views of the 13th and 14th holes of the Harbour Town Golf Course. Situated on over half an acre with spectacular water & golf views, this luxurious coastal retreat blends relaxed luxury with timeless design Featuring a dream kitchen, stunning great room, soaring ceilings, designer lighting, 2 owner suites, spacious guest ensuites, and 2 fireplaces, this home is filled with natural light and offers seamless indoor-outdoor living. Truly an amazing property for easy living and entertaining with incredible privacy surrounded by natural beauty.

20 Turnberry Lane, Hilton Head Island

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

$2,999,000

A modern masterpiece in Leamington, this brand-new 2024 home offers luxury living just a short golf cart ride to the private beach club. Overlooking the Arthur Hills Golf Course and lagoon, it blends sleek design with functionality, featuring a floating stair system, custom lighting, and a gourmet kitchen. Double wraparound balconies capture the breathtaking views. The outdoor oasis boasts a heated/cooled pool with a sun ledge, marble pavers, multiple fire features, a grilling station, and a lounge/bar area. With 10,000 sq ft under roof, ample parking, an elevator, and hurricane-grade windows/doors, this stunning retreat has it all.

5 Beds ⋅ 5 Baths ⋅ 5,080 SqFt. ⋅ HILTONHEAD-451467 MLS

A modern masterpiece in Leamington, this brand-new 2024 home offers luxury living just a short golf cart ride to the private beach club. Overlooking the Arthur Hills Golf Course and lagoon, it blends sleek design with functionality, featuring a floating stair system, custom lighting, and a gourmet kitchen. Double wraparound balconies capture the breathtaking views. The outdoor oasis boasts a heated/cooled pool with a sun ledge, marble pavers, multiple fire features, a grilling station, and a lounge/bar area. With 10,000 sq ft under roof, ample parking, an elevator, and hurricane-grade windows/doors, this stunning retreat has it all.

50 Leamington Lane, Hilton Head Island

Listing courtesy of Maxey Blackstream Christie's International Real Estate. Selling Office: Premier Properties of Hilton Head Island.

$1,825,000

Investor Alert! Palmetto Dunes retreat generated $172,000 in short-term rental income in 2024! Designed for entertaining & relaxation, this home sits on a large corner lot with golf course views & features heated pool, firepit, patio & multiple outdoor spaces. Inside, the freshly painted open floor plan offers seamless flow, with primary suites on both levels, a game room & a well-appointed kitchen.Thoughtfully designed for comfort & convenience, this home is moments from world-class beaches, championship golf, and premier dining. Whether you're seeking a high-performing investment or a private coastal retreat, this turnkey opportunity is it!

5 Beds ⋅ 5 Baths ⋅ 5,047 SqFt. ⋅ HILTONHEAD-451783 MLS

Investor Alert! Palmetto Dunes retreat generated $172,000 in short-term rental income in 2024! Designed for entertaining & relaxation, this home sits on a large corner lot with golf course views & features heated pool, firepit, patio & multiple outdoor spaces. Inside, the freshly painted open floor plan offers seamless flow, with primary suites on both levels, a game room & a well-appointed kitchen.Thoughtfully designed for comfort & convenience, this home is moments from world-class beaches, championship golf, and premier dining. Whether you're seeking a high-performing investment or a private coastal retreat, this turnkey opportunity is it!

2 High Water, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Century 21 Diamond Realty.

$3,000,000

HUGE PRICE IMPROVEMENT - Your 'Private Compound' awaits. Escape to a world of unparalleled privacy and refined elegance in this exceptional coastal retreat. More than a home, this is a meticulously crafted compound designed for both grand entertaining and intimate family living, all just steps from the tranquil sound and ocean. This is more than a residence, it's a lifestyle. Immerse yourself in the warm, intimate atmosphere of this coastal sanctuary, where every detail has been carefully curated for your comfort and enjoyment. This is your opportunity to own a truly exceptional piece of paradise

6 Beds ⋅ 7 Baths ⋅ 5,672 SqFt. ⋅ HILTONHEAD-451335 MLS

HUGE PRICE IMPROVEMENT - Your 'Private Compound' awaits. Escape to a world of unparalleled privacy and refined elegance in this exceptional coastal retreat. More than a home, this is a meticulously crafted compound designed for both grand entertaining and intimate family living, all just steps from the tranquil sound and ocean. This is more than a residence, it's a lifestyle. Immerse yourself in the warm, intimate atmosphere of this coastal sanctuary, where every detail has been carefully curated for your comfort and enjoyment. This is your opportunity to own a truly exceptional piece of paradise

3 Heyward Place, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty. Selling Office: Luxury Homes of Hilton Head.

$6,125,000

There is nothing quite like this home on Hilton Head Island. This modern architectural masterpiece offers unparalleled waterfront living w/ breathtaking dual water views of Broad Creek to the East and the shimmering Calibogue Sound to the West. Inside, 4 spacious ensuite bedrooms, custom Italian glass doors & a German-made gourmet kitchen elevate the art of living. Enjoy the Living Room w/ soaring 21-foot ceilings & natural light throughout. Step outside to discover a private oasis: a negative-edge upper pool cascades into 75' lap pool, a generously sized covered deck w/ space for future outdoor kitchen & separate 600 sqft Studio/Pool House.

4 Beds ⋅ 6 Baths ⋅ 7,183 SqFt. ⋅ HILTONHEAD-451285 MLS

There is nothing quite like this home on Hilton Head Island. This modern architectural masterpiece offers unparalleled waterfront living w/ breathtaking dual water views of Broad Creek to the East and the shimmering Calibogue Sound to the West. Inside, 4 spacious ensuite bedrooms, custom Italian glass doors & a German-made gourmet kitchen elevate the art of living. Enjoy the Living Room w/ soaring 21-foot ceilings & natural light throughout. Step outside to discover a private oasis: a negative-edge upper pool cascades into 75' lap pool, a generously sized covered deck w/ space for future outdoor kitchen & separate 600 sqft Studio/Pool House.

73 Brams Point Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - The Cottage Group, LLC. Selling Office: Premier Properties of Hilton Head Island.

$4,750,000

The ultimate home, perfect for entertaining! Spacious 2nd-row, 6 BR | 6 BA | 2 HB home on Armada in Palmetto Dunes just steps from 3 miles of award-winning beach. Freshly painted with coastal-chic décor, this home has a spectacular 1st floor featuring a chef's eat-in kitchen, dining room, living room, wet bar off the leisure room, powder room & sunroom. Offers a 3-stop elevator & three primary suites on the 2nd-floor. Outdoor entertainment area offers an idyllic wooded view, a covered lounging & dining area with a wet bar and grill, & a large pool with a spa. Ample parking with a large driveway & garage. Guests and owners have access to all the amenities in Palmetto Dunes: golf, tennis, pickleball, an 11-mile lagoon, golf at the Arthur Hills Golf Course in Leamington, and much more. Short walk or bike ride to the heart of Palmetto Dunes. Seasonal Dunes Buggy is available throughout Palmetto Dunes and the Shelter Cove area. Short walk or bike ride to resort amenities!

6 Beds ⋅ 8 Baths ⋅ 6,741 SqFt. ⋅ HILTONHEAD-451281 MLS

The ultimate home, perfect for entertaining! Spacious 2nd-row, 6 BR | 6 BA | 2 HB home on Armada in Palmetto Dunes just steps from 3 miles of award-winning beach. Freshly painted with coastal-chic décor, this home has a spectacular 1st floor featuring a chef's eat-in kitchen, dining room, living room, wet bar off the leisure room, powder room & sunroom. Offers a 3-stop elevator & three primary suites on the 2nd-floor. Outdoor entertainment area offers an idyllic wooded view, a covered lounging & dining area with a wet bar and grill, & a large pool with a spa. Ample parking with a large driveway & garage. Guests and owners have access to all the amenities in Palmetto Dunes: golf, tennis, pickleball, an 11-mile lagoon, golf at the Arthur Hills Golf Course in Leamington, and much more. Short walk or bike ride to the heart of Palmetto Dunes. Seasonal Dunes Buggy is available throughout Palmetto Dunes and the Shelter Cove area. Short walk or bike ride to resort amenities!

9 Armada Street, Hilton Head Island

Listing courtesy of Schembra Real Estate Group.

$2,975,000

THE VIEW! Unobstructed sound views from this elegant 5BD/6BTH estate w/ direct beach access & private front courtyard. 2 story foyer opens to a beautifully renovated large living area w/ hardwood floors & glass sliders across back of home capturing the expansive water views. Formal dining rm, bar/study w/ full bth & living rm. Exquisite kitchen remodel, large sitting & eating area, amazing bonus suite over garage w/ laundry rm/kitchenette. Large primary suite w/ 2 bths. Upstairs, library w/ fireplace & 4 bdrms. Outdoor living w/ expansive deck, a lower covered patio w/ manicured lawn & a bridge over marsh to the private beach & water’s edge.

5 Beds ⋅ 6 Baths ⋅ 6,543 SqFt. ⋅ HILTONHEAD-450370 MLS

THE VIEW! Unobstructed sound views from this elegant 5BD/6BTH estate w/ direct beach access & private front courtyard. 2 story foyer opens to a beautifully renovated large living area w/ hardwood floors & glass sliders across back of home capturing the expansive water views. Formal dining rm, bar/study w/ full bth & living rm. Exquisite kitchen remodel, large sitting & eating area, amazing bonus suite over garage w/ laundry rm/kitchenette. Large primary suite w/ 2 bths. Upstairs, library w/ fireplace & 4 bdrms. Outdoor living w/ expansive deck, a lower covered patio w/ manicured lawn & a bridge over marsh to the private beach & water’s edge.

18 Oyster Shell Lane, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: EXP Realty LLC.

$4,250,000

Stunning deep-water residence in Sea Pines features a private, oversized dock with a boat lift, offering unparalleled waterfront access. Spanning nearly 6,000 square feet, the open floor plan showcases breathtaking, unobstructed water views. The entertainer’s dream kitchen boasts a 60” Viking gas range, double stainless steel refrigerator, walk-in pantry, and a striking 12-foot granite bar complete with a wine cooler and ice maker. The outdoor living space features a circular driveway with pervious pavers, a resort-style private pool and hot tub, and a fire pit—all set within over 3,000 square feet of beautifully designed patio space. OSCREA

6 Beds ⋅ 6 Baths ⋅ 6,000 SqFt. ⋅ HILTONHEAD-450230 MLS

Stunning deep-water residence in Sea Pines features a private, oversized dock with a boat lift, offering unparalleled waterfront access. Spanning nearly 6,000 square feet, the open floor plan showcases breathtaking, unobstructed water views. The entertainer’s dream kitchen boasts a 60” Viking gas range, double stainless steel refrigerator, walk-in pantry, and a striking 12-foot granite bar complete with a wine cooler and ice maker. The outdoor living space features a circular driveway with pervious pavers, a resort-style private pool and hot tub, and a fire pit—all set within over 3,000 square feet of beautifully designed patio space. OSCREA

25 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of DOT REAL ESTATE.

$14,234,500

The most sensational & remarkable home is under construction! Brand New masterpiece in World-Class Sea Pines Resort. Magnificent Oceanfront parcel, in the sought after South Beach Area. Finest finishes, trim, accessories, appliances, cabinets, flooring & fixtures. In addition to 6 ensuite bedrooms (3 master suites) there's an office, a sitting/wine tasting room, Butler's Pantry, huge 2nd floor recreation room w/wetbar opens up to a sprawling upper deck. Amazing pool, spa & outdoor areas. Main floor Master Suite suitable for Royalty; steam shower, free standing tub, double entry curb-less shower. Under parking for up to 8 vehicles. Elevator. Please see the extensive description in documents.

6 Beds ⋅ 9 Baths ⋅ 7,000 SqFt. ⋅ HILTONHEAD-450301 MLS

The most sensational & remarkable home is under construction! Brand New masterpiece in World-Class Sea Pines Resort. Magnificent Oceanfront parcel, in the sought after South Beach Area. Finest finishes, trim, accessories, appliances, cabinets, flooring & fixtures. In addition to 6 ensuite bedrooms (3 master suites) there's an office, a sitting/wine tasting room, Butler's Pantry, huge 2nd floor recreation room w/wetbar opens up to a sprawling upper deck. Amazing pool, spa & outdoor areas. Main floor Master Suite suitable for Royalty; steam shower, free standing tub, double entry curb-less shower. Under parking for up to 8 vehicles. Elevator. Please see the extensive description in documents.

9 Brown Pelican Road, Hilton Head Island

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

$6,350,000

This rare oceanfront opportunity sits in one of Hilton Head’s premier gated communities, offering direct access to the island’s finest beaches. Surrounded by pristine dunes and open space, the home features a private path leading directly to the sand. Designed with exquisite woodwork and fine craftsmanship, the home’s expansive interior has been lightly used as a secondary residence, ensuring exceptional condition. Enjoy breathtaking ocean views and stunning sunrises, embracing a coastal lifestyle. This property provides an unparalleled opportunity to own a refined oceanfront escape in one of Hilton Head’s most exclusive enclaves.

5 Beds ⋅ 7 Baths ⋅ 6,346 SqFt. ⋅ HILTONHEAD-450493 MLS

This rare oceanfront opportunity sits in one of Hilton Head’s premier gated communities, offering direct access to the island’s finest beaches. Surrounded by pristine dunes and open space, the home features a private path leading directly to the sand. Designed with exquisite woodwork and fine craftsmanship, the home’s expansive interior has been lightly used as a secondary residence, ensuring exceptional condition. Enjoy breathtaking ocean views and stunning sunrises, embracing a coastal lifestyle. This property provides an unparalleled opportunity to own a refined oceanfront escape in one of Hilton Head’s most exclusive enclaves.

28 Planters Row, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Maxey Blackstream Christie's International Real Estate.

$4,340,000

Offered for the first time, this 5th-row coastal, multi-generational retreat w/golf & lagoon views will captivate the most discerning buyer who is seeking location, luxury, & privacy all w/in a 3 min walk to the Sea Pines sun-kissed beaches. Enjoy 1st & 2nd floor owner suites, two family living spaces + a private upper deck, perfect for sunning or stargazing! The custom millwork, coffered ceilings, two fireplaces, gourmet kitchen w/double islands, an office or 6th BD plus a 3-car garage make this an exceptional home. All topped off by a spacious screened porch to enjoy evening breezes overlooking the resort-style pool, spa & lush landscaping.

5 Beds ⋅ 7 Baths ⋅ 6,631 SqFt. ⋅ HILTONHEAD-450515 MLS

Offered for the first time, this 5th-row coastal, multi-generational retreat w/golf & lagoon views will captivate the most discerning buyer who is seeking location, luxury, & privacy all w/in a 3 min walk to the Sea Pines sun-kissed beaches. Enjoy 1st & 2nd floor owner suites, two family living spaces + a private upper deck, perfect for sunning or stargazing! The custom millwork, coffered ceilings, two fireplaces, gourmet kitchen w/double islands, an office or 6th BD plus a 3-car garage make this an exceptional home. All topped off by a spacious screened porch to enjoy evening breezes overlooking the resort-style pool, spa & lush landscaping.

58 N Sea Pines Drive, Hilton Head Island

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