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$3,295,000
4 Beds 4 Baths HILTONHEAD-511945 MLS
Oceanfront living takes center stage at this inviting residence in Ocean Point, a private section of the prestigious Port Royal community on Hilton Head Island. Set along the Atlantic, the home enjoys an exceptional coastal setting, with the oceanfront property between the residence and beach maintained by Ocean Point-providing owners the beauty of this remarkable landscape without the responsibility of maintaining it themselves.Inside, the home offers a comfortable blend of classic character and refreshed coastal style, with spacious living areas designed to complement the spectacular setting. Warm heart-of-pine floors, a natural connection between the kitchen and Carolina Room, and multiple bedrooms with ocean views create an inviting island retreat. The first-floor primary suite offers a private escape, while generous gathering spaces are ideal for family and entertaining.Ocean Point owners enjoy a private pool immediately adjacent to the property, as well as exclusive beach access. Port Royal's exceptional amenities add even more to the lifestyle, including an oceanfront Olympic-size pool, Beach House, playground, fire pits, pickleball and tennis courts, leisure trails, and private security.Thoughtfully refreshed and beautifully appointed, this special oceanfront residence offers a rare opportunity to enjoy the best of Hilton Head Island-where the ocean, exceptional amenities, and relaxed coastal living are right outside your door.

13 Ocean N Point, Hilton Head Island

Listing courtesy of Charter One Realty.

$3,995,000
5 Beds 7 Baths HILTONHEAD-512060 MLS
Waterfront living in Wexford doesn't get much better than this and 20 Castlebridge Court 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.

$899,000
3 Beds 2 Baths HILTONHEAD-512211 MLS
Excellent opportunity to own a full-size home in Palmetto Dunes ocean community! Located on the 4th hole of the Robert Trent Jones Golf course. A little over a mile from the white sand beach of Hilton Head Island. Recently renovated with new luxury vinyl planking floors. New interior and exterior paint. Kitchen has new cabinets with quartz counter-tops and new stainless appliances. Primary and guest baths have new cabinets and quartz counter-tops. Primary bath has double vanity plus walk-in shower. Full size lot with numerous specimen oak trees. Close to all amenities including golf, tennis, pickleball, restaurants, and shopping. Amazing opportunity to own a single-family home on a full size lot for the cost of a condo or villa.

66 Off Shore, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,475,000
3 Beds 4 Baths HILTONHEAD-512115 MLS
Rarely does a like-new home in Hilton Head Plantation pair this level of renovation with a premier address, a private saltwater swimming pool, and screened lanai. Beautifully reimagined in 2026, this private (single-story) residence features, tall ceilings, gorgeous plank flooring, current color selections, and an intelligently designed floor plan. The fully remodeled kitchen is an absolute showcase... Complete with quartz countertops, a downdraft vent range, updated stainless steel appliances, and a generous pantry behind craftsman-style barn doors. The three (en-suite) bathrooms have all been completely transformed and offer a modern and luxurious feel. The private pool was resurfaced in 2025 and includes new pool equipment! The house-wide plumbing was replaced with PEX for additional peace-of-mind! Add to the list spacious bedroom suites, a gas fireplace, a private office nook, epoxy floors in the garage, abundant closets/cabinetry, and professional landscaping outside. This is a high-elevation lot with a pleasant golf backdrop on a quiet, (limited traffic) street near Hilton Head Plantation's main gate. Virtually staged photos are meant to provide spatial information and decor inspiration. No structural modifications have been made.

43 Knollwood Drive, Hilton Head Island

Listing courtesy of Collins Group Realty.

$295,000
2 Beds 1 Baths HILTONHEAD-512198 MLS
One of the nicest Marshsides to hit the market! Welcome to this light & bright, 2br. and 2bath end-unit villa in popular Marshside Villas. Offered fully furnished and featuring peaceful, double lagoon views, this inviting one-story home has been thoughtfully updated and is ready to enjoy! Completely turnkey, the refreshed kitchen features newer, stainless appliances (all just a few years old), new sink, breakfast bar with additional storage and seating, new lighting and ample cabinet space. The great room with cathedral ceiling and wood-burning fireplace features: smooth ceilings, built-ins, new ceiling fan and added cabinets and shelves. Wood-like laminate flooring throughout, the home features two remodeled baths with custom showers. The end-unit location offers additional privacy and natural light, while the lagoon setting creates a relaxing low country backdrop. Owner occupied with love and care since 2021, a great deal lot of thought has been put into storage and outdoor living space. Furniture, fixtures, TV's, etc all convey as a convenience to the purchaser and seller. Marshside has an excellent reputation for a well-run regime and great location near schools and hospitals.

5 Gumtree Road Unit F-5, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$1,290,000
4 Beds 4 Baths HILTONHEAD-512173 MLS
Beautifully updated home in Moss Creek, one of the Hilton Head Island area's premier private golf and marina communities. Offering 3,480 square feet, this spacious mid-century modern Lowcountry home features 4 large bedrooms, including 2 primary suites, and 3.5 beautifully updated baths. The flexible layout includes a private guest suite with 2 bedrooms and a full bath, plus an additional primary suite with ensuite bath - ideal for family and guests. The completely updated kitchen features quartz countertops, new appliances, soft-close cabinetry, and elegant gold hardware. French oak wide-plank flooring flows throughout the main living areas, complemented by smooth ceilings, high-end lighting, and fresh interior and exterior paint. Enjoy the sought-after Moss Creek Lowcountry lifestyle with two 18-hole golf courses, private marina, tennis and pickleball, fitness and clubhouse amenities, all in a gated community conveniently located between Hilton Head Island and Bluffton, SC. A beautifully updated home offering space, flexibility, and the golf-and-marina lifestyle that makes Moss Creek such a special place to call home.

55 Saw Timber Drive, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$899,000
4 Beds 4 Baths HILTONHEAD-512036 MLS
This stunning four-bedroom home located on a cul-de-sac street sits on a great lot with views of the Oyster Reef Golf Course. Even better, it's just around the corner from the access point for the Dolphin Head Bluff Path. This home boasts an incredible floor plan with two primary bedroom suites, one downstairs and one upstairs. You will enjoy the renovated kitchen with stainless steel appliances, custom cabinets, all open to the main living areas. There is so much natural light throughout and tons of storage space. This home has beautiful crown moldings and great ceiling height throughout.Living in the Low Country means outdoor living space is a must, and this has an incredible back yard/patio with exceptional golf views of #8 of the Oyster Reef Course. Updated bathrooms recently painted and the roof was replaced a year ago, you can move in worry free. Hilton Head Plantation has low fees and incredible amenities: Golfers have four championship 18-hole courses within the community (Bear Creek, Dolphin Head, Oyster Reef and the Country Club of Hilton Head). Private beach lovers enjoy a private shoreline along the Port Royal Sound in Dolphin Head Park. HHP has a resort-style zero-entry pool with lazy river and splash pad anchors Spring Lake Recreation Area. There's even a Marina just inside the community and for garden lovers, Seabrook Farms is a place where residents can rent beds to grow vegetables, fruits, and flowers.

16 Yellow Rail Lane, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$799,000
6 Beds 8 Baths HILTONHEAD-512129 MLS
Own one-eighth of this professionally managed, turnkey home by Pacaso. Bald Eagle sits on a quiet third-row lot on Hilton Head Island, just a short walk from the Atlantic through a private beachside community. The exterior has a covered front porch, classic columns and a shingled roofline that feels considered and unhurried against the island's natural landscape. Inside, the entry foyer has a custom curved staircase, ornate columns, coffered ceilings and light hardwood floors that run throughout the main level. The great room has box beam ceilings, a traditional fireplace with a modern tile surround and built-in storage, opening directly into the dining area with French doors to the backyard. The kitchen has dark stone countertops, a premium range hood, glass-front cabinetry, a quartz-topped island and a separate breakfast bar. The primary bedroom opens to the backyard patio and has a spa-caliber en suite bath with a freestanding soaking tub, tiled shower and dual vanities. Five additional bedrooms, each with private baths, and a bonus room with wet bar complete the layout across three floors connected by a four-stop elevator. The heated pool, overflowing hot tub and outdoor cooking area sit within mature landscaping that gives the backyard a private, enclosed quality. The beach is a short walk through the community's private beachside access. Harbour Town and its iconic lighthouse, the Quarterdeck's waterfront dining and the Sea Pines Resort's golf courses and trails are all within easy reach. Bald Eagle is professionally designed, appointed and managed by Pacaso. Owners arrive to find the home ready at every visit, with nothing left to coordinate before the stay begins.

8 Bald Eagle Road, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$850,000
3 Beds 3 Baths HILTONHEAD-512111 MLS
Tucked away on a private cul-de-sac in Hilton Head Plantation, this bright and spacious3BR/3BA home offers single-level living, excellent bedroom separation and a gated courtyard entry. Enjoy views of the 10th hole of Oyster Reef Golf Club from your backyard stone patio, with no homes directly across the street, and walk to Oyster Reef Golf Club and Loggerhead Tavern. The light-filled living room features vaulted ceilings, while the updated eat-in kitchen offers top-of-the-line appliances, stone countertops, bamboo cabinetry, imported tile floors and greenhouse windows for a contemporary feel. A 2+ car garage, updated plumbing and roof less than 10 years old add to the appeal. Hilton Head Plantation amenities include four 18-hole golf courses, a chilled Lazy River and pool, tennis, pickleball, miles of leisure trails and the beautiful recently renourished Dolphin Head Beach. Priced to reflect the opportunity for updates and personalization, this home is ready for you to make it your own and enjoy all Hilton Head has to offer!

14 Oyster Reef Cove, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$649,000
2 Beds 2 Baths HILTONHEAD-511687 MLS
This charming two bedroom home is one not to be missed!. Two story ceiling in living room with fireplace. Walls of windows allowing natural light to flow inside all day long! Updated kitchen appliances and counters. Tile and wood floors throughout, no carpet! Primary suite on first floor with cathedral ceiling, fireplace and large walk-in closet. Ensuite second bedroom and loft/sitting room/office on second floor. Rarely offered in these patio homes is a 2-car garage! Perfect for year-round living in beautiful Moss Creek! Enjoy all MC has to offer; amenities include 2 championship golf courses. beautifully remodeled clubhouse, 4 pickleball courts, Racket Center with 7 Har Tur Courts, Equestrian Center, 5 Fishing/crabbing docks, marina, 2 nature preserves, Bocce Courts, Dog Park, firepits and miles of leisure trails. Don't miss this special opportunity!

20 Toppin Drive, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - The Cottage Group, LLC.

$950,000
2 Beds 2 Baths HILTONHEAD-512086 MLS
Premier investment in Sea Pines Resort's South Beach Marina Village and less than 1/4 mile to the beach. This 1-floor 2BR/2BA Lagoon Villa features brand new impact rated windows and doors. While this unit has never been rented other rentals in this regime rent VERY well. Highly desirable location near the beach, South Beach Marina, dining, and entertainment. Features include vaulted ceilings, a spacious living area, and a private lagoon-view patio. Sea Pines remains Hilton Head Island's most established short-term rental market, making this an exceptional opportunity for immediate income, appreciation potential, and personal enjoyment. (Virtual enhancement has been used in some photographs)

226 S Sea Pines Drive Unit 1588, Hilton Head Island

Listing courtesy of Charter One Realty.

$609,000
2 Beds 3 Baths HILTONHEAD-511985 MLS
Here's your opportunity to own a meticulously maintained villa in the heart of Shipyard that has been totally renovated and is TURN-KEY! Do not miss this chance to see this well cared for villa unit that has been used as a second home by current owner! There have been over 37k in recent renovations to bring in a nicely appointed kitchen with all new cabinets with quart countertops, sink/faucet and new microwave. This open galley kitchen is perfectly appointed and uses every inch wisely. Brand new pavers have been installed on both the oversized front porch entrance/service area and the spacious back patio! The bedrooms upstairs have cathedral ceilings and both bathrooms have been updated and are coastal chic! Each bedroom has a patio as another area to sit and relax and enjoy the beauty that Hilton Head has to offer. The primary bedroom has an oversized sliding glass door that provides a beautiful view of the Galleon golf course. The downstairs is an open concept and incorporates neutral 16 inch tiles throughout for easy wear.....the kitchen is also open to the living area and it's easy to stay connected to the visitors while the cook is in the kitchen. There is a full laundry room with extra space for well needed storage. Shipyard is a thriving and excellent plantation to enjoy all that is offered on Hilton Head Island. There are 3 nine hole golf courses, a restaurant and golf pro shoppe, Van Der Meer tennis facility and a newer beach club that offers storage underneath for those that are interested! The Shipmaster complex provides a spacious pool and tennis courts that are included in your regime fee. Shipyard has two separate entrances including one off of Highway 278 and the other on Pope Avenue which offers easy access to Coligny Plaza....considered by many to be the 'downtown' of HHI! This villa can be used as a primary, secondary or a rental property so it is very flexible...and animals are welcome for owners! Come see this villa TODAY! It won't last long!

63 Shipyard Drive Unit 704, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$7,800,000
6 Beds 8 Baths 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.

$739,000
3 Beds 3 Baths HILTONHEAD-511979 MLS
Overlooking the 6th hole of Moss Creek's South Course, this move-in ready 3-bedroom, 2.5-bath home offers the perfect blend of Lowcountry charm, thoughtful design, and effortless living in one of the area's most sought-after communities.Step inside to discover beautiful pine floors, soaring ceilings, and timeless architectural details throughout. Designed for both everyday living and entertaining, the open floor plan features a spacious kitchen that flows seamlessly into the vaulted great room, complete with a cozy fireplace and custom built-ins. A separate dining room with an elegant tray ceiling provides the perfect setting for family dinners and holiday gatherings.The main-level primary suite offers a private retreat with dual walk-in closets and a spacious bath featuring dual vanities, a soaking tub, a beautifully tiled walk-in shower, and a private water closet. Upstairs, two generously sized guest bedrooms, a full bath, and an oversized storage closet provide excellent separation and privacy for family and visitors.Step outside to the private deck and enjoy peaceful golf course views framed by mature landscaping. Additional highlights include a new roof (2026), new carpet (2026), oversized two-car garage, paver driveway and front walkway, laundry room, powder room, and a low-maintenance homesite designed for easy living. Residents of Moss Creek enjoy an exceptional lifestyle with two championship 18-hole golf courses, a deep-water marina, tennis and pickleball courts, fitness center, clubhouse, waterfront pool complex, nature trails, and Mackay's Grill. Offering the convenience of primarily one-level living, quality finishes, and a highly functional floor plan, this home is ideal as a full-time residence or a lock-and-leave Lowcountry retreat.

21 Wax Myrtle Court, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$1,195,000
4 Beds 5 Baths HILTONHEAD-511954 MLS
Offered for the first time by its original owners, 342 Long Cove Drive is a rare opportunity to own one of Long Cove Club's distinctive custom residences. Thoughtfully designed and impeccably maintained since its construction, including a new roof in 2025, this timeless brick home blends enduring craftsmanship with exceptional architectural character. Privately sited on a beautifully landscaped homesite, the residence enjoys sweeping golf-to-lagoon views while offering remarkable privacy. Soaring ceilings, expansive windows, and light-filled living spaces create an open, airy atmosphere throughout, while the home's unique design offers warmth, flexibility, and timeless appeal. Designed for comfortable everyday living and gracious entertaining, the floor plan features two spacious primary suites, one on each level, elevator access to all levels, a dedicated office, generous gathering spaces, and a detached two-car garage. The private front brick courtyard surrounds a sparkling swimming pool, creating a secluded outdoor retreat unlike any other. Lovingly cared for over the years, the home presents an outstanding opportunity for its next owner to personalize the interiors while preserving the quality and architectural integrity that make it so special. Combining classic design, exceptional maintenance, and one of Long Cove's most desirable settings, this is a truly rare offering in one of Hilton Head Island's premier private communities. Long Cove Club is a community that features world-class amenities, including a top ranked Pete Dye designed golf course, deep water marina facilities, Jr. Olympic size pool, tennis, pickleball, bocce ball, basketball court, dog park, playground and community garden.

342 Long Cove Drive, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$1,985,000
3 Beds 4 Baths HILTONHEAD-511813 MLS
An absolute standout in Sea Pines. This exceptional home was worth the wait... but is not expected to last long! Relaxed and comfortable meets modern and sophisticated. Prepare to be captivated by this exceptionally cool, single-level stunner! A private (gated) front courtyard enhances the arrival experience, while the private backyard setting is unmatched. Inside you will find an open-concept interior that is complimented by numerous design enhancements. The design-forward, chef-style kitchen will reignite your love of both cooking and entertaining, boasting quartz counters, impressive cabinetry, designer lighting, updated appliances, gas cooking, beverage refrigerator, pantry, and an expansive flat-top island. The home naturally flows out to an inviting screened porch, extending comfortable living space outdoors. The spacious owner's suite enjoys tranquil water views and a spa-like bath, while the two private guest rooms offer beautifully remodeled en-suite baths as well. Embrace a year-round outside lifestyle with a refreshing (heated) saltwater pool, firepit area, peaceful lagoon and private backyard lawn. The property features a durable TPO roofing system, valued for its energy efficiency, longevity, and low-maintenance performance. Set on nearly a half-acre with open space on two sides, this high-elevation property stands apart! Ideally positioned in Sea Pines on a quiet street almost directly between the Sea Pines Beach Club and the Harbourtown Yacht Basin! Tastefully furnished for immediate gratification!

41 Willow Oak W Road, Hilton Head Island

Listing courtesy of Collins Group Realty.

$2,995,000
4 Beds 6 Baths HILTONHEAD-511890 MLS
Rare opportunity to own one of Wexford's most distinctive residences, perfectly situated on an oversized corner double lot with picturesque harbor and Broad Creek water views and a 65 foot boat slip. This exceptional townhome combines the ease of low-maintenance living with the privacy, space, and amenities typically found in a single-family home.Designed for effortless living, the home features a private elevator providing convenient access to every level. The spacious, open-concept floor plan centers around a beautifully appointed kitchen that flows seamlessly into the dining room and living areas, making it ideal for entertaining but with the primary bedroom, laundry room and outdoor kitchen on the same level, this is perfect for easy living. Dedicated Library and office space, wine room and open third floor living space offer endless opportunity and something for everyone. Expansive windows fill the home with natural light while framing the tranquil waterfront setting and stunning multi level fountain.Outdoor living is equally impressive, with inviting spaces to relax, dine, and enjoy coastal breezes while overlooking the Broad Creek and harbor in both directions. A rare 6-8-car garage offers exceptional flexibility for automobile collectors, golf carts, recreational equipment, workshop space, and abundant storage.Recent improvements include a new roof, providing added value and peace of mind. Residents will also appreciate being just moments from Wexford's newly completed Harbour Center, featuring enhanced marina amenities, waterfront gathering spaces, and a vibrant social atmosphere.Located within the prestigious, gated Wexford community, residents enjoy world-class amenities including a championship golf course, deep-water marina with lock system, tennis and pickleball courts, swimming pool, clubhouse, fine dining, and an active lifestyle in one of Hilton Head Island's most sought-after private communities.Experience luxury waterfront living where exceptional views, outstanding amenities, and an unbeatable location come together at 2 Wexford on the Green.

2 Wexford On The Green, Hilton Head Island

Listing courtesy of BESTNEST By Beverly Serral.

$779,000
4 Beds 3 Baths HILTONHEAD-511026 MLS
Updated 4 BR, 3 BA home overlooking scenic Henri's Pond in the gated community of Moss Creek. July 2026 - freshly painted throughout with popcorn ceiling removed and LVP installed in first floor halls, dining room, kitchen, living room and primary bedroom. A highlight of the home is the new large screened-in back porch overlooking Henri's Pond, creating the perfect setting for morning coffee, outdoor dining, or relaxing while enjoying the ever-changing views of the water and surrounding wildlife. The current owner further enhanced the property with a spacious 1-car garage and attached carport, providing exceptional convenience and additional storage. Owner had paver driveway and walkway installed from the street to the front door as well as outdoor decking area facing Henri's Pond. Conveniently located near Bostwick Park, featuring 2 pools, fitness center, and deep-water marina. Moss Creek amenities include 2 private 18-hole golf courses, tennis and pickleball courts, dog park, and nature trails. Move-in ready and ideally suited for enjoying the Lowcountry lifestyle. All major home items - roof, new HVAC and ductwork, PEX piping - recently updated.

283 Moss Creek Drive, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$1,849,500
3 Beds 3 Baths HILTONHEAD-511596 MLS
Classic Hilton Head Island architecture, perfectly preserved and completely reimagined. Set on a rare corner estate lot of more than three-quarters of an acre in Shipyard Plantation, 37 Kingston Road offers a level of finish and scale rarely found at this price point among the Island's premier gated communities. A complete renovation from top to bottom includes brand new HVAC systems with all new ductwork, a stunning new pool with a Pennsylvania flagstone deck, and designer finishes throughout. Vaulted ceilings, skylights, and thoughtful millwork bring warmth, character, and natural light to every room. The kitchen blends timeless design with tasteful updates, featuring white shaker cabinetry, stone countertops, stainless steel appliances, updated hardware and fixtures, and a center island. The split floor plan offers ideal separation between the primary suite and guest bedrooms, while the generous lot provides the opportunity to add a guest house or casita. The primary suite is spacious and serene, with direct access to the pool and a beautifully renovated bath featuring a marble walk-in shower and double vanity. Every bathroom reflects the same level of craftsmanship and attention to detail found throughout the home. Outside, the new pool and Pennsylvania flagstone deck create a private outdoor retreat surrounded by mature live oaks and classic Lowcountry landscaping. The bonus Carolina room extends the living space, creating a seamless connection between the home's interior and outdoor living areas. Offered furnished and available for immediate enjoyment, the home is just a five-minute bike ride to the Shipyard Beach Club and the Sonesta Resort, and only minutes from some of the Island's best dining, shopping, golf, and recreation. Short-term rental projections are available upon request. Whether the goal is a primary residence, a multigenerational retreat, a second home, or an income-producing investment property, 37 Kingston Road is uniquely positioned to deliver. A rare corner estate, completely renovated, furnished, and ready, at a price that rewards the discerning buyer who knows this market. *Owner is SCREA.

37 Kingston Road, Hilton Head Island

Listing courtesy of ELEVE PROPERTIES Brokered by EXP Realty.

$1,150,000
3 Beds 5 Baths HILTONHEAD-511807 MLS
Excellent value on updated, superbly maintained lifestyle home with private pool/spa and panoramic lagoon views on quiet cul de sac street in popular Hilton Head Plantation. Features include soaring, smooth vaulted & tray ceilings, wood & tile flooring, granite & composite counters, high end appliances (Forno 8 burner gas range & double Ovens, etc.), custom cabinetry/vanities/built-ins, plantation shutters, skylights, recessed lighting, ceiling fans, walls of windows to pool & lagoon views, 17 SEER high efficiency HVAC system, newer roof (2022) & mechanicals, etc. Very livable floor plan offers Chef's dream kitchen (large island, coffee/wet bar, butlers pantry, max cabinet & counter space), open to casual and formal dining, expansive great room, bonus/media room, much desired screened porch, 3 BR suites including well-appointed primary suite w/private courtyard, 2 ample guest BR's with updated baths (glass & tile surround showers, new vanities, counters, lighting), secluded den/study, 2 powder rooms, 2nd floor loft, walk-in attic space, 2 car garage and ample closet/storage space. All with charming curb appeal, circular drive, specimen live oaks, palms, azaleas, etc. and proximity to Crooked Pond Pool/Tennis, front gate & shopping/dining/entertainment + HHP's Spring Lake Pool Complex, Dolphin Head Recreational Area and newly refurbished Pine Island Beach Park!

3 Twisted Cay Lane, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,200,000
3 Beds 3 Baths HILTONHEAD-511804 MLS
Location, location, location...Experience the very best of Sea Pines from this beautifully updated Fairway Oaks villa. Privately situated at the end of a quiet cul-de-sac, this 2,200-square-foot home offers a rare combination of privacy, natural beauty, and convenience-with an attached two-car garage, an uncommon and highly sought-after feature in Sea Pines villas. The home features 3 bedrooms and 2 full and 1 half bath including a spacious first-floor primary suite featuring soaring ceilings, an oversized custom walk-in closet, a luxurious steam shower, heated towel rack, and spa-inspired finishes. Upstairs, two generously sized guest bedrooms and a full bath create an inviting retreat for family and friends.The beautifully renovated kitchen showcases Brazilian quartzite and quartz countertops, custom floor-to-ceiling cabinetry, new appliances, and a beverage center with wine cooler and kegerator. Walls of windows fill the living areas with natural light and frame peaceful lagoon views. Step onto the expansive rear decks, where a charming water feature creates a serene setting beneath the towering evergreens..Fairway Oaks is one of Sea Pines' most desirable villa communities, uniquely surrounded by tranquil lagoons and the scenic fairways of Heron Point Golf Course. Residents enjoy a private swimming pool, tennis and pickleball courts, and the peace of mind that comes with no short-term rentals allowed. Just a short walk or bike ride from Harbour Town's iconic lighthouse, marina, waterfront dining, boutique shopping, and miles of scenic trails, this exceptional villa offers the very best of the Lowcountry lifestyle. Whether you are searching for a full-time residence or an elegant coastal getaway, this is more than a home--- It is the lifestyle you have been waiting for. OSCREA

40 Planters Wood Drive Unit 2516, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$1,695,000
4 Beds 4 Baths HILTONHEAD-511697 MLS
Extremely rare opportunity! No expense spared in this 100% remodeled luxury penthouse villa with sweeping Skull Creek & ICW views. Top of the line, curated finishes by award winning design team throughout including wide plank maple flooring, soaring smooth ceilings, built-ins & millwork by master craftsmen, walls of windows & private terraces to view, high end designer fixtures, hardware, window treatments, wall & door coverings (MDF panels, polished stainless steel, leathered, etc.), lighting (crystal waterfall & raindrop chandeliers, sconces, pendant, niche, accent, recessed LED), stainless steel & glass staircase railings, dramatic floor to ceiling fireplace w/ herringbone tile surround, ultra custom cabinetry, limestone & quartz counters, acid etched mirrored backsplash, 800 series Bosch & Fisher-Paykel appliances, dual Fagor wine coolers, tankless water heater, floating vanities, glass & tile surround showers, wall-mounted fixtures, integrated Alexa system & built-in speakers, etc. Thoughtfully designed floor plan for living and entertaining includes first floor Chef's peninsula kitchen & breakfast bar open to spacious dining area, handsome den w/wet bar, awe-inspiring great room & water view sitting area, lavish primary suite with stunning bath, guest BR & bath + laundry room. 2nd floor offers game area, media area, office nook, ensuite BR's 3 & 4 with well-appointed baths + storage & mechanical access. A stunning transformation with a breathtaking locale... All with covered parking, large storage unit & private complex pool and cabana. And just down the street from CCHH, waterfront dining & entertainment + Spring Lake pool complex, Dolphin Head Recreational Area & recently renourished Pine Island Beach Park.

4 Village North Drive Unit 43, Hilton Head Island

Listing courtesy of Charter One Realty.

$489,000
3 Beds 2 Baths HILTONHEAD-511701 MLS
Welcome to 17 Monticello Drive, a charming, move-in ready home nestled in the highly desirable Chinaberry Ridge community on Hilton Head Island. This inviting residence offers a spacious, open floor plan with vaulted ceilings, abundant natural light, and beautifully maintained living spaces perfect for everyday living or entertaining. The home features comfortable bedrooms, updated flooring, a bright kitchen and dining area, and a large two-car garage. Outside, you'll enjoy a private backyard surrounded by mature landscaping, creating a peaceful setting for relaxing or entertaining. Conveniently located near top-rated schools, parks, shopping, restaurants, beaches, and the Intracoastal Waterway, this home offers an exceptional opportunity for first-time buyers, retirees, or investors seeking the perfect blend of comfort, location, and value.

17 Monticello Drive, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$4,495,000
4 Beds 5 Baths HILTONHEAD-511638 MLS
A remarkable expression of Lowcountry luxury, this exceptional custom residence is perfectly positioned on a quiet cul-de-sac in the prestigious Port Royal community, offering the rare opportunity to enjoy both breathtaking marsh front living and easy access to the beach. Here, you don't have to choose between sweeping tidal marsh views and walking distance to the beach, this home offers both. Encompassing more than 4,600 square feet of thoughtfully designed single-level living, the home captures panoramic vistas of Fish Haul Creek, the tidal marsh, and the Atlantic Ocean beyond while blending timeless architecture with impeccable craftsmanship. From the impressive front elevation and grand wrought-iron staircase to the custom wood and glass entry doors, every detail has been carefully curated. Inside, soaring ceilings, custom millwork, coquina-shell columns, extensive stone flooring, designer lighting, walls of glass, and multiple fireplaces create warm yet sophisticated living spaces designed to showcase the surrounding natural beauty. The gourmet kitchen is a chef's dream, featuring premium Wolf, Viking, Bosch, and Sub-Zero appliances, custom cabinetry, generous prep space, and an adjoining butler's pantry with wet bar-ideal for entertaining. The luxurious primary suite serves as a private retreat with veranda access, custom walk-in closets, and a spa-inspired bath complete with heated stone floors, a soaking tub, oversized walk-in shower, and skylight. Two additional guest suites, a dedicated office, elevator access, and a spacious six-car climate-controlled garage provide exceptional flexibility for family and guests alike. Designed for year-round enjoyment, the outdoor living spaces are equally impressive. Expansive covered verandas, exposed cypress beams, an outdoor fireplace, built-in grilling area, professionally designed gardens, a custom hot tub with waterfall, and a private dock with a floating dock on Fish Haul Creek create an extraordinary setting for entertaining or simply enjoying the peaceful waterfront surroundings. Whether you're launching a kayak from your backyard, spending the afternoon on the beach just moments away, or watching spectacular sunsets over the marsh from your veranda, this one-of-a-kind estate offers an unparalleled coastal lifestyle in one of Hilton Head Island's most coveted communities.

127 Fort Walker Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$244,900
1 Beds 1 Baths HILTONHEAD-511617 MLS
Essentially new following a major studs-out renovation, this one-bedroom villa enjoys a grassy front lawn, majestic shade tree, and tranquil lagoon views from the sunny rear deck. Formerly a studio, the redesigned layout now offers a private bedroom retreat while retaining the lower studio-level HOA assessment. Updates include reinforced 12-inch-on-center floor joists, new subflooring and insulation, PEX plumbing, smooth volume ceilings, luxury plank flooring, lighting, doors, trim, and slider glass. The all-new kitchen features white quartz counters, expanded cabinetry, subway tile, and new appliances. The remodeled bath offers designer wave tile, a soaking tub, new fixtures, and updated lighting. Enjoy a wood-burning fireplace, abundant storage, a storm door with roll-down screen, and new rear gutter system. Exterior painted July 2026 new water heater relocated outside. Low POA fees, with all 2026 exterior and insurance assessments paid.

5 Gumtree Road Unit H-17, Hilton Head Island

Listing courtesy of Collins Group Realty.

$1,250,000
4 Beds 4 Baths HILTONHEAD-511553 MLS
42 Ashton Cove Drive is a rare South Island opportunity! Beautifully updated throughout, this home features an open-concept floor plan, chef's kitchen, high-end finishes, and three spacious bedrooms with resort-style baths. The lower level offers a private one-bedroom apartment with a full kitchen, full bath, laundry, and flexible living space-ideal for guests, in-laws, a home office, or rental potential (where permitted). Enjoy expansive covered porches with breathtaking marsh views, an outdoor kitchen with beverage refrigerator, a large back yard, fire pit, and multiple entertaining areas. The oversized lower level also includes a 3+ car garage, workshop, and abundant storage. Community amenities include a pool and racquet courts. Offered furnished (excluding personal items). No short-term rentals.

42 Ashton Cove Drive, Hilton Head Island

Listing courtesy of Lowcountry Live Oak Realty.

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