Refine Search
Sort by
17 Old Stoney Lane, Hilton Head Island
$649,000
4 Beds ⋅ 4 Baths ⋅ 1,943 SqFt. ⋅ HILTONHEAD-513344 MLS
Low maіntenancе lіving, mіnіmаl stаіrs and a fully fenced bаckуard in this nearly new townhome! This 4 bedroom 3 and a half bath townhome provides a first floor primary bedroom with an additional primary suite on the second floor. Both primary bedrooms include an attached bath with double sinks, shower and walk in closets. Built in 2023, this home has an efficient layout with a designer kitchen, open flow floor plan and an expansive two-story living room. A screened back porch with a fully fenced and landscaped backyard provides comfortable outdoor enjoyment for all seasons. Old Stoney Village is a pet and golf cart friendly community with a low HOA and close proximity to community waterfront parks, some of the Islands best waterfront dining, schools & Island Rec Center. Located on the north end of Hilton Head Island creating easy access to all of the Island and Bluffton. Nearby pool and fitness center access available for additional membership fee to the Country Club of Hilton Head.

17 Old Stoney Lane, Hilton Head Island

Listing courtesy of Condomaximum Concepts Inc.

136 S Shore Drive, Hilton Head Island
$4,795,000
4 Beds ⋅ 5 Baths ⋅ 4,386 SqFt. ⋅ HILTONHEAD-512195 MLS
Oceаnfront Livіng, Εlevаtеd. Ѕet dіrеctly along the Atlantіc Οcean within Leamington, Palmetto Dunes, 136 South Shore Drive offers an exceptional combination of oceanfront living, privacy, and refined coastal comfort. Tasteful interiors and a spacious floor plan create an inviting setting for both everyday living and entertaining. Just beyond the residence, owners can enjoy the beach, pool, and the natural beauty of Hilton Head Island's coastline. South Shore's intimate setting provides a distinctive advantage. With no short-term rentals, the community maintains a quieter, more private residential atmosphere while remaining conveniently close to the golf, tennis, pickleball, dining, biking, and recreational amenities of Palmetto Dunes.136 South Shore Drive is a rare opportunity to enjoy a beautiful oceanfront residence in one of Hilton Head Island's most desirable and private coastal settings.

136 S Shore Drive, Hilton Head Island

Listing courtesy of Keller Williams Realty.

5 Sailwing Lane, Hilton Head Island
$2,550,000
4 Beds ⋅ 5 Baths ⋅ 3,710 SqFt. ⋅ HILTONHEAD-512736 MLS
Expеriencе thе beѕt οf Ηiltοn Ηead Island waterfrοnt livіng at 5 Sailwing Lane, a spacious harbour-front townhome in the coveted Windmill Harbour community. Offering over 3,700 square feet with four bedrooms - four full baths & 1 half bath, this distinctive residence combines generous living spaces with an enviable Lowcountry setting. The thoughtfully designed floor plan features a beautiful kitchen, dining room, family room, and den (or office or extra BR), providing abundant space for everyday living and entertaining. The curved staircase showcases one of the many exquisite touches throughout the home. The first floor in-law suite offers exceptional flexibility for extended family, guests, a private office, or a separate retreat featuring a spacious BR, full BT, family room (or media room) plus a kitchen area. The elevator services the first, second and top floor. Built with durable Hebel block construction, the home offers the benefits of this energy-efficient, resilient building system while providing the comfort and spaciousness expected in a premier island residence. Need extra storage space? The upper floor (just under 800 sq ft.) is heated and cooled and ready for all your storage needs or future expansion. Positioned directly on the harbour, this home captures the quintessential Hilton Head lifestyle, set within the private and picturesque community of Windmill Harbour. Residents will enjoy a distinctive Lowcountry lifestyle surrounded by water, beautiful landscaping, and a vibrant boating atmosphere. From relaxed mornings overlooking the boats to entertaining family and friends in the expansive living areas, 5 Sailwing Lane offers a rare combination of space, construction quality, flexibility, and prime harbour-front location. A special opportunity to own a substantial four-bedroom, four-bath waterfront townhome in one of Hilton Head Island's most desirable boating communities. The South Carolina Yacht Club is just steps away from your door - It is the perfect club to enjoy a world class meal, vibrant social activities and a competitive fitness environment. Why wait- Your new life awaits!

5 Sailwing Lane, Hilton Head Island

Listing courtesy of Charter One Realty.

20 Old Stoney Lane, Hilton Head Island
$699,990
4 Beds ⋅ 4 Baths ⋅ 1,871 SqFt. ⋅ HILTONHEAD-512410 MLS
Welcome to 20 Old Stoney Lane in Old Stoney Village, a beautifully designed 4-bedroom, 3.5-bathroom townhome built in 2023 on Hilton Head Island with a fully fenced backyard and garage. Offering a rare combination of space, functionality, and value, this is an excellent opportunity for buyers looking to be under $700,000 on HHI. The thoughtfully designed floor plan features dual primary suites, with one conveniently located on the main level and a second spacious primary suite with high ceilings upstairs. The upper level also includes two additional bedrooms, a full bathroom, and the laundry room, complete with cabinets above the washer and dryer for added storage. The main level features an inviting kitchen with gorgeous cabinetry, granite countertops, and stainless-steel appliances, opening to the living and dining areas. The living room makes a dramatic impression with a very high, two-story ceiling, creating an exceptionally open and spacious feel. Hard-surface flooring runs through the kitchen and living room. Step outside to the screened-in porch and fully fenced backyard, offering a comfortable private outdoor space for relaxing, entertaining, or enjoying the island lifestyle. With a one-car garage and a driveway that can hold four cars, you'll have plenty of convenient parking and storage. The north end location provides easy access to nearby recreation and conveniences ~ a rowing center, biking and walking trails, and restaurants (like Benny's and Crazy Crab super close by) ~ plus the home is just a short distance from the public-school complex. This is an exceptional value for buyers seeking a better-than-new townhome with plenty of room, flexible living arrangements, and easy access to everything the Lowcountry has to offer! Add charming 20 Old Stoney Lane to your Must See List!

20 Old Stoney Lane, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

7 Windflower Court, Hilton Head Island
$499,900
3 Beds ⋅ 2 Baths ⋅ 1,462 SqFt. ⋅ HILTONHEAD-512479 MLS
Beautiful & updated coastal townhome for under $500,000 in highly desired Hilton Head Plantation! This stunning 3BD/2BA lock and leave townhome is perfect for anyone looking for maintenance free living. With a newer roof and a short walk to Spring Lake Pavillion where all your world class amenities are, this location is ideal. Spacious floor plan with large living area, one bedroom and full bathroom on the first floor. Find two additional bedrooms and one full bathroom upstairs. Step outside to a generous deck and patio area surrounded by natural foliage-ideal for morning coffee, evening gatherings, or simply enjoying the quiet Lowcountry setting. With its cul-de-sac location, proximity to Dolphin Head, miles of leisure trails, and the Plantation's signature amenities, this home delivers both privacy and convenience. Maintenance free living with regime covering trash, pest control and landscaping. Come enjoy everything Hilton Head Plantation has to offer with their high-end amenities and beautiful nature that surrounds the community!

7 Windflower Court, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

315 Ceasar Place, Hilton Head Island
$489,000
4 Beds ⋅ 4 Baths ⋅ 2,022 SqFt. ⋅ HILTONHEAD-512139 MLS
Offering a level of space and flexibility rarely found in townhome living, this four-bedroom, 3.5-bath Allenwood residence pairs a versatile multi-level floor plan with peaceful lagoon views and multiple outdoor living spaces. Front and rear balconies extend from the main living level, creating natural places to enjoy the Lowcountry setting.A defining feature of the home is the private fourth-bedroom suite located off the garage, complete with a full bath, walk-in closet, and its own waterfront porch. Separated from the primary living areas, this space creates exceptional flexibility for guests, extended family, a home office, or additional living space.Inside, generous living areas accommodate both everyday life and entertaining, while the oversized one-car garage provides valuable parking and storage. Offered partially furnished and move-in ready, the home is well suited for a primary residence, second home, or investment property.Allenwood is a gated Hilton Head Island community offering a neighborhood pool and a convenient location near beaches, dining, shopping, recreation, leisure trails, and the Hilton Head Island school campus. With four bedrooms, abundant outdoor living, water views, and a floor plan that offers genuine versatility, this residence brings together space, privacy, and the ease of island living. Some images have been virtually enhanced with conceptual furnishings.

315 Ceasar Place, Hilton Head Island

Listing courtesy of Engel & Volkers.

7 Genoa Court, Hilton Head Island
$1,990,000
6 Beds ⋅ 7 Baths ⋅ 2,786 SqFt. ⋅ HILTONHEAD-512306 MLS
Stepѕ away frοm thе famеd 18th grееn liеѕ a unique opportunіty іn the heart of Sea Pines' iconic Harbour Town. This turnkey furnished home boasts 6 en-suite bedrooms, perfect for family gatherings and countless vacation memories. Rows of sliders lead guests from the newly renovated kitchen and double-story living area to the freshly resurfaced swimming pool and spa. This unique home features a rooftop deck with views to Calibogue Sound and is walking distance to the famous lighthouse, Liberty Oak, and family friendly dining and retail. The Sea Pines trolley is a short stroll away with transportation to the Sea Pines Beach Club, Sea Pines Center and South Beach amenities. With an established rental history, premier location and sleeping space for 20 this home is truly an investor's dream.

7 Genoa Court, Hilton Head Island

Listing courtesy of The Hilton Head Agency.

40 Old Stoney Lane, Hilton Head Island
$739,000
4 Beds ⋅ 5 Baths ⋅ 2,206 SqFt. ⋅ HILTONHEAD-512194 MLS
One of the only semi-custom floor plans in Old Stoney Village! This 4 bedroom 4.5 bath is full of custom home features including: each bedroom having its own ensuite bath, luxury LED lighted vanity mirrors, dining room bay window, living room built ins, upgraded closet shelving, oversized kitchen island with custom cabinets, full hop up quartz kitchen backsplash, enlarged tile showers, a gas range, dual laundry hookups on both floors, and an additional office/den. This home also features dual primary bedrooms (one on both first and second floor), garage, a grilling deck with propane hook up, front porch and the option to fence in the back yard. Set on a wooded corner lot, located off a quiet cul de sac, making this one of the most private lots in the neighborhood. Old Stoney Village is a pet and golf cart friendly community with a low HOA and close proximity to community waterfront parks, some of the islands best waterfront dining, schools and the Island rec center. Located on the north end of Hilton Head creating easy access to all of Hilton Head and Bluffton.

40 Old Stoney Lane, Hilton Head Island

Listing courtesy of Condomaximum Concepts Inc.

4 Honeysuckle Court, Hilton Head Island
$635,000
3 Beds ⋅ 2 Baths ⋅ 1,602 SqFt. ⋅ HILTONHEAD-511997 MLS
Opportunity to own a beautifully updated 3-bedroom townhouse in Hilton Head Plantation for under $700,000. This is one of those homes you truly have to see to appreciate. Stunning renovated kitchen from top to bottom has it all, while the great room features a custom wood-trim ceiling that adds warmth and character. LVP extends throughout the first floor. The bathrooms have been thoughtfully updated with today's finishes. The versatile floor plan includes a 1st floor bedroom or den along with two 2nd floor bedrooms. Outside, you'll find a generously sized fenced front service yard that can also be used as a dog run. The expansive private rear stone patio, complete with a fire pit, creates a peaceful retreat for relaxing alone or with family and friends. Storage is another feature, with 2 separate storage areas--one is exceptionally large and could be a workshop. New Anderson sliding doors add both beauty and energy efficiency. This townhome checks all the boxes, making it a great property for a primary residence, 2nd home, starter home, or long-term rental. It is a low-maintenance lifestyle home, allowing you to enjoy all Hilton Head has to offer. As the saying goes, "Don't judge a book by its cover." This home has been transformed with remarkable updates and is one you won't want to miss.

4 Honeysuckle Court, Hilton Head Island

Listing courtesy of Charter One Realty.

3 Leeward Passage, Hilton Head Island
$1,195,000
4 Beds ⋅ 5 Baths ⋅ 2,914 SqFt. ⋅ HILTONHEAD-511946 MLS
Beautifully updated and lovingly maintained, this Charleston-style townhome offers timeless Lowcountry charm in Windmill Harbour, one of Hilton Head Island's most desirable gated waterfront communities. The property sits mere steps from the marina and South Carolina Yacht Club, providing a direct connection to the island's coastal lifestyle. Situated on one of the neighborhood's charming and peaceful streets, this corner townhome spans three stories with a private elevator, four ensuite bedrooms, and a layout designed to balance privacy with inviting spaces to gather and connect. Classic Charleston architecture is showcased through double balconies with traditional haint blue ceilings, while the interiors feature distinctive dentil crown molding and curated finishes throughout.Recent improvements include a renovated kitchen with quartz countertops, a custom Venetian plaster range hood, premium appliances, and a custom-built wine bar. The exterior has been repainted, and two new HVAC systems were installed in July 2026, offering modern efficiency and peace of mind. With its low-maintenance design and ideal setting, this townhome offers the ease of a true lock-and-leave lifestyle, perfectly suited for full-time living or coastal getaways.

3 Leeward Passage, Hilton Head Island

Listing courtesy of I Save Realty.

2 Wexford On The Green, Hilton Head Island
$2,950,000
4 Beds ⋅ 6 Baths ⋅ 6,366 SqFt. ⋅ HILTONHEAD-511890 MLS
WATERFRΟNT. DOUΒᏞE ᏞΟΤ. 65-FΟΟT BOAT SLΙP. ΕXCEPTIONAL GARAGE.This distinctive Wexford residence offers a rare combination of space, waterfront views, and effortless coastal living. Ideally positioned on an oversized corner double lot, the home captures picturesque Broad Creek and harbor views in both directions and includes a 65-foot boat slip.More than a traditional townhome, this exceptional residence lives like a private single-family home while offering the convenience of low-maintenance living within one of Hilton Head Island's premier gated communities. A private elevator provides easy access to every level, while the thoughtfully designed floor plan offers exceptional flexibility for both everyday living and entertaining.The main living level is centered around a beautifully appointed kitchen that opens seamlessly to the dining and living areas, creating an inviting setting for gatherings. The primary suite, library, laundry room, and outdoor kitchen are conveniently located on the same level for effortless one-level living. Additional spaces include a dedicated library, private office, wine room, and expansive third-floor living area-providing room for work, guests, hobbies, and relaxation.Expansive windows bring abundant natural light throughout the home while showcasing tranquil water views and the property's striking multi-level fountain. Multiple outdoor living areas provide the perfect setting for dining, entertaining, or simply enjoying the coastal breezes and ever-changing waterfront scenery.A truly exceptional 6-8-car garage provides rare flexibility for automobile enthusiasts, golf carts, recreational equipment, workshop space, and extensive storage. Recent improvements include a new roof, adding valuable peace of mind.Just moments from Wexford's newly completed Harbour Center, residents enjoy enhanced marina amenities, waterfront gathering spaces, and an inviting social atmosphere. Wexford's private amenities include a championship golf course, deep-water marina with lock system, tennis and pickleball courts, swimming pool, clubhouse, fine dining, and an active coastal lifestyle.For the buyer seeking something beyond an ordinary townhome, 2 Wexford on the Green offers an extraordinary combination of waterfront living, generous indoor and outdoor space, boating access, and an unparalleled location within Wexford. Seller is also willing to consider creative financing options, providing additional flexibility for a qualified buyer.

2 Wexford On The Green, Hilton Head Island

Listing courtesy of BESTNEST By Beverly Serral.

35 Lake Forest Drive Unit APT 3304, Hilton Head Island
$699,000
2 Beds ⋅ 2 Baths ⋅ 1,400 SqFt. ⋅ HILTONHEAD-511765 MLS
Discover this diamond in the rough! A 2-bedroom, 2-bath townhouse in the heart of Sea Pines Resort. This light filled villa offers approximately 1,400 square feet of single-level living with vaulted ceilings, an open floor plan, and peaceful lagoon views from the living room, primary suite, and spacious rear deck. Enjoy added privacy along with a welcoming front porch and excellent bedroom separation.Perfect as a primary residence, vacation home, or investment property with short-term rental potential, this villa also offers access to a community pool and tennis courts.Ideally located near the Sea Pines Forest Preserve, Harbour Town and pristine beaches, championship golf, bike trails, marinas, shopping, and dining, this is an outstanding opportunity to enjoy the very best of Hilton Head Island living. Brand new front and rear decks!

35 Lake Forest Drive Unit APT 3304, Hilton Head Island

Listing courtesy of ERA Wilder Realty, Inc.

135 Harbour Passage, Hilton Head Island
$1,195,000
3 Beds ⋅ 4 Baths ⋅ 2,772 SqFt. ⋅ HILTONHEAD-511567 MLS
Welcome to Windmill Harbour, one of Hilton Head Island's premier gated waterfront communities. This beautifully maintained 3-bedroom, 3.5-bath home offers the perfect blend of Lowcountry charm, comfort, and functionality. The thoughtfully designed floor plan features spacious living areas filled with natural light, creating an inviting atmosphere for both everyday living and entertaining. Enjoy multiple outdoor living spaces, including front and rear balconies and a private deck, all perfectly positioned to take in breathtaking Intracoastal Waterway and serene marsh views. Whether you're enjoying your morning coffee or unwinding at sunset, the picturesque Lowcountry scenery provides an ever-changing backdrop. Each bedroom offers privacy and comfort, making the home ideal for family and guests alike. Residents of Windmill Harbour enjoy access to the world-renowned lock-controlled marina, the South Carolina Yacht Club, scenic walking paths, and beautifully landscaped grounds. Conveniently located just minutes from Hilton Head's beaches, championship golf, dining, and shopping, this exceptional property offers the perfect combination of waterfront beauty, luxury, and the unmatched Lowcountry lifestyle.

135 Harbour Passage, Hilton Head Island

Listing courtesy of Charter One Realty.

148 Windward Village Drive, Hilton Head Island
$619,000
2 Beds ⋅ 3 Baths ⋅ 1,220 SqFt. ⋅ HILTONHEAD-511442 MLS
Located in the desirable Windward Village enclave within the prestigious gated Shipyard community, this beautifully updated 2-bedroom, 2.5-bath villa offers a peaceful golf course setting, thoughtful upgrades, and an exceptional Hilton Head Island lifestyle. The spacious floor plan features soaring cathedral ceilings, abundant natural light, and a first-floor primary suite with an updated en-suite bath, enclosed walk-in closet with cedar shelving, and private deck. The living area opens to a screened porch with views through the mature trees toward the golf course, creating an inviting extension of the living space. The current owners completed extensive improvements between 2020 and 2022, including impact-resistant windows and two sliding glass doors, updated kitchen cabinetry and appliances, uniform tile flooring throughout, and beautifully renovated bathrooms. The two downstairs bathrooms feature heated tile floors, while the guest bath also includes a heated towel rack. Additional improvements include a screened porch with updated screening and tile flooring, HVAC system (2023), water heater (2023), and dishwasher (November 2025). Windward Village residents enjoy their own community pool, spa, and fire pit, all within the 800-acre Shipyard community. Shipyard offers private beach access via the Shipyard Beach Club, miles of leisure trails for walking and biking, 24-hour gated security, the 27-hole Shipyard Golf Club, Van Der Meer Tennis & Pickleball Center, Sonesta Resort Hilton Head Island, Hilton Head Health wellness resort, and a convenient south-end location just minutes from Coligny Plaza, shopping, dining, and entertainment. Whether you're searching for a primary residence, second home, or investment opportunity, this move-in-ready villa offers the perfect combination of comfort, quality, and coastal living.

148 Windward Village Drive, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

125 Greenwood Drive Unit APT 3407, Hilton Head Island
$719,000
2 Beds ⋅ 3 Baths ⋅ 1,238 SqFt. ⋅ HILTONHEAD-510644 MLS
Come sеe this tοtаlly RΕΝΟVAΤΕD FEE SIMPLΕ homе Located in the exquisite Carolina Place community in the heart of the Low Country where you can live out your dreams of enjoying the island! This 2 bedroom 2 and 1/2 bath townhome has the ideal layout, location and VIEW! Complete privacy and serene view with wonderful wild life including deer, various Southern birds and so much more! Having been recently updated it is a turn-key opportunity to have a permanent primary, secondary or investment home in Sea Pines Plantation. The first floor is spacious and open with a HUGE screened-in back porch that runs the entire width of the townhome and is fully enclosed. It adds a welcome dimension to the living space and adds a variety of space for hosting friends and family. The view is peaceful and tranquil with the lagoon and the protected forest preserve backdrop behind it with only the natural wildlife as your neighbors. You can sit on your covered fully enclosed back porch and enjoy all the beauty that the Low Country has to offer! Both bedrooms are located upstairs and each have their own private updated bathrooms. This home is easy in and located in close proximity to the ample amenities that Carolina Place has to offer! It has a large swimming pool with on sight spa with tennis and pickle ball courts too! Sea Pines Plantation has so much to offer with biking trails that run throughout the area taking you throughout Sea Pines including Harbour Town, South Beach Marina or the Beach Club....there's also a private access beach for owners of Sea Pines Properties.....not to mention the 4 different golf courses, tennis, pickle ball, boating, shopping and all the water sports imaginable!! There's a reason this particular area has so many happy owners.....come see for yourself and become a Sea Pines Residential owner TODAY!!

125 Greenwood Drive Unit APT 3407, Hilton Head Island

Listing courtesy of Keller Williams Realty.

17 Lake Forest Drive Unit APT 3347, Hilton Head Island
$775,000
2 Beds ⋅ 3 Baths ⋅ 1,610 SqFt. ⋅ HILTONHEAD-509566 MLS
Tucked within the world-renowned community of Sea Pines, this beautifully updated 2-bedroom, 2.5-bath villa offers the perfect blend of Lowcountry charm, investment opportunity, and resort lifestyle. Enjoy tranquil lagoon views from a spacious floor plan featuring a fully renovated lower level designed with today's coastal buyer in mind. Partially furnished with bedroom furnishings included, this turnkey retreat is ideal as a second home, vacation getaway, or income-producing short-term rental. Owners and guests enjoy access to pristine beaches, miles of leisure trails, and three championship golf courses including legendary Harbour Town Golf Links, home of the annual RBC Heritage. Just moments from Harbour Town's iconic marina, dining, shopping, and entertainment, this is an exceptional opportunity to own in one of Hilton Head's most sought-after destinations.

17 Lake Forest Drive Unit APT 3347, Hilton Head Island

Listing courtesy of Real Broker, LLC.

9 Old Stoney Lane, Hilton Head Island
$559,000
3 Beds ⋅ 3 Baths ⋅ 1,628 SqFt. ⋅ HILTONHEAD-508118 MLS
Welcomе to 9 Old Stοnеy Ꮮаnе, a bеаutifully crafted 2023-built tοwnhomе offering modern Lowcountry living in one of the most desirable areas of Hilton Head Island. This practically new 3-bedroom, 2.5-bath residence features a bright and open-concept floor plan designed for both everyday comfort and effortless entertaining. The main living space flows seamlessly into a stylish kitchen with high-end finishes, creating a warm and inviting atmosphere throughout. Upstairs, the spacious bedrooms provide privacy and flexibility, with a well-appointed primary suite offering a relaxing retreat. Ideally located just minutes from Hilton Head?s renowned beaches, golf courses, dining, and shopping, this low-maintenance townhome presents an exceptional opportunity as a primary residence, second home, or investment property. Move-in ready and built with today?s standards in mind, 9 Old Stoney Lane combines location, quality, and convenience in one compelling offering!

9 Old Stoney Lane, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

2065 Deer Island Road, Hilton Head Island
$1,055,000
1 Beds ⋅ 2 Baths ⋅ 816 SqFt. ⋅ HILTONHEAD-507877 MLS
Searсhing for a trulу рrivаtе Ѕeа Ρines retreat with unmаtchеd views just steps from Harbour Town? 2065 Deer Island Road offers a rare end-of-the-road setting in the coveted Sea Pines Resort, delivering breathtaking views of the marsh and out to the Calibogue Sound. Tucked away at the end of a quiet road, this unique home is surrounded by nature, where walls of windows flood the home with natural light and frame stunning water and wildlife views from every angle. Thoughtfully updated with luxurious finishes, the home features high-end appliances including a Sub-Zero refrigerator, JennAir range, and Bosch dishwasher and microwave, along with quartz countertops and an open-concept living space designed for relaxed coastal living. Heart pine floors upstairs and bamboo flooring on the lower level add warmth and character, while multiple decks provide the perfect setting to take in unforgettable sunsets over the water. The upstairs level of all Deer Island properties are similar and can be re-configured to accommodate various bedroom and bathroom layouts. This flexible layout lives beautifully as a second home or income-producing rental, offering a peaceful, private escape just a short walk or bike ride to the Harbour Town Lighthouse, the Quarterdeck Restaurant, and the shops, dining, and amenities of Harbour Town. A rare opportunity to own one of the most scenic and private homes in Sea Pines.

2065 Deer Island Road, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

285 Ceasar Place, Hilton Head Island
$539,000
4 Beds ⋅ 4 Baths ⋅ 2,042 SqFt. ⋅ HILTONHEAD-506353 MLS
Welcomе to 285 Ceaѕаr Plасе, a bеаutifully maintained 4‐bedrοom, 3.5-bath townhome located on the desirable north end of the island, just minutes from top-rated schools, shopping, dining, and everyday conveniences. Offering 2,042 square feet of thoughtfully designed living space, this home blends comfort, flexibility, and Lowcountry lifestyle. The versatile first-floor suite features a private full bath, making it ideal for multigenerational living, a guest retreat, home office, or potential lockout. This level also opens to a screened-in porch, creating a private outdoor retreat for guests or extended living space. Upstairs, the open-concept main living area is bright and inviting, perfect for both relaxing and entertaining. Extend your living space outdoors with a second screened-in porch off the main level-ideal for year-round enjoyment. A third open-air balcony at the front of the home adds additional outdoor space and charm. Enjoy peaceful lake views with a tranquil fountain, providing a serene backdrop to everyday living. This well-kept property also includes a spacious 1-car garage and has been meticulously maintained, offering true move-in-ready appeal. Located within a gated community, residents enjoy access to a clubhouse and pool, combining security with resort-style amenities. Whether you're seeking a primary residence, second home, or investment opportunity, this property offers exceptional value in a prime island location.

285 Ceasar Place, Hilton Head Island

Listing courtesy of COAST - Brokered by EXP Realty.

109 Windward Village Drive, Hilton Head Island
$509,900
2 Beds ⋅ 2 Baths ⋅ 1,061 SqFt. ⋅ HILTONHEAD-506348 MLS
Refreshеd and move‐іn reаdу! Grеat οрportunity to be in Ѕhiрyard! This light and bright end-unit villa features a rare first-floor living floor plan and is ideally located in the hidden gem of Windward Village. Just inside the back gate of Shipyard, this fee-simple home offers walkable access to everything the Coligny area has to offer while enjoying the peace and privacy of a gated community with three 9-hole golf courses and an on-site pool with hot tub. The first-floor primary suite allows for easy, stair-free living and includes a newly remodeled full bath and generous closet space. Also on the main level are a spacious living room, built-in office alcove, and a large dining area highlighted by a wall of windows with unobstructed golf course views. The kitchen is equipped with all-new stainless steel appliances. Upstairs, you'll find a large, versatile loft currently used as a second bedroom, complete with a full bath and an oversized walk-in closet. Recent upgrades include a newly rebuilt rear deck, composite front deck, updated plumbing, new carpeting, and luxury vinyl flooring. This charming villa is ideal for full-time living, a vacation retreat, or taking over a successful 5-star rated short-term rental program with bookings already in place.

109 Windward Village Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

1 Grandview Court, Hilton Head Island
$1,125,000
3 Beds ⋅ 4 Baths ⋅ 2,216 SqFt. ⋅ HILTONHEAD-505579 MLS
Built by Grаves Conѕtruсtiοn іn 2022, thіs 3 bеd/3.5 bаth luxury townhome end-unіt iѕ move-in ready and close to the many amenities within Hilton Head Plantation. The first floor main living area has a high elevation (20.8 ft) and high ceilings that give plenty of natural light. Kitchen has quartz counters, soft-hinge drawers, under hood vent, tiled backsplash and plenty of storage. Spacious screened porch with new plantings just outside. Living area has built-in shelves/cabinets and a propane fireplace. Primary bed/bath on the 1st floor. 2nd floor has 2 bed/2 baths and a compact living area that's perfect for an office. Elevator goes from the 2-car garage area to all floors. Garage area has almost 1,400 extra sq ft of unfinished space with a new epoxy floor coating. Can be used as a home gym, workshop or for extra storage. Steps away from the pool, fitness center and food/beverage within the Country Club of Hilton Head. Hilton Head Plantation includes miles of walking/bike trails, 4 golf courses, Dolphin Head Rec area with a mile-plus waterfront leisure path overlooking the Port Royal Sound, recently renourished Pine Island Beach Park, tennis, nature preserve, marina and more.

1 Grandview Court, Hilton Head Island

Listing courtesy of The Ocean Broker.

5 Grandview Court, Hilton Head Island
$1,149,999
3 Beds ⋅ 4 Baths ⋅ 2,317 SqFt. ⋅ HILTONHEAD-504283 MLS
"The Lοck-And‐Ꮮeаvе Ꮮifе: Ηilton Head Stylе"- Јust steps from Skull Creek Marina and the Country Club of Hilton Head, this beautifully appointed 2024-built townhome delivers the ultimate Hilton Head lock-and-leave lifestyle. Designed for effortless living and entertaining, this 3-bedroom, 3.5-bath residence combines elevated finishes, thoughtful functionality, and an unbeatable location within Hilton Head Plantation. Step inside and immediately appreciate the open-concept design, private elevator, and abundance of natural light. The spacious living area features a stunning three-sided fireplace and custom floor-to- ceiling built in creating an inviting space to relax after a day on the water or at the beach. The adjoining kitchen and dining area flow seamlessly to a screened porch- an ideal spot for morning coffee, cocktails or casual entertaining. The first-floor primary suite offers exceptional convenience and privacy, while the second floor provides two additional bedrooms and a versatile sitting area. A private elevator makes every level easily accessible, with an additional 650 square feet of climate-controlled flex space-perfect for a home office, studio, fitness room, hobby space, or simply exceptional storage. A mini-split HVAC system keeps this bonus area comfortable all year round. The lower level features high-end wood-look ceramic tile for both style and durability. Everyday living is enhanced by premium upgrades including a Culligan whole-house water filtration system, built in dehumidifier, smart thermostats, custom window treatments and more. And then there's the location. Walk to Skull Creek Marina and the Country Club of Hilton Head in 2 minutes. Enjoy exceptional amenities including a private sandy beach on Port Royal Sound, a lazy river community pool, 12 tennis courts, bocce courts, pickleball, playgrounds, scenic trails, 2 nature conservancies with boardwalks, beautiful Bluff walking path on the Port Royal Sound and more. With its newer construction, private elevator, exceptional storage, flexible bonus space, and proximity to the water, this is a rare opportunity to enjoy Hilton Head on your own terms. Come for the boating. Stay for the lifestyle, Leave the maintenance behind!!

5 Grandview Court, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

55 Wexford On The Green, Hilton Head Island
$3,800,000
4 Beds ⋅ 6 Baths ⋅ 5,912 SqFt. ⋅ HILTONHEAD-503338 MLS
Currently under construction, this modern custom townhome offers marsh front views and scenic vistas of the Wexford golf course, just a short distance from the clubhouse and community pool. Thoughtfully designed for elevated Lowcountry living, the home features a chef's kitchen with custom cabinetry, premium appliances, and a dedicated scullery, opening to a spacious family room with fireplace. The primary suite is located on the first floor and includes a spa-inspired bath with custom vanity, a generous walk-in closet with direct access to the laundry room. Also on the main level are a private office and elevator access to all floors. The second floor offers an additional living room with gas fireplace and kitchenette, a second laundry room, and three ensuite guest bedrooms. A dedicated spa room provides space for a sauna and/or workout area and opens to a rooftop garden. The third floor features a versatile bonus space ideal for a media room, game room, or lounge, complete with built-ins, wet bar, fireplace, art room, and additional storage. Step outside to a private balcony with hot tub and a real wood-burning fireplace with gas starter. Additional highlights include a six-car garage with extensive walk-in storage and dedicated golf cart parking for up to three carts, spray foam insulation, tankless water heater, and modern construction throughout. Enjoy the Wexford lifestyle with a private marina on Broad Creek with a lock system, championship golf, tennis and pickleball, clubhouse dining, community pool, and a gated setting just minutes from Hilton Head Island beaches, dining, and shopping.

55 Wexford On The Green, Hilton Head Island

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

14 Grandview Court Unit 12, Hilton Head Island
$1,495,900
4 Beds ⋅ 4 Baths ⋅ 2,201 SqFt. ⋅ HILTONHEAD-450640 MLS
Luxury New Construction Townhomes with Deep Water Views! Don't miss this rare opportunity to own a brand-new townhome in the highly sought-after Hilton Head Plantation. These thoughtfully designed residences feature exceptional floor plans, two-car garages, and breathtaking deep water views of the Intracoastal Waterway. Ideally located just steps from Skull Creek Marina, home to the Freedom Boat Club, and moments from the vibrant amenities and activities at the Country Club of Hilton Head. The setting is further distinguished by its proximity to the historic Talbird Cemetery, a preserved and active cemetery that remains an important part of the island's heritage. Located behind the new Waterway phase, it serves as a meaningful reminder of Hilton Head's rich history and has been respectfully maintained as part of the surrounding landscape.

14 Grandview Court Unit 12, Hilton Head Island

Listing courtesy of Charter One Realty.

12 Grandview Court Unit 10, Hilton Head Island
$1,550,900
4 Beds ⋅ 4 Baths ⋅ 2,546 SqFt. ⋅ HILTONHEAD-450638 MLS
Luxury New Construction Townhomes with Deep Water Views! Don't miss this rare opportunity to own a brand-new townhome in the highly sought-after Hilton Head Plantation. These thoughtfully designed residences feature exceptional floor plans, two-car garages, and breathtaking deep water views of the Intracoastal Waterway. Ideally located just steps from Skull Creek Marina, home to the Freedom Boat Club, and moments from the vibrant amenities and activities at the Country Club of Hilton Head. The setting is further distinguished by its proximity to the historic Talbird Cemetery, a preserved and active cemetery that remains an important part of the island's heritage. Located behind the new Waterway phase, it serves as a meaningful reminder of Hilton Head's rich history and has been respectfully maintained as part of the surrounding landscape.

12 Grandview Court Unit 10, Hilton Head Island

Listing courtesy of Charter One Realty.

10 Grandview Court Unit 8, Hilton Head Island
$1,695,900
4 Beds ⋅ 4 Baths ⋅ 2,563 SqFt. ⋅ HILTONHEAD-450637 MLS
Luxury New Construction Townhomes with Deep Water Views! Don't miss this rare opportunity to own a brand-new townhome in the highly sought-after Hilton Head Plantation. These thoughtfully designed residences feature exceptional floor plans, two-car garages, and breathtaking deep water views of the Intracoastal Waterway. Ideally located just steps from Skull Creek Marina, home to the Freedom Boat Club, and moments from the vibrant amenities and activities at the Country Club of Hilton Head. The setting is further distinguished by its proximity to the historic Talbird Cemetery, a preserved and active cemetery that remains an important part of the island's heritage. Located behind the new Waterway phase, it serves as a meaningful reminder of Hilton Head's rich history and has been respectfully maintained as part of the surrounding landscape.

10 Grandview Court Unit 8, Hilton Head Island

Listing courtesy of Charter One Realty.

board logo

We do not attempt to independently verify the currency, completeness, accuracy or authenticity of the data contained herein. It may be subject to transcription and transmission errors. Accordingly, the data is provided on an “as is” “as available” basis only and may not reflect all real estate activity in the market. © 2026 REsides, Inc. All rights reserved. Certain information contained herein is derived from information, which is the licensed property of, and copyrighted by, REsides, Inc.