Wildhorse/Squire/Gumtree Homes for Sale

Welcome to Wildhorse, Squire, and Gumtree—three of Hilton Head Island's most charming and desirable neighborhoods nestled in the heart of Beaufort County, South Carolina. This picturesque region is renowned for its stunning landscapes, vibrant community spirit, and close proximity to pristine beaches, making it an ideal destination for families, retirees, and anyone seeking the ultimate coastal lifestyle.

Homes for sale in Wildhorse, Squire, and Gumtree offer a delightful array of architectural styles, from cozy single-family homes to elegant estates. Many properties feature spacious layouts, modern amenities, and beautiful outdoor spaces perfect for entertaining or simply enjoying the serene surroundings. With an emphasis on natural beauty, these neighborhoods often boast lush greenery, tranquil ponds, and scenic walking trails that encourage an active and healthy lifestyle.

Living in this area means you’re just a stone's throw away from the island's world-class golf courses, gourmet dining options, and vibrant shopping districts. The community is also known for its family-friendly atmosphere, with excellent schools and numerous recreational activities available for residents of all ages. Whether you're an outdoor enthusiast eager to explore the nearby nature preserves or someone who enjoys the finer things in life, Wildhorse, Squire, and Gumtree have something to offer everyone.

If you’re ready to find your dream home in one of Hilton Head Island’s most sought-after neighborhoods, browse our listings today and discover the endless possibilities that await you in Wildhorse, Squire, and Gumtree! Your coastal paradise is just a click away.

Newest Wildhorse/Squire/Gumtree Homes for Sale

$505,000

3 Beds ⋅ 2 Baths ⋅ 1,597 SqFt. ⋅ HILTONHEAD-512647 MLS

This home is nestled in a charming, quiet community, this inviting single-level home offers the perfect blend of comfort and convenience. Designed for easy main-floor living, it's an ideal fit for first-time buyers, growing families, or empty nesters seeking low-maintenance lifestyle. Best of all, you're just minutes from top-rated schools, NEW Town Park, local dining, everyday shopping, and healthcare facilities. Private backyard for the Landscape and Gardening enthusiasts! New HVAC and Luxury Vinyl Plank flooring, roof approximately 10 years old, all exterior siding is Hardie Plank.

1 Chinaberry Circle, Hilton Head Island

Listing courtesy of Hilton Head Area Properties, LLC.

$1,299,000

4 Beds ⋅ 3 Baths ⋅ 2,298 SqFt. ⋅ HILTONHEAD-512456 MLS

No HOA! Rare find! .74 acres with marsh frontage. Enough land to subdivide into 2 lots, possibly 3. One existing home with 4 bedrooms and 3 bathrooms. This beautiful home has vaulted ceilings with wood and tile flooring throughout. A huge shaded Southern porch lends itself to an inviting and relaxing atmosphere while the rear sundeck off the kitchen offers additional outside space. Lush landscape and flower beds, including loquat and fruit trees add to the Lowcountry feel. The home has a large custom patio with a surrounding tiled seating area and fire pit. The attached 2nd story apartment has its own entrance, vaulted ceilings and 2 oversized light filled rooms with a separate kitchen. The lower level has 3 studio apartments, each with its own private entrance, full bath, individual heat and air units. This entire attached former garage and upstairs apartment can be reconfigured to a full size home, mother-in-law suite, ADU, or another garage with endless possibilities. This spacious .74 acreage has unlimited potential and is zoned for a 2nd residence, possibly 3. The sprawling driveway and yard offers room to store your, boat, toys, equipment, RV and more. Tucked away off the main road and five minutes to a boat launch and bridge to the mainland, creating a private compound. Walking distance to restaurants, bars, multiple town parks, schools, and the Island Recreation Center offering swimming, basketball, gym and much more. Current long-term rental income is $90K+ per year. Owner financing with 10% down, and/or open to trades. Owner is SCREA

23 Reggies Road, Hilton Head Island

Listing courtesy of Hilton Head Properties.

$425,000

3 Beds ⋅ 2 Baths ⋅ 1,170 SqFt. ⋅ HILTONHEAD-512389 MLS

This North End home is located in the NON-HOA section of the Chinaberry Ridge Community. Sitting on a spacious lot, this one-level, 3-bedroom, 2-bathroom home has tall ceilings in living area with sliding doors that lead out to the large/ partially fenced backyard. Inside, there is good storage and many closets. The kitchen has a new refrigerator, new dishwasher, newer washer and dryer, the roof is 2019, water heater is 2019, HVAC heatpump is 2017. The things that you always ask about in the age of a home are already taken care of for peace of mind for the next owner. You don't want to miss this great home and lot on Hilton Head Island.

47 Chinaberry Drive, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$1,195,000

5 Beds ⋅ 3 Baths ⋅ 3,420 SqFt. ⋅ HILTONHEAD-511733 MLS

Experience Lowcountry living at its finest in this beautifully updated home within one of Hilton Head Island's most private gated waterfront communities. Perfectly positioned to capture peaceful Intracoastal Waterway and pond views, this home offers exceptional privacy with no homes behind and only one neighboring home visible from the expansive porches and rooftop deck. Designed for both everyday living and entertaining, recent improvements include new pine flooring in the kitchen and living rooms, refinished hardwood floors, luxury carpet, fresh interior paint, HVAC, water heater, resurfaced rooftop deck, updated landscaping, new stucco, French drains, and an oversized two-car garage with workshop space, plus two large storage rooms. A three-stop elevator provides effortless access to every level, while the upstairs bonus room offers flexibility as a fifth bedroom, office, or media room. Enjoy coffee overlooking the water as coastal breezes, abundant wildlife, wading birds, and even the occasional bald eagle create an unforgettable setting. Spend evenings watching boats cruise the Intracoastal or take the short stroll down tropical walking trail to the community's newly renovated private dock, where dolphins are frequent visitors, fishing is just steps away, and spectacular sunsets never disappoint. Marina slips are available for only $125 per month, along with a convenient day dock. Residents enjoy low HOA fees of just $1,800 annually, a community pool within near distance, scenic waterfront trails, and quick access to some of Hilton Head's favorite waterfront restaurants including Benny's Coastal Kitchen, Hudson's Seafood House on the Docks, Dockside, and Skull Creek Boathouse. With multiple routes to Beach, the bridge, and Bluffton, this home offers the perfect blend of luxury waterfront tranquility, convenience, and island living.

42 Bermuda Pointe Circle, Hilton Head Island

Listing courtesy of Realty One Group - Lowcountry.

$629,000

5 Beds ⋅ 3 Baths ⋅ 2,363 SqFt. ⋅ HILTONHEAD-511641 MLS

Need 5 bedrooms? Take another look! This light and bright Hilton Head Island home offers 4 bedrooms plus wonderfully flexible space that can easily evolve with you-think optional 5th bedroom, home office, TV den, or even two separate work-from-home spaces. There's also room to add a shower to the downstairs bath, creating even more possibilities. With NO HOA fees, this is an exciting option for a primary residence, second home, or investor exploring long- or short-term rental potential. Inside, you'll find an easy-flowing floor plan with a welcoming foyer, dining room, spacious great room, eat-in kitchen, LVP flooring, abundant storage, and attached 2-car garage. Outside, the private wooded backyard brings the vacation vibes with a large deck, Tiki hut, and fire pit. All of this in a convenient north-end location close to schools, the Rec Center, bike paths, Main Street, Skull Creek, Islanders Beach, shopping, Bluffton, and Cross Island access. HVAC 2022. A home with space to live, work, play-and plenty of possibilities for what's next.

20 Hanahan Lane, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$484,000

3 Beds ⋅ 2 Baths ⋅ 1,524 SqFt. ⋅ HILTONHEAD-511701 MLS

Welcome to Northends sought after Community Chinabury Ridge, a charming, move-in ready home nestled in the 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.

$575,000

3 Beds ⋅ 2 Baths ⋅ 1,829 SqFt. ⋅ HILTONHEAD-509111 MLS

Tucked away on a quiet cul-de-sac within the charming Squiresgate community on Hilton Head Island, this beautifully renovated 3-bedroom, 2-bathroom coastal bungalow offers the perfect blend of comfort, style, and convenience. Set on a generous .34-acre corner lot, the home welcomes you with a bright, open living space filled with natural light, flowing effortlessly into a warm and inviting family room overlooking a private, fenced backyard framed by lush, mature tropical landscaping. Thoughtfully updated throughout, recent improvements include a fully renovated kitchen and bathrooms, new flooring, interior paint, custom built-ins, doors, lighting, and fixtures-creating a fresh, modern feel with a relaxed boho-inspired aesthetic.Designed for both everyday living and entertaining, the main living areas transition seamlessly to an expansive patio, offering an ideal outdoor retreat with ample space for dining, lounging, or future enhancements such as a screened porch, outdoor kitchen and pool. Additional highlights include a 2-car garage, expanded parking pad with room for a boat or small trailer, and extra storage for recreational vehicles. Located in a golf cart-friendly neighborhood with low POA fees and minimal restrictions, Squiresgate is one of the island's hidden gems-just moments from waterfront dining along Skull Creek, local restaurants, public schools, and easy access on and off the island. Residents also have the option to join the nearby Country Club of Hilton Head, offering premier golf, tennis, pool, fitness, and spa amenities. This inviting home delivers a rare opportunity to enjoy relaxed coastal living in a peaceful, well-connected setting.

20 Kings Court, Hilton Head Island

Listing courtesy of Schembra Real Estate Group.

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