Wildhorse/Squire/Gumtree Homes under $500,000

Welcome to the enchanting Wildhorse, Squire, and Gumtree neighborhoods of Hilton Head Island, South Carolina—where coastal charm meets suburban tranquility. Nestled within the picturesque Beaufort County, this inviting area is perfect for families, retirees, and anyone seeking a serene lifestyle in one of the Lowcountry’s most sought-after locations.

Wildhorse, Squire, and Gumtree are known for their beautiful homes and lush landscapes, offering a variety of architectural styles that cater to diverse tastes. Here, you can find an impressive selection of homes priced under $500,000, making it an ideal choice for first-time buyers, those looking to downsize, or anyone wanting to invest in a slice of paradise without breaking the bank.

Residents enjoy easy access to the island's stunning beaches, world-class golf courses, and an array of outdoor activities, from biking along scenic trails to kayaking in tranquil waters. The community is also conveniently located near shopping centers, fine dining, and vibrant local markets, ensuring that everything you need is just a stone's throw away.

Wildhorse, Squire, and Gumtree are not just neighborhoods; they are a lifestyle. With a warm sense of community and an abundance of recreational opportunities, it’s no wonder that many are drawn to this charming area. Whether you’re looking to build your dream home or find a cozy retreat, the homes in this region offer an exceptional value for those seeking the Hilton Head Island experience. Come explore the possibilities today!

Newest Wildhorse/Squire/Gumtree Homes under $500,000

$450,000

4 Beds ⋅ 3 Baths ⋅ 2,000 SqFt. ⋅ HILTONHEAD-512587 MLS

If you've been searching for a Hilton Head Island property that gives you more than just a place to call home, this is the one to put at the top of your list. Set on a generous over half-acre in the desirable Squire Pope area, this spacious 4-bed, 2.5-bath home delivers something that's increasingly hard to find on HHI: space, flexibility, privacy, and possibilities. Whether you're an entrepreneur looking for room to run your business, a contractor or tradesperson needing garage and storage space, a creative who wants a workshop, or simply someone who refuses to be boxed in by an HOA, this property gives you the freedom to think bigger. The detached garage and multiple sheds provide an abundance of storage and workspace options - perfect for equipment, tools, hobbies, projects, or that business venture you've been dreaming about. And with no HOA, you have the flexibility to personalize and utilize your property in a way that fits your lifestyle. The over a half-acre lot gives you breathing room that's becoming increasingly rare on Hilton Head Island. And then there's the location. Tucked away in the sought-after Squire Pope area, you'll enjoy a peaceful, private setting while still being just minutes from the best of Hilton Head - pristine beaches, restaurants, shopping, boating, entertainment, and all the coastal lifestyle that makes the island so special. This isn't just a home - it's a property with potential. Bring your business, your projects, your toys, your ideas, and your vision. If you're looking for a little more elbow room and a lot more freedom on Hilton Head Island, you've just found it.

58 Cobia Court, Hilton Head Island

Listing courtesy of Coastal Luxury Real Estate.

5 Gumtree Road Unit M-20, Hilton Head Island

$375,000

2 Beds ⋅ 2 Baths ⋅ 1,080 SqFt. ⋅ HILTONHEAD-512488 MLS

Welcomе to 5 Gum Treе Rοad, Unіt Μ20, а deѕіrable 2-bedroom, 2-bаth end‐unit villa in Marshside on Hilton Head Island. Enjoy peaceful lagoon views and the added privacy and natural light that come with an end-unit location. The well-designed layout offers comfortable living spaces, two generously sized bedrooms, and a relaxing Lowcountry setting that makes this villa ideal as a primary residence, second home, or island retreat. Marshside Villas offers a convenient Hilton Head location with easy access to the island's beaches, dining, shopping, golf, and miles of leisure trails. Whether you're enjoying your morning coffee overlooking the lagoon, heading out for a day at the beach, or exploring everything Hilton Head has to offer, M20 provides an opportunity to enjoy the island lifestyle in a quiet, established community. End unit, lagoon views, two bedrooms, two full baths, and a Hilton Head Island address-come see what makes this villa special.

5 Gumtree Road Unit M-20, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

5 Gumtree Road Unit F-20, Hilton Head Island

$369,900

2 Beds ⋅ 2 Baths ⋅ 1,080 SqFt. ⋅ HILTONHEAD-512645 MLS

One of thе niceѕt Μarѕh Ѕіde vіllаs you'll find! This bеautіfully remodeled 2 bedroom, 2 full bath end-unit villa offers a tranquil lagoon view and exceptional attention to detail throughout. The villa has been thoughtfully updated with a brand-new kitchen featuring stone countertops, new cabinetry, and stainless-steel appliances. Additional improvements include luxury vinyl plank flooring, new windows, completely remodeled bathrooms with tiled showers/baths and new vanities, a newly tiled fireplace, recessed lighting, and new ceiling fans. Beyond the cosmetic updates, this villa has also undergone important structural improvements, including a newly supported subfloor and foundation-adding peace of mind to an already exceptional property. As an end unit, the villa benefits from additional windows and a cathedral ceiling that bring in abundant natural light. Other features include a storage shed and a private back deck overlooking the peaceful lagoon setting. Best of all, this villa is conveniently located just a short distance from the community pool and fitness center. One-level villas with this caliber of remodeling, desirable end-unit location, and tranquil lagoon view rarely come available. This is a special opportunity you won't want to miss!

5 Gumtree Road Unit F-20, Hilton Head Island

Listing courtesy of Charter One Realty.

$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.

$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.

5 Gumtree Road Unit D3, Hilton Head Island

$379,900

2 Beds ⋅ 3 Baths ⋅ 1,120 SqFt. ⋅ HILTONHEAD-511966 MLS

Completely renovated 2bd/2.5 bath townhome on slab foundation with wood burning fireplace. This condo has been completely remodeled to include LVP flooring, PEX plumbing and water heater moved to storage closet on front porch, new kitchen with quartz countertops, new carpet, new bathrooms and much more! This condo is located near the community pool, tennis courts, gym and playground - and getting off the island is a breeze as it is close to the HHI bridge.

5 Gumtree Road Unit D3, Hilton Head Island

Listing courtesy of Coastal Realty Group.

$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.

5 Gumtree Road Unit H-17, Hilton Head Island

$215,000

1 Beds ⋅ 1 Baths ⋅ 600 SqFt. ⋅ HILTONHEAD-511617 MLS

Essеntially nеw fοllowіng а mаjοr ѕtuds-out renovatiοn, thiѕ 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.

5 Gumtree Road Unit L-20, Hilton Head Island

$379,000

2 Beds ⋅ 2 Baths ⋅ 1,080 SqFt. ⋅ HILTONHEAD-509080 MLS

#L-20 offers a rare opportunity to own a marsh-view villa tucked in a remarkably private corner of Marsh Side. Positioned to capture marsh views and Lowcountry sunsets, this 2-bedroom, 2-bath villa fills with natural light and offers open-concept living. Both bedrooms are en-suite, providing comfort and separation for owners and guests, alike. The primary bath adds smart everyday functionality with built-in outlets, dedicated hot-tool storage, and custom drawer organization. Improvements add significant substance and style, including a brand-new wood-burning fireplace and chimney, new stainless-steel appliances, custom countertops, and a new sliding glass door opening toward the marsh. Subfloors have been replaced throughout the majority of the villa, while hardwood flooring, shiplap accents, smooth ceilings, designer finishes, and fresh interior paint create a polished, cohesive feel. Located just off the Cross Island Parkway, Marsh Side offers convenient access to Hilton Head's south end, Bluffton, and Highway 278. Residents are within minutes of the Island Rec Center, local schools, parks, boating docks, waterfront restaurants, coffee shops, healthcare, and retail shopping. Combining community amenities, privacy, convenience, and intentional design, this villa offers an exceptionally easy, elevated Hilton Head Island lifestyle.

5 Gumtree Road Unit L-20, Hilton Head Island

Listing courtesy of ELEVE PROPERTIES Brokered by EXP Realty.

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