Wildhorse/Squire/Gumtree Homes with Pool Amenities

Welcome to the enchanting neighborhood of Wildhorse/Squire/Gumtree, nestled in the heart of Hilton Head Island, South Carolina. This picturesque area, located in Beaufort County, is known for its lush landscapes, serene surroundings, and a vibrant community atmosphere that perfectly embodies the charm of coastal living.

Wildhorse/Squire/Gumtree is characterized by its beautiful homes that blend seamlessly with the natural beauty of the island. Many properties in this desirable region feature stunning pool amenities, providing the perfect oasis for relaxation and entertainment. Imagine basking in the warm South Carolina sun by your private pool, hosting summer barbecues, or enjoying peaceful evenings under the stars with family and friends. Whether you’re an avid swimmer or simply love lounging poolside with a good book, these homes cater to your every desire.

The community is also conveniently located near some of Hilton Head Island's finest attractions. With easy access to pristine beaches, world-class golf courses, and a variety of dining and shopping options, residents of Wildhorse/Squire/Gumtree enjoy the best of island living. This area is perfect for families, retirees, and anyone looking to embrace a laid-back lifestyle while still being close to all the action.

If you’re seeking a home that combines luxury, comfort, and a touch of Southern charm, look no further than Wildhorse/Squire/Gumtree. Experience the joy of living in a community that feels like a vacation destination all year round, complete with your very own pool to enjoy!

Newest Wildhorse/Squire/Gumtree Homes with Pool Amenities

$375,000

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

Welcome to 5 Gum Tree Road, Unit M20, a desirable 2-bedroom, 2-bath 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.

$369,900

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

One of the nicest Marsh Side villas you'll find! This beautifully 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.

$499,990

4 Beds ⋅ 4 Baths ⋅ 1,936 SqFt. ⋅ HILTONHEAD-512638 MLS

Pristine, polished, and ready to go! This beautifully maintained 4-bedroom, 3.5-bath townhome in gated Allenwood is an absolute standout. Built in 2019. The main level features a gorgeous white kitchen with granite countertops (all appliances conveying), an inviting living room, half bath, and a large screened-in porch overlooking a lagoon with fountain ~ the perfect spot to start your day or wind down. Upstairs, the primary suite with high ceilings features a walk-in closet, dual sink extra-long vanity, and a view out to the lagoon. You'll also find two additional bedrooms, a full bath, and laundry on the top floor. The fourth bedroom and its full bath are located at the rear of the garage and offer a wonderful bonus: another screened-in porch ~ creating an ideal guest suite, office, or whatever you decide ~ the world is your oyster. 98% hard-surface flooring - carpeting only in the 4th bedroom. A one-car garage plus an extra-long two-car driveway provides plenty of parking. Allenwood has a great community pool, sidewalks, and is convenient to the public schools and fabulous waterfront restaurants. Available immediately and exceptionally pristine - this one is truly move-in ready and better than new!

207 Ceasar Place, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$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.

$199,000

1 Beds ⋅ 2 Baths ⋅ 813 SqFt. ⋅ HILTONHEAD-512397 MLS

THE LEAST EXPENSIVE CONDO ON HILTON HEAD AND IN ONE OF THE MOST DESIRABLE COMMUNITIES ON THE NORTH END OF HILTON HEAD ISLAND. WHEN YOU PURCHASE A MARSH SIDE CONDO YOUR GETTING MUCH MORE THAN A PLACE TO LIVE. MARSH SIDE HAS MORE COMMUNITY AMENITIES THAN ANY COMMUNITY ON THE ENTIRE ISLAND INCLUDING SALTWATER POOL, TENNIS COURTS, PLAYGROUND, PICNIC AREA AND 24 HOUR FITNESS CENTER AND LAUNDRY FACILITY. CLOSE TO SCHOOLS AND MAIN STREET SHOPPING AND DINING. FOUR GREAT WATERFRONT RESTAURANTS WITH THE BEST SUNSET VIEWS RIGHT DOWN GUM TREE ROAD.THIS POPULAR 1BR 1 AND 1/2 BATH LOFT VILLA OFFERS AN INVITING LIVING SPACE FEATURING A COZY FIREPLACE IN THE LIVINGROOM OPEN TO THE KITCHEN AND CONVENIENT HALF BATH ON THE FIRST FLOOR . PERFECT PERMANENT RESIDENCE, SECOND HOME OR RENTAL INVESTMENT PROPERTY. NEW AC 3YR OLD, WATER HEATER 2YR OLD, AND LARGE STACKABLE WASHER AND DRYER ONE YEAR OLD. LARGE OUTSIDE STORAGE ROOM AT FRONT DOOR FOR BI843KES OR BEACH CHAIRS. LARGE WALK IN CLOSET OFF THE MASTER BEDROOM ON THE SECONDFLOOR WITH FULL BATH. EXTERIOR PAINTED JULY 2026. LOW POA FEES, ON-SITE PROPERTY MANAGERS AND OVERNIGHT PATROLS. YOU CAN ENJOY THE ISLAND BENEFITS WITHOUT THE WORRY OF OUTSIDE MAINTENCE. CLOSE TO THE ISLAND RECCREATION CENTER, PARKS, PUBLIC BOAT LANDINGS, SAILING & ROWING CENTER, CROSS ISLAND PARKWAY, THE LIBRARY, MEDICAL OFFICES, THE HOSPITAL, BANKS, GROCERY STORES AND THE HILTON HEAD ISLAND AIRPORT AND MILES OF WALKING AND BIKE TRAILS. THIS ONE WON'T LAST. CONDO SOLD AS IS INSPECTONS WELCOME SELLER TO MAKE NO REPAIRS.

5 Gumtree Road Unit E-10, Hilton Head Island

Listing courtesy of Premier Properties of 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.

$1,295,000

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.

$234,900

1 Beds ⋅ 1 Baths ⋅ 600 SqFt. ⋅ 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.

$384,900

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.

$555,000

4 Beds ⋅ 4 Baths ⋅ 2,042 SqFt. ⋅ HILTONHEAD-506353 MLS

Welcome to 285 Ceasar Place, a beautifully maintained 4-bedroom, 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 2,032 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.

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