St Helena Island Homes with Trail(s) Association amenities

St Helena Island Homes with Trail(s) Association amenities

Our website features the best real estate search for homes, condos, land and foreclosure properties available in St_Helena_Island and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Newest St Helena Island Homes with Trail(s) Association amenities

$959,000
3 Beds 3 Baths 2,728 SqFt. HILTONHEAD-512447 MLS
Beautifully updated and ideally situated on Longfield Lake in the private community of Dataw Island, this 3-bedroom, 2.5-bath home offers exceptional Lowcountry living with a thoughtful, easy-flowing floor plan. Built by Jim May of Mayfair Homes, one of Dataw Island's premier builders, the residence features beautiful pine wood floors, a first-floor primary suite, and a dedicated study-perfect for a home office, den, or quiet retreat.The first-floor primary suite provides both convenience and privacy. The updated primary bath features an oversized walk-in shower, Kohler plumbing fixtures, marble-topped dual vanities, a large soaking tub, Visual Comfort lighting, a private water closet, and an extra-large linen closet. The spacious primary bedroom closet includes a custom organization system.The updated kitchen is both stylish and functional, featuring a Thermador gas cooktop, KitchenAid dishwasher, microwave and oven, granite countertops, and Visual Comfort lighting.Upstairs, two additional bedrooms, an updated bath, and a loft area provide comfortable accommodations for family and guests. A large, climate-controlled storage room offers exceptional additional space for seasonal items, hobbies, or personal belongings.The detached two-car garage includes an additional bay for a golf cart, providing ample room for vehicles, golf equipment, and additional storage. Outdoor features include a tabby driveway, inviting front porch, screened porch, and spacious rear patio.Recent improvements include a new roof and two new HVAC systems, both installed in 2025. Additional features include a tankless water heater, custom cabinetry, and beautifully landscaped grounds.Properly maintained and thoughtfully updated, this exceptional home combines classic Lowcountry character with modern amenities, all in a serene setting overlooking Longfield Lake on Dataw Island.

160 Dataw Drive, St Helena Island

Listing courtesy of Charter One Realty.

$350,000
HILTONHEAD-511905 MLS
Rare opportunity to own one of the few remaining waterfront homesites in the private, gated community of Bermuda Bluff Island. Lot 72 offers an impressive .72 acres of pristine Lowcountry landscape, perfectly positioned along the salt marshes and deep waters of the Beaufort River. Framed by gorgeous, mature Live Oaks and native palm trees, this exceptional property serves as the ultimate canvas for a custom luxury home. Wake up to awesome, panoramic water views and enjoy front-row seating to the changing tides, coastal wildlife, and golden sunsets that define South Carolina's sea islands. Bermuda Bluff successfully blends remote, natural tranquility with modern convenience and upscale neighborhood amenities. Property owners enjoy direct water access via the community's private tidal creekRare opportunity to own one of the few remaining waterfront homesites in the private, gated community of Bermuda Bluff Island. Lot 72 offers an impressive .72 acres of pristine Lowcountry landscape, perfectly positioned along the salt marshes and deep waters of the Beaufort River. Framed by gorgeous, mature Live Oaks and native palm trees, this exceptional property serves as the ultimate canvas for a custom luxury home. Wake up to awesome, panoramic water views and enjoy front-row seating to the changing tides, coastal wildlife, and golden sunsets that define South Carolina's sea islands. Bermuda Bluff successfully blends remote, natural tranquility with modern convenience and upscale neighborhood amenities. Property owners enjoy direct water access via the community's private tidal creek boat launch, a fabulous deep-water dock with a day docking float, a clubhouse, tennis courts, and a refreshing community swimming pool. While the setting feels like a private island retreat, you are only a short 15 minute drive from convenient shopping/grocery centers and just 20 minutes from the historic charm, shopping, and dining of downtown Beaufort. Bring your custom builder and design a coastal masterpiece tailored to take full advantage of this unparalleled and increasingly rare riverfront location.--

72 Front Street, St Helena Island

Listing courtesy of Point South Realty.

$1,475,000
3 Beds 3 Baths 2,700 SqFt. HILTONHEAD-510785 MLS
Situated on a scenic tidal creek with deep water access within Dataw Island, this exceptional waterfront home offers a private dock, boat lift, and breathtaking views of Jenkins Creek, capturing the very best of Lowcountry living. Whether your ideal day includes boating, kayaking, paddleboarding, crabbing from your dock, or simply enjoying the peaceful waterfront setting, this property offers an unmatched connection to the water. Designed to maximize the views, the home captures picturesque vistas from the living room, dining area, and chef's kitchen. The open floor plan features spacious gathering areas, a chef's kitchen, and two wood-burning fireplaces, creating a warm and inviting atmosphere for everyday living and effortless entertaining.Outdoor living is equally exceptional, with welcoming front and rear porches, a screened porch overlooking Jenkins Creek, and an expansive deck perfectly positioned to enjoy the surrounding natural beauty. The primary suite is a private retreat featuring a spa-inspired bath, custom built-ins, and a custom walk-in closet. Two guest bedrooms share a Jack-and-Jill bath, while the finished room above the garage offers flexible space for a home office, bonus room, or additional guest accommodations. Residents of Dataw Island enjoy access to two championship golf courses, a full-service marina, tennis and pickleball courts, swimming pools, a fitness center, dining, and an active club lifestyle. Whether you're heading out for a day on the water, exploring the surrounding creeks by boat, or unwinding on the porch after sunset, this home offers an authentic waterfront lifestyle in one of the Lowcountry's most sought-after private communities.

153 Dataw Drive, St Helena Island

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

Start Your Search
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.