Hilton Head Island Homes with Trail(s) Association Amenities

Welcome to Hilton Head Island, South Carolina, a stunning coastal paradise nestled in Beaufort County. Renowned for its breathtaking beaches, lush landscapes, and vibrant community, Hilton Head Island is the perfect blend of relaxation and adventure. With its temperate climate and year-round sunshine, this island offers an idyllic setting for those seeking a serene lifestyle or an active outdoor experience.

One of the standout features of Hilton Head Island is its commitment to preserving natural beauty while providing a wealth of amenities for residents. The Homes with Trail(s) Association embodies this spirit, offering residents exclusive access to scenic trails that wind through the island's picturesque landscapes. Imagine stepping out of your front door and onto a network of well-maintained paths that meander through lush greenery, tranquil marshes, and along the stunning coastline. Whether you enjoy walking, jogging, or biking, these trails provide the perfect opportunity to explore the island's natural wonders.

The Homes with Trail(s) Association also fosters a strong sense of community, with organized events and activities that encourage neighbors to connect and enjoy the outdoors together. From guided nature walks to community picnics, residents can immerse themselves in the vibrant lifestyle that Hilton Head Island has to offer.

In addition to the trails, residents benefit from the island's world-class amenities, including golf courses, tennis clubs, and gourmet dining options. With a variety of shopping and cultural experiences nearby, Hilton Head Island truly has something for everyone. Come discover your dream home in this enchanting coastal haven, where adventure and tranquility await!

Newest Hilton Head Island Homes with Trail(s) Association Amenities

$417,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512313 MLS

Welcome to Admirals Row, a Hilton Head Island villa offering ocean views and resort-style living. This beautifully updated 2BD/2BA unit features NEW smooth ceilings throughout, sunrise views from the private balcony, and easy beach access. Enjoy a modern kitchen with granite countertops and stainless steel appliances. Sold FULLY FURNISHED and move-in ready! BEST PRICED UPDATED 2-BEDROOM in all of Beach & Tennis. Amenities include pools, restaurants, beach bar, bike rentals, tennis, and 12 brand-new pickleball courts. Great rental income potential!

40 Folly Field Road Unit 340, Hilton Head Island

Listing courtesy of Peirce Group Brokered by EXP Realty LLC.

$985,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512084 MLS

Welcome home to this beautifully maintained 3-bedroom, 3-bath residence offering exceptional curb appeal and a warm, welcoming atmosphere in the desirable Headlands section of Hilton Head Plantation. Perfectly positioned to enjoy picturesque golf views of the 18th hole of Bear Creek Golf Club, this move-in ready home has been lovingly cared for by its current owner. Inside, you'll find luxury vinyl plank flooring throughout most of the home, creating a seamless and stylish living space. The inviting living room features a cozy gas fireplace, while the kitchen is equipped with stainless steel appliances. The enclosed porch has been thoughtfully converted into an additional living space, providing even more room to relax, entertain, or simply enjoy the beautiful golf course views year-round. A brand-new HVAC system adds peace of mind, making this home as practical as it is inviting. Combining comfort, quality, and an outstanding location, this home is truly move-in ready and offers the perfect opportunity to enjoy the Hilton Head Plantation lifestyle. Virtually staged photos are meant to provide spatial information and decor inspiration. No structural modifications have been made.

5 Oyster Rake Court, Hilton Head Island

Listing courtesy of Collins Group Realty.

$1,095,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512031 MLS

Open ocean views, proven rentals, and Leamington prestige! 410 Barrington Court is a 2-bedroom / 2-bathroom villa with proven rental performance and projected annual gross rental revenue over $84K, offering a strong blend of income opportunity and second-home enjoyment within Palmetto Dunes Oceanfront Resort. Tucked in one of the most peaceful sections on Ocean Lane, the villa opens to an expansive private balcony designed for dining, lounging, and enjoying oceanfront views, with ocean views carried into both bedrooms. Consistently well maintained by the original owner, the villa features an ideal floor plan with spacious living and dining areas, bedrooms positioned on opposite sides for privacy, and a generous master suite with balcony access and a beautifully renovated walk-in shower. Recent improvements include all new LVP flooring, renovated bathrooms, fresh paint throughout including doors/trim/baseboards, HVAC (2020), dishwasher (2026), and new bedding (not pictured). Barrington Court offers an oceanfront pool and hot tub, pool pavilion with restrooms, grilling area, outdoor showers, covered parking, and designated owner storage locker in the garage for beach gear, golf clubs, and more-all set among beautiful lagoons, lush landscaping, and scenic walkways. Enjoy access to Palmetto Dunes' three miles of beach, tennis/pickleball, three golf courses, 11-mile lagoon system, trails, and dining, plus easy access across William Hilton Parkway to Shelter Cove Harbour & Marina for waterfront dining, shopping, watersports, seasonal activities and live entertainment.

77 Ocean Lane Unit 410, Hilton Head Island

Listing courtesy of Greenplate Group Brokered by eXp Realty.

$435,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512305 MLS

Welcome to a rare opportunity in South Forest Beach: a completely updated, open concept layout, turn-key 2-bedroom, 2-bath villa in the sought-after Dunes Villas community, just a short walk from Hilton Head Island's world-renowned beaches. This beautifully renovated upper-level end unit offers the ideal combination of coastal living, privacy, convenience, and investment potential. Thoughtfully updated throughout and sold fully furnished, the villa is ready to enjoy as a personal beach retreat, second home, or income-producing short-term rental. Dunes Villas offers a community pool and on-site parking, while its prime location places you within minutes of the beach, Coligny Plaza, restaurants, shopping, entertainment, and Hilton Head's extensive network of bike paths. With its turnkey condition, desirable 2-bedroom, 2-bathroom layout, pet-friendly appeal, and exceptional location in the heart of the island, this is a very rare opportunity to own a truly special Hilton Head property!

6 Woodward Avenue Unit I2, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$879,000

3 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512297 MLS

Welcome to effortless Lowcountry living in the desirable Club Course neighborhood of world-famous Sea Pines Resort. This beautifully maintained 3-bedroom, 2-bath Hilton Head Island home is light, bright, and move-in ready, offering the perfect combination of comfort, location, and island lifestyle. Thoughtful updates include new LVP flooring, fresh paint, updated primary bathroom, Trex decking, and a 2025 Trane HVAC system. The spacious back deck is ideal for outdoor dining, entertaining, or relaxing, while the large backyard offers space for a pool and for creating a private oasis. Located near the main gate of Sea Pines, this home provides quick and convenient access to everything Hilton Head Island has to offer while still enjoying the privacy and amenities of one of the island's most iconic communities. Sea Pines is home to three renowned public golf courses, miles of pristine beaches, numerous restaurants, Harbour Town, private owner and guest beach access at Tower Beach, and the exciting redevelopment of South Beach. From biking beneath moss-draped live oaks to golf, boating, dining, and days spent on the beach, the Sea Pines lifestyle is truly hard to beat. Hilton Head Island has also been recognized as the #1 Island in the U.S. for nine consecutive years, further reinforcing why so many people choose to call this special place home. Whether you're searching for a primary residence in Sea Pines, a Hilton Head Island second home, or a short-term rental investment / coastal getaway, this turnkey property is ready for its next owner. Move in, unpack, and start enjoying the Hilton Head Island lifestyle from day one. Schedule your in-person or live video walkthrough today.

157 Otter Road, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$760,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512291 MLS

Turnkey single-level 3-bedroom, 3-bath home blending Lowcountry charm and refined design on over 1/3 acre with peaceful views of Hilton Head Plantation's venerable Dolphin Head Golf Course. Reimagined from the studs in 2019, the light-filled layout with exposed wood beams, tray ceilings, tongue-and-groove accents, custom trim and premium fixtures throughout. The bright eat-in kitchen features Fantasy Brown dolomitic marble, Walker Zanger tile, soft-close cabinetry, high-end Bosch and GE Profile appliances including induction cooktop. Both the primary suite and sunken living room open to the tabby shell back patio with hot tub and grilling area. Inside, the woodburning fireplace and vaulted living room ceiling add warmth and character. Major systems replaced in 2019 include: new roof, energy-efficient windows, HVAC, ductwork, water heater, plumbing, wiring, new LVP, tile flooring and a refreshed garage with epoxy floors, craftsman-inspired lighting and carriage-style door. A short walk or ride to the clubhouse, Dolphin Cafe and Hilton Head Plantation's resort amenities. A beautifully upgraded retreat ready to welcome you home.

27 Pineland Road, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$1,049,000

4 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512033 MLS

Welcome to Your Beachside Retreat in Folly Field! Located just minutes from Folly Field beach, this beautifully updated 4-bedroom, 2.5-bath, 2339 square foot home offers the perfect blend of coastal charm and modern comfort. Step inside to find an updated kitchen featuring quartz countertops, stainless steel appliances, and ample storage. The open kitchen to dining area overlooks the landscaped fenced backyard. The living area is ideal for entertaining, complete with LVP floors. The spacious fourth bedroom or den on the first level provides great flexibility, perfect as a guest suite, home office, or playroom. The main suite is on the first floor and has a newly renovated ensuite bath and hardwood flooring. Enjoy the privacy of your fenced backyard oasis, ideal for relaxing afternoons or hosting summer BBQs with family and friends. Nestled in a quiet and sought-after neighborhood in the Folly Field area, you'll love being close to the beach, top tier shopping, dining, and everything Hilton Head has to offer. Don't miss this incredible opportunity to own a move-in ready home in one of the islands most desirable communities! Rental income projected at $75,000 gross income without a pool and $95,000 with a pool installed.

10 Camellia Street, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$199,000

HILTONHEAD-512270 MLS

Solitude on this remote street, yet a short path to amenities makes this the perfect blend of privacy and convenience on this meticulously maintained, oversized lot. Featuring immaculate stamped concrete pad and extensive landscaping, this site easily accommodates a 45-foot motorcoach. Priced unfurnished. Just steps from the pool, racquet sports, clubhouse, playground and laundry facilities. Beyond the front gates, enjoy convenient access to shopping, dining, the beach, bike paths and the town trolley. Experience the #1 Motorcoach Resort on the #1 island destination in America - an exceptional blend of lifestyle and investment.

133 Arrow Road Unit 81, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$5,500,000

5 Beds ⋅ 7 Baths ⋅ HILTONHEAD-511760 MLS

BREATHTAKING Mediterranean Estate Home overlooking the 16th Fairway of the Robert Trent Jones Ocean Golf Course in Palmetto Dunes just a Short Walk to the Beach. 7,051 Square Feet with Outstanding Craftsmanship showcases Chef's Kitchen with Spacious Island & Butler's Pantry and Small Laundry Room, 5 Bedroom Suites, Custom Wood Paneled Parlor with Full Bar and Travertine Floored Foyer to a Two-Story Entry with a Grand Marble Staircase. Spacious Second Floor Laundry Room. BEAUTIFUL Raised Invisible Edge Pool and Spa. 5 Covered Porches, Fireplace and Built-In Grill. 6-Car Drive Through Garage, Elevator, Terra Cotta Tile Roof, Paver Driveway and Mature Landscaping. Perfect Home for Relaxing and Entertaining Family, Friends, or Business Outings. Truly EXCEPTIONAL in every way. Come Enjoy the Best of Life at 11 Sea Lane on Hilton Head Island!

11 Sea Lane, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$875,000

2 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512261 MLS

Beautifully RENOVATED and fully FURNISHED, this END UNIT villa at 27 Water Oak is ideally situated directly on the first fairway of the Robert Trent Jones Golf Course in the heart of Palmetto Dunes. Gorgeous NEW flooring throughout, HIGH END furnishings give the villa an elevated coastal feel that is fresh, sophisticated and inviting. The unique floor plan offers no steps to the front door, a first-floor primary suite, a powder room, and two spacious bedrooms, each with a private ensuite bath and deck. A generous LOFT provides flexible space for additional sleeping, a home office or extra living space. Enjoy expansive fairway VIEWS and sensational SUNSETS from the WRAPAROUND deck. The community pool is just across the street and the BEACH is a short walk away. Palmetto Dunes offers three championship golf courses, an 11-mile lagoon, world class tennis and pickleball, restaurants, a general store and the complimentary Dunes Buggy. Whether a place to call home, a weekend retreat or an investment opportunity, this exceptional villa is ready to be enjoyed from day one.

21 Haul Away Unit 27, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,150,000

4 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511846 MLS

Rare Dolphin Head opportunity in Hilton Head Plantation. This 4BR/3BTH, 3357 SF home on a 0.42-acre homesite w/stunning lagoon views stretching to the 18th fairway of the Dolphin Head Golf Club-wide unobstructed views, gorgeous sunsets over the water, 50 year roof installed in 2014 and bright light/windows galore. This home was loved and lived in for 25 years. $10,000 seller credit toward updating. Buyers can move in with confidence. Clean stucco report and home inspection completed 7/7/2026. This is a true lagoon-fairway retreat minutes from groceries, Hospital Medical Pavilion, Schools, Spring Lake pool and tennis/pickle-ball and island beaches. HHP is voted over & over as "best community to live in" on the north end of Hilton Head Island.

11 China Cockle Way, Hilton Head Island

Listing courtesy of Charter One Realty.

$569,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511988 MLS

Welcome to the highly-desired St. Andrews Common community in world-renowned Palmetto Dunes Resort! This beautifully updated 2BD / 2BA villa offers a light, inviting retreat in one of Hilton Head Island's most ideal locations. The spacious layout provides plenty of room for both everyday living and entertaining, making this a perfect primary residence, second home, or turnkey investment opportunity. Offered fully furnished and ready to rent - having achieved nearly $45K in gross rentals just last year! Enjoy the peaceful surroundings of St. Andrews Common, complete with a community pool and picturesque lagoon and landscape views throughout the neighborhood. You'll have easy access to miles of pristine beaches, championship golf, tennis and pickleball, dining, shopping, biking, kayaking and everything that makes the Hilton Head lifestyle so special.

20 Queens Folly Road Unit 1659, Hilton Head Island

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

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