Hilton Head Island Homes with Trail(s) Association amenities

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 pristine beaches, lush landscapes, and vibrant culture, Hilton Head is more than just a vacation destination; it's a lifestyle. With its warm climate and friendly community, this island gem offers an idyllic setting for families, retirees, and anyone seeking a serene escape from the hustle and bustle of everyday life.

One of the many highlights of living in Hilton Head Island is the access to the Homes with Trail(s) Association amenities. This exclusive community is designed for those who love the outdoors and appreciate the beauty of nature. Residents enjoy miles of scenic trails perfect for walking, biking, or simply soaking in the breathtaking views of the island’s natural surroundings. Whether you’re an avid hiker or prefer a leisurely stroll, the trails offer something for everyone.

In addition to the trails, the Homes with Trail(s) Association provides a range of amenities that enhance the quality of life for its residents. Enjoy access to community pools, fitness centers, and social clubs that foster a sense of belonging and camaraderie among neighbors. The close-knit community atmosphere encourages residents to engage in various activities, from yoga classes to seasonal events, making it easy to forge lasting friendships.

Living in Hilton Head Island means embracing a lifestyle filled with adventure, relaxation, and unparalleled beauty. Discover your dream home in this enchanting locale and experience all that the Homes with Trail(s) Association and Hilton Head Island have to offer!

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

$1,750,000
4 Beds ⋅ 4 Baths ⋅ 2,790 SqFt. ⋅ HILTONHEAD-513156 MLS
A rare opportunity in Sea Pines, 10 Fox Lane is a beautifully finished 2023 home tucked within the peaceful Club Course area of one of Hilton Head Island's most iconic communities. Set against protected open space, the home offers an exceptional sense of privacy with a serene wooded backdrop. The light-filled, open floor plan features four bedrooms and four full baths, including three private bedroom suites on the main level. Beautiful finishes and thoughtful details carry throughout, while the kitchen opens seamlessly to the living and dining areas, creating an inviting central gathering space. Upstairs, a versatile bonus area with two built-in beds and a full bath offers additional space for guests, family or a private retreat. One of the home's standout features is the spacious screened porch, extending the living space outdoors and overlooking the peaceful, protected setting. Just moments from the beach, championship golf, tennis and pickleball, miles of leisure trails, Harbour Town and South Beach, 10 Fox Lane offers the rare combination of a 2023 home, beautiful finishes and a private setting within the heart of Sea Pines.

10 Fox Lane, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate.

$1,245,000
3 Beds ⋅ 3 Baths ⋅ 3,544 SqFt. ⋅ HILTONHEAD-513054 MLS
More to come including professional photos.

1 Shaftsbury Lane, Hilton Head Island

Listing courtesy of Charter One Realty.

$2,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-513142 MLS
Your late Summer Spicebush week 36 Awaits! Tucked within the heart of Hilton Head Island's prestigious Sea Pines community, this ownership places you just moments from the Sea Pines Beach Club and Plantation Club Golf Course. Perfectly situated, your Spicebush Week 36 offers effortless access to world-class golf, pristine beaches, waterfront dining, and the island's most celebrated events. Embrace coastal living at its best-start your mornings by the sea, unwind beneath golden sunsets, and savor the timeless charm of Sea Pines Resort. With refined, low-maintenance ownership, your annual island escape is always ready when you are.

124 N Sea Pines Drive Unit 567, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$649,000
2 Beds ⋅ 3 Baths ⋅ 1,647 SqFt. ⋅ HILTONHEAD-513045 MLS
Enjoy beautiful marina views from this exceptional 4th-floor, two-story villa in the heart of Shelter Cove Harbour & Marina. This spacious 2-bedroom, 2.5 bath villa features an inviting living and dining area, well-appointed kitchen, powder room, and a large private balcony overlooking the harbour - the perfect place to relax and take in the views. Upstairs the owner's suite features a Jacuzzi tub and separate walk-in shower, while a supplemental A/C unit provides added comfort. Additional features include a Wi-Fi controlled thermostat and convenient elevator access located directly across from the villa. Step outside to waterfront dining, boutique shopping, live entertainment, seasonal events, and all the activity of the marina. Owners and guests also enjoy access to the Harbourside I pool and Palmetto Dunes Resort amenities, including beach access via the seasonal Dunes Buggy, golf, tennis, pickleball, and miles of leisure trails. A wonderful opportunity to enjoy the Shelter Cove lifestyle and the very best of Hilton Head Island.

13 Harbourside Lane Unit 7170, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$899,000
3 Beds ⋅ 3 Baths ⋅ 1,576 SqFt. ⋅ HILTONHEAD-513137 MLS
Beautifully updated 3-bedroom, 3-bath villa in Turnberry Village, ideally situated along the George Fazio Golf Course in the heart of Palmetto Dunes. This light-filled villa offers an open and inviting floor plan with a beautifully updated kitchen featuring quartz countertops, stainless steel appliances, generous cabinet space, and a large peninsula with bar seating overlooking the dining and living areas. The spacious living room opens to a large private Trex deck with sweeping golf course views, creating the perfect setting for relaxing or entertaining. The first-floor primary suite offers convenient main-level living with a private bath, while upstairs you'll find two additional spacious bedrooms, each with access to its own full bath. Turnberry Village offers a community pool and playground and is conveniently located less than a mile from the beach, with easy access by bike or the seasonal Dunes Buggy. Enjoy all that Palmetto Dunes has to offer, including world-class golf, tennis and pickleball, dining, shopping, miles of leisure trails, and beautiful beaches. Whether you're looking for a second home or investment property, this is a wonderful opportunity to own in one of Hilton Head Island's most desirable resort communities.

59 Carnoustie Road Unit 279, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,950,000
4 Beds ⋅ 5 Baths ⋅ 2,957 SqFt. ⋅ HILTONHEAD-513113 MLS
This bright 4-bedroom, 4.5-bath Sea Pines home offers a rare combination of space, privacy, and location. Never rented, the elevated home sits on a .4-acre lot with a fully fenced backyard and room for a pool. A spacious back deck overlooks a lagoon and the 18th fairway of Sea Pines Country Club, with a peek-a-boo marsh view beyond the golf course. Inside, the light-filled living room features vaulted ceilings, a brick fireplace, oversized windows, and transoms that bring in abundant natural light while showcasing the views. The floor plan also includes a separate dining room, an eat-in kitchen that opens to the family room, and a 2-car garage. Three generously sized bedrooms are located on the main level, while the fourth large bedroom is privately situated over the garage with its own full bath. Additional features include beautiful wood floors throughout the main living areas, two newer HVAC systems, and a desirable location close to Sea Pines Country Club. With a fenced yard, flexible living space, and an attractive price point for Sea Pines, this home is move-in ready and offers an excellent opportunity.

56 Governors Road, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$2,849,000
4 Beds ⋅ 5 Baths ⋅ 3,925 SqFt. ⋅ HILTONHEAD-512812 MLS
Fully remodeled and beautifully appointed, this exceptional harbourfront home in Wexford offers a relaxed Lowcountry lifestyle with harbour views, private pool, 3,925 square feet of living space, and a private dock that can accommodate a 70' vessel. The home features 4 bedrooms, 4 full and 1 half baths, and 2-car plus golf cart garage. Wexford's private marina and harbour provide direct access to the Broad Creek and the Intracoastal Waterway through its 24/7 lock system, one of only three on the East Coast. Upon entering, the formal living room makes an immediate impression with soaring ceilings, exposed beams, a propane fireplace, and expansive windows that fill the space with natural light. Doors open directly to the pool deck, creating an effortless connection between indoor and outdoor living. The inviting family room features high ceilings, floor-to-ceiling windows, an electric fireplace, and direct access to the pool deck. At the heart of the home is a stunning, fully remodeled kitchen with a bright, open design, double islands, top-of-the-line appliances, quartz countertops, and a walk-in pantry. The spacious first-floor primary suite features a beautifully remodeled bath with a zero-entry shower, a soaking tub, and a generous walk-in closet. A first-floor laundry room adds everyday convenience. Three guest rooms with fully remodeled ensuite baths provide flexibility and room for guests. The outdoor living spaces have been thoughtfully enhanced with a brand-new covered area overlooking the pool and harbour, creating an inviting space for relaxing and entertaining. The newly plastered pool and resurfaced pool deck provide a refreshed outdoor retreat. This home also has a built in generator for added piece of mind. The generous lot offers plenty of room and privacy, while the 2-car plus golf cart garage provides storage and convenience. Wexford members enjoy a premier private club lifestyle, including an Arnold Palmer Signature golf course, tennis, pickleball, croquet, pool complex, private harbour, fire pit, and newly opened Clubhouse and Harbour Center. Combined with a vibrant social calendar and Wexford's unique marina lifestyle, this is an exceptional opportunity to enjoy the best of private club living on Hilton Head Island.

44 Wexford Club Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$4,400,000
6 Beds ⋅ 6 Baths ⋅ 4,796 SqFt. ⋅ HILTONHEAD-513002 MLS
Like NEW, this State of the Art Lowcountry 6BR/5.5BA Beach Home approx 8000+ sq ft under roof offering 2 living rooms, 2 screened porches, huge garage, workshop and large private pool was designed for the way you actually want to live on Hilton Head Island. Open, comfortable, private, premium finishes, with perfectly designed outdoor spaces, all just moments from the residents only private beach . Hardwood floors, custom millwork, built-ins and walls of windows carry throughout the home. The kitchen is a showstopper, with an oversized island, custom cabinetry, high-end appliances and a true walk-in pantry. The primary suite is equally impressive withhis & her bathrooms w/freestanding soaking tub, oversized tiled shower and custom his & hers walk-in closets. Outside is where this home really separates itself. Two screened porches create an incredible amount of year-round living space, including an upper porch with fireplace, built-in grill and dining area. Downstairs, another oversized screened living area opens to the private pool, hot tub and beautifully landscaped backyard. Add an elevator, dedicated office, game area, workshop and more storage than you expect to find in an island home, and there's very little this house leaves you wanting. One of the finest homes ever offered for sale in Port Royal situated on a premium oversized extremely private lot in close proximity to the Residents Private Beach & Beach Club. The private gated community of Port Royal on Hilton Head is an Outdoor Enthusiast Dream offering Tennis. Golf. Pickle Ball. Bike Paths. Swimming. Gardening. Beach Activities

51 Scarborough Head Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$309,000
1 Beds ⋅ 1 Baths ⋅ 540 SqFt. ⋅ HILTONHEAD-513107 MLS
Turnkey and renovated in 2024, C217 offers Lowcountry marsh and wooded views with convenient beach access. Used exclusively as the owners' private retreat, the villa has been carefully maintained and is located in a building with an elevator. The open kitchen and living area feature quartz countertops, new cabinetry and stainless steel appliances, LVP flooring and a built-in sound system. A new HVAC system was installed in 2026. The villa is offered fully furnished and includes fresh paint in a coastal color and a custom designed bedroom closet. The redesigned bathroom features a white quartz-topped vanity and a tiled walk-in shower with a glass enclosure. Expansive living room windows bring natural light into the living area and frame the private marsh and wooded surroundings. The balcony offers sunrise views overlooking the marsh and trees where birds are frequently seen and heard. Shaded from direct afternoon sun, it creates a great place to relax after a day at the beach. Hilton Head Beach and Tennis Resort amenities include tennis and pickleball courts, swimming pools, on-site dining, a fitness center, playground, laundry facilities and 24-hour security. This villa can easily be used as a primary residence, vacation home or investment property.

40 Folly Field Road Unit C217, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$735,000
2 Beds ⋅ 3 Baths ⋅ 1,600 SqFt. ⋅ HILTONHEAD-513104 MLS
Enjoy the best of the Sea Pines lifestyle from this beautifully updated and nicely furnished 2-bedroom Heritage Villa, ideally located just minutes from Harbour Town. The light and inviting interior features stylish LVP flooring, comfortable living spaces, and thoughtful updates throughout, making this villa truly move-in ready. Enjoy a pleasant view of the community pickleball courts and easy access to all that Sea Pines has to offer. An excellent vacation rental opportunity, the villa has generated $29,264 in gross rental income year-to-date. Whether you're looking for a full-time residence, vacation getaway, or income-producing investment, this villa offers exceptional convenience to Harbour Town, world-class golf, dining, shopping, biking trails, and more. Offered furnished and ready to enjoy!

107 Lighthouse Road Unit 2289, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$1,800,000
3 Beds ⋅ 3 Baths ⋅ 2,178 SqFt. ⋅ HILTONHEAD-513103 MLS
Just 300 steps to the beach in North Forest Beach! Welcome to this beautifully rebuilt beach cottage in the highly sought-after North Forest Beach area, just steps from the beach and withing easy walking distance of Coligny Plaza's restaurants, shops and entertainment. The home features 3 bedrooms and 2.5 baths along with a 2 car garage, one half of which has been thoughtfully converted into a comfortable, air-conditioned office. Outside, enjoy a large private swimming pool, surrounded by a fenced backyard and beautiful, easy-care landscaping. Completely rebuilt in 2017, the home offers two inviting outdoor living spaces, one screened porch and a spacious screened lanai - perfect for relaxing after a day at the beach. There is also abundant storage beneath the enclosed areas. The property features a convenient semicircular driveway, plus additional parking along the side of the home, making it idea for family, friends, and guests. For years, the owners successfully rented the home for approximately 10 peak-season weeks, and it consistently attracted repeated visitors and stayed booked. Location on popular Jacana Street, this home offers an exceptional combination of beach access, privacy, outdoor living, and convenience. Whether you're looking for a personal beach retreat, an investment property, or both, this North Forest Beach cottage is ready to enjoy.

145 Jacana Street, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$399,000
2 Beds ⋅ 1 Baths ⋅ 960 SqFt. ⋅ HILTONHEAD-513044 MLS
The location of this villa truly cannot be beat. Completely renovated from top to bottom, this turnkey, second-floor Dunes Villa is the ultimate coastal retreat. Situated just steps from the ocean, this property offers a seamless island lifestyle whether you are looking to generate immediate rental income as an investment, relax in your own second home, or settle into a low-maintenance primary residence. Every detail of this turn-key two-bedroom, one-bath home was thoughtfully designed for maximum style and comfort. The light and bright kitchen features renovated cabinetry and modern appliances, while the updated bathroom provides a crisp, contemporary space to rinse off after a day in the sun. What sets this property apart is its unbeatable combination of location, community amenities, and low regime fee. Just steps away you can feel the ocean breeze, or walk down the block to dine at one of the nearby restaurants. A quick five minute stroll takes you straight to the Lowcountry Celebration Park and Coligny Plaza. Hilton Head's Coligny area is a vibrant downtown area where you will find over 20 restaurants, local shopping, and lively entertainment. Dunes Villas offers hassle-free parking, the rare island luxury of a year-round swimming pool, and is pet-friendly exclusively for owners. An opportunity to own a completely updated villa this close to the beach and Coligny Plaza rarely presents itself. Claim your piece of Hilton Head's paradise today.

6 Woodward Avenue Unit C3, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

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