Hilton Head Island Homes with Trail(s) Amenities

Welcome to Hilton Head Island, South Carolina, a coastal paradise nestled in Beaufort County that beckons with its stunning landscapes, pristine beaches, and vibrant community spirit. Known for its lush greenery and breathtaking ocean views, Hilton Head Island is not just a destination; it’s a lifestyle. With a year-round mild climate, outdoor enthusiasts can indulge in a myriad of activities, from golfing on world-renowned courses to biking along scenic trails.

For those seeking the perfect home in this idyllic setting, properties with trail amenities offer an unparalleled living experience. Imagine waking up to the sound of waves and the gentle rustle of leaves, with direct access to a network of trails that wind through the island’s natural beauty. These homes are thoughtfully designed to cater to an active lifestyle, providing easy access to walking, jogging, and biking paths that meander through picturesque landscapes, marshes, and along the coastline.

Living in a home with trail amenities means you can enjoy leisurely strolls or invigorating runs right at your doorstep, all while soaking in the stunning vistas that Hilton Head Island has to offer. Whether you’re a nature lover, a fitness enthusiast, or simply someone who appreciates the tranquility of outdoor spaces, these homes are perfect for you.

Embrace the charm of Hilton Head Island, where coastal living meets adventure. Discover your dream home today and step into a world where every day feels like a vacation!

Newest Hilton Head Island Homes with Trail(s) Amenities

$1,249,000

3 Beds ⋅ 2 Baths ⋅ 2,156 SqFt. ⋅ HILTONHEAD-512887 MLS

It's a great house!

41 Stoney Creek Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$675,000

3 Beds ⋅ 3 Baths ⋅ 1,941 SqFt. ⋅ HILTONHEAD-512886 MLS

Welcome to 137 Cordillo Parkway, Suite 6002, a beautifully furnished 3-bedroom, 2.5-bath Hilton Head Island retreat offered at $675,000.Whether you are searching for your own beach getaway or an investment opportunity, this property offers the perfect combination of comfort, convenience, and island lifestyle. The spacious floor plan comfortably sleeps up to eight guests and comes fully furnished, making it easy to begin enjoying the property from day one.One of the highlights of the home is the relaxing back patio and porch area-the perfect place to unwind after a day at the beach. Community amenities include three swimming pools, convenient elevator access, and a private walkway providing direct access toward the beach.Enjoy an approximately eight-minute scenic walk along the shaded pathway to the sand, with convenient access to a wonderful beachfront restaurant along the way. Whether spending the day by the pool, relaxing on the beach, enjoying nearby dining, or simply taking in the laid-back Hilton Head atmosphere, this property offers an exceptional coastal experience.Ideal for an owner-occupant, second-home buyer, or investor seeking rental potential. Forecasted rental projections are available upon request.Schedule your private showing today and come experience everything this Hilton Head Island property has to offer.

137 Cordillo Parkway Unit 6002, Hilton Head Island

Listing courtesy of Douglas Lane Real Estate Group.

$1,625,000

3 Beds ⋅ 3 Baths ⋅ 2,431 SqFt. ⋅ HILTONHEAD-512571 MLS

Located within the coveted Heritage Woods neighborhood of Sea Pines Resort, this classic three bedroom, three bath home represents a dynamic real estate opportunity. This single floor property boasts dual living areas, large bedrooms and peaceful reading and relaxation nooks. A flexible room on the home's opposite side offers a rare fourth sleeping space or quiet office - complete with a full bath. The home's private swimming pool is framed by Brazilian hardwood decking and wrap-around rear fencing ensures upmost privacy for family and guests. The spacious floor plan offers modern functionality while enduring touches such as the brick fireplace and built in bookshelves lend a timeless charm. Hilton Head Island's award wining beaches are within walking distance via Sea Pines' convenient beach paths while the leisurely pursuits of Harbour Town and South Beach are within a short biking distance. This fully furnished home is currently on the short term rental market and represents a turnkey opportunity for a buyer seeking an immediate investment or a ready canvas to create their own island escape.

8 Old Military Road, Hilton Head Island

Listing courtesy of The Hilton Head Agency.

$1,600,000

4 Beds ⋅ 5 Baths ⋅ 3,505 SqFt. ⋅ HILTONHEAD-512875 MLS

Welcome home to 21 Ribaut Dr. on Hilton Head Plantations prestigious Ribaut Island in a private gate with 63 homesites. Take advantage and enjoy the private amenities of a community pool, dock and tennis/pickleball courts. Sitting on just under a half an acre lot, this wonderful, updated floor plan has 4 bedrooms, & 4.5 bathrooms. The office is just off the primary suite. Enjoy the open updated kitchen/family room and cooking on your propane stove and oven while entertaining friends and family. The Primary bath has been renovated with large soaking tub. There are wood floors in the living areas and carpet in the bedrooms. The home is equipped with an extended 2 car garage with workshop space and a large storage closet. Storage galore with many closets and a walk-in floored attic. Located within the gates of Hilton Head Plantation, residents enjoy an outstanding array of amenities, including four championship golf courses, the Country Club of Hilton Head, Spring Lake Recreation Area, Dolphin Head Recreation Area, a full-service marina, tennis and pickleball courts, miles of leisure trails, a community pool, and 24-hour security-all just minutes from Hilton Head Island's beaches, shopping, and dining.

21 Ribaut Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,295,000

4 Beds ⋅ 4 Baths ⋅ 2,672 SqFt. ⋅ HILTONHEAD-512804 MLS

Discover the outdoor lifestyle that draws so many to Hilton Head at 56 Sussex Lane, where privacy, tranquility, and resort-style living come together. Enjoy your own private pool and spa, along with a spacious screened-in porch overlooking a beautiful long lagoon view--the perfect setting for relaxing, entertaining, and enjoying the Lowcountry lifestyle. Tucked away on a quiet cul-de-sac in Indigo Run, one of Hilton Head Island's most sought-after communities, this meticulously maintained home offers a wonderful combination of privacy and convenience. The spacious four-bedroom, three-and-a-half-bath home has a dedicated office and features high ceilings and an inviting great room that opens directly to the screened-in porch. The well-appointed kitchen flows seamlessly into a comfortable family room, with easy access to the new, high-end heated pool and spa and outdoor living areas. Used as a second home by its owners, 56 Sussex is truly move-in ready and a "must-see." With shopping just five minutes away and the beach approximately ten minutes from your door, this home makes it easy to enjoy everything Hilton Head has to offer.

56 Sussex Lane, Hilton Head Island

Listing courtesy of Charter One Realty.

$610,000

2 Beds ⋅ 2 Baths ⋅ 1,371 SqFt. ⋅ HILTONHEAD-512852 MLS

Completely updated inside and out, this charming coastal cottage with golf view at 52 Stable Gate offers move-in-ready, single-story living in sought-after Moss Creek. More than a surface renovation, major improvements include a new roof (2021), HVAC and ductwork (2024), updated electrical and smoke detectors, plus new Anderson kitchen window and two sliders with a 20-year warranty.Enjoy an updated kitchen and baths, automatic primary bedroom window treatments, a wraparound patio and private screened courtyard. The newly sodded yard features irrigation and an invisible fence, plus exterior storage.Just minutes from Hilton Head Island, Moss Creek offers an exceptional Lowcountry lifestyle with deep-water boat slips, launch and storage, waterfront pool, full-featured fitness center, golf, tennis, pickleball and countless other recreational and social amenities.

52 Stable Gate Road, Hilton Head Island

Listing courtesy of ERA Wilder Realty, Inc - Bluffton.

$2,200,000

4 Beds ⋅ 3 Baths ⋅ 2,484 SqFt. ⋅ HILTONHEAD-512850 MLS

Beautifully renovated and fully updated 4 bed/3 bath home just minutes from the beach! This stunning property has been thoughtfully transformed from top to bottom, offering stylish finishes, modern upgrades, and all new furnishings inside and out. The freshly painted interior features new doors & hardware, ceiling fans, lighting, and fixtures throughout. The completely renovated kitchen showcases new cabinetry and appliances, while all three bathrooms have been beautifully updated, including a reconfigured primary bath designed for improved functionality and style. Major improvements include new plumbing, ductwork, roof, and gutter systems, providing peace of mind for years to come. Outside, enjoy a serene private pool area overlooking a lagoon, with updated landscaping and pool surrounds creating the perfect setting for relaxing or entertaining. With its exceptional location near the beach and extensive renovations inside and out, this turnkey home is ready to be enjoyed!

15 Wagon Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

$489,000

2 Beds ⋅ 3 Baths ⋅ 1,346 SqFt. ⋅ HILTONHEAD-512849 MLS

Excellent Investment Opportunity in South Forest Beach! This beautifully remodeled, turnkey 2BR/2.5BA Courtside Villa offers the ideal combination of coastal comfort, exceptional location, and proven rental appeal. Situated in Hilton Head Island's desirable South Forest Beach, the villa is just a short distance from the Atlantic Ocean and minutes from Coligny Plaza's renowned dining, shopping, and entertainment. Celebration Park is also an easy stroll away. Thoughtfully remodeled and ready to enjoy, the villa features a beautifully updated kitchen, two spacious bedrooms - each with its own en-suite bath and a convenient half bath for guests. The bright, open floor plan creates a welcoming setting for relaxed island living and memorable beach getaways. Courtside Villas is a well-maintained community offering two swimming pools and direct access to the Van Der Meer Tennis Center, providing owners and guests with an array of resort-style amenities just steps from the villa. Whether you're seeking a personal island retreat, a vacation home, or an income producing investment, this exceptional property delivers the quintessential Hilton Head lifestyle in one of the island's most sought after locations.

15 Deallyon Avenue Unit 47, Hilton Head Island

Listing courtesy of Charter One Realty.

$824,999

3 Beds ⋅ 2 Baths ⋅ 1,853 SqFt. ⋅ HILTONHEAD-512421 MLS

Here's the perfect opportunity to create your forever home in Hilton Head Plantation. This home is located on one of the best streets in HHP because it's light, bright and quiet. Located on the cul-de-sac at the very end of the street you will ALWAYS enjoy your drive back to your house. Every square inch of this home is used smartly and it presents as light and bright which is such a huge asset! There is an open foyer as soon as you enter connected to the spacious living area and large dining area. The glass doors at the back of the house allow in all the South Carolina light and there's a beautiful oversized backyard with peek-a-boo views to the 17th hole of the Oyster Reef golf course-one of 4 golf courses in the plantation. Immediately behind the lot line there is an open area that gives the area an expanded spacious feel. There are 3 bedrooms and 2 full baths and they are situated for privacy. The primary bedroom has a beautiful bay window that faces the back of the property and nice space to create the perfect room. The primary bathroom is spacious and has both a shower and an oversized tub. This lot is almost a half acre and serene with the extra common space immediately behind the lot line. There's a full two car garage with an outside access door, a sink and a full laundry room as you enter the house through the garage. One step through the front door and it's OBVIOUS this home has been well maintained and loved. The roof was replaced in November 2025 so it has a full lifetime left. Hilton Head Plantation has TONS to offer anyone wanting to live on this island-it has 4 golf courses, a huge pool complex with a lazy river, tennis/pickleball and walking paths. The entire dolphin head beach area has been renovated to include a public pickle ball court, a newly renourished beach area, children's playground and a new community building!

28 Oyster Bay Place, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$265,000

1 Beds ⋅ 1 Baths ⋅ 540 SqFt. ⋅ HILTONHEAD-512847 MLS

Steps to the Beach! This nicely updated villa offers a convenient location, comfortable living space, and an established rental history. Features include an updated kitchen, a new bathroom with a beautiful walk-in shower, and tile flooring throughout. The cozy bunk beds make great use of the space, while the private balcony provides a nice spot to relax and enjoy the outdoors. Resort amenities include an oceanfront pool with seasonal food service, lighted tennis courts and pro shop, fitness center, playground, on-site restaurants, and 24-hour security. With the beach just steps away and plenty of amenities to enjoy, this villa is a great opportunity for a beach getaway or investment property.

40 Folly Field Road Unit C147, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$2,100,000

4 Beds ⋅ 5 Baths ⋅ 2,256 SqFt. ⋅ HILTONHEAD-512797 MLS

This fully furnished third-row ocean home is ideally located a short distance from the beach via a dedicated path through a winding grove of trees. Situated in the highly sought-after Forest Beach area and conveniently close to the Ocean Gate of Sea Pines Resort. It is perfectly suited for vacation getaways, a second home, or investment rental. With 4 bedrooms and 4.5 baths, this home features welcoming front porches on both the first and second floors, plus two side porches, including a screened porch for relaxing outdoors. You enter the home into a separate first floor living space with a sitting room, TV, a wet bar and refrigerator. This provides a unique area for the guests to separate from the main kitchen, dining and living room, making it easy for all to enjoy their own space. You then enter into the open concept main living area. You have a modern kitchen, counter barstools, a large dining room table, and a big living room with TV plus a small game table. The laundry room and half bath are also located on the main level. All four bedrooms are on the second level, offering access to wide porches-perfect for enjoying the coastal breeze and lush surroundings. After a day at the beach, retreat to the private, fenced side yard featuring a pool, spa, and spacious patio area, ideal for afternoon swims and cookouts. This Forest Beach gem captures the best of the Hilton Head Island lifestyle with exceptional flexibility and appeal.

6 Cassina Lane, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$990,000

3 Beds ⋅ 3 Baths ⋅ 2,350 SqFt. ⋅ HILTONHEAD-512751 MLS

Welcome to 7 McGuire - the epitome of Hilton Head Island living. Perfectly situated on a quiet cul-de-sac in the Palmetto Hall community, this Lowcountry-inspired residence beautifully combines design, location, and exceptional value. From the moment you arrive, a classic covered front porch invites you to slow down and stay awhile. Step through the front door to find an expansive, light-filled open floor plan crowned by elegant coffered ceilings. The thoughtfully designed layout features rich hardwood floors, excellent bedroom separation for maximum privacy, and a kitchen built for entertaining. Outside, the backyard serves as a private, lushly landscaped oasis bordering the golf course-giving you the unique choice to maintain your secluded retreat or trim the greenery to reveal expansive fairway views. As the only home available in Palmetto Hall under $1M (outside of Tucker Ridge), this rare opportunity won't last long.

7 Mcguire Court, Hilton Head Island

Listing courtesy of Hilton Head Properties.

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