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

$795,000

3 Beds ⋅ 3 Baths ⋅ 1,831 SqFt. ⋅ HILTONHEAD-512905 MLS

Probably the nicest Avalon ever listed for sale, including a location in the community that offers the utmost in private outdoor living. Completely updated with an outstanding open floorplan with 3 bedroom and 3 full baths plus a 2 car garage.

15 Indigo Run Drive Unit 21, Hilton Head Island

Listing courtesy of Charter One Realty.

$638,000

2 Beds ⋅ 2 Baths ⋅ 1,230 SqFt. ⋅ HILTONHEAD-512903 MLS

Walk/Bike to Beach. Private 3rd Floor Villa with stunning golf views and convenient elevator access!! Just around the corner from the Sea Pines Beach and Plantation Clubs ... offering panoramic golf and ocean views from their individual restaurant locations. This beautifully appointed villa offers an open-concept kitchen and living area with upgraded luxury vinyl plank flooring and a private balcony to enjoy the outdoor living environment. This villa complex also has a private pool for it's homeowners just within steps of the entrance to this property. 2 BR/2 BA. This villa is being offered fully furnished and turnkey for your personal convenience or as an investment property. Island living at your fingertips!!

22 Lighthouse Road Unit 525, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

$1,299,000

3 Beds ⋅ 3 Baths ⋅ 1,652 SqFt. ⋅ HILTONHEAD-512787 MLS

A sophisticated top-floor retreat in the heart of Harbour Town, where direct marina, lighthouse, and Calibogue Sound views define every level. This 3-bedroom, 3-bath, two-story penthouse offers a rare vantage point above Sea Pines' most storied address - steps from the shops, restaurants, and marina energy of Harbour Town, yet elevated well above it. The two-story layout gives the living space real scale and separation while keeping the lighthouse and sound as the constant backdrop. Move-in ready as a personal getaway, or well-suited as a short-term rental - direct marina and lighthouse views like this are consistently the strongest driver of rental demand and rate in Harbour Town. This villa is sold furnished. A location, elevation, and view combination that rarely comes to market. Schedule a private showing.

18 Lighthouse Lane Unit 1043, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$715,000

2 Beds ⋅ 3 Baths ⋅ 1,380 SqFt. ⋅ HILTONHEAD-512876 MLS

Carefree Island living - Fairway Views and close to the Beach. This fully renovated 1,380 sq ft villa in Shipyard Plantation is the vacation home that makes everything easy. Two bedrooms, two and a half baths, and an open, light-filled layout built for both entertaining and quiet downtime - with golf course fairways views right outside and the beach just a short walk away. Sold fully furnished and truly turnkey - arrive with your suitcase and nothing else. Rent it when you're away, keep it just for you, or do both. Either way, this home is ready the moment you are. Shipyard Plantation adds resort-style amenities to the mix: golf, tennis, beach club, and gated privacy, all close to shops, dining, and more! Easy to show - schedule your appointment now.

113 Shipyard Drive Unit 109, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$259,000

1 Beds ⋅ 1 Baths ⋅ 540 SqFt. ⋅ HILTONHEAD-512890 MLS

BEST VALUE FOR A 1BR OCEANFRONT VILLA AT HILTON HEAD BEACH & TENNIS!**- SELLER MOTIVATED!** Ready to own your own piece of Hilton Head Island? This turnkey, oceanfront 1BR/1BA villa at Hilton Head Beach & Tennis Resort is priced with a quick sale in mind, and all reasonable offers will be considered! The seller has simply reached a point where they are no longer enjoying their beach trips, creating an opportunity for the next owner to make this renovated villa their own Hilton Head getaway, second home, or short-term rental investment. Located on the first floor with peak a boo ocean views, this fully furnished villa is ready to enjoy or rent. The updated kitchen, renovated in 2022-2023, features stainless steel appliances, while luxury vinyl plank flooring and thoughtful updates create a comfortable coastal feel. Built-in bunk beds with mounted TVs are a fantastic bonus for families and guests, allowing the villa to comfortably sleep up to six. Step outside to your private balcony and take in the ocean views-or head downstairs and enjoy one of Hilton Head's most amenity-rich beachfront resorts. Resort amenities include direct beach access, one of the largest oceanfront pools on Hilton Head Island, two outdoor pools, tiki bar, on-site restaurant and sports bar, tennis courts, pickleball courts, fitness center, bike rentals, outdoor grilling areas, playground, 24/7 gated security, and cable and internet included. The villa also features a brand-new HVAC system installed June 2025, adding peace of mind for both owners and guests. Whether you're looking for a beachfront second home, a turnkey vacation rental, or an affordable way to own on Hilton Head Island, this is an opportunity worth seeing. **Seller is motivated, priced for a quick sale, and will consider all offers. Bring your offer and make this oceanfront Hilton Head retreat yours!**

40 Folly Field Road Unit A134, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$1,850,000

4 Beds ⋅ 3 Baths ⋅ 3,000 SqFt. ⋅ HILTONHEAD-512889 MLS

Beautifully positioned along a picturesque lagoon, this inviting home combines an exceptional setting with spacious interiors, thoughtful updates, and wonderful indoor-outdoor living. Soaring ceilings, expansive windows, designer lighting, and serene water views create a light-filled atmosphere from the moment you enter. Open kitchen features quartz counters, soft-close cabinetry, eat-in island and stainless appliances, flowing to the living, dining and family rooms. First-floor owner suite enjoys serene water views and a beautifully updated bath. Two additional spacious guest suites offer generous closets and share a beautifully finished bath. Flexible 4th BR offers room to add a bath. One of the home's most special features is its incredible connection to the water. Just off the kitchen, there is a screened porch features and an open deck that's ideal for grilling, relaxing, and watching the abundant Lowcountry wildlife. For those who love to fish, it doesn't get much better than stepping into your own backyard to reel in redfish, black drum, and flounder. Whether your perfect day includes a morning bike ride, a round of golf, an afternoon on the beach, boating from Harbour Town, or simply relaxing at home, this location puts the best of Sea Pines within easy reach. From the expansive water views and beautifully updated interiors to the exceptional screened porch, and welcoming neighborhood atmosphere, this home offers a wonderful opportunity to enjoy the relaxed Lowcountry lifestyle.

50 Hearthwood Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,425,000

5 Beds ⋅ 3 Baths ⋅ 3,235 SqFt. ⋅ HILTONHEAD-512885 MLS

Experience the ultimate Lowcountry lifestyle in this impeccably maintained home located in the sought-after Hilton Head Plantation. This stunning residence offers tranquil golf and lagoon views, providing a peaceful backdrop for both everyday living and entertaining. The gourmet kitchen features quartz countertops, a large center island, a spacious pantry, and premium stainless steel appliances, all flowing seamlessly into the formal dining room and a grand living area defined by soaring cathedral ceilings and a cozy gas fireplace. A bright, airy Carolina room extends the living space, leading out to a private paver patio and a heated saltwater pool. The main-level primary suite is a true retreat, boasting a spa-like ensuite bath, two oversized walk-in closets, and direct access to a private screened porch. There are also two additional spacious bedrooms on the first floor. Upstairs, a versatile loft serves as an ideal home office or media area, accompanied by two spacious guest bedrooms that share a full bath and ample storage. Additional highlights include professional landscaping, a generous driveway, and an unbeatable location just a three-minute stroll from the Port Royal Sound or a five-minute bike ride to Dolphin Head Beach. Residents of Hilton Head Plantation enjoy world-class gated amenities, including private beach access, a marina, tennis and pickleball courts, leisure trails, bocce courts and a resort-style community pool with a lazy river. This home perfectly balances comfort, privacy, and the quintessential Hilton Head Island experience.

24 Angel Wing Drive, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$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 near 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.

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