Heritage Woods Homes with Trail(s) Amenities

Welcome to Heritage Woods, a hidden gem nestled within the picturesque Hilton Head Island, South Carolina. This charming community in Beaufort County offers a unique blend of natural beauty and modern convenience, making it an ideal destination for those seeking a serene coastal lifestyle.

Heritage Woods is renowned for its enchanting trails that wind through lush landscapes, providing residents with an opportunity to immerse themselves in the stunning surroundings. Whether you’re an avid jogger, a leisurely walker, or simply someone who enjoys the tranquility of nature, the well-maintained trails are perfect for daily exercise or peaceful strolls. Imagine starting your day with a refreshing morning run or unwinding in the evening with a scenic walk as the sun sets over the horizon.

The homes in Heritage Woods are thoughtfully designed, combining elegance and functionality. With a variety of styles and sizes, there’s something to suit every taste and preference. Many properties feature open-concept layouts, expansive windows that invite natural light, and outdoor spaces perfect for entertaining or simply enjoying the serene environment.

Living in Heritage Woods means more than just beautiful homes; it’s about embracing a lifestyle filled with outdoor adventures and community spirit. Residents enjoy easy access to the stunning beaches of Hilton Head Island, renowned golf courses, and vibrant dining and shopping options.

Discover the charm and tranquility of Heritage Woods, where nature and luxury harmoniously coexist. Whether you’re looking to relocate, invest, or find your dream home, this community is sure to captivate your heart. Come explore the possibilities that await you in this idyllic coastal haven!

Newest Heritage Woods Homes with Trail(s) Amenities

$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.

$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.

$1,495,000

5 Beds ⋅ 3 Baths ⋅ 2,504 SqFt. ⋅ HILTONHEAD-512460 MLS

Some homes give you a place to stay in Sea Pines. 15 Dewberry gives you a reason to stay in. This five-bedroom home in Greenwood Forest pairs the Sea Pines lifestyle with the kind of amenities that make the house itself part of the vacation. And yes, the bikes come with the house. THE PUTTING GREEN: A professionally designed three-hole green spans 35 to 38 feet with an 11 stimp rating and real break, good for a morning warm-up or one more round after dinner. THE HANGOUT: A separate in-law suite with its own kitchenette turned wet bar, ice maker included. One of the home's five bedrooms currently serves as the suite's living room, and flexes just as easily into a bunk room when more sleeping space is needed. THE SPACE: Brazilian hardwood floors, a tongue and groove ceiling, quartz counters, and GE Cafe appliances run throughout the single story home, with new flooring added in the bedrooms. A Carolina room with a daybed and porch swing gives everyone one more place to land. THE NEIGHBORHOOD: Greenwood Forest is one of the few pockets of Sea Pines with its own community pool, tennis and pickleball, and a playground, a short distance from the Shops at Sea Pines and Beach Trolley access through a wooded community path. Easy distance to either HarbourTown or the Beach! Already an active vacation rental, the home has a confirmed booking of 91 nights for 2027 alone, worth more than $19,000, a sign of how much demand a house like this can hold.

15 Dewberry Lane, Hilton Head Island

Listing courtesy of Luxury Homes of Hilton Head.

$2,900,000

4 Beds ⋅ 4 Baths ⋅ 3,895 SqFt. ⋅ HILTONHEAD-511549 MLS

Filled with natural light and thoughtfully designed for comfortable living and entertaining, this exceptional home offers soaring ceilings, striking slate flooring, and an open, flowing floor plan. The spacious chef's kitchen seamlessly connects to the living room, dining area, family room, and breakfast nook, creating inviting spaces for gathering with family and friends. Offering four bedrooms and three-and-a-half baths, the home provides generous accommodations for both everyday living and hosting guests. Outside, enjoy a private fenced backyard complete with a sparkling pool, covered outdoor living area, and beautifully designed hardscape and mature landscaping-perfect for relaxing, grilling, and entertaining. Ideally located just moments from the iconic Harbour Town Golf Links, home of the annual RBC Heritage, this home places you in the heart of everything Sea Pines has to offer. Enjoy miles of leisure trails, pristine beaches, the Sea Pines Beach Club, Harbour Town Marina, South Beach Marina, Lawton Stables, world-class dining and shopping, and three championship golf courses. This is a rare opportunity to enjoy one of Hilton Head Island's most sought-after lifestyles.

75 Baynard Cove Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$2,249,900

4 Beds ⋅ 4 Baths ⋅ 2,922 SqFt. ⋅ HILTONHEAD-504552 MLS

Experience Lowcountry living at its finest in this bright, airy home designed for seamless indoor-outdoor enjoyment. Expansive floor to ceiling windows and sliding doors flood the main living area with natural light while opening directly to the outdoor entertaining spaces. The gourmet kitchen features premium appliances, generous island seating, a cozy breakfast nook, and a separate formal dining area, perfect for both casual meals and elegant gatherings. Four bedrooms plus a versatile flex room provide plenty of space for family, guests, or a home office. Step outside to your private backyard oasis, complete with a saltwater pool and spa, spacious deck for al fresco dining, and lush landscaping that frames peaceful lagoon views. Ideally located just 1.2 miles from the beach and minutes from world class golf, tennis, and Harbour Town, this residence offers effortless indoor-outdoor living and a lifestyle rich with recreation.

30 Plantation Drive, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate.

Start Your Search

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.