Windward Village Homes with Trail(s) Association Amenities

Welcome to Windward Village, a hidden gem nestled in the heart of Hilton Head Island, South Carolina. This charming subdivision is the perfect blend of coastal living and community spirit, making it an ideal place for families, retirees, and anyone looking to embrace the island lifestyle.

Windward Village boasts a variety of beautifully designed homes that cater to diverse tastes and preferences. From cozy cottages to spacious family residences, each home is thoughtfully constructed to provide comfort and style. The community is known for its picturesque landscapes, featuring lush greenery and serene surroundings that create a peaceful retreat from the hustle and bustle of everyday life.

One of the standout features of Windward Village is its incredible association amenities, including scenic walking and biking trails that wind through the neighborhood. These trails offer residents the perfect opportunity to enjoy leisurely strolls or invigorating bike rides while taking in the natural beauty of the area. Imagine starting your day with a refreshing walk surrounded by the sounds of nature or unwinding in the evening with a sunset bike ride.

In addition to the trails, Windward Village fosters a strong sense of community, with friendly neighbors and organized events that bring everyone together. Whether you’re looking to socialize at community gatherings or simply enjoy the tranquility of your surroundings, Windward Village has something for everyone.

Experience the charm and warmth of Windward Village, where your dream home awaits in this idyllic Hilton Head Island community. Embrace the coastal lifestyle and make memories that will last a lifetime!

Newest Windward Village Homes with Trail(s) Association Amenities

$639,000

2 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511442 MLS

Located in the desirable Windward Village enclave within the prestigious gated Shipyard community, this beautifully updated 2-bedroom, 2.5-bath villa offers a peaceful golf course setting, thoughtful upgrades, and an exceptional Hilton Head Island lifestyle. The spacious floor plan features soaring cathedral ceilings, abundant natural light, and a first-floor primary suite with an updated en-suite bath, enclosed walk-in closet with cedar shelving, and private deck. The living area opens to a screened porch with views through the mature trees toward the golf course, creating an inviting extension of the living space. The current owners completed extensive improvements between 2020 and 2022, including impact-resistant windows and two sliding glass doors, updated kitchen cabinetry and appliances, uniform tile flooring throughout, and beautifully renovated bathrooms. The two downstairs bathrooms feature heated tile floors, while the guest bath also includes a heated towel rack. Additional improvements include a screened porch with updated screening and tile flooring, HVAC system (2023), water heater (2023), and dishwasher (November 2025). Windward Village residents enjoy their own community pool, spa, and fire pit, all within the 800-acre Shipyard community. Shipyard offers private beach access via the Shipyard Beach Club, miles of leisure trails for walking and biking, 24-hour gated security, the 27-hole Shipyard Golf Club, Van Der Meer Tennis & Pickleball Center, Sonesta Resort Hilton Head Island, Hilton Head Health wellness resort, and a convenient south-end location just minutes from Coligny Plaza, shopping, dining, and entertainment. Whether you're searching for a primary residence, second home, or investment opportunity, this move-in-ready villa offers the perfect combination of comfort, quality, and coastal living.

148 Windward Village Drive, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

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