Windward Village Homes with Trail(s) Association amenities

Welcome to Windward Village, a picturesque subdivision nestled in the heart of Hilton Head Island, South Carolina, within the charming Beaufort County. Known for its stunning coastal landscapes and vibrant community spirit, Windward Village is the perfect place for those seeking a serene yet engaging lifestyle.

This idyllic neighborhood features a range of beautifully designed homes that cater to diverse tastes and preferences. With a blend of contemporary architecture and classic southern charm, each residence is thoughtfully crafted to provide comfort and style. The lush greenery and well-maintained landscaping create an inviting atmosphere, making every stroll through the neighborhood a delight.

One of the standout features of Windward Village is its commitment to outdoor living and community engagement. The Homes with Trail(s) Association offers a wealth of amenities that enhance the quality of life for its residents. Enjoy leisurely walks or invigorating bike rides along the scenic trails that wind through the community, allowing you to immerse yourself in the natural beauty of Hilton Head Island.

In addition to the trails, residents can take advantage of the community's social events, fostering connections with neighbors and creating lasting friendships. Whether you're enjoying a peaceful afternoon by the pool or participating in a neighborhood gathering, Windward Village is designed to cultivate a sense of belonging.

With its prime location, stunning homes, and a vibrant community, Windward Village is more than just a place to live—it's a lifestyle waiting for you to embrace. Come and discover the charm of this beautiful subdivision, where your dream home awaits!

Newest Windward Village Homes with Trail(s) Association amenities

$619,000

2 Beds ⋅ 3 Baths ⋅ 1,220 SqFt. ⋅ 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.

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.