Windward Village Homes with Pool Association amenities

Welcome to Windward Village, a hidden gem nestled in the heart of Hilton Head Island, South Carolina. This charming subdivision offers a perfect blend of coastal living and community spirit, making it an ideal choice for families, retirees, and anyone seeking a serene lifestyle. With its lush landscapes and picturesque surroundings, Windward Village embodies the essence of island living.

One of the standout features of this desirable community is the exclusive Homes with Pool Association. Residents enjoy access to a stunning pool area that serves as a social hub for neighbors and friends alike. Imagine warm afternoons spent lounging by the pool, soaking up the sun, or hosting delightful gatherings with loved ones. The pool area is meticulously maintained, providing a refreshing escape just steps from your front door.

In addition to the pool, Windward Village boasts an array of amenities designed to enhance your lifestyle. Whether you’re taking leisurely strolls along the scenic pathways, enjoying the nearby parks, or taking advantage of the close proximity to pristine beaches, every day feels like a vacation. The community fosters a welcoming atmosphere, encouraging residents to connect and engage through various social events and activities throughout the year.

With its prime location in Beaufort County, Windward Village offers easy access to Hilton Head Island's vibrant dining, shopping, and recreational options. Experience the perfect blend of relaxation and adventure as you explore the island's natural beauty and rich cultural offerings.

Discover your dream home in Windward Village, where every day is a delightful escape in paradise!

Newest Windward Village Homes with Pool 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.

$509,900

2 Beds ⋅ 2 Baths ⋅ 1,061 SqFt. ⋅ HILTONHEAD-506348 MLS

Refreshed and move-in ready! Great opportunity to be in Shipyard! This light and bright end-unit villa features a rare first-floor living floor plan and is ideally located in the hidden gem of Windward Village. Just inside the back gate of Shipyard, this fee-simple home offers walkable access to everything the Coligny area has to offer while enjoying the peace and privacy of a gated community with three 9-hole golf courses and an on-site pool with hot tub. The first-floor primary suite allows for easy, stair-free living and includes a newly remodeled full bath and generous closet space. Also on the main level are a spacious living room, built-in office alcove, and a large dining area highlighted by a wall of windows with unobstructed golf course views. The kitchen is equipped with all-new stainless steel appliances. Upstairs, you'll find a large, versatile loft currently used as a second bedroom, complete with a full bath and an oversized walk-in closet. Recent upgrades include a newly rebuilt rear deck, composite front deck, updated plumbing, new carpeting, and luxury vinyl flooring. This charming villa is ideal for full-time living, a vacation retreat, or taking over a successful 5-star rated short-term rental program with bookings already in place.

109 Windward Village Drive, Hilton Head Island

Listing courtesy of Charter One 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.