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$639,000
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.

$1,150,000
4 Beds ⋅ 4 Baths ⋅ 2,486 SqFt. ⋅ HILTONHEAD-511190 MLS
A rare 4-bedroom villa in Shipyard that lives more like a home than a condo! Not used as a rental, this spacious residence offers an ideal primary-home feel with generous living areas, a gated front courtyard, fireplace, plantation shutters, smooth ceilings, solid-core doors, cherry wood flooring, and high-end finishes throughout. The impressive kitchen will please any chef, and three sets of updated French doors bring in natural light and provide access to an oversized rear patio. Set within an approximately 23-acre regime with a lighted paver walkway to the pool, this property benefits from a strong regime with reserves, no special assessments, and fees that include insurance, cable, internet, and water. Buildings were recently painted in 2026. A special opportunity in Shipyard with rare size, quality, and flexibility - the seller would like to sell in 2026 and welcomes all offers.

63 Shipyard Drive Unit 1806, Hilton Head Island

Listing courtesy of Collins Group Realty.

$599,000
2 Beds ⋅ 3 Baths ⋅ 1,530 SqFt. ⋅ HILTONHEAD-508444 MLS
Beautifully furnished and updated 2 bedroom, 2.5 bath villa in very popular Shipmaster community. Great outdoor spaces. Large bedrooms can accommodate multiple bedding configurations for rental market. The living area has an oversized slider that overlooks an extended patio in a park like setting. The second floor has 2 large bedrooms with ensuite baths and sliding doors to private balconies. Walk, bike or drive .7 miles to the Shipyard Beach Club and boardwalk access. Close to private community pool and private tennis/pickleball court and a short walk to beach. Amazing rental potential, ideal for a primary residence or relaxing getaway.

63 Shipyard Drive Unit 1703, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

$35,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-508179 MLS
Coastal Retreat! This is your opportunity to own a deeded 2-bedroom, 2-bath quartershare at Brigantine Quarters in Shipyard with 13 rotating weeks yearly. Unit 292 offers serene lagoon from the back porch. This mini-resort includes tennis, pickleball, pools, playground, and private beach gate for BQ owners and guests. Maintenance charge covers appliances, furniture, maintenance upkeep, taxes, Shipyard HOA, and more, ensuring a stress-free experience, ideal for personal use, trade, or rentals.

55 Barcelona N Road Unit 292B, Hilton Head Island

Listing courtesy of The Homesfinder Realty Group.

$749,000
3 Beds ⋅ 3 Baths ⋅ 2,000 SqFt. ⋅ HILTONHEAD-507555 MLS
Beautiful and bright 3BR 3BA. End unit. Spacious & inviting living & dining areas with a vaulted ceiling & open to a kitchen with stainless appliances & all the essentials for cooking & entertaining. A large Carolina room can provide cozy space or become your work from home office while enjoying a lovely long lagoon view. Large master suite with generous master bath & large walk in closet. Each guest bedroom has its own private bath. Beautifully appointed with very tasteful furniture, light fixtures & accessories including smooth ceilings. Community pool, tennis and pickleball court. Perfect as primary home or as an investment property.

1 Gloucester Road Unit J-2, Hilton Head Island

Listing courtesy of Charter One Realty.

$559,000
2 Beds ⋅ 3 Baths ⋅ 1,200 SqFt. ⋅ HILTONHEAD-504659 MLS
Move-in ready, year-round vacation cottage, located along the Brigantine course in Hilton Head's private Shipyard community. Fully furnished and move-in ready with flooring, kitchen counters, backsplash and appliances updated in 2022. The home has been tastefully decorated with a blend of beach casual and updated finishes. Enjoy lower cost of ownership with Cottages II parking and drive recently resurfaced as well as new roofing installed. Perfect unit for Hilton Head gateway or investment/rental property. Shipyard is a great, gated community with all the amenities one expects such as golf, tennis, pools, beach access. Nearby Sonesta Resort offers use of pool and beach access for a daily fee through Resortpass.com. Convenient access to both William Hilton Parkway and Pope Avenue provide easy access to Hilton Head's popular dining, entertainment, and shopping options. Come see for yourself!

12 Valencia Road Unit 20, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$35,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-503793 MLS
Coastal Retreat! This is your opportunity to own a deeded 2-bedroom, 2-bath quartershare at Brigantine Quarters in Shipyard with 13 rotating weeks yearly. Unit 292 offers serene lagoon from the back porch. This mini-resort includes tennis, pickleball, pools, playground, and private beach gate for BQ owners and guests. Maintenance charge covers appliances, furniture, maintenance upkeep, taxes, Shipyard HOA, and more, ensuring a stress-free experience, ideal for personal use, trade, or rentals.

55 Barcelona Road Unit 292C, Hilton Head Island

Listing courtesy of The Homesfinder Realty Group.

$850,000
3 Beds ⋅ 4 Baths ⋅ 2,500 SqFt. ⋅ HILTONHEAD-503372 MLS
Great opportunity to make this Hilton Head Island home your own. Just minutes from the beach and surrounded by world-class golf! Overlooking a beautiful golf course view, this property features 3 spacious bedrooms, each with private ensuites, oversized living areas, and abundant storage, offering comfort and functionality for every lifestyle. Situated near the back gate of Shipyard, you'll enjoy easy access to Coligny Plaza, Celebration Park, shopping, dining, and entertainment, all while being tucked away in a peaceful setting. Imagine starting your mornings with a bike ride along the islands scenic paths, spending afternoons on the world-famous beaches, and evenings exploring Hilton Heads vibrant culinary scene. This home is ideal as a primary residence, vacation retreat, or income-producing investment. With the ability to be used as a short-term rental, it provides outstanding flexibility and potential. Discover the perfect blend of coastal charm, golf course living, and investment opportunity in one of Hilton Heads most desirable locations!

52 Cordillo Parkway, Hilton Head Island

Listing courtesy of Maxey Blackstream Christie's International Real Estate.

$1,375
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-502467 MLS
Carolina Club by Spinnaker - Hilton Head Island - 1 float week -You pick the week in advance and BOOK IT! VALUE here the 2026 maint. fee has been paid! The unit / townhome villa features two-bedrooms are suited for up to six people. This quiet townhome contains a fully equipped kitchen, washer and dryer, spacious dining and living area with entertainment center. You can also relax outside on the private deck.Hilton Head is truly a destination with a bit for everybody, relaxation, beaches, sport activities, bike trails, walking areas, shopping, evening fun just to name a few.Amenities are like two on-site pools, clubhouse, tennis courts, a playground, complimentary bicycle rental, children's activities and golf privileges at Golden Bear Course and more.Yearly maintenance fee is $1K.

200 Southwind Drive Unit # 225, Hilton Head Island

Listing courtesy of Realty One Group - Lowcountry.

$40,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-501788 MLS
Welcome to your coastal getaway! Own a deeded 2BR, 2BA quartershare at Brigantine Quarters in Shipyard. Enjoy 13 rotating weeks a year in this beautifully designed residence with vaulted ceilings and a large balcony. This mini-resort includes tennis, pickleball, pools, playground, and private beach gate for BQ owners and guests. Maintenance charge covers appliances, furniture, maintenance upkeep, taxes, Shipyard HOA, and more, ensuring a stress-free experience, ideal for personal use or rentals.

55 Barcelona Road Unit 226-1, Hilton Head Island

Listing courtesy of The Homesfinder Realty Group.

$32,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-501467 MLS
Great opportunity in the highly desired Brigantine Quarters behind the gates of Shipyard! With 13-weeks of annual usage, this 2 BR/2 BA second floor flat is on a rotating schedule and has an incredible long lagoon view. Your maintenance fee covers everything from taxes, insurance, to toasters! It's a great way to have a worry-free place at the beach. Two community pools (one heated seasonally) - plus allt he amenities that go along with Shipyard!

55 Barcelona Road Unit 274B, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$579,000
2 Beds ⋅ 2 Baths ⋅ 1,270 SqFt. ⋅ HILTONHEAD-500510 MLS
This updated first-floor villa in Shipyard is the second home (or full-time escape) you've been looking for. With peaceful lagoon views and a peek at the fairway beyond, this 2-bedroom, 2-bath retreat makes island living easy. Tucked inside one of Hilton Heads most sought-after gated communities, it's all about comfort, simplicity, and coastal style. Inside, the single-level layout flows easily from the open living and dining area into a renovated kitchen with granite counters, modern cabinetry, and smooth ceilings. The flooring has been upgraded, both bathrooms have a clean, updated look, and the entire space feels fresh and inviting. It's being sold fully furnished so just bring your suitcase. Whether you're using it as a second home, renting it out, or moving in full-time, this place is ready to go. It's also smartly set up for real life. The guest room has bunk beds for extra sleeping space, and there's a private outdoor storage closet for your bikes, beach gear, or golf clubs. As a ground-floor villa, its super accessible. No large stairway to climb! The walk-out balcony puts you just steps from the lagoon. Location-wise, you're in the sweet spot. A short stroll takes you to the beach path, with Shipyards private Beach Club, golf courses, and top-notch tennis and pickleball courts nearby. The community's bike trails wind through gorgeous Lowcountry scenery, mature oaks, quiet lagoons, and peaceful roads. When you're done exploring, the pool is the perfect place to cool off or catch up with neighbors. Shipyard is known for its ideal south-island location. It's close to restaurants, shops, and everything else Hilton Head has to offer. Whether you're after a vacation base, rental property, or a full-time home, this one checks all the right boxes. Clean, comfortable, turnkey, and in one of the islands most charming communities. Don't let this one slip by.

200 Colonnade Drive Unit 201, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$499,000
2 Beds ⋅ 2 Baths ⋅ 1,086 SqFt. ⋅ HILTONHEAD-453890 MLS
Discover coastal living at its finest in this beautifully maintained 2 bed, 2 bath home nestled in a secluded enclave within the prestigious 24-hour gated community of Shipyard. Vaulted ceilings and abundant natural light enhance the open living space, while the updated primary bathroom adds a touch of modern luxury. Enjoy serene mornings on the expansive front porch and take advantage of ample storage with attic space and a rare 2-car garage. No weekly rentals ensure a peaceful, family-friendly atmosphere. With beach access, scenic walking paths, golf, and tennis amenities just moments away, this is Lowcountry living at its best.

30 Valencia Drive Unit 7B, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

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