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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.

$509,500
1 Beds 2 Baths 1,215 SqFt. HILTONHEAD-511373 MLS
Escape to this beautifully appointed, fully furnished, spacious 1-bedroom, 1.5-bath villa located in the prestigious Shipyard Community. Offering comfort, convenience, and easy access to Hilton Head's best attractions, this two-story townhome is an ideal getaway for couples, small families, or a relaxing solo retreat. Villa Highlights: Primary Suite is a spacious upstairs bedroom with a king-sized bed, ample storage, and a private ensuite bath. Additional Sleeping Space: Queen sleeper sofa in the living area. Open Living Area: Bright and inviting main level with comfortable seating, cable TV, books, and board games for unwinding after a day of adventure. Chef's Kitchen: Fully equipped with ample pantry space, cookware, and everything you need for meal preparation and entertaining - SS appliances & granite countertops accent the space. New water heater in 2026. Private Outdoor Deck: Cozy seating for morning coffee or evening cocktails. Laundry Convenience: Full-sized washer and dryer tucked into the upstairs hallway closet. Community Features: Beach Access: A scenic 10-15 minute walk along shaded paths to Shipyard's Beach Access Boardwalk. Pool & Sundeck: The community pool is conveniently located just outside your front door and open daily from sunrise to sunset (April 1-October 31).Tennis & Golf: Access Van Der Meer Tennis Club, Shipyard Racquet Club, and a 27-hole championship golf course. Biking Trails: Miles of picturesque paths wind through Shipyard and connect to the island's scenic routes.

113 Shipyard Drive Unit 162, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$659,000
2 Beds 3 Baths 1,380 SqFt. HILTONHEAD-511116 MLS
Come to the beach! This beautifully updated villa features newly remodeled bathrooms, a renovated kitchen and downstairs living area with an open-concept design. New Air Conditioner and Hot water heater, Smooth ceilings, recessed lighting, with an abundance of natural light creating a bright modern atmosphere, while the spacious living area overlooks the 7th fairway of the Shipyard Galleon Golf Course. Ideally located just steps from the beach, Van Der Meer Tennis Center, and The Sonesta Resort, this villa offers the perfect blend of relaxation and convenience. Residents and guests can also enjoy an oversized community pool and pool house. Whether you're looking for a high-performing short-term rental investment, a second home, or a full-time residence on Hilton Head Island, this exceptional property is an outstanding opportunity. Home can be fully furnished by Staging company for approximately $10,000.00.

113 Shipyard Drive Unit 200, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$569,000
2 Beds 3 Baths 1,548 SqFt. HILTONHEAD-507543 MLS
Beautifully updated 2-bedroom, 2.5-bath townhome in Golfmaster, located within the gated Shipyard community. This villa offers spacious living with an open-concept floor plan, abundant natural light, and scenic golf and lagoon views. The main level features a bright living and dining area with crown molding, fireplace, and access to a private porch overlooking the golf course and lagoon. The kitchen is well-appointed with granite countertops, stone backsplash, and a breakfast bar, opening seamlessly to the dining area. Upstairs, both bedrooms offer en-suite baths and private access to a second-floor balcony with elevated golf and lagoon views. The primary suite includes a walk-in tile shower and separate soaking tub. Additional highlights include multiple outdoor living spaces and a functional layout ideal for full-time living or a second home. Golfmaster amenities include a private pool, tennis courts, and pickleball courts. Shipyard offers gated security, leisure trails, golf, and access to beach amenities.

1 Gloucester Road Unit 103, Hilton Head Island

Listing courtesy of Charter One Realty.

$700,000
2 Beds 3 Baths 1,400 SqFt. HILTONHEAD-508081 MLS
Ideally positioned just off the beach path in Shipyard, this updated villa offers easy access to both the sand and pool, along with a strong history as a short-term rental. Set in the closest building to the beach within the villa complex, the location offers a distinct advantage for both owners and guests. This beautifully updated villa, renovated within the past five years, is a proven short-term rental with a solid track record. The interior features quality upgrades throughout, including custom tile showers, updated flooring, and a well-designed kitchen and living area that balance style and functionality. Step outside to a spacious rear deck that opens directly to the beach path, offering quick and easy access to the sand. The community pool is just steps away, creating an ideal setup for vacationers seeking both beach and pool access. Shipyard is a gated, 800-acre community located in the heart of Hilton Head's south end, known for its convenient access by bike to beaches, golf, tennis, and nearby amenities. Residents and guests enjoy direct beach access via the Shipyard Beach Club, as well as access to Van Der Meer Tennis Center and Shipyard Golf Club's 27 holes. The community's central location near Coligny makes it especially attractive for both personal use and rental demand. An excellent opportunity for investors or second-home buyers seeking a turn-key property with proven income potential in one of Hilton Head's most established resort communities.

125 Shipyard Drive Unit 124, Hilton Head Island

Listing courtesy of ELEVE PROPERTIES Brokered by EXP Realty.

$635,000
2 Beds 3 Baths 1,536 SqFt. HILTONHEAD-508226 MLS
Rare Sailmaster 2 bedroom, 2 1/2 bath directly overlooking the golf course. Enter through a private fenced gate to your own front courtyard. Featuring LVP throughout the unit, fresh paint & remodeled with many updates. Kitchen is updated & equipped with all appliances & everything needed down to the silverware. Upstairs bathrooms are updated & the bedrooms each have a private bath. New lighting fixtures with ceiling fans installed in every room. Both bedrooms have sliders going out to sitting balconies. Walk outside the main living area through sliding glass doors to your own private patio with grill, table, chairs & over look the golf course fairway. Pets only allowed by Owners. Fully furnished with everything you see, except the current tenants personal belongings. Including Brand New Flat Screen TV's in all rooms! Long Term Rental in place - lease expires 2/28/2027 - must honor lease. Buyers to verify all information

26 Sailmaster Common Unit 26, Hilton Head Island

Listing courtesy of Hilton Head Real Estate Partners.

$1,325,000
3 Beds 3 Baths 2,122 SqFt. HILTONHEAD-504945 MLS
Beautifully renovated 3-bedroom, 2.5-bath home set on a private 0.75-acre lot in the gated, beachfront community of Shipyard Plantation. This home is in excellent condition and has been thoughtfully redesigned throughout, featuring new white oak hardwood flooring, an updated kitchen with all new appliances, smooth painted ceilings, and new Andersen Windows. Additional upgrades include new attic insulation, and a new HVAC system with updated ductwork. The spacious layout offers a first-floor dedicated office and large primary suite complete with a sunroom, while two generously sized guest bedrooms are located upstairs-providing excellent separation and flexibility. The living room showcases high ceilings and abundant natural light, enhanced by elegant finishes, new lighting fixtures, and ceiling fans. All bathrooms have been fully and tastefully renovated with tile showers, a jetted tub, new vanities, and marble flooring, it's all been done for you. Custom wood trim work and molding can be found throughout, adding a refined touch to every space. The exterior features durable new siding, and a newly added side-entry two-car garage enhances both functionality and curb appeal. Each bedroom includes sliding doors with access to a patio or private balcony, seamlessly blending indoor and outdoor living. Surrounded by over 100 beautiful trees, the property offers exceptional privacy along with scenic golf views, creating a peaceful, resort-like setting. There is also ample room to add a full-size pool. Residents of Shipyard enjoy outstanding amenities, including private beach access, miles of leisure trails, golf, tennis facilities, and the security of a gated community-all in a prime location close to everything Hilton Head has to offer. Bike to the beach with ease and enjoy the best of coastal living

20 Gloucester Road, 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.

$740,000
3 Beds 3 Baths 1,987 SqFt. HILTONHEAD-504572 MLS
This beautiful 3BR/3BA fully furnished villa offers the perfect blend of luxury & comfort. This serene getaway offers views overlooking the 6th fairway on Shipyard's Clipper golf course. Vaulted ceilings enhance the sense of space and light throughout the main living areas, while plentiful windows invite natural light and connect the indoors to the beautiful natural surroundings. A sunny Carolina Room with a fireplace and large windows invites natural light and fresh coastal breezes, perfect for enjoying an early cup of coffee or evening cocktail while gazing at the lush landscape and the fairway. Boasting 3 large bedrooms and 3 full bathrooms, a sunny Primary bedroom with an ensuite full bath with oversized garden tub and separate shower. The 2 secondary bedrooms complete the bedroom layout: one with an ensuite bath, the other with access to the 3rd full bath. This villa is designed to accommodate both families and guests comfortably. The floorplan provides desirable separation between the generous primary suite and the secondary bedrooms, ensuring privacy for all. Smart TVs are found throughout the villa. The beautifully updated kitchen is complete with new kitchen cabinets & SS appliances; it offers ample cabinetry and countertop space - perfect for meal preparation, entertaining, or simply enjoying a quiet morning at home. Residents and guests will love Golfmaster II's amenities, featuring a gated community pool with bathroom facilities, walking distance to pickleball/tennis and basketball courts, and a seasonal shuttle stop for quick trips to the Shipyard Beach Club. Just minutes from private beach access & HHI's South End, providing an ideal setting for a relaxing coastal escape. Miles of leisure trails & a short drive or bike ride to Coligny Plaza's local shops & restaurants or the many golf courses offered both in Shipyard and on HHI.

1 Gloucester Road Unit E-2, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$775,000
3 Beds 4 Baths 1,820 SqFt. HILTONHEAD-503593 MLS
Just steps to the beach, this 3-bedroom, 3.5-bath Beachwalk villa in Shipyard Plantation on Hilton Head Island is the perfect blend of income potential and easy coastal living. Designed with vacationers in mind, the flexible floor plan features two separate living areas-ideal for relaxing after beach days or accommodating multiple guests. The updated kitchen showcases white wood cabinetry and stainless steel appliances delivering the fresh, coastal look renters love. Newly renovated bathrooms and freshly painted interiors set the tone throughout, while charming coastal shiplap accents add texture and character. Light-filled interiors, numerous updates, and spacious bedrooms offer comfort for owners and guests alike. Sold turn-key and fully furnished, with short-term rentals allowed, this villa is ready to enjoy as a second beach home while generating rental income when not in use. Located in gated Shipyard Plantation with 24-hour security, golf, tennis, bike paths, and more--this is Hilton Head Island living at its best.

125 Shipyard Drive Unit 110, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$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.

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