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$259,990
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511405 MLS
Recently refreshed with fresh paint and stylish new furnishings, this ocean-oriented 2-bedroom villa is truly turnkey and ready to enjoy. Whether you're searching for a personal vacation getaway, an income-producing investment, or the perfect combination of both, 4104 Hilton Head Resort presents an exceptional opportunity. With existing reservations already in place, this villa offers immediate rental income potential while giving future owners the flexibility to enjoy everything Hilton Head Island has to offer. Located within the gated Hilton Head Resort community, owners and guests enjoy an impressive collection of resort-style amenities, including indoor and outdoor pools, tennis courts, a fitness center, game room, private beach access, and Coco's on the Beach. Conveniently situated near championship golf courses, shopping, dining, and miles of pristine beaches, this low-maintenance villa makes island living effortless. Whether you're expanding your investment portfolio, purchasing your own coastal retreat, or seeking a property that offers the best of both worlds, this beautifully updated villa delivers outstanding value in one of Hilton Head Island's most amenity-rich beach communities.

663 William Hilton Parkway Unit 4104, Hilton Head Island

Listing courtesy of Real Broker, LLC.

$975,000
2 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511564 MLS
Beautifully renovated 2BR/2.5BA home in the heart of Sea Pines offering exceptional privacy on a corner lot backing to protected open space and an adjacent unbuildable lot. From the charming courtyard entry with privacy gate to the expansive outdoor living space, every detail has been designed for comfortable everyday living and effortless entertaining. Open kitchen, dining and living areas, separate den with fireplace and built-ins, smooth ceilings, parquet floors, renovated kitchen and owner's bath, spacious guest suite, expansive deck with covered pergola, 2016 roof and 2023 Lennox HVAC, and parking for 3 cars. Located in one of Sea Pines' most welcoming neighborhoods where neighbors truly know one another. Located within the world-renowned Sea Pines Resort, owners enjoy easy access to miles of leisure trails, championship golf, beaches, tennis, pickleball, Harbour Town, South Beach Marina, restaurants, shopping, and countless outdoor activities. Whether you're searching for a primary residence, second home, or Lowcountry getaway, 33 Oak Court delivers privacy, comfort, and timeless appeal in one of Hilton Head Island's most sought-after communities.

33 Oak Court, Hilton Head Island

Listing courtesy of Charter One Realty.

$4,495,000
4 Beds ⋅ 5 Baths ⋅ HILTONHEAD-511638 MLS
A remarkable expression of Lowcountry luxury, this exceptional custom residence is perfectly positioned on a quiet cul-de-sac in the prestigious Port Royal community, offering the rare opportunity to enjoy both breathtaking marsh front living and easy access to the beach. Here, you don't have to choose between sweeping tidal marsh views and walking distance to the beach, this home offers both. Encompassing more than 4,600 square feet of thoughtfully designed single-level living, the home captures panoramic vistas of Fish Haul Creek, the tidal marsh, and the Atlantic Ocean beyond while blending timeless architecture with impeccable craftsmanship. From the impressive front elevation and grand wrought-iron staircase to the custom wood and glass entry doors, every detail has been carefully curated. Inside, soaring ceilings, custom millwork, coquina-shell columns, extensive stone flooring, designer lighting, walls of glass, and multiple fireplaces create warm yet sophisticated living spaces designed to showcase the surrounding natural beauty. The gourmet kitchen is a chef's dream, featuring premium Wolf, Viking, Bosch, and Sub-Zero appliances, custom cabinetry, generous prep space, and an adjoining butler's pantry with wet bar-ideal for entertaining. The luxurious primary suite serves as a private retreat with veranda access, custom walk-in closets, and a spa-inspired bath complete with heated stone floors, a soaking tub, oversized walk-in shower, and skylight. Two additional guest suites, a dedicated office, elevator access, and a spacious six-car climate-controlled garage provide exceptional flexibility for family and guests alike. Designed for year-round enjoyment, the outdoor living spaces are equally impressive. Expansive covered verandas, exposed cypress beams, an outdoor fireplace, built-in grilling area, professionally designed gardens, a custom hot tub with waterfall, and a private dock with a floating dock on Fish Haul Creek create an extraordinary setting for entertaining or simply enjoying the peaceful waterfront surroundings. Whether you're launching a kayak from your backyard, spending the afternoon on the beach just moments away, or watching spectacular sunsets over the marsh from your veranda, this one-of-a-kind estate offers an unparalleled coastal lifestyle in one of Hilton Head Island's most coveted communities.

127 Fort Walker Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,599,000
6 Beds ⋅ 4 Baths ⋅ HILTONHEAD-511679 MLS
Sandcastles by the Sea is a gated community gem centrally located mid-island and a 5-min walk (by direct bike path) to one of Hilton Head Island's most desired public beaches. This 6BR|4BA versatile luxury property has an array of opportunities including primary or secondary residence, multigenerational utilization, short/long term rental revenue or corporate investment for perks & prospects. Enjoy year-round swimming in the heated private pool or throw your cares to the southern breeze from a large balcony overlooking a wildlife haven in the neighborhood lagoon. An elevator provides seamless access to all three levels, offering everyday convenience while enhancing the home's comfort and refined design. Nestled within a gated, golf cart and low-speed vehicle-friendly community with nightly security patrols, this exceptional property offers the perfect blend of privacy, convenience, and coastal elegance. Just moments from the beach, the spacious residence is designed for effortless indoor-outdoor living, making it a rare opportunity to own a premier luxury retreat in one of Hilton Head Island's most desirable beachfront communities. Excellent rental history available upon request. House will be sold FULLY FURNISHED.

124 Sandcastle Court, Hilton Head Island

Listing courtesy of Beach House Boutique.

$7,950,000
HILTONHEAD-511653 MLS
An extraordinary opportunity to create a legacy oceanfront estate in one of Sea Pines most coveted locations. Offering an exceptional 100 feet of direct Atlantic Ocean frontage, this remarkable homesite is the first oceanfront lot to become available in this area in a long time. A rare opportunity. Tucked just off South Beach Lane, this premier property offers the chance to design and build a custom coastal retreat perfectly tailored to your vision. Wake to panoramic sunrises over the Atlantic, step directly onto the beach, and enjoy the privacy, prestige, and unmatched lifestyle that only true oceanfront ownership in Sea Pines can provide. Opportunities like this are extraordinarily scarce. If you've been waiting for the right oceanfront homesite to build your dream home, this is the moment.

15 Green Wing Teal Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$675,000
3 Beds ⋅ 4 Baths ⋅ HILTONHEAD-511291 MLS
Outstanding curb appeal and a quiet cul-de-sac location make this 3-bedroom, 3.5-bath home a rare opportunity in highly sought-after Hilton Head Plantation. Fresh interior paint creates a bright, inviting atmosphere, while the spacious floor plan is designed for comfortable everyday living and effortless entertaining. Enjoy a private, wooded homesite that offers peace, privacy, and beautiful natural surroundings. The home features generous living spaces, a butler's pantry, a dedicated laundry room, and an attached one-car garage. With its functional layout and timeless appeal, this home provides the perfect opportunity to make it your own. Hilton Head Plantation offers an exceptional coastal lifestyle with championship golf, tennis and pickleball, a deep-water marina, Dolphin Head Recreation Area, Spring Lake, miles of leisure trails, waterfront parks, and 24-hour gated security. Just minutes from beaches, shopping, dining, and all that Hilton Head Island has to offer. Private wooded views, outstanding curb appeal, and an unbeatable location combine to make this a home you won't want to miss.

34 Sweet Bay Lane, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$5,900,000
7 Beds ⋅ 8 Baths ⋅ HILTONHEAD-511606 MLS
Properties of this caliber are increasingly difficult to find in Sea Pines. 7 Bedroom/6.5 Baths PLUS Pool Bath, 2022 construction, designer furnished and just a 3-minute walk to the beach. Set on an oversized nearly 1/3-acre 3rd row homesite, this is the rare combination discerning buyers wait years to find. Custom construction and incredibly designed for effortless coastal living, the home showcases sophisticated finishes, soaring ceilings, a gourmet kitchen with a separate prep kitchen, and seamless indoor-outdoor living centered around a covered porch with an outdoor fireplace, summer kitchen, heated pool, and spa. Seven beautifully appointed bedrooms-including a first-floor primary suite and four ensuite guest suites-provide exceptional comfort and privacy, while multiple gathering spaces make the home ideal for entertaining family and friends. Combining exceptional quality, an oversized homesite, beach proximity, and one of Sea Pines' most desirable locations, this is a true legacy property offering the very best of coastal living. Current rental projections of approximately $349,000 annually.

10 Bald Eagle Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$1,370,000
3 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511499 MLS
Turn-key, fully renovated beach home in the highly sought-after Forest Beach area of Hilton Head Island, just a short walk to the beach, Coligny Plaza, restaurants, shopping, and grocery stores. Whether you're looking for a primary residence, second home, or vacation rental investment, this property checks every box. Pride of ownership is evident throughout. The updated kitchen features stainless steel appliances, a center island, and opens seamlessly to the spacious living room with a cozy fireplace, creating the perfect gathering space. The generous primary suite offers a private ensuite bath, while two additional bedrooms comfortably accommodate family and guests. Step outside to your own private backyard retreat featuring a fenced yard, oversized swimming pool, spa, putting green, cornhole area, hammock, grilling space, and outdoor shower, perfect for relaxing after a day at the beach or entertaining year-round. With no POA or HOA fees and an unbeatable North Forest Beach location, this move-in ready Hilton Head home offers exceptional flexibility as a personal getaway or income-producing investment.

8 Flamingo Street, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

$929,500
4 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511490 MLS
Discover the perfect Sea Pines getaway in this upgraded, fully furnished 4-bedroom, 3-bath townhome offering 1,820 sq ft of comfort and style. This beautifully updated villa overlooks a serene lagoon, creating the ideal Lowcountry backdrop for morning coffee or evening unwinding. With room to sleep 8 (possibly more) and short-term rental eligibility, it's an exceptional investment and a turnkey vacation retreat. Enjoy easy access to the community pool, tennis and pickleball courts, plus all the world-class amenities Sea Pines Resort is known for. A rare opportunity to own a spacious, move-in-ready home with views, convenience, and rental potential all in one!

7 Lake Forest Drive Unit APT 3366, Hilton Head Island

Listing courtesy of Real Broker, LLC.

$5,500,000
4 Beds ⋅ 5 Baths ⋅ HILTONHEAD-511537 MLS
Oceanfront Luxury in a Private Gated Community on Hilton Head Island. Experience the ultimate in coastal living with this exceptional oceanfront residence, perfectly positioned within one of Hilton Head Island's most private gated communities. Offering breathtaking Atlantic Ocean views, direct beach access, and thoughtfully designed living spaces, this remarkable home is the perfect blend of elegance, comfort, and Lowcountry charm. Designed for both everyday living and effortless entertaining, the home features four spacious bedrooms, including two luxurious primary suites, five full bathrooms, and two separate living areas, providing exceptional flexibility for family and guests. The light-filled main living area showcases soaring vaulted ceilings, expansive windows, a fireplace, and walls of glass that frame spectacular ocean views. Enjoy relaxing on the upstairs deck allowing you to enjoy the sights and sounds of the Atlantic from nearly every angle. The generous primary suites offer private retreats complete with spa-inspired baths and tranquil coastal vistas. The first floor living area also offers a fireplace. Stroll outside to a private pool, expansive patio, lush tropical landscaping, and a private walk leading directly to one of Hilton Head Island's most pristine beaches create an unparalleled outdoor experience. Towering live oaks provide timeless Lowcountry character while preserving privacy and natural beauty. Whether you're seeking a luxurious primary residence, a second home, or an extraordinary oceanfront retreat, this exceptional property delivers the rare combination of privacy, sophistication, and direct beachfront living in one of Hilton Head Island's most coveted locations.

21 Barnacle Road, Hilton Head Island

Listing courtesy of Hilton Head Real Estate Partners.

$3,499,995
5 Beds ⋅ 6 Baths ⋅ HILTONHEAD-511517 MLS
Welcome to 164 Mooring Buoy-where timeless coastal elegance meets one of Palmetto Dunes' most coveted beachside locations. Perfectly positioned on the second row with direct access to the beach walkway, this exceptional five-bedroom, five-and-a-half-bath residence offers an effortless connection to more than three miles of Hilton Head Island's pristine Atlantic shoreline. Thoughtfully designed for sophisticated coastal living, this remarkable home blends timeless architecture, generous living spaces, and exceptional indoor-outdoor entertaining. A majestic canopy of centuries-old live oaks and a gracious circular drive create a memorable arrival, while the two-car garage and abundant parking provide convenience for family and guests alike. Impeccably maintained and thoughtfully updated, every detail reflects the pride of ownership and quality craftsmanship that define this extraordinary property. At the heart of the home, the beautifully appointed kitchen flows seamlessly into the expansive great room, where walls of glass invite natural light and open to an impressive outdoor living space. Step onto the spacious rear deck overlooking a sparkling heated pool and spa-your own private sanctuary for afternoon relaxation, evening gatherings, or peaceful mornings surrounded by the beauty of the Lowcountry. The luxurious main-level primary suite offers comfort and privacy, while four additional ensuite guest bedrooms provide elegant accommodations for family and friends. Multiple living and gathering spaces ensure everyone has room to relax, entertain, or create lasting memories after a day on the beach, golf course, or tennis courts. Whether hosting unforgettable celebrations, enjoying quiet moments beneath the oaks, or embracing the endless recreational opportunities of Palmetto Dunes, this home embodies the very essence of refined island living. Equally suited as a distinguished primary residence, an exceptional coastal retreat, or a premier investment with outstanding rental potential, 164 Mooring Buoy presents a rare opportunity to own an extraordinary beachside home within one of Hilton Head Island's most prestigious resort communities.

164 Mooring Buoy, Hilton Head Island

Listing courtesy of Charter One Realty.

$500,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511533 MLS
Unlike any Admiral's Row villa you've seen before, this extraordinary 2 bedroom, 2 bath end-unit ocean view villa has been reimagined from the studs out into a stunning, open-concept coastal retreat. Brand new to the market, every detail has been thoughtfully redesigned to create a spacious, modern floor plan that offers exceptional functionality, comfort, and style.No expense was spared in this top-to-bottom renovation, including all new electrical wiring, plumbing, ductwork, HVAC system, water heater, flooring, drywall, cabinetry, quartz countertops, appliances, lighting, fixtures, and finishes. Both bathrooms feature beautiful walk-in tiled showers with integrated heaters, and dehumidification systems to provide year-round comfort in Hilton Head's coastal climate. Both sliding glass doors have been upgraded with impact-rated hurricane sliders, providing peace of mind and energy efficiency.Designed for everyday living as much as vacation enjoyment, this villa offers abundant storage rarely found in beach properties, making it an ideal primary residence, second home, or high-performing investment property. Wide hallways and oversized doorways provide easy accessibility for wheelchairs and walkers, offering convenience without sacrificing style.As a desirable 4th floor end unit, not far from the elevator, you'll enjoy added privacy, extra natural light, and fabulous ocean views, all just steps from the sandy beaches of the Atlantic Ocean. The extensive improvements continue beyond the villa itself, with the building featuring a brand-new fire sprinkler system and the $40,000 special assessment already paid in full by the seller, offering tremendous value for the next owner.Located in the heart of Hilton Head Island's popular Folly Field beach area, Admiral's Row offers an exceptional resort lifestyle with direct beach access, an oceanfront Olympic-size swimming pool, beach bar and café, sports bar, tennis courts, pickleball courts, fitness center, and beautifully maintained grounds. Explore more than 60 miles of Hilton Head Island's renowned leisure pathways, with shopping, dining, golf, entertainment, and everyday conveniences just minutes away.Whether you're looking for your forever beach home, a luxurious island getaway, or a proven income-producing vacation rental, this one-of-a-kind ocean view villa offers a rare opportunity to own one of the most extensively renovated residences in Admiral's Row.

40 Folly Field Road Unit 434, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$329,900
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511507 MLS
Beautifully updated, fully furnished 2-bedroom, 2-bath end-unit villa located in the highly sought-after Hilton Head Beach & Tennis Resort. Whether you're looking for a turnkey vacation home, a full-time residence, or an established investment property, this villa offers the perfect combination of comfort, convenience, and coastal living. The bright, open floor plan features luxury vinyl plank flooring, an updated kitchen with newer appliances, tasteful coastal décor, and a private balcony overlooking the pickleball courts. Being offered fully furnished, this villa is truly move-in or rental ready. Located just a short walk from the beach, owners and guests enjoy access to an impressive array of resort amenities, including one of Hilton Head's largest oceanfront pools, three on-site restaurants, a beach bar, pickleball and tennis courts, a fitness center, bike rentals, playground, 24-hour gated security, and beautifully maintained grounds. Ideally situated near Coligny Plaza, Shelter Cove, Harbour Town, championship golf courses, shopping, dining, and miles of scenic bike paths, this property offers everything buyers love about Hilton Head Island. With a strong rental history and exceptional resort amenities, this is a rare opportunity to own a beautifully maintained coastal retreat with outstanding investment potential.

40 Folly Field Road Unit APT E17, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$35,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511529 MLS
Why own more than you can use? Premium location and walking distance to the beach! Ocean Palms is a 1/5th deeded fractional ownership property allowing each owner 10 weeks of use per year on a calendar rotation of 2 weeks back to back 5 times annually. Management by the Westin Oceanfront Resort & Spa allows use of the hotel amenities, fitness center, oceanfront pool complex, beach access and resort shuttle. A great golf & tennis package is included with ownership. This wonderful 2 bedroom/2 bath designer furnished 2nd floor Sanibel floor plan has 1350 htd sq ft, screened porch & balcony, and overlooks the front pool area. Onsite open house/model villa open most days.

14 Wimbledon Court Unit 204-1, Hilton Head Island

Listing courtesy of Hilton Head Properties.

$1,850,000
4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-511500 MLS
Experience the best of Hilton Head living in this beautifully designed home within the highly sought-after Port Royal Community. Perfectly positioned directly across from the residents' beach path, the Atlantic Ocean is less than 0.3 miles away, making beach days part of everyday life.Thoughtfully designed with exceptional bedroom separation, this predominantly single-story home offers 4 bedrooms and 4 baths, including a guest suite above the garage that can be closed off from the main home offering comfortable space for extended family or homeowners. The welcoming floor plan features a gracious foyer, formal dining room, spacious living room with a fireplace, and an inviting kitchen with counter seating, a sun-filled breakfast nook, and an adjoining great room with a second fireplace. The screened porch and expansive deck overlook the 11th fairway of the Barony Course, creating a peaceful backdrop for relaxing or entertaining.The spacious primary suite offers a calm and restful setting with a walk-in closet, dual vanities, a soaking tub, a separate shower, and a water closet. Two additional ensuite guest rooms are privately situated in their own wing.Set on a generous 0.636-acre homesite with room for a pool, this 3,218-square-foot home is part of one of Hilton Head Island's premier residential communities, where short-term rentals are prohibited. Residents enjoy private beach access, an oceanfront beach house, leisure trails, tennis, pickleball, gardens, 24-hour security, and optional membership to the Port Royal Golf Club.

108 S Port Royal Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$825,000
3 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511473 MLS
Experience the charm of coastal living at 45 Night Heron, a beautifully positioned Sea Pines beach cottage just a five-minute stroll to Hilton Head Island's renowned beaches. This light-filled 3-bedroom, 2-bath retreat offers an open floor plan with soaring vaulted ceilings, creating an inviting space for gathering and relaxing. Ample enclosed storage beneath the home provides room for beach gear, bicycles, and more. Night Heron has its own private community pool. Harbour Town, South Beach, Sea Pines Beach Club, & the Plantation Golf Club are just moments away by way of 17 miles of picturesque leisure trails. Located near the Ocean Gate for easy island access and only minutes from the shopping, dining, and entertainment of Coligny Plaza, this property is perfectly suited as a primary residence, vacation home, or high-performing rental investment.

45 Night Heron Lane, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$399,500
3 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511307 MLS
Lowest-Priced 3-Bedroom Condo on Hilton Head Island. Turnkey Short-Term Rental Steps from the Beach. Discover the most affordable 3-bedroom villa on Hilton Head Island, a rare opportunity for investors and vacation home buyers alike. This spacious 3-bedroom, 2-bathroom condo sits just steps from the beach and Coco's oceanfront restaurant and bar. Completely transformed with stylish laminate flooring, smooth ceilings, and updated tile showers, it offers a fresh, modern feel throughout. Sold fully furnished with in-unit laundry, the villa is entirely move-in ready, whether for guests or your own getaway, and comes with a proven short-term rental history that helps generate income to offset ownership costs. Residents also enjoy a gated, resort-style community with 24/7 security, a fitness center, indoor track, indoor pool and spa, game room, pickleball, an on-site restaurant, six tennis courts, and two outdoor pools. With unbeatable amenities and a price point unmatched on the island, this villa won't last. Schedule your showing today.

663 William Hilton Parkway Unit 3321, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$7,400,000
4 Beds ⋅ 6 Baths ⋅ HILTONHEAD-511454 MLS
Cross your private bridge into one of Hilton Head Island's most discreet and protected oceanfront enclaves. Stella del Mare is one of only three beachfront communities on Hilton Head Island where short-term rentals are not permitted, ensuring year-round privacy, security, and a consistently quiet residential environment. This 4-bedroom, 5.5-bath Mediterranean estate offers a rare alternative to the island's oceanfront rentals. Positioned along the coveted Bradley Beach shoreline, this gated enclave of three Oceanfront homes and two 2nd row parcel provides expansive Atlantic views without the weekly rental influx common elsewhere. Originally featured nationally for its design and architectural significance, Stella del Mare set a new benchmark for luxury construction. Built by skilled European craftsmen using imported and timeless materials, the residence showcases hand-laid walnut flooring, carved travertine, silk wall coverings, Venetian glass, and custom wrought-iron detailing. Many architectural elements were sourced internationally to achieve authenticity and permanence rarely replicated today. Constructed using the Hebel Block system for superior durability, strength, and insulation, this home was designed to endure for generations. Every detail reflects substance over trend. Outdoor living includes a private courtyard, freshly renovated pool and spa, elevator access, and multiple oceanfront balconies designed for quiet sunrise mornings and uninterrupted coastal views - without the transient traffic associated with short-term rental communities. Recent enhancements include complete exterior stucco refinishing in 2024; replacement of numerous exterior windows, new geothermal HVAC system, and complete pool renovation demonstrating continued investment and meticulous care. This property presents the perfect offering for the discerning buyer seeking a legacy beachfront residence in a gated, owner-focused community - where privacy, architectural integrity, and long-term enjoyment take precedence.

3 Stella Del Mare Manor, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$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.

$317,500
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511441 MLS
1st floor action packed Hilton Head Beach and Tennis resort; bike, tennis, swim, and of course pickle ball! Really clean 1st floor corner unit great views of the lagoon and courts. Freshly painted and cleaned.

40 Folly Field Road Unit E1, Hilton Head Island

Listing courtesy of Realty One Group - Lowcountry.

$2,499,000
4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-510784 MLS
Welcome to this 4 bedroom Sea Pines getaway! Lagoon and majestic live oaks in the backyard with private pool, gazebo and beautiful guest cottage. This updated single-level home offers the relaxed coastal lifestyle that makes Sea Pines one of Hilton Head Island's most sought-after destinations. Thoughtfully renovated and offered beautifully furnished, the home blends timeless Lowcountry charm with modern updates, making it ready to enjoy from day one.Inside, the open-concept floor plan is designed for gathering. The updated kitchen flows seamlessly into a bright and inviting family room with custom built-ins and a convenient desk nook for remote work or vacation planning. New flooring, updated lighting, and stylish finishes create a fresh, welcoming atmosphere throughout.The main house features three spacious bedrooms, while a separate guest cottage provides additional space for extended family, friends, or vacation guests. The flexible layout is ideal for second-home owners looking to maximize both enjoyment and rental potential.Step outside and discover the true magic of this property. A private Savannah brick courtyard surrounds the sparkling pool, creating an intimate outdoor retreat perfect for entertaining, relaxing, and making memories. Beyond the pool, a picturesque lagoon meanders through the backyard beneath a canopy of live oaks, providing a beautiful natural backdrop filled with Lowcountry wildlife and year-round scenery. A charming waterside gazebo offers the perfect spot for morning coffee, afternoon reading, or evening cocktails as the sun filters through the trees.Located in the heart of Sea Pines, owners and guests enjoy easy access to beaches, championship golf, miles of leisure trails, Harbour Town, South Beach Marina, shopping, dining, and all the amenities that have made Hilton Head Island a premier vacation destination for generations.Whether you're searching for a family retreat, a second home, or an investment property with proven vacation rental appeal, this exceptional Sea Pines residence delivers the best of island living.

37 Woodbine Place, Hilton Head Island

Listing courtesy of Hilton Head Properties.

$35,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511423 MLS
Why own more than you can use? Premium location and walking distance to the beach! Ocean Palms is a 1/5th deeded fractional ownership property allowing each owner 10 weeks of use per year on a calendar rotation of 2 weeks back to back 5 times annually. Management by the Westin Oceanfront Resort & Spa allows use of the hotel amenities, fitness center, oceanfront pool complex, beach access and resort shuttle. A great golf & tennis package is included with ownership. This wonderful 2 bedroom/2 bath designer furnished 2nd floor Sanibel floor plan has 1350 htd sq ft, a screened porch & balcony, and overlooks the front pool area. Onsite open house/model villa open daily.

14 Wimbledon Court Unit 202-1, Hilton Head Island

Listing courtesy of Hilton Head Properties.

$2,100,000
4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-511413 MLS
Located in the heart of Harbour Town within Sea Pines, this beautifully appointed home offers the perfect blend of luxury, comfort and coastal charm. Enjoy easy access to iconic Harbour Town Yacht Basin, Lighthouse, shops, waterfront dining, renowned golf, miles of leisure trails and a short drive or shuttle to magnificent Hilton Head beaches. The home features 4 bedrooms and 4 bathrooms with expansive deck and pool. Ideal for entertaining, unwinding from a day at the beach or golf course. Whether you're seeking a full-time residence, vacation retreat or an investment property, this exceptional home captures the very best of the Sea Pines lifestyle.

8 Windjammer Court, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate.

$25,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511398 MLS
Why own more than you can use? Premium location and walking distance to the beach! Ocean Palms is a 1/5th deeded fractional ownership property allowing each owner 10 weeks of use per year on a calendar rotation of 2 weeks back to back 5 times annually. Management by the Westin Oceanfront Resort & Spa allows use of the hotel amenities, fitness center, oceanfront pool complex, beach access and resort shuttle. A great golf & tennis package is included with ownership. This wonderful 2 bedroom/2 bath designer furnished 1st floor Captiva floor plan has 1300 htd sq ft, a spacious back deck, and overlooks the back pool area. Onsite open house/model villa open daily.

14 Wimbledon Court Unit 135-5, Hilton Head Island

Listing courtesy of Hilton Head Properties.

$1,199,000
5 Beds ⋅ 6 Baths ⋅ HILTONHEAD-511235 MLS
Private Golf Course Estate with Guest House, Bonus Suite & Climate-Controlled Workshop - Nestled within the highly sought-after community of Hilton Head Plantation, this exceptional golf course property offers a rare combination of privacy, flexibility, and space. Surrounded by mature trees and enhanced by an adjacent non-buildable lot, the property provides a peaceful setting while remaining close to all the amenities Hilton Head Island has to offer. The main residence features generous living areas, abundant natural light, and beautiful golf course views. Designed for comfortable everyday living and entertaining alike, the home offers spacious gathering areas and seamless access to outdoor living spaces. A standout feature of the property is the private guest residence with its own entrance, full kitchen, laundry, living area, one bedroom, and one-and-a-half baths. Whether used for extended family, visiting guests, a home office, or private retreat, the space offers exceptional versatility. Car enthusiasts, hobbyists, and makers will appreciate the detached three-car garage, including a climate-controlled bay ideal for a workshop, collector vehicle, fitness area, golf simulator, or year-round projects. Above the garage, a finished bonus suite complete with a full bathroom and closet provides additional flexible living space perfect for guests, recreation, work-from-home needs, or a private studio. Outdoor living is equally impressive. A spacious paver patio overlooks the mature landscape and golf course setting, creating an inviting space for entertaining, dining, and relaxing throughout the year. A full-yard irrigation system helps keep the grounds looking their best with minimal effort. Significant improvements provide added peace of mind, including a roof replacement in 2016 and three HVAC systems replaced within the last five years. This is a rare opportunity to own a property that offers the flexibility of multiple living spaces, the privacy of an oversized setting, and the lifestyle advantages of one of Hilton Head Island's premier gated communities.

14 Field Sparrow Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$2,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511359 MLS
Owner is also selling Week 17 (Unit 2900) and is open to offering a discounted price if both weeks are purchased together - an excellent opportunity to enjoy two consecutive weeks in paradise! Experience the relaxed sophistication of Hilton Head Island during deeded Week 16, ideally positioned in the last week of April, when spring is in full bloom and the island is at its most beautiful. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of Hilton Head's most sought-after communities. This desirable end-unit villa, located next to the pool, offers added privacy, extra natural light, and exceptional convenience. Overlooking the lush fairways of the golf course, it provides peaceful views and a tranquil backdrop throughout your stay. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and the vibrant coastal arts and culture that make Sea Pines so special. Imagine beginning your mornings with refreshing ocean breezes and serene golf course views before setting out to bike beneath towering live oaks along miles of shaded pathways. Spend your afternoons on award-winning fairways, relaxing on the beach, or exploring the island's natural beauty before unwinding with spectacular waterfront sunsets. Late April offers warm, comfortable temperatures, colorful spring blooms, and ideal conditions for beach walks, outdoor dining, dolphin cruises, tennis, and all that Sea Pines has to offer-before the peak summer crowds arrive. Whether you prefer championship golf, coastal adventures, or simply relaxing on your private balcony overlooking the greens, everything you need is right at your doorstep. With the option to purchase the adjoining Week 17 at a discounted package price, this is a rare opportunity to enjoy two consecutive weeks in one of Hilton Head Island's premier vacation destinations.

70 Lighthouse Road Unit 2896, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$1,900
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511357 MLS
Owner is also selling Week 16 (Unit 2896) and is open to offering a discounted price if both weeks are purchased together-an excellent opportunity to enjoy two consecutive weeks in paradise! Enjoy the relaxed sophistication of Hilton Head Island during deeded Week 17, ideally positioned in the first week of May when the island is at its springtime best. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most sought-after settings. This desirable villa overlooks the lush fairways of the golf course, providing peaceful views and a tranquil backdrop throughout your stay. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and a vibrant coastal arts and culture scene. Imagine beginning your mornings with refreshing ocean breezes and serene golf course vistas, then setting out to bike beneath towering live oaks along miles of shaded pathways. Spend your afternoons on award-winning fairways, relaxing on the beach, or exploring the island's natural beauty before unwinding with spectacular waterfront sunsets. May's comfortable temperatures and blooming landscapes create the perfect setting for beach walks, outdoor dining, dolphin cruises, and all that Sea Pines has to offer-without the crowds of peak summer. Whether you prefer championship golf, coastal adventures, or simply relaxing on your private balcony overlooking the greens, everything you need is right at your doorstep. With the option to purchase the adjoining Week 17 at a discounted package price, this is a rare opportunity to enjoy two consecutive weeks in one of Hilton Head Island's premier vacation destinations.

70 Lighthouse Road Unit 2900, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$935,000
3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511355 MLS
Pristine, thoughtfully updated residence with Sams Point Pond and distant tidal marsh views on quiet/private "eyebrow" street in much preferred Elliott Point area of popular HHP. Features and recent updates include soaring vaulted/tray smooth ceilings, custom built-ins throughout by master craftsmen, quartz counters, designer fixtures/hardware/lighting/window treatments, wood/tile/carpet flooring, stainless steel appliances, wood burning fireplace w/marble hearth, ceiling fans, walls of windows, sliding glass doors to view, skylights & transom windows providing excellent natural light, whole house dehumidifier system, impressive closet & storage space, pocket doors, etc. Very livable open floor plan boasts expansive great room, dining room, comfortable 4 season Carolina Room, well-appointed island kitchen (max cabinet & counter space), casual dining, stylish wet bar, powder room, laundry, ample primary suite (4 closets including 2 large walk-in closets), guest BR suite, Den/Media Rm/3rd BR and 2 car garage. Exterior offers attractive/durable cypress wood exterior, secluded rear deck, aggregate shell walkway, professionally maintained, mature plantings & lawn, specimen trees & irrigation system. All with charming curb appeal and primo location close to all HHP has to offer including Spring Lake Village Pool Complex, CCHH, Safe Harbor Marina, waterfront Dolphin Head Recreational Area and recently renourished Pine Island Beach Park. What's not to love about this home and Hilton Head Plantation!

312 Seabrook Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$448,000
1 Beds ⋅ 1 Baths ⋅ HILTONHEAD-511346 MLS
Another fantastic direct oceanfront villa at HHBT. This one has an open bedroom with lovely luxury vinyl flooring throughout. Lovely backsplash in kitchen. Sit on your sofa and view the ocean. Need more room? Buy A 224 and A 225 to accommodate a larger family.

40 Folly Field Road Unit A225, Hilton Head Island

Listing courtesy of C 21 A Low Country Realty.

$3,450,000
5 Beds ⋅ 5 Baths ⋅ HILTONHEAD-511130 MLS
Built in 2018 by May River Custom Homes, 24 Rum Row delivers luxury coastal living in a coveted Palmetto Dunes location, where high-end construction is notably enhanced with wide (11-mile) lagoon views, a private dock, and convenient beach access! Impressively designed and professionally decorated, this FIVE-bedroom retreat features wide-plank wood floors, 8' solid-core doors, coffered ceilings, upgraded lighting, a gas fireplace, multiple laundry rooms, and impressive open living spaces on both levels. The chef-style kitchen shines with quartz countertops, a large island, a professional gas range, a pot filler, a pantry, and current features/finishes. Seamless indoor/outdoor living includes a large (screened) porch, private swimming pool, a covered poolside kitchen with a Napoleon grill, outdoor lounging/dining areas, and tranquil pool-to-lagoon views. High Quality throughout, numerous coastal-inspired finishes, a double garage, strong rental appeal, and offered fully furnished.

24 Rum Row, Hilton Head Island

Listing courtesy of Collins Group Realty.

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