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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.

$310,000
2 Beds ⋅ 2 Baths ⋅ 888 SqFt. ⋅ 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.

40 Folly Field Road Unit E1, Hilton Head Island

Listing courtesy of Realty One Group - Lowcountry.

$2,499,000
4 Beds ⋅ 4 Baths ⋅ 2,982 SqFt. ⋅ 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 ⋅ 3,531 SqFt. ⋅ 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.

$825,000
3 Beds ⋅ 3 Baths ⋅ 2,446 SqFt. ⋅ HILTONHEAD-511207 MLS
Located in the desirable Skull Creek area of Hilton Head Plantation, this great 3BR, 2.5BA home with a two car garage is awaiting its next owner. The hardcoat stucco, lagoon and golf course views, cul-de-sac street and easy access from both gates add to the appeal. The current owners have enjoyed the property as a second home and have done numerous updates over the years. Priced to allow the new owner to put their personal touch, the home is being sold "as is" however inspections are welcomed.

12 Golden Hind Drive, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$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.

$1,250,000
5 Beds ⋅ 6 Baths ⋅ 4,083 SqFt. ⋅ 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.

$965,000
3 Beds ⋅ 3 Baths ⋅ 2,588 SqFt. ⋅ 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 ⋅ 540 SqFt. ⋅ 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 ⋅ 4,240 SqFt. ⋅ 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.

$269,000
1 Beds ⋅ 1 Baths ⋅ 540 SqFt. ⋅ HILTONHEAD-511205 MLS
Own a piece of paradise on the Atlantic Ocean at an affordable price. Cute 1 bedroom top floor condo located in the open Y of the building and close to the elevator at Hilton Head Beach and Tennis Resort. Located on the quiet marsh side of Building C with some ocean views from the balcony. Fully furnished and turnkey ready making rental income. Enjoy all of the amenities that HHBT ocean front resort offers including a huge beach front pool, seasonal beach/pool cafe, year-round on-site restaurant, gated with 24-hour security, onsite pickleball, tennis, and gym. Come and see this one as its perfect for renting and/or second home.

40 Folly Field Road Unit C302, Hilton Head Island

Listing courtesy of Beechee Coastal Properties, LLC.

$2,500,000
3 Beds ⋅ 4 Baths ⋅ 2,869 SqFt. ⋅ HILTONHEAD-511247 MLS
Experience the quintessential beachside lifestyle in this residence reminiscent of historic, coastal cottages of years past. The home's interior wraps you in rich character with washed pine walls, crisp painted wood ceilings, and beautifully refinished pine floors, striking balance between nostalgic coastal elegance and modern sophistication. The heart of the home kitchen appointed with 6-burner Viking gas cooktop, convenient refrigerator drawers, a warming drawer, wine cooler and spacious pantry. Included are stone countertops and island with bar seating, open to Great Room and Carolina Room/Dining overlooking water view. Split-floorplan prioritizes privacy with the Owners ensuite and lounge occupying one wing overlooking the water view separated by a gallery hallway leading to two private guest ensuites in separate wing. Enjoy peace of mind with updated operating systems including backup whole-house generator, newer HVAC and ductwork, tankless water heater, new plumbing pipes, young roof & spray foam insulation beneath main floor. Exterior painted within the last 4 years and features high-end permeable driveway & walkway pavers, blending curb appeal with eco-friendly design. Just an easy, short stroll away from two community pools and the sandy shore, this home offers move-in-ready, oceanside living at its finest!

31 Ocean S Point, Hilton Head Island

Listing courtesy of Charter One Realty.

$6,295,000
6 Beds ⋅ 8 Baths ⋅ 4,247 SqFt. ⋅ HILTONHEAD-510633 MLS
Experience the pinnacle of oceanfront luxury with endless, unobstructed views of the Atlantic Ocean from this spectacular beachfront retreat on Singleton Beach. Perfectly positioned on one of Hilton Head Island's most coveted stretches of shoreline, this exceptional residence (remodeled in 2021) captures breathtaking eastern sunrises, panoramic coastline views, and the soothing sound of waves gently rolling onto the beach.Designed for effortless coastal living, this fully furnished, turnkey home spans three beautifully appointed levels and features six spacious bedrooms and seven and one-half bathrooms. The open-concept main living area is thoughtfully designed for gathering and entertaining, seamlessly connecting the gourmet kitchen, dining area, and expansive great room with breathtaking Atlantic Ocean views.Outdoor living is equally exceptional. A private oceanfront pool with an elevated sun deck overlooks the beach, creating the perfect setting for entertaining or quiet relaxation. Covered balconies on every level invite you to enjoy sweeping ocean vistas and refreshing coastal breezes, while a private boardwalk provides direct access to the pristine white sands of Singleton Beach.Thoughtfully designed for both comfort and convenience, the home also features an elevator serving all three levels, an oversized garage, abundant storage, and a spacious secondary living room that offers the perfect gathering space for family and guests.Whether envisioned as a primary residence or an extraordinary coastal retreat, this remarkable property presents a rare opportunity to own one of Hilton Head Island's premier oceanfront homes.Life on Singleton Beach is defined by natural beauty, tranquility, and effortless recreation. Enjoy more than 12 miles of pristine sandy beaches, spectacular Atlantic sunrises, refreshing ocean breezes, and all the world-class amenities that have made Hilton Head Island one of America's most celebrated coastal destinations. Every sunrise over the Atlantic reminds you that this is more than a home-it's one of Hilton Head Island's most extraordinary oceanfront experiences.

10 Collier Beach Road, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

$2,700,000
3 Beds ⋅ 3 Baths ⋅ 2,060 SqFt. ⋅ HILTONHEAD-511230 MLS
3 bedroom, 3 bath direct oceanfront The Sea Crest Villa located in North Forest Beach area. Excellent rental history but can be permanent residence. Open floor plan with nice balcony. The Sea Crest has a fitness center, community pool, direct oceanfront access and elevator for easy entry. Located directly across from The Sea Crest is Coligny Plaza with many restaurants, shopping, and grocery store. These units rarely come available.

10 N Forest Beach Drive Unit 3203, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$845,000
3 Beds ⋅ 3 Baths ⋅ 1,876 SqFt. ⋅ HILTONHEAD-511226 MLS
Take advantage of this unique opportunity to own an updated 3-Bedroom home in the sought-after Hilton Head Plantation. Ideally located just a short distance from Dolphin Head Beach Park & Pine Island, the home also sits conveniently between Dolphin Head Recreation Area and the Spring Lake Pool & Tennis Complex, offering easy access to some of the community's most desirable amenities. Adding to its appeal, the property comes with a long-term tenant in place through July 1, 2027, providing immediate rental income of $3,700 per month plus utilities. This is an excellent opportunity to purchase at today's prices while generating steady income until you're ready to make Hilton Head Plantation your permanent residence, seasonal retreat, or retirement home.

3 Deerfield Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,099,000
3 Beds ⋅ 2 Baths ⋅ 2,047 SqFt. ⋅ HILTONHEAD-511126 MLS
STEPS TO THE BEACH AND PRICED AT LOT VALUE!! Discover the perfect blend of Lowcountry charm, privacy, and coastal living in this beautifully maintained 3-bedroom, 2-bath home, ideally situated on a sprawling and exceptionally private .58-acre golf course homesite beneath a magnificent canopy of mature specimen oak trees. Located in the highly sought-after Port Royal Plantation, this one-level residence offers effortless living with an inviting open floor plan designed for both everyday comfort and entertaining.Just steps from Port Royal's private beach access, you'll enjoy morning walks along the Atlantic shoreline, breathtaking sunrises, and the relaxed lifestyle that makes Hilton Head Island one of the country's premier coastal destinations. Whether you're searching for a primary residence, second home, or investment opportunity, this property offers an unbeatable combination of location, privacy, and community amenities.Inside, the spacious open-concept layout seamlessly connects the living, dining, and kitchen areas, creating a bright and welcoming atmosphere. A huge all-seasons Carolina Room overlooks the expansive backyard and golf course, providing the perfect space to relax, entertain guests, or simply enjoy the peaceful views year-round.Recent improvements provide peace of mind, including all new plumbing throughout the home allowing you to move in and immediately enjoy everything this exceptional property has to offer. The one-car garage provides convenient storage for your vehicle, beach gear, and outdoor equipment.The oversized homesite is one of the property's most remarkable features, offering incredible privacy, abundant outdoor living potential, and stunning mature landscaping rarely found today. Towering live oaks create a picturesque Lowcountry setting while framing beautiful golf course views. This lush oasis also features plenty of room for a pool. Ownership in Port Royal Plantation includes access to an outstanding collection of private amenities. Residents enjoy two championship 18-hole golf courses, a private oceanfront community pool, a beachfront clubhouse exclusively for property owners, an exceptional tennis center, walking and leisure trails, 24-hour gated security, and one of Hilton Head Island's most pristine stretches of private beach.This is a rare opportunity to own a beautifully updated home on one of Port Royal Plantation's largest and most private golf course lots-all within an easy stroll to the beach.

4 Robbers Row, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$299,000
2 Beds ⋅ 2 Baths ⋅ 843 SqFt. ⋅ HILTONHEAD-511168 MLS
Beautifully Renovated 2-Bedroom Villa with Direct Pool Views - Closest Building to the Beach! This is the beach getaway you've been waiting for! This stunning, fully renovated 2-bedroom villa at Hilton Head Resort offers a beautiful direct view of the heated outdoor pool from your front porch. No detail has been overlooked in this top-to-bottom renovation. Upgrades include shiplap accent walls, stylish barn doors, smooth ceilings, new ductwork, luxury vinyl plank flooring with a coastal feel, recessed lighting, closet lighting, all-new ceiling fans and light fixtures, a completely remodeled kitchen with new cabinetry, countertops, and appliances, plus beautifully updated bathrooms. The primary bath even features a lighted makeup magnifying mirror for added convenience. Sold fully furnished, this villa is truly turnkey - start enjoying it immediately after closing, whether as your personal beach retreat or a vacation rental investment. Hilton Head Resort offers an outstanding lineup of resort-style amenities, including: 7-minute walk to the beach or seasonal golf cart shuttle service. Poolside restaurant just downstairs. Oceanfront bar and grill. Indoor heated pool. Two outdoor pools, including another heated pool just outside your kitchen window! Indoor 1/10th mile jogging track, Hot tub, sauna, and steam room. Tennis and pickleball courts, Beach volleyball, Fitness center, Kiddie pool and Picnic area with BBQ grills. Whether you're looking for a second home, investment property, or both, this beautifully updated villa combines an unbeatable location, exceptional amenities, and true move-in-ready convenience. Come experience everything this incredible property and The Hilton Head Resort have to offer!

663 William Hilton Parkway Unit 1223, Hilton Head Island

Listing courtesy of Hilton Head Isl Realty.

$325,000
2 Beds ⋅ 2 Baths ⋅ 831 SqFt. ⋅ HILTONHEAD-511159 MLS
Welcome to Unit 4129 at Hilton Head Resort, a beautifully furnished 2-bedroom, 2-bath villa offering the perfect blend of comfort, convenience, and resort-style living. This turnkey property features durable tile and laminate flooring throughout, making it ideal as a primary residence, vacation getaway, or investment property.The fully equipped kitchen boasts granite countertops, maple cabinetry, and a cozy dinette area for casual dining. Have peace of mind knowing the HVAC was just replaced 2023! The villa is being sold fully furnished and includes TVs in every room, a sleeper sofa for additional guests, and everything needed to begin enjoying the coastal lifestyle immediately.Relax on the private covered porch overlooking the outdoor tennis courts and swaying palm trees-a peaceful setting to enjoy your morning coffee or unwind after a day at the beach.Hilton Head Resort offers an exceptional array of amenities, including private beach access via a scenic boardwalk or complimentary golf cart shuttle, six free tennis courts, two outdoor pools, an indoor heated pool, indoor hot tub, sauna, steam room, fitness center with Nautilus equipment, indoor running track, badminton, volleyball, picnic areas, bicycling, and nearby surfing opportunities. Owners and guests also enjoy the oceanfront cabana and Coco's on the Beach, the resort's popular beachfront bar and grill. Free Wi-Fi is available throughout the resort. Ideally located just minutes from Palmetto Dunes, Shelter Cove, championship golf, shopping, dining, entertainment, and all that Hilton Head Island has to offer, Unit 4129 is your opportunity to own an affordable slice of paradise with outstanding rental potential.

663 William Hilton Parkway Unit 4129, Hilton Head Island

Listing courtesy of Family Tides Real Estate LLC.

$250,000
2 Beds ⋅ 2 Baths ⋅ 917 SqFt. ⋅ HILTONHEAD-510820 MLS
Turnkey Hilton Head rental-ready villa with an outstanding rental track record and a practical layout designed for easy everyday use, a beach getaway, or income-producing ownership...the interior offers comfortable living space, a defined kitchen area, and an easy flow that keeps the unit simple to use, maintain, and rent...located just a short walk to the ocean, this property gives owners and guests convenient access to Hilton Head beaches, shopping, dining, and resort-style amenities...the community offers BEACH ACCESS, 2 outdoor pool areas, an indoor pool, heated/solar community pool, sauna, fitness center, tennis, pickleball, basketball, walking paths, playground, picnic area, outdoor grilling, security gate, on-site management, continual security, and landscape maintenance...monthly regime fee includes cable, internet, water, sewer, pest control, building maintenance, landscaping, garbage service, and insurance.

239 Beach City Road Unit 3234, Hilton Head Island

Listing courtesy of Real Broker, LLC.

$999,000
3 Beds ⋅ 3 Baths ⋅ 2,410 SqFt. ⋅ HILTONHEAD-510685 MLS
Beautifully updated and thoughtfully designed, this 3BR/2.5BA home in Hilton Head Plantation offers the kind of light-filled living that never goes out of style. Soaring ceilings, skylights, and expansive windows create an open, airy feel, while mature landscaping and golf course views provide a peaceful backdrop from nearly every room. The updated eat-in kitchen is the heart of the home, featuring plenty of storage, a large island, and an easy flow into the family room, living room, and Carolina Room. The spacious primary suite offers a private retreat with generous closet space and an updated bath complete with dual vanities, a soaking tub, and a large walk-in shower. Two additional bedrooms provide plenty of room for family, guests, or a home office. Step outside to enjoy the expansive patio and beautifully landscaped yard overlooking the golf course, where privacy, nature, and outdoor living come together effortlessly. Complete with a two-car garage and located in amenity-rich Hilton Head Plantation, this is a home that feels as good as it looks.

11 Annabella Lane, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$2,850,000
5 Beds ⋅ 5 Baths ⋅ 3,220 SqFt. ⋅ HILTONHEAD-510715 MLS
Welcome to your dream coastal retreat on Hilton Head Island. Nestled in the highly sought-after Hammock Breeze community, this stunning like-new waterfront home offers an unparalleled blend of luxury, convenience, and breathtaking natural beauty. Breathtaking views of the Atlantic Ocean and Port Royal Sound call to you from multiple expansive porches, while a newly built, private, secured walkway provides direct access to the pristine shores of Fish Haul Beach, one of the island's most beautiful waterfront parks.Inside, high-end touches and sophisticated craftsmanship abound across five spacious bedrooms and four elegant bathrooms. The newly refreshed interior features custom cabinetry in the kitchen and baths, deluxe flooring throughout, and cozy fireplaces that add warmth to the living room, family room, and bedrooms. On the lower level, a large and flexible tech/exercise room adapts effortlessly to your lifestyle, whether you envision a high-tech media hub, home office, or private gym. Complete with a brand-new back porch added in 2026, a spacious two-car garage, and a private elevator for ultimate convenience, this estate delivers the pinnacle of luxury waterfront living. This is the perfect home for beach lovers or investors looking for excellent short-term rental income.

34 Hammock Breeze Way, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$290,000
1 Beds ⋅ 1 Baths ⋅ 540 SqFt. ⋅ HILTONHEAD-511062 MLS
Beautifully REMODELED FIRST-FLOOR villa in the desirable A Building at Hilton Head Beach & Tennis Resort... this light-filled beach condo has been thoughtfully redesigned with a clean coastal feel, smart use of space, and a warm, inviting layout that feels comfortable from the moment you walk in... the kitchen is a true standout with CUSTOM CABINETS extended to the ceiling for a finished designer look, additional CUSTOM CABINETRY surrounding the refrigerator, full-sized stainless steel appliances, TILE BACKSPLASH, beautiful GRANITE countertops, and a large island with stool seating, extra storage, and generous prep space... the island serves as both a dining area and functional gathering space, creating a more open and comfortable floor plan... the layout also features KIDS BUNKS, POCKET DOORS for efficient use of space, SMOOTH CEILINGS, updated lighting, and LVP FLOORING throughout... the updated bathroom offers quality finishes, attractive coastal touches, and excellent craftsmanship... tucked along the quieter wing of the building, this villa enjoys a more private setting with less hallway traffic, refreshing breezes through the bedroom window, and peaceful views toward the Magnolia courtyard... offered FULLY FURNISHED and RENTAL READY, this villa is ideal as a primary residence, vacation home, or investment property... located just steps from the beach, owners and guests enjoy outstanding resort amenities including an oceanfront pool, beach bar and restaurant, tennis courts, pickleball courts, fitness center, playground, bike rentals, on-site laundry, 24-hour gated security, and easy access to one of Hilton Head Island's widest stretches of beachfront.

40 Folly Field Road Unit A145, Hilton Head Island

Listing courtesy of Real Broker, LLC.

$1,850
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511051 MLS
Enjoy the peaceful elegance of Hilton Head Island during deeded Week 45, perfectly timed for the crisp beauty of late autumn and, in many years, the Thanksgiving holiday. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most coveted settings. 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 island's rich coastal arts and culture scene.Imagine beginning your mornings with cool ocean breezes and uncrowded beaches, biking beneath majestic live oaks draped in Spanish moss, or spending leisurely afternoons on award-winning fairways before gathering with family and friends for memorable holiday meals or spectacular waterfront sunsets. Whether you're seeking a relaxing seasonal escape, an active golf retreat, or a warm-weather destination for Thanksgiving celebrations, Week 45 offers the perfect blend of tranquility, natural beauty, and island charm; all with the flexibility and convenience of deeded ownership.

70 Lighthouse Road Unit 2875, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$389,000
2 Beds ⋅ 2 Baths ⋅ 917 SqFt. ⋅ HILTONHEAD-511039 MLS
Enjoy breathtaking Port Royal Sound and lagoon views from this beautifully remodeled, prime villa at The Spa. The stunning kitchen features granite countertops, stainless steel appliances, and modern finishes. Both bathrooms have been completely renovated, including a spa-inspired tiled walk-in shower. Luxury vinyl plank flooring flows throughout, creating a fresh, Lowcountry modern feel. Relax on the spacious deck while taking in the peaceful water views. This turnkey property is an exceptional primary residence, vacation getaway, or high-performing rental. Resort-style amenities include 24-hour gated security, three outdoor pools, an indoor heated pool, hot tub, fitness center, tennis courts, and your own private beach just steps from the door. Everything has been thoughtfully updated-simply arrive, unpack, and enjoy coastal living at its best! Move right in and start making memories today!

239 Beach City Road Unit 1221, Hilton Head Island

Listing courtesy of Redfin Corporation.

$825,000
3 Beds ⋅ 2 Baths ⋅ 1,279 SqFt. ⋅ HILTONHEAD-510993 MLS
Turnkey Sea Pines Retreat with Proven Rental Income. Welcome to this beautifully updated single-level 3-bedroom, 2-bath townhouse nestled in one of Sea Pines' most peaceful and desirable communities. Offering the ease of one-level living, this furnished, move-in-ready home is the perfect primary residence, vacation retreat, or investment property, combining comfort, convenience, and outstanding income potential. The thoughtfully updated interior features luxury vinyl plank flooring, fully renovated bathrooms, vaulted ceilings in both the living room and primary bedroom, and an open, light-filled layout designed for relaxed coastal living. Recent improvements include a new water heater (2023), new HVAC system (2024), and freshly repainted exterior (2024), providing peace of mind for years to come. Enjoy your morning coffee on the private east-facing deck overlooking a tranquil lagoon, where herons, turtles, and other lowcountry wildlife create a peaceful natural setting. Multiple parking spaces are conveniently located directly outside the front door. Outdoor enthusiasts will appreciate being just a short walk from the Sea Pines Forest Preserve, offering miles of scenic walking trails and fishing lakes, as well as nearby Lawton Stables with horseback riding and a popular petting zoo. The Beach Club is just a 15-20 minute bike ride away, while the nearby Greenwood Gate provides quick and convenient access in and out of Sea Pines. The community features a large swimming pool with gazebo and grills, tennis courts, pickleball courts, well-maintained landscaping, and a low HOA. As a Sea Pines property owner, you'll enjoy access to world-class amenities including championship golf, tennis, the Sea Pines Beach Club, the private owner-only Tower Beach, Harbour Town, South Beach Marina, miles of leisure trails, dining, shopping, and everything that makes Sea Pines one of Hilton Head Island's premier resort communities. Being sold fully furnished, this turnkey property has generated $57,000 annually in documented annual short-term rental income while still allowing 15 weeks of owner use, a rare combination of strong investment performance and generous personal enjoyment. An elevation certificate is available, with the finished floor elevation measured at 7.3 feet, providing valuable information for insurance planning.

125 Greenwood Drive Unit 3423, Hilton Head Island

Listing courtesy of C 21 A Low Country Realty.

$1,175,000
3 Beds ⋅ 4 Baths ⋅ 2,842 SqFt. ⋅ HILTONHEAD-510376 MLS
A rare opportunity to create your own Hilton Head Island retreat inside Port Royal Plantation, one of the island's most established private coastal communities. Set on a generous .65-acre homesite, 10 Robbers Row offers 2,842 heated square feet, a spacious setting, and the kind of location, lifestyle, and long-term potential that is increasingly hard to find. Designed by noted Hilton Head architect Kurt Herrman, the home offers architectural character, light-filled living spaces, soaring 10-foot ceilings, and true hard-coat stucco construction. For the buyer with vision, this is more than a renovation opportunity - it is a chance to preserve, refresh, and reimagine a home with island pedigree in a sought-after Port Royal setting. Here is your chance to create something special in Port Royal Plantation - a custom Lowcountry retreat that can be personalized around the way you want to live on Hilton Head Island. Offered as-is and ready for its next chapter, 10 Robbers Row provides thefoundation, setting, and opportunity to bring that vision to life.

10 Robbers Row, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$850,000
3 Beds ⋅ 3 Baths ⋅ 1,970 SqFt. ⋅ HILTONHEAD-510798 MLS
Lightly lived in 3 bedroom, 2 full bath home on a Club Course cul-de-sac backing up to Newhall Nature Preserve.

12 Club Course Lane, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

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