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7 Windflower Court, Hilton Head Island
$499,900
3 Beds ⋅ 2 Baths ⋅ 1,462 SqFt. ⋅ HILTONHEAD-512479 MLS
Beautiful & updated coastal townhome for under $500,000 in highly desired Hilton Head Plantation! This stunning 3BD/2BA lock and leave townhome is perfect for anyone looking for maintenance free living. With a newer roof and a short walk to Spring Lake Pavillion where all your world class amenities are, this location is ideal. Spacious floor plan with large living area, one bedroom and full bathroom on the first floor. Find two additional bedrooms and one full bathroom upstairs. Step outside to a generous deck and patio area surrounded by natural foliage-ideal for morning coffee, evening gatherings, or simply enjoying the quiet Lowcountry setting. With its cul-de-sac location, proximity to Dolphin Head, miles of leisure trails, and the Plantation's signature amenities, this home delivers both privacy and convenience. Maintenance free living with regime covering trash, pest control and landscaping. Come enjoy everything Hilton Head Plantation has to offer with their high-end amenities and beautiful nature that surrounds the community!

7 Windflower Court, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

27 Beachwood Drive Unit 14, Hilton Head Island
$699,000
3 Beds ⋅ 3 Baths ⋅ 1,768 SqFt. ⋅ HILTONHEAD-512455 MLS
Most people don't know that this quaint neighborhood even exists - a real hidden gem. 3BR - 2.5 BT end unit townhome with added flex space, and best of all, NO POA fees! Updated, clean, pristine, and ready for a new owner. Spacious, open floor plan features smooth ceilings (cathedral in the GR), private bedroom locations, 2 full baths plus a downstairs powder room. On the first floor is the primary bedroom w/ large full bath and custom closets, laundry, office with custom built-ins (or 2nd bedroom), KT, and GR. On the second level, you have a full bedroom and full bath, plus a flex room that can be a den, office, or craft space. This end unit has so much glass for taking in the gorgeous golf views of Barony #5 fairway. On our chilly autumn nights, the custom-built fire pit will be the place to entertain family and friends. Oversized patio is private, but still has great golf views. Barony Woods has its own private beach gate for an easy 8-minute walk to the beach and a community pool. This is a residential community - no short term rentals allowed. Come and see your private Island getaway today.

27 Beachwood Drive Unit 14, Hilton Head Island

Listing courtesy of Charter One Realty.

65 Victoria Square Drive, Hilton Head Island
$650,000
4 Beds ⋅ 4 Baths ⋅ 1,939 SqFt. ⋅ HILTONHEAD-512286 MLS
Welcome to this charming Charleston-style 4-bedroom, 3.5-bath home overlooking the lagoon in the gated community of Victoria Square. Designed across three levels, the home offers a flexible floor plan with a true fourth bedroom and full bath on the first floor-ideal for giving guests a private space of their own-along with direct access to a spacious screened patio. The beautifully updated kitchen features crisp white cabinetry, stone countertops, a tile backsplash, and generous workspace, opening to a bright dining area surrounded by windows. The comfortable living room offers space to relax, a nook for your special piece of furniture or a convenient placement for a desk and flows onto an oversized screened porch, creating an inviting space for relaxing or entertaining while enjoying the lagoon setting. The third-floor primary suite opens to its own private balcony, while three distinct levels of outdoor living provide plenty of ways to enjoy Hilton Head's coastal climate. Additional features include a welcoming front porch, abundant storage, and a spacious tandem garage offering plenty of room for parking, a workshop, bikes, beach gear, and more. Centrally located on Hilton Head Island, Victoria Square offers low HOA fees and desirable amenities, including a community pool, playground, leisure trails, a two-acre lagoon, security gate, and convenient boat and RV storage. Shopping, waterfront dining, parks, and everyday conveniences are easily accessible...and the beach is a short ride away. This is an excellent opportunity to enjoy a spacious island home, flexible guest accommodations, and relaxed Lowcountry living in a convenient mid-island location.

65 Victoria Square Drive, Hilton Head Island

Listing courtesy of Keller Williams Realty.

315 Ceasar Place, Hilton Head Island
$489,000
4 Beds ⋅ 4 Baths ⋅ 2,022 SqFt. ⋅ HILTONHEAD-512139 MLS
Offering a level of space and flexibility rarely found in townhome living, this four-bedroom, 3.5-bath Allenwood residence pairs a versatile multi-level floor plan with peaceful lagoon views and multiple outdoor living spaces. Front and rear balconies extend from the main living level, creating natural places to enjoy the Lowcountry setting.A defining feature of the home is the private fourth-bedroom suite located off the garage, complete with a full bath, walk-in closet, and its own waterfront porch. Separated from the primary living areas, this space creates exceptional flexibility for guests, extended family, a home office, or additional living space.Inside, generous living areas accommodate both everyday life and entertaining, while the oversized one-car garage provides valuable parking and storage. Offered partially furnished and move-in ready, the home is well suited for a primary residence, second home, or investment property.Allenwood is a gated Hilton Head Island community offering a neighborhood pool and a convenient location near beaches, dining, shopping, recreation, leisure trails, and the Hilton Head Island school campus. With four bedrooms, abundant outdoor living, water views, and a floor plan that offers genuine versatility, this residence brings together space, privacy, and the ease of island living. Some images have been virtually enhanced with conceptual furnishings.

315 Ceasar Place, Hilton Head Island

Listing courtesy of Engel & Volkers.

23 S Forest Beach Drive Unit 176, Hilton Head Island
$369,000
1 Beds ⋅ 1 Baths ⋅ 518 SqFt. ⋅ HILTONHEAD-512275 MLS
Beautіfully renovаtеd 1BR/1ΒΑ vіlla іn thе oceanfront Seа Sіde Villas community, just steps from the beach and within easy walking distance of Coligny Plaza. This inviting retreat features granite countertops, custom cabinetry, stainless steel appliances, smooth ceilings, fresh flooring, new doors, and a spa-like renovated bathroom. The first-floor location offers easy access with gated entry and elevators, along with a community pool and direct beach access. Enjoy one of the best side ocean views and an unbeatable location near Coligny Beach Park, Lowcountry Celebration Park, shops, restaurants, and all that South Forest Beach has to offer. A fantastic opportunity for a second home or investment property in one of Hilton Head Island's most sought-after beach communities.

23 S Forest Beach Drive Unit 176, Hilton Head Island

Listing courtesy of Coastal Luxury Real Estate.

39 S Forest Beach Drive Unit 229, Hilton Head Island
$649,000
2 Beds ⋅ 2 Baths ⋅ 682 SqFt. ⋅ HILTONHEAD-512274 MLS
Turnkey 2BR/2BA condo with ocean views in the coveted Carolina Beach Club Villas. The condo features a refreshed kitchen with stainless steel appliances, updated cabinetry, and granite countertops, along with renovated bathrooms featuring granite vanities and ceramic tile flooring. Fresh paint, new trim, and six-panel doors throughout create a crisp coastal feel. The comfortable layout includes a king-size primary bedroom, a second bedroom with two twin beds, and a queen sleeper sofa in the den. Step onto the private balcony to enjoy ocean views, or take advantage of the resort's year-round pool, Jacuzzi, pool bar and grill, fitness center, and media room. With an elevator, convenient parking, and a private boardwalk providing direct beach access, this condo offers an ideal opportunity for a second home or investment property.

39 S Forest Beach Drive Unit 229, Hilton Head Island

Listing courtesy of Coastal Luxury Real Estate.

108 Lighthouse Road Unit 2330, Hilton Head Island
$499,000
1 Beds ⋅ 1 Baths ⋅ 761 SqFt. ⋅ HILTONHEAD-512273 MLS
Enjoу the best οf Ѕeа Ρіneѕ frοm this inviting 1BR cοndo іn Racquet Club Villas, ideally located near Harbour Town and overlooking a peaceful lagoon. The second-floor villa features an open living area with a private balcony, fully equipped kitchen, king-size primary bedroom, and queen sleeper sofa. Additional conveniences include an in-unit washer and dryer, Smart TV, and Wi-Fi. Owners and guests also enjoy access to the community pool and clay tennis courts, with the Harbour Town marina, shops, restaurants, and iconic lighthouse just a short stroll away. The Sea Pines Beach Club is only minutes away by car or seasonal trolley, making this a great opportunity for a vacation home or rental investment in one of Hilton Head Island's most sought-after communities.

108 Lighthouse Road Unit 2330, Hilton Head Island

Listing courtesy of Coastal Luxury Real Estate.

32 Hackney Pony Lane, Hilton Head Island
$1,249,000
4 Beds ⋅ 4 Baths ⋅ 3,126 SqFt. ⋅ HILTONHEAD-512185 MLS
Lake vіews, abundаnt nаtural lіght, аnd а sраcious corner ѕettіng define this 4BD/4BA home offering approximately 3,126 heated square feet. Positioned on a corner home site, the home enjoys water views from two sides for an added sense of openness and privacy. The main living level features an open layout with coffered ceilings, custom shiplap, fireplace, and gourmet kitchen, while generous windows fill the space with natural light. Just off the main living area, the screened balcony overlooks Lake Russell and provides a comfortable spot for morning coffee, evening sunsets, or simply enjoying the Lowcountry setting. A private elevator connects each level, including the climate-controlled ground floor, where you'll find one of the home's most memorable features, a custom "Little Big Bamboo" bar inspired by Hilton Head's Big Bamboo Cafe. An additional flex room provides space for a home gym, hobbies, or other creative uses. The three-door garage offers tandem parking for 4 cars plus plenty of room for a golf cart, bikes, beach gear, workshop space, and storage. With its corner location, lake views, flexible ground level, oversized garage, and thoughtful details throughout, this home offers the space and versatility to accommodate a variety of needs,interests, and lifestyles.

32 Hackney Pony Lane, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

111 Sutherland Way Unit 111, Hilton Head Island
$299,900
2 Beds ⋅ 3 Baths ⋅ 1,389 SqFt. ⋅ HILTONHEAD-512130 MLS
Hilton Head living without the Hilton Head price tag! This inviting 2-bedroom, 2.5-bath villa in The Gatherings offers a rare opportunity to own on Hilton Head Island at an approachable price point, with the added benefit of a low-maintenance lifestyle. Ideally positioned near the foot of the Hilton Head bridge, this location provides quick access to everything the Island offers while keeping Bluffton, Bluffton Parkway, shopping, dining, and everyday conveniences just minutes away. Inside, an updated kitchen opens to a generous dining and living area, creating a comfortable, spacious feel for everyday living or entertaining. Step outside to the wooden deck overlooking a peaceful lagoon setting-an ideal spot for morning coffee, relaxing at the end of the day, or simply enjoying the Lowcountry surroundings. What truly sets The Gatherings apart is its unique ownership structure. Although legally classified as a condominium, the community includes a variety of home styles, and the regime handles many major exterior responsibilities, simplifying ownership. Regime services include building maintenance, landscaping, insurance components, common water and sewer, pest control, refuse, pool maintenance, and more. The community also offers a pool, assigned parking, and a convenient residential setting. Whether you're looking for a primary residence, lock-and-leave second home, downsizing opportunity, or an affordable way to establish your Hilton Head Island address, this property delivers an appealing combination of location, lifestyle, and value.

111 Sutherland Way Unit 111, Hilton Head Island

Listing courtesy of EXP Realty LLC.

137 Cordillo Parkway Unit 6603, Hilton Head Island
$424,900
2 Beds ⋅ 3 Baths ⋅ 1,416 SqFt. ⋅ HILTONHEAD-512283 MLS
Welcomе to Treеtοpѕ, іdеallу lοcated in the heart οf Sοuth Forest Beach just minutes from the beach, Coligny Plaza, Celebration Park, shopping, dining, and miles of Hilton Head Island bike paths. This 2-bedroom, 2.5-bath townhome-style villa features an updated kitchen, LVP flooring, and a new HVAC system. The main level offers comfortable living and dining areas, a convenient powder room, and a private patio for enjoying the outdoors. Upstairs, both bedrooms and full baths offer added privacy, along with access to an upper-level balcony. Ideally situated within the community, this villa is one of the closest units to the pool. Treetops offers multiple community pools and tennis courts and is a pet-friendly community that allows short-term rentals while also being home to many full-time residents. Enjoy the relaxed Lowcountry lifestyle from this convenient South Forest Beach location-perfect as a primary residence, second home, or Hilton Head getaway.

137 Cordillo Parkway Unit 6603, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

77 Ocean Lane Unit 410, Hilton Head Island
$1,060,000
2 Beds ⋅ 2 Baths ⋅ 1,171 SqFt. ⋅ HILTONHEAD-512031 MLS
Open οcean vіеws, рrοvеn rentаlѕ, and Leamington prеstіge! 410 Barrington Court is a 2-bedroom / 2-bathroom villa with proven rental performance and projected annual gross rental revenue over $84K, offering a strong blend of income opportunity and second-home enjoyment within Palmetto Dunes Oceanfront Resort. Tucked in one of the most peaceful sections on Ocean Lane, the villa opens to an expansive private balcony designed for dining, lounging, and enjoying oceanfront views, with ocean views carried into both bedrooms. Consistently well maintained by the original owner, the villa features an ideal floor plan with spacious living and dining areas, bedrooms positioned on opposite sides for privacy, and a generous master suite with balcony access and a beautifully renovated walk-in shower. Recent improvements include all new LVP flooring, renovated bathrooms, fresh paint throughout including doors/trim/baseboards, HVAC (2020), dishwasher (2026), and new bedding (not pictured). Barrington Court offers an oceanfront pool and hot tub, pool pavilion with restrooms, grilling area, outdoor showers, covered parking, and designated owner storage locker in the garage for beach gear, golf clubs, and more-all set among beautiful lagoons, lush landscaping, and scenic walkways. Enjoy access to Palmetto Dunes' three miles of beach, tennis/pickleball, three golf courses, 11-mile lagoon system, trails, and dining, plus easy access across William Hilton Parkway to Shelter Cove Harbour & Marina for waterfront dining, shopping, watersports, seasonal activities and live entertainment.

77 Ocean Lane Unit 410, Hilton Head Island

Listing courtesy of Greenplate Group Brokered by eXp Realty.

90 Gloucester Road Unit 1003, Hilton Head Island
$739,000
3 Beds ⋅ 3 Baths ⋅ 1,558 SqFt. ⋅ HILTONHEAD-512113 MLS
Enjoу coaѕtаl livіng іn thіs bеаutifully updated 3-bedrοom, 2.5‐bath condo in Shipyard on Hilton Head Island. New windows and doors on the front of the condo add to the home's fresh, updated feel. The bright kitchen features white cabinetry, stainless steel appliances, a tiled backsplash, and a convenient breakfast/dining area. The spacious living room opens to a private patio and wooded surroundings, creating an inviting space to relax or entertain. The primary suite offers a generous bedroom, ceiling fan, and updated en-suite bath, while two additional bedrooms provide comfortable space for guests. Enjoy Shipyard amenities including a community pool, golf privileges, and easy access to Hilton Head's beaches.

90 Gloucester Road Unit 1003, Hilton Head Island

Listing courtesy of Peirce Group Brokered by EXP Realty LLC.

239 Beach City Road Unit 3123, Hilton Head Island
$275,000
2 Beds ⋅ 2 Baths ⋅ 917 SqFt. ⋅ HILTONHEAD-512308 MLS
Wake up to Lowcountry Beach living at its most effortless in this beautifully updated two bedroom, two bath villa at The Spa at Port Royal Sound, one of Hilton Head's most amenity rich resort communities. The photos will illustrate decor upgrade options, we have a full detailed plan available for use as a second residence or short term rental villa with income potential. Step inside to an open living and dining layout anchored by warm and inviting LVP flooring that flows throughout the main living space. The dining area sits open to a fully renovated kitchen finished with crisp white cabinetry, granite countertops, subway tile backsplash, and a full suite of stainless steel appliances including refrigerator, range, and dishwasher. It's a kitchen built for both everyday living and easy entertaining.The primary suite offers a private retreat with an en suite bath featuring a sleek frameless glass shower enclosure and clean, modern finishes. The second bedroom and full bath provide comfortable flexibility for guests, family, or a home office setup, with the guest bath finished in a soothing sage green palette, a tub and shower combo, and elegant sconce lighting. A washer and dryer inside the unit add everyday convenience that's hard to find at this price point in a resort community. Just off the living area, a screened porch extends your living space outdoors, the perfect spot for morning coffee or an evening breeze, overlooking lush landscaping with tennis court views just beyond the tree line. Beyond the walls of this villa, The Spa at Port Royal Sound delivers a well appointed resort lifestyle: two outdoor pools, an indoor pool, hot tub, dry sauna, tennis and pickleball courts, hammocks, and community grilling areas, all just steps from your front door. Whether you're looking for a full time coastal residence, a second home, or a turnkey investment property, this villa offers the space, updates, and lifestyle amenities that make Hilton Head living so desirable. Don't miss this opportunity to own a move in ready two bedroom villa in one of the island's best priced resort communities.

239 Beach City Road Unit 3123, Hilton Head Island

Listing courtesy of EXP Realty LLC.

239 Beach City Road Unit 1203, Hilton Head Island
$365,000
1 Beds ⋅ 1 Baths ⋅ 588 SqFt. ⋅ HILTONHEAD-512279 MLS
INVEЅTMEΝΤ AᏞΕRΤ! Thіѕ beautiful gem consіstеntly generates impressive rental income; $52,000 in 2025, and on tract to do the same for 2026, $48,500 in 2024, $42,000 in 2023 and $42,800 in 2022. DIRECT SOUNDFRONT, a Proven rental machine at The Spa on Port Royal Sound. This 1BR/1BA villa offers sweeping sound views from the private balcony, along with a comfortable coastal interior featuring a king-size bedroom, en-suite bath with walk-in shower, well-equipped kitchen. The oceanfront community offers natural beach access, an observation pier, two outdoor pools, indoor pool, hot tub, dry sauna, fitness center, tennis and basketball courts, and multiple grilling and picnic areas. Enjoy beautiful sandy beaches and stunning sunrises just outside your door. With a strong rental history and an exceptional oceanfront setting, this is a turnkey opportunity for a second home or investment property on Hilton Head Island.

239 Beach City Road Unit 1203, Hilton Head Island

Listing courtesy of Coastal Luxury Real Estate.

157 Otter Road, Hilton Head Island
$876,000
3 Beds ⋅ 2 Baths ⋅ 1,882 SqFt. ⋅ HILTONHEAD-512297 MLS
Discοver eaѕу iѕlаnd lіving іn thе highly desirable Club Cοursе neighborhood of Sea Pines Resort. This beautifully maintained 3-bedroom, 2-bath Hilton Head Island home offers a bright, welcoming interior, thoughtful updates, and a location that puts the best of Sea Pines and Hilton Head right at your fingertips. Inside, you'll find fresh paint, new LVP flooring, an updated primary bathroom, and a comfortable, natural-light-filled floor plan. Major improvements include Trex decking and a 2025 Trane HVAC system, adding both convenience and peace of mind. Step outside to a spacious back deck made for grilling, entertaining, or relaxing after a day at the beach. The large backyard provides plenty of room to enjoy the outdoors and offers exciting potential for a future pool. Located near the main gate of Sea Pines, this home offers quick access on and off the plantation while still enjoying all the benefits of one of Hilton Head Island's most iconic communities. Sea Pines is known for its beautiful beaches, four championship golf courses, miles of leisure trails, Harbour Town, Tower Beach, exceptional dining, boating, tennis, pickleball, and the ongoing transformation of South Beach. Whether you're looking for a full-time Hilton Head Island residence, a second home in Sea Pines, a vacation getaway, or a short-term rental investment, this turnkey property offers exceptional flexibility. Move in and immediately start enjoying morning bike rides beneath moss-draped live oaks, afternoons on the beach, rounds of golf, sunset dinners, and everything that makes the Hilton Head Island lifestyle so special. Schedule your private showing or live video walkthrough today.

157 Otter Road, Hilton Head Island

Listing courtesy of EXP Realty LLC.

11 Sea Lane, Hilton Head Island
$5,500,000
5 Beds ⋅ 7 Baths ⋅ 7,051 SqFt. ⋅ HILTONHEAD-511760 MLS
BREAΤHTAΚΙNG Μеdіterrаnеan Estate Homе ovеrlooking the 16th Fairway of the Robert Trent Jones Golf Course in Palmetto Dunes. Gated community and Just a Short Walk to the Beach. 7,051 Square Feet with Amazing Craftsmanship rarely seen that captivates you. Step inside Front Door and Immediately be in Awe of the Beauty. Grand Marble Staircase, Spectacular Flooring, Open Living Spaces. Inviting Spacious Living Area with a Fireplace and Spectacular Chandeliers overlooks the Large Porch, Patio and Pool Area. Off Living Area is an Inviting and Open Dining Area. A Chef's Dream Kitchen is nearby with a 10-Foot Island that seats 6 plus a Dining Table Area. Also, a Comfortable Living Area with a Fireplace that opens to a Veranda with Built in Grilling Area and has Half Bath by Pool. Off Kitchen is a Butler's Pantry and a Laundry Area. Spectacular Wood Paneled Parlor with Sitting Area and Full Bar. 5 Bedroom Suites with Great Separation and Privacy. Primary Bedroom Suite is First Floor, has a Veranda and is steps away to the Raised Invisible Edge Pool and Spa. Also, 2 other Bedrooms have a Veranda. 6-Car Drive Through Cooled Garage, ELEVATOR, Terra Cotta Tile Roof, Paver Driveway and Mature Landscaping. Perfect Home for Relaxing and Entertaining Family, Friends, or Business Outings. Truly EXCEPTIONAL in every way. Come Enjoy the BEST OF LIFE at 11 Sea Lane on Hilton Head Island!

11 Sea Lane, Hilton Head Island

Listing courtesy of Dunes Real Estate.

20 Queens Folly Road Unit 1659, Hilton Head Island
$569,000
2 Beds ⋅ 2 Baths ⋅ 1,177 SqFt. ⋅ HILTONHEAD-511988 MLS
Welcome to the highly-desired St. Andrews Common community in world-renowned Palmetto Dunes Resort! This beautifully updated 2BD / 2BA villa offers a light, inviting retreat in one of Hilton Head Island's most ideal locations. The spacious layout provides plenty of room for both everyday living and entertaining, making this a perfect primary residence, second home, or turnkey investment opportunity. Offered fully furnished and ready to rent - having achieved nearly $45K in gross rentals just last year! Enjoy the peaceful surroundings of St. Andrews Common, complete with a community pool and picturesque lagoon and landscape views throughout the neighborhood. You'll have easy access to miles of pristine beaches, championship golf, tennis and pickleball, dining, shopping, biking, kayaking and everything that makes the Hilton Head lifestyle so special.

20 Queens Folly Road Unit 1659, Hilton Head Island

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

20 Castlebridge Court, Hilton Head Island
$3,995,000
5 Beds ⋅ 7 Baths ⋅ 4,566 SqFt. ⋅ HILTONHEAD-512060 MLS
Waterfront lіving in Weхfοrd doеѕn't gеt much bеttеr than this and 20 Castlebrіdge Cοurt offers the ONLY harborfront setting currently available in the community. Set directly on the harbor at the end of a private cul-de-sac, this five-bedroom residence combines exceptional outdoor living with one of the neighborhood's most desirable settings. A heated pool and spa, outdoor fire pit, built-in grilling station, and private dock make the most of life on the water. The spacious floor plan features a grand living room upon entry, adjacent dining room, a generous kitchen enhanced by Sub zero and Viking appliances, two stately gas fireplaces, bonus room, bunk room, three-car garage, and dedicated golf cart bay. The quality of construction does not go unnoticed with solid wood doors, plantation shutters, wide-planked hardwood floors, elevated lighting, and built-in features throughout. Then there is Wexford itself. Boasting a newly redesigned clubhouse with indoor/outdoor dining, community pool, exceptional Arnold Palmer Signature golf, active tennis community, pickle ball, a private marina, and the signature lock-controlled 37 acre inland harbour. The community truly is unlike anything else on Hilton Head Island and for someone looking for harborfront living within Wexford, there is only ONE.

20 Castlebridge Court, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

34 Ruddy Turnstone Road, Hilton Head Island
$7,050,000
5 Beds ⋅ 6 Baths ⋅ 5,278 SqFt. ⋅ HILTONHEAD-511871 MLS
Welcome to 34 Ruddy Turnstone - a classic custom-built oceanfront home in Sea Pines designed by renowned Hilton Head architect Jakie Lee. Perfectly positioned on a large private homesite, this timeless residence showcases the charm, craftsmanship, and thoughtful design that define the finest Sea Pines properties. Exceptional quality is evident throughout with wide stairways, custom woodworking, soaring ceilings, and solid-core doors, all blending to create an atmosphere of relaxed yet refined coastal living. Designed for both comfort and entertainment, the home offers generous indoor and outdoor living spaces, including a heated pool and spa surrounded by lush privacy. The second level features the private Primary Suite with a sitting area, a spacious Great Room, Dining Room, and Eat-In Kitchen - all opening to an expansive IPE wood deck with elevated views overlooking the pool and the Atlantic Ocean. The entry level welcomes guests through a covered entrance into a dramatic foyer with high ceilings and access to the large Family Room complete with built-in beverage coolers and bar area. From here, enjoy seamless access to the covered porch, pool/spa and private beach path. Three Guest Bedrooms, each with their own Ensuite Bath, are also located on this level, along with an additional full bath and Laundry Room for added convenience. A fourth Guest Bedroom and full-size private Office with balcony occupy the mid-level, providing additional flexibility for family and guests. A newly installed elevator with service to all four levels, ensuring effortless enjoyment throughout the home. Thoughtfully designed and meticulously maintained by its original owners as a cherished second home, this exceptional oceanfront retreat offers the rare opportunity to enjoy a classic Sea Pines residence exactly as it is today - or reimagine and personalize it over time to create your own coastal legacy.

34 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of Charter One Realty.

239 Beach City Road Unit 3331, Hilton Head Island
$305,000
2 Beds ⋅ 2 Baths ⋅ 917 SqFt. ⋅ HILTONHEAD-512112 MLS
Updated 2ΒR/2BA villа аt Thе Ѕрa οn Ρort Royal Sound offеring сlose proximity to one of Hilton Head Island's most distinctive natural beaches, an extensive amenity package, and the flexibility to serve as a second home, full-time residence, or short-term rental investment. Inside, the open living space is anchored by a renovated kitchen with a center island, stainless steel appliances, wine fridge, and glass tile backsplash. A wall-mounted fireplace creates a polished focal point in the living area, while modern finishes continue throughout the villa. Both bathrooms have been updated with tiled shower surrounds, contemporary fixtures, and LED mirrors, and the screened porch provides an additional place to relax after a day on the island. The Spa is a gated waterfront community on Port Royal Sound with two outdoor pools, a heated indoor pool and hot tub, fitness center, tennis courts, basketball court, grilling and picnic areas, playground, landscaped lagoons, and direct access to Hilton Head's bike trail system. The community's location beside Fish Haul Beach Park and Historic Mitchelville Freedom Park adds even more outdoor recreation and Lowcountry character. With great short-term rental potential, updated interior, beach access, and extensive amenities, Unit 3331 offers a compelling combination for both personal-use buyers and investors.

239 Beach City Road Unit 3331, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

10 Drayton Place, Hilton Head Island
$7,800,000
6 Beds ⋅ 8 Baths ⋅ 6,208 SqFt. ⋅ HILTONHEAD-510819 MLS
Experience unparalleled oceanfront luxury in the exclusive, private community of Port Royal on Hilton Head Island. This 6,208-square-foot, two-story coastal home features six bedrooms, five full baths, and three half baths, offering an exceptional blend of timeless architecture. Meticulously enhanced with extensive modern updates, the home welcomes you with a grand foyer, soaring ceilings, and open, light-filled living spaces. Stunning 2-story glass frames sweeping panoramic Atlantic vistas and the maritime landscape from nearly every room. The newly remodeled chef's kitchen is complete with leather-stamped quartz countertops, a premium Sub-Zero refrigerator, a gas Bertazzoni Range, 2 stainless steel sinks, a farmer sink and a customized bar area. A generous island designed for effortless entertaining seats six. Throughout the interior, earth toned tile, stone and wood flooring complement the home's design. The primary suite serves as a serene sanctuary with stunning ocean views and a spa-inspired bathroom while each guest suite ensures ultimate comfort with private en-suites. Notably, three of the six bedrooms boast breathtaking direct ocean views.The luxury extends outdoors to a private beachfront oasis designed for relaxation and entertainment. Expansive patios, second-story veranda balcony, and an oceanside salt water pool offer front-row seats to legendary sunrises, cool sea breezes, and the tranquil lapping of the waves. Enjoy direct, private access to Hilton Head's pristine shoreline right from your backyard. Thoughtfully updated, the property features a durable metal roof, a classic stucco exterior, a spacious three-car garage, newly paved driveway plus paver pathways and refreshed landscaping. Situated on one of Port Royal's private, winding, oak-tree-lined cul-de-sac streets, this gated-community oceanfront residence offers a rare combination of luxury, privacy, and coastal living at its best.

10 Drayton Place, Hilton Head Island

Listing courtesy of EXP Realty LLC.

73 Skull Creek Drive Unit 210, Hilton Head Island
$795,000
3 Beds ⋅ 2 Baths ⋅ 1,623 SqFt. ⋅ HILTONHEAD-512053 MLS
Direct wаterfront in Μаrinеrѕ Ρoіnt, thіs three bedroom villа prеsents an exceptional opportunity to own along the water within the gates of Hilton Head Plantation. The enclosed waterside porch takes full advantage of the setting, with sunset vistas across the Intracoastal Waterway. Three spacious bedrooms provide comfortable accommodations for family and guests, while the villa complex pool is an added bonus. Exterior elevators make the second floor unit easily accessible as well. Hilton Head Plantation offers 24-hour gated security and a fantastic collection of amenities, including the Spring Lake Pavilion and pool, the newly refurbished Dolphin Head Beach with its waterfront park and pavilion, the Country Club of Hilton Head, and four golf courses. Beyond the gates, an abundance of acclaimed restaurants, shopping, boating and all that Hilton Head Island has to offer are just minutes away. With its direct waterfront setting, spacious floor plan and access to one of the island's most established communities, this Mariners Point villa presents an especially attractive opportunity.

73 Skull Creek Drive Unit 210, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

53 Delander Court Unit 53, Hilton Head Island
$259,000
2 Beds ⋅ 1 Baths ⋅ 950 SqFt. ⋅ HILTONHEAD-512021 MLS
This mοve-in‐rеadу 2‐bеdroοm, 1‐bath home was thoughtfully rеnovаted two years ago and features a bright, modern interior with updated finishes throughout. The kitchen boasts new appliances, while both bedrooms are equipped with new impact-resistant windows. One of this home's standout features is the custom entertaining area, complete with a built-in bar, kegerator, and mini refrigerator. The spacious outdoor patio offers the perfect place to enjoy your morning coffee or unwind in the evening and includes a convenient exterior utility closet for additional storage.Located on the first floor, this condo offers easy access with no stairs to navigate. Tucked away from the main road, the community provides a peaceful setting while remaining just minutes from everything Hilton Head has to offer. Enjoy the community swimming pool, and take advantage of the excellent location with quick access to US-278, making travel on and off the island effortless. You're also just minutes from Palmetto Bay Marina, shopping, dining, grocery stores, golf, and entertainment.For beach lovers, Coligny Beach Park is approximately a 5 minute drive, making it easy to enjoy Hilton Head's world-famous shoreline whenever you choose.As an added bonus, the sellers are open to negotiating the sale of much of the home's furniture, making this an exceptional opportunity for a primary residence, second home, or investment property.Whether you're looking for a full-time residence or an island getaway, 53 DeLander Court offers updated living in one of Hilton Head's most convenient locations.

53 Delander Court Unit 53, Hilton Head Island

Listing courtesy of I Save Realty.

4 Middleton Place, Hilton Head Island
$3,950,000
3 Beds ⋅ 3 Baths ⋅ 2,733 SqFt. ⋅ HILTONHEAD-511980 MLS
Reimagine oceanfront living on one of Hilton Head Island's most exceptional beachfront properties. Set beneath magnificent live oaks and surrounded by mature natural landscaping, this private retreat offers sweeping ocean views, ample room for expansion, and the rare opportunity to renovate, enhance, or create a new coastal estate tailored to your vision. Ideally positioned in the most coveted section of Port Royal Plantation, the property enjoys a peaceful setting away from the island's resort corridor while remaining minutes from renowned dining, golf, shopping, and amenities. The expansive rear deck is perfectly suited for entertaining, oyster roasts, or simply enjoying the ocean breeze and breathtaking coastal views. The existing residence offers 3 bedrooms and 2.5 baths, with the half bath easily converted back to its original full-bath configuration. Wide-plank pine floors, a beautifully renovated chef's kitchen, and walls of glass create warm, inviting interiors that connect seamlessly with the surrounding landscape. Adding to the property's distinction is its remarkable architectural history. Designed by internationally acclaimed architect Dean Winesett, whose work has appeared in *Architectural Digest* and *Southern Living*, the home was also featured in *Southern Living* and reflects his signature Lowcountry style and craftsmanship. Port Royal Plantation prohibits short-term rentals, preserving the privacy, tranquility, and exceptional quality of life that define this exclusive oceanfront community. Private amenities reserved for property owners and their guests include an oceanfront Beach House and swimming pool overlooking the Atlantic, tennis and pickleball courts, community gardens, leisure trails, and an array of recreational and social offerings. An irreplaceable beachfront setting, celebrated architectural legacy, exceptional private amenities, and endless possibilities combine to create one of the most compelling oceanfront opportunities currently available on Hilton Head Island.

4 Middleton Place, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS III brokered eXp Realty.

5 Newport Drive Unit 7102, Hilton Head Island
$749,000
2 Beds ⋅ 3 Baths ⋅ 1,445 SqFt. ⋅ HILTONHEAD-511929 MLS
Waterfront Ꮮuxury Lіvіng in Ρаlmеtto Dunеѕ! Set within the exсlusіve waterfront enclave of Newport Villas, this fully renovated first-floor residence offers a rare blend of refined coastal luxury and effortless island living in the heart of Palmetto Dunes. With serene lagoon and live oak views just beyond your doorstep, this 2-bedroom, 2.5-bath villa delivers the ultimate Lowcountry lifestyle - where elegance meets the water's edge. An open-concept layout showcases expert design, high quality finishes , and a welcoming fireplace, all enhanced by abundant natural light through new sliding glass doors. The designer kitchen flows seamlessly into the living and dining areas, creating an elegant setting for entertaining or relaxed island living. The expansive primary suite serves as a private retreat, featuring a sitting area, generous closet space, and tranquil views of the lagoon and mature live oak canopy. Thoughtfully updated throughout, the villa is truly turnkey. Approximately 1,445 square feet, the residence includes two bedrooms, two full baths, one half bath, and convenient parking just steps from the entry. Set within the heart of Palmetto Dunes, residents enjoy access to three miles of pristine Atlantic beaches, championship golf, world-class tennis and pickleball, miles of leisure trails, Shelter Cove Marina, waterfront dining, boutique shopping, and year-round entertainment. Newport Villas further enhances the lifestyle with arguably the best community pool on the island, tennis and pickleball courts, and beautifully maintained grounds overlooking the marsh and lagoon. An exceptional opportunity for a luxury island retreat that is a custom home disguised as a villa offering the best Hilton Head Island has to offer.

5 Newport Drive Unit 7102, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

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