Hilton Head Island SC Historical Real Estate, Homes for Sale

2 Beds ⋅ 2 Baths ⋅ 1,883 SqFt. ⋅ HILTONHEAD-511684 MLS

Selling a dream located 4th row on Whistling Swan to build your new custom home! Steps away from SP Beach Club restaurants, beach bar and the sandy white beach and Plantation Golf Club. Lot dimensions are 107 X 133 X 103 X 150 = .34/acre. Selling "As- Is"; "Where-Is" with seller making no repairs. No inspections. Possible lease back needed.

1 Whistling Swan Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - The Cottage Group, LLC.

$1,875,000

3 Beds ⋅ 4 Baths ⋅ 2,721 SqFt. ⋅ HILTONHEAD-511600 MLS

Nestled on prestigious Plantation Drive, in amenity-rich Sea Pines Community, this quintessential Tom Parker-designed Sea Pines home enjoys an exceptional location, beneath magnificent live oaks, perfectly situated within near distance to Harbour Town & the SP Beach Club. Set on just under a half-acre overlooking the 8th fairway of Heron Pointe Golf Course, this beautifully updated home offers more than 2,700 square feet of light-filled living space w/timeless charm, elevated first-floor construction, classic brick accents & serene golf course views.Step inside to a welcoming slate-floored entry that opens to hardwood flooring throughout the main living areas & bedrooms.The open-concept kitchen, family room, & living area create an ideal setting for everyday living & entertaining, anchored by a stunning floor-to-ceiling quartz gas fireplace. The beautifully renovated kitchen features custom cabinetry, GE Café & Bosch appliances, a gas range, gorgeous countertops w/hand-made back splash & updated lighting.The thoughtfully designed floor plan includes the primary suite & a guest suite on the main level, w/a spacious third en-suite bedroom above the garage that serves perfectly as a second primary suite or a private guest retreat. All bedrooms feature en-suite baths, & an additional half-bath is conveniently located for guests. The fabulous 550+ square-foot 2025 primary suite addition, offers breathtaking golf course views, a generous walk-in closet, & a luxurious spa-inspired bath featuring a double-sink vanity w/marble countertops & a custom-tiled walk-in shower. Add'l improvements include a comprehensive 2020 renovation with 3 new hurricane-impact sliding glass doors, a beautifully updated kitchen, & new lighting throughout. A GE wash/dryer & a new water heater were installed in 2021, while 2025 upgrades include a new furnace, ductwork, & hurricane-impact garage doors.Outdoor living is equally impressive w/a newly added (2025) covered screened porch measuring approximately 19' x 14', offering stunning golf course views & an adjacent elevated patio-perfect for relaxing or entertaining family & friends.Enjoy the best of Sea Pines with an easy walk or bike ride to Harbour Town or SP Beach Club. Owners enjoy access to miles of pristine beaches, a pvt residents' beach, world-class golf, tennis, marinas, a nature preserve, equestrian stables & countless other amenities. Experience the Sea Pines Lifestyle at its finest, you deserve to love where you live!

50 Plantation Drive, Hilton Head Island

Listing courtesy of C 21 A Low Country Realty.

$1,700,000

4 Beds ⋅ 3 Baths ⋅ 2,015 SqFt. ⋅ HILTONHEAD-511511 MLS

Location is everything! This ocean-oriented, four-bedroom, 3.5-bath condominium is just steps from the Atlantic Ocean and all the amenities of South Beach Marina Village in Sea Pines. Ideally located beside the new community pool, the residence features a private rear deck and an upstairs deck off the primary bedroom. Enjoy easy access to the beach, bike paths, pickleball, shops, restaurants, and entertainment. Start making your Hilton Head memories today!

225 S Sea Pines Drive Unit 1401, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$5,500,000

4 Beds ⋅ 5 Baths ⋅ 3,590 SqFt. ⋅ 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.

$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.

$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.

$1,375,000

3 Beds ⋅ 3 Baths ⋅ 1,850 SqFt. ⋅ HILTONHEAD-510483 MLS

Stunning turn key 3 bed 3 bath unit in Hilton Head Beach Villas-Coming Soon!

37 S Forest Beach Drive Unit 9, Hilton Head Island

Listing courtesy of SERHANT. Selling Office: COAST PROFESSIONALS Brokered by EXP Realty.

$1,275,000

4 Beds ⋅ 3 Baths ⋅ 1,966 SqFt. ⋅ HILTONHEAD-510200 MLS

Welcome to 10 Myrtle Lane.

10 Myrtle Lane, Hilton Head Island

Listing courtesy of EXP Realty LLC. Selling Office: Island Getaway, Ltd.

$419,000

2 Beds ⋅ 2 Baths ⋅ 1,064 SqFt. ⋅ HILTONHEAD-508597 MLS

What a find for owning on Hilton Head Island! Located directly across from the beach path, this 2-bedroom villa has been enjoyed for years as a special family getaway and is ready for its next chapter. You can spend your mornings by the ocean and your evenings grilling on the patio while enjoying the large outdoor space. The villa has been well maintained and is comfortable to enjoy immediately, as it is sold fully furnished. One of the best villa locations in this complex and priced for a buyer to add their own personal style and updates now or in the future. Owners may have pets, and the large community pool is only steps away. You will love the proximity to the shops of Coligny, parks, restaurants, shopping, entertainment, and everything people enjoy about the Forest Beach lifestyle.

32 S Forest Beach Unit 70, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$955,000

3 Beds ⋅ 2 Baths ⋅ 1,545 SqFt. ⋅ HILTONHEAD-508893 MLS

Nestled just steps from the ocean, this charming beach cottage offers the perfect blend of coastal comfort and relaxed seaside living. Three bedrooms and two full baths plus a huge kitchen, breakfast room and light-filled great room. A huge laundry room/mud room is great for extra storage. A one-car carport keeps your car out of the sun. The massive backyard is fenced and has an oversized deck with a hot tub, a sandy area great for your hammock, and a storage shed. The impressive live oak tree welcomes you as you drive up. With sunlit interiors, breezy open spaces, and thoughtfully curated décor inspired by the ocean, the cottage creates a warm and inviting weekend getaway or permanent beach home. Spend mornings on the back deck enjoying a cup of coffee, afternoons spent on sandy beaches, and evenings under stunning coastal sunsets. Whether you're seeking a peaceful getaway or a memorable beachside escape, this cottage provides a cozy haven where every day feels like a vacation. Folly Field is a quaint community just a short stroll to Nalas Beach Bar, a short bike ride to Shelter Cove, and all of its fun spots (restaurants, shopping, nightlife, and waterfront activities). This home has been lovingly updated and you will be totally impressed!

8 Azalea Street, Hilton Head Island

Listing courtesy of Charter One Realty.

$850,000

2 Beds ⋅ 2 Baths ⋅ 1,088 SqFt. ⋅ HILTONHEAD-507799 MLS

Beautifully remodeled with modern coastal finishes, this 2BR/2BA Woodbine Villa combines an unbeatable walk-to-the-beach location with serene golf views! Both Sea Pines Beach Club and Plantation Golf Club are just a quick stroll down the bike path, while #47 Woodbine still provides a peaceful, private, cul de sac location in Sea Pines. Flanked by ancient live oaks and giant magnolia trees, this corner unit overlooking the 12th green on Atlantic Dunes golf course and has been completely refreshed with wide plank engineered wood floors, white quartz kitchen counters, stainless appliances, smooth ceilings with recessed lighting and subway tile accents in the kitchen and baths. Nothing was left untouched! Unwind on the brick paver back patio watching golf, or relax in a stunning, light-filled sunroom wrapped in walls of windows. A light bright, single level, pet-friendly community in Sea Pines. Absolutely perfect as your 2nd home beach retreat, vacation rental investment or primary bungalow. This property is a WOW and won't last!

2 Woodbine Place Unit 47, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty. Selling Office: Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

$425,000

2 Beds ⋅ 2 Baths ⋅ 1,316 SqFt. ⋅ HILTONHEAD-507511 MLS

Great south-end location with no HOA and Short-Term Rentals allowed. Rare opportunity for investors or renovation enthusiasts. Significant cleanup work has already been completed, including extensive tree removal and full clearing of the home and grounds. Clean slate ready for your vision. Sold as-is.

25 Bay Pines Drive, Hilton Head Island

Listing courtesy of COAST - Brokered by EXP Realty. Selling Office: Engel & Volkers.

$855,000

2 Beds ⋅ 2 Baths ⋅ 1,088 SqFt. ⋅ HILTONHEAD-507385 MLS

Rare opportunity to own a beautifully upgraded end unit in the desirable Woodbine Villas within Sea Pines Resort. Meticulously maintained and in pristine condition, this villa offers a bright, open floor plan with excellent bedroom separation, ideal for both personal enjoyment and guests. Enjoy serene lagoon and phenomenal golf course views overlooking Heron Point by Pete Dye from the spacious indoor-outdoor patio and Carolina Room. Perfectly positioned just a short stroll to Sea Pines Beach Club, Fraser's Tavern, and miles of leisure trails beneath iconic Live Oaks. This villa is not only a peaceful retreat but also a strong investment opportunity, this is a rare chance to own a standout property in one of Hilton Head's most sought-after communities.

2 Woodbine Place Unit 56, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate. Selling Office: Greenplate Group Brokered by eXp Realty.

$975,000

3 Beds ⋅ 2 Baths ⋅ 2,150 SqFt. ⋅ HILTONHEAD-506917 MLS

Enjoy breathtaking waterfront views and endless potential at 11 Big Oak Street. This property features a spacious lot with direct water access and an existing dock structure. Whether you choose to renovate or build new, this is a rare chance to create your own Lowcountry waterfront escape. Tucked away in a peaceful setting yet close to Hilton Head's amenities, this property is perfect for those seeking location, views, and opportunity. Property sold as-is.

11 Big Oak Street, Hilton Head Island

Listing courtesy of RE/MAX Island Realty. Selling Office: Maxey Blackstream Christie's International Real Estate.

$3,295,000

5 Beds ⋅ 6 Baths ⋅ 4,334 SqFt. ⋅ HILTONHEAD-505653 MLS

Set on more than one acre in the heart of Sea Pines, this 5-bedroom, 5.5-bath home offers 270-degree golf views across two of the most celebrated courses on Hilton Head Island. Enjoy sweeping fairway vistas of the 1st and 18th holes at Heron Point by Pete Dye and the 5th and 6th holes at Atlantic Dunes by Davis Love III-a rare vantage point that places you at the center of the Sea Pines golf and beach lifestyle. Properties with this level of acreage, privacy, and panoramic golf views in Sea Pines are exceptionally rare. Designed as a sprawling open ranch, the home celebrates the natural beauty that defines Sea Pines. Expansive windows frame spectacular golf course views and invite the outdoors in, creating a light-filled interior connected to the surrounding landscape. The layout reflects a timeless philosophy-homes designed to flow seamlessly with nature. Outdoor living shines with extensive patio spaces for dining, entertaining, and relaxing, all set against the dramatic backdrop of championship golf. A private pool offers a peaceful retreat after a day at the beach or on the course, making the property ideal as a Sea Pines vacation home, luxury second home, or Hilton Head Island investment property. Located in one of the most sought-after areas of Sea Pines, the home is walkable to the beach, Sea Pines trolley stops, and multiple restaurants and amenities. Currently featured as a vacation rental property with Sea Pines Resort, it offers immediate income potential while also serving as an exceptional private retreat within Sea Pines.

34 N Live Oak Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$1,695,000

4 Beds ⋅ 4 Baths ⋅ 3,144 SqFt. ⋅ HILTONHEAD-504477 MLS

Rarely do you find this much space so close to the beach at this price point. Located just moments from the ocean and Coligny's popular shops and restaurants, this spacious Forest Beach home offers an exceptional coastal lifestyle in one of Hilton Head's most desirable locations. Situated on an oversized corner homesite shaded by majestic oaks, the property features 4 bedrooms, 4 bathrooms, and over 3,000 square feet of comfortable, light-filled living space. The open floor plan provides generous room for gathering and entertaining, while recent improvements-including a brand-new roof, new HVAC and remodeled storage building that add immediate value and functionality. With abundant parking, plenty of room for family and guests, and an unbeatable location near the beach, dining, and recreation, this nicely appointed beach home is well-suited as a primary residence, second home, or investment opportunity.

1 Gannet Street, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$2,295,000

4 Beds ⋅ 4 Baths ⋅ 3,087 SqFt. ⋅ HILTONHEAD-505673 MLS

A Rare Point Comfort Peninsula Property. Tucked away on one of the most remarkable homesites on Hilton Head Island, this classic coastal home sits on approximately 1.25 acres at the end of a private peninsula, surrounded by over 180 degree views of marsh and deep water. Properties with this combination of land, privacy, and views are extraordinarily rare on the island today. Even more rare is the Point Comfort lifestyle, a relaxed authentic Lowcountry way of living. Residents can enjoy access to the community boat landing w/ direct water access, allowing you to keep your boat right at home then head out on the water whenever the tide and weather call. Enjoy golf cart rides and spend time with neighbors within this friendly enclave, a place where life moves at an easy pace. Built during the island's early era of thoughtful coastal contemporary design in the 1960s, the home reflects the architectural style that helped define Hilton Head, simple, understated Lowcountry modernism designed to live in harmony with the landscape. Large windows frame the water and marsh from nearly every angle, while the open floor plan invites the outdoors inside, capturing the island's breezes, light, and ever-changing skies. The setting is nothing short of magical. World-class sunsets stretch across the marsh each evening, casting warm light across the water and surrounding vegetation. Mature trees and natural landscaping create a sense of privacy that is increasingly difficult to find on the island. Inside, the two-story layout offers generous living space and flexibility. The main living areas are designed for relaxed coastal living and entertaining, while the lower level provides ideal accommodations for a mother-in-law suite, multi-generational living or just additional living/office space. Step outside to a large private patio, perfect for quiet mornings. Enjoy the sunset from the second floor deck. A private drive leads to the home and carport, further enhancing the sense of seclusion. For decades, this home has been the backdrop for generational memories-family gatherings, sunset dinners, and life along the water. It now awaits its next steward to continue that tradition. With low annual dues $500.00, minimal restrictive covenants, extraordinary land size, sweeping water views, and unmatched natural beauty, this Point Comfort property represents a truly unique opportunity on Hilton Head Island.

18 Nautilas Road, Hilton Head Island

Listing courtesy of SERHANT.

$515,000

2 Beds ⋅ 2 Baths ⋅ 1,064 SqFt. ⋅ HILTONHEAD-505468 MLS

Best location in the complex! This desirable front-row end-unit villa offers easy access to the beach-simply step out your front door and walk directly to the beach path. Impeccably maintained and gently used as a second home, this villa has been thoughtfully updated with numerous recent upgrades, including a new kitchen, luxury flooring, updated bathroom, new HVAC, doors, and windows, along with tasteful furnishings throughout. Comfortable, stylish, and move-in ready, this charming coastal retreat is the perfect place to enjoy summer at the beach or start generating rental income. A wonderful opportunity in an unbeatable location!

32 S Forest Beach Unit 9, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Charter One Realty.

$1,212,500

3 Beds ⋅ 3 Baths ⋅ 1,465 SqFt. ⋅ HILTONHEAD-505133 MLS

Rarely Available Hilton Head Beach Villa - South Forest Beach. This stunning 4-bedroom, 3-bath villa offers breathtaking ocean views from a spacious back deck. One of only 30 units in a privately gated community, it's just minutes from Coligny Plaza, fine dining, shopping, and entertainment. Features include a carport with storage, a laundry room, and a short-term rental history that performs exceptionally. Don't miss this beachfront gem!

37 S Forest Beach Drive Unit 15, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty. Selling Office: Charter One Realty.

$3,895,000

4 Beds ⋅ 5 Baths ⋅ 3,656 SqFt. ⋅ HILTONHEAD-505062 MLS

A rare Beach Lagoon opportunity in Sea Pines: second-row location on an oversized half-acre lot with serene lagoon views in the front and golf course views in the rear. Just steps to the beach bridge and an easy stroll to the Sea Pines Beach Club for dining, cocktails, and oceanfront living.This well-maintained 4-bedroom, 4.5 bath home features brick and wood floors, excellent bedroom separation, and a kitchen with granite countertops designed for entertaining. Each bedroom offers a private en-suite bath plus a convenient half bath for guests.Whether used as a luxury beach retreat, income-producing investment, or incredible full-time residence, this property offers unmatched versatility. Opportunities to own a lagoon-to-golf view, oversized lot on the ocean side of Sea Pines are extraordinarily limited.Sea Pines at its finest - invest, enjoy, and build lasting value in one of the resort's most coveted ocean neighborhoods.

28 W Beach Lagoon Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$2,225,000

6 Beds ⋅ 4 Baths ⋅ 3,130 SqFt. ⋅ HILTONHEAD-504973 MLS

Phenomenal 5th Row Beach home in North Forest Beach! Currently utilized as a thriving investment rental home. This fully furnished 6 bedroom, 4 bathroom coastal retreat boasts an additional loft- providing extra sleeping quarters with a full bathroom. Admire the stunning rooftop deck that overlooks the spacious green space, courtyard with barbecue area and custom in ground pool + large paver patio surround! (2018 new pool equipment) The updated kitchen displays delightful custom cabinetry, granite countertops and stainless steel appliances. Enjoy low maintenance living with luxury vinyl plank flooring throughout, not only is it easy to clean but its waterproof + scratch resistant, giving peace of mind (especially with the pool and beach right there!) Easily rinse off after the beach at your own personal outdoor shower and benefit from plenty of space for storage of beach/pool essentials right around the corner. This gorgeous turnkey home has so much to offer, the list just keeps going! Both HVAC system (2021- with yearly maintenance) insures a place to escape from the heat when you aren't enjoying the private fenced yard or direct beach access at the end of the street. This place has survived numerous hurricanes in its lifetime, likely due to how structurally sound it is-metal roof, cement block walls with brick overlay. This location is ideal! The North Forest Beach Area is perfect for heading away from the traffic and submerging in tranquility but not too far to take advantage of endless options for shopping dining and entertainment the Coligny Beach Park and Plaza offer! Whether you want to make this a short-term rental goldmine or your permanent beach residence, prepare to embrace the island life!

2 Nighthawk Street, Hilton Head Island

Listing courtesy of Family Tides Real Estate LLC.

$910,000

7 Beds ⋅ 5 Baths ⋅ 3,803 SqFt. ⋅ HILTONHEAD-502548 MLS

Welcome to the Bay Pines community on the south end of Hilton Head Island. This unique property includes the adjoining Lot 28A directly behind the home, which will convey with the sale. With no homeowner's association, the property offers excellent flexibility, including the potential for short-term rentals. The home features 3,803 square feet of living space with 7 bedrooms and 5 bathrooms. The first floor includes a private apartment with its own entrance, offering 4 bedrooms and 3 bathrooms-ideal for guests, extended family, or rental income. The second floor features 3 additional bedrooms and 2 bathrooms, providing comfortable living space for the main residence. Covered porch with oversized 1 car garage.

14 Bay Pines Drive, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty. Selling Office: COAST PROFESSIONALS Brokered by EXP Realty.

$1,350,000

3 Beds ⋅ 3 Baths ⋅ 1,950 SqFt. ⋅ HILTONHEAD-502981 MLS

Welcome to the best buy on a 3 bedroom villa in South Beach! With brand new Living Room furniture and Dining Room table, you will love the light, bright, and perfectly updated villa offering easy living just steps from all the fun that South Beach has to offer; Salty Dog, Shops, Restaurants, boat excursions and more! Enjoy an updated kitchen with new countertops and most appliances, smooth ceilings, wood floors, and refreshed bathroom vanities-including a brand-new primary shower. A main level bedroom adds convenience, while the screened porch can be enclosed for more year round space. Plus, an extra room ideal for a 4th bedroom, office, or storage. The ocean views from the primary sundeck and screen porch are a special and unique feature! South Beach Villas owners and guests now enjoy the completed newest private pool in all of South Beach which will certianly increase rentals!! Now's the time to own 1406 South Beach Villa, with the new Salty Dog waterfront restaurant expected to boost area values once completed!

225 S Sea Pines Drive Unit 1406, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - The Cottage Group, LLC. Selling Office: Daniel Ravenel Sotheby's International Realty.

$880,000

2 Beds ⋅ 2 Baths ⋅ 1,100 SqFt. ⋅ HILTONHEAD-502880 MLS

Experience true luxury at 72 Fairway Lane Villas, a beautifully renovated 2-bedroom, 2-bath Villa situated on one of Sea Pines Plantation's most expansive & serene Golf & lagoon views. This stunning Villa has been meticulously transformed, boasting a complete top-to-bottom renovation that includes brand-new kitchen, baths, flooring, ceiling changes, plus too many upgrades to include here. The open-concept living spaces are bright & airy, perfectly designed for entertaining or a quiet family retreat. The updated kitchen features high-end appliances & finishes, while the spacious bedrooms & elegant bathrooms offer comfort & sophistication. Step outside to the expansive paver patio & enjoy the tranquil Golf & Lagoon views creating your own personal oasis. Beyond the doors of this magnificent property, you are immersed in the unparalleled lifestyle of Sea Pines Plantation. This world-renowned gated community is a playground of amenities, from championship golf courses like the famous Harbour Town Golf Links & Atlantic Dunes to the top-tier Sea Pines Racquet Club. One of the most significant advantages of this location is the easy access to the Atlantic Ocean beach. A short walk or bike ride from 72 Fairway Lane Villas puts you at the Sea Pines beachfront via numerous direct beach access paths for a more secluded experience. A short distance to Sea Pines Beach Club, a world-class oceanfront destination with dining, restrooms, & a relaxed atmosphere. The community also offers additional amenities including the iconic Harbour Town with its famous lighthouse, diverse dining & shopping at South Beach Marina Village, & the serene Sea Pines Forest Preserve. In addition to its appeal as a primary residence or personal getaway, 72 Fairway Lane Villas presents an exceptional short-term rental investment opportunity. Sea Pines Plantation is one of the most desirable & high-demand rental markets on the East Coast and, with a consistent flow of visitors year-round. The comprehensive renovation means the property will likely command top-tier rental rates & attract five-star reviews from guests who appreciate modern amenities & a turn-key experience. The property's convenient location with easy access to the beach, bike paths, & all of Sea Pines' world-class attractions ensures strong occupancy & repeat bookings. Sea Pines is one of the few communities on the island where short-term rentals are a core part of the economy, & the demand for quality properties is robust.

13 Lawton Drive Unit 72, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: RE/MAX Island Realty.

$1,225,000

3 Beds ⋅ 3 Baths ⋅ 1,388 SqFt. ⋅ HILTONHEAD-502545 MLS

Golfer's dream condo with beautiful golf and lagoon views. Just a short walk to the Sea Pines Beach Club and ocean. This 3 bedroom, 3 bathroom villa features a first-floor primary suite. Enjoy on-site tennis, nearby Forest Preserve trails, and world-class Sea Pines amenities including golf, beaches, dining, and Harbour Town.

13 Lawton Drive Unit 79, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate. Selling Office: Keller Williams Realty.

$260,000

2 Beds ⋅ 1 Baths ⋅ 725 SqFt. ⋅ HILTONHEAD-502498 MLS

Enjoy island living at an incredible value! This charming single-story, 2-bedroom, 1-bath villa is ideally located just minutes from the South End of Hilton Head, close to beaches, shopping, and dining. Features include new LVP flooring, updated lighting, and a refreshed bathroom. Perfect for a primary residence, investment property, or second home, with easy access on and off the island via the Cross Island Parkway. Regime fee includes water/sewer, trash pickup, landscaping of common areas, pool maintenance, insurance and building upkeep (with the exception of doors and windows). Some photos are virtually staged. Minutes to Folly Field, Burkes Beach, Shelter Cove, and Coligny, this villa offers the best of Hilton Head's coastal lifestyle- relaxed, convenient, and move-in ready!

6 Point Comfort Road Unit 9A, Hilton Head Island

Listing courtesy of COAST - Brokered by EXP Realty. Selling Office: RE/MAX Island Realty.

$3,600,000

4 Beds ⋅ 5 Baths ⋅ 3,900 SqFt. ⋅ HILTONHEAD-502424 MLS

Welcome to 3,900 square feet of coastal perfection, where every detail has been thoughtfully reimagined for modern living. This 4-bedroom, 4.5-bath showstopper sits in the sweet spot, just three rows back from the beach with the beach path running right behind the property.Completely new redesign with today's open concept in mind, this home flows effortlessly from room to room with top-tier finishes throughout. Two first floor master bedrooms,one with a wet room master bath and two walk-in closets.The second master features an office with fireplace.The custom-built bunk room is perfect for hosting friends and family (or maxing out rental income). Complete interior renovation including all mechanicals . Renovated pool and patio in a backyard that backs directly onto the Atlantic Dunes Golf Course.New siding, roof and hurricane-rated Marvin windows were recently replaced for peace of mind.Grab your bike and you're minutes from Harbour Town, South Beach Marina, Coligny Plaza, plus golf and tennis. This isn't just proximity, this is the Hilton Head lifestyle on tap.Whether it's your primary residence, vacation escape, or investment property, this home delivers on all three. The beach is calling, answer it.

167 Sea Pines Drive, Hilton Head Island

Listing courtesy of May River Realty. Selling Office: Sea Pines Real Estate - The Cottage Group, LLC.

$1,100,000

5 Beds ⋅ 4 Baths ⋅ 3,408 SqFt. ⋅ HILTONHEAD-502108 MLS

Location is everything! Just 3rd row from the ocean and steps from the private Port Royal beach, this 5-bedroom, 3.5-bath home sits on an extra-large almost half an acre! The property features a private pool, screened porch, and beautiful lagoon views, offering endless potential to create your dream Lowcountry retreat. The kitchen opens to a spacious family room and dining area, with heart pine floors, a wet bar, plantation shutters, and a separate formal dining room. The primary bath has been remodeled, and the home offers an inviting floor plan ideal for both relaxing and entertaining. While the property is being sold as-is and would benefit from some updating, its priced to sell and the location and lot size are unmatched. A rare opportunity to own in the sought-after private beachfront community of Port Royal!

98 S Port Royal Drive, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Peirce Group Brokered by EXP Realty LLC.

$2,400,000

4 Beds ⋅ 3 Baths ⋅ 3,327 SqFt. ⋅ HILTONHEAD-501945 MLS

Fantastic location just five rows from the ocean and directly on the walkway to the beach! This beautifully renovated 4-bedroom, 3-bath home features a private pool and an open, inviting floor plan. The kitchen has been completely updated with new appliances, backsplash, cabinetry, and fixtures, showcasing a high-quality remodel that feels fresh and modern. The bright, clean interior is move-in ready. The living room centers around a stunning fireplace that serves as a perfect focal point, complemented by plantation shutters throughout. Each bathroom has been tastefully redone with stylish finishes, tiled and glass-enclosed showers, and updated fixtures. Additional highlights include smooth-painted ceilings, new flooring throughout, and a beautifully finished living area that exudes warmth and comfort. Used only as a second home, the property has been meticulously maintained and would make an exceptional primary residence, vacation home, or high-income rental investment. Outdoor living is superb, with generous deck space and a private plunge pool, perfect for relaxing or entertaining. Enjoy easy beach access, simply follow the walkway from your backyard to the ocean!

6 Black Skimmer Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Collins Group Realty.

$1,050,000

3 Beds ⋅ 3 Baths ⋅ 1,388 SqFt. ⋅ HILTONHEAD-501591 MLS

Updated 3 BR/3BA Fairway Lane villa with arguably the best view of the large serene lagoon, huge live oak, and golf beyond. Enjoy a day at the beach just across Sea Pines Drive, followed by some tennis or putting on the private putting green, and then relax on the back patio and enjoy a beautiful sunset. This completely updated villa offers tile flooring, cathedral ceiling, tons of natural light, updated kitchen, baths, beautiful furnishings etc.

13 Lawton Drive Unit 82, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach. Selling Office: Charter One Realty.

$392,000

2 Beds ⋅ 2 Baths ⋅ 1,064 SqFt. ⋅ HILTONHEAD-501402 MLS

Steps to the Beach! Walk to Coligny Plaza | 2BR Villa with Back Patio and Community Pool. Welcome to your perfect Hilton Head Island escape! Location, convenience, and coastal charm come together in this beautiful 2-bedroom, 1.5-bath villa at Hilton Head Cabanas. Walking distance to Coligny Plaza and directly across the street from the beach access path, this villa offers the ideal island lifestyle -- whether you are looking for a vacation getaway, investment opportunity, or full-time residence. The first floor features a functional layout with a cozy family room, a fully equipped kitchen, a dining area, and a convenient half bath. Open the sliding doors and step into your uncovered back patio and enjoy lush landscaping, serene views, and direct access to the community pool -- perfect for relaxing after a day at the beach. Upstairs, you will find two comfortable bedrooms, a full bathroom, and generous closet space throughout. The unit also includes designated parking and guest parking -- a valuable bonus in this sought-after South Forest Beach location. Don't miss your chance to own a piece of paradise just steps from shopping, dining, entertainment, and Hilton Head Island beaches.

32 S Forest S Beach Unit 12, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: EXP Realty LLC.

$1,675,000

3 Beds ⋅ 3 Baths ⋅ 1,851 SqFt. ⋅ HILTONHEAD-501124 MLS

Take this moment to stop and think about how amazing your life would be, owning a home only steps from the beautiful world-famous beaches of Hilton Head Island. Imagine the memories you will make with family and friends, enjoying this fantastic home with a community private beach access, and everything else the island has to offer, within a short drive to over 200 restaurants and bars, 19 public golf courses, many marinas for boating and fishing, and so many more world-class island amenities. If you've been waiting for the perfect home, your wait is over! Located in Folly Field, one of the island's original oceanfront communities, 4 Moonshell is a 2nd Row, newer 2017 construction (tax records are incorrect) 3BR/3BA home designed and built with every detail in mind. It offers space for everyone, and the pool area with a pool bar is the oasis you'll never want to leave. The oversized 3-car garage provides space for your island toys. You'll appreciate the peace of mind that impact-resistant windows throughout and spray foam insulation provide in terms of low energy consumption and safety against adverse weather conditions. More pluses added with a new HVAC in 2023, exterior paint in 2025, and a newer electric pool heater. This home has been lovingly cared for and has never been a rental, although it would generate a fantastic income of $135k+ on the short-term rental market. A change in family plans brought this special home to market, so jump on this opportunity before someone else does!

4 Moonshell Road, Hilton Head Island

Listing courtesy of Real Life Brokered By EXP Realty LLC. Selling Office: William Raveis - Carolina LLC.

$699,000

2 Beds ⋅ 2 Baths ⋅ 1,600 SqFt. ⋅ HILTONHEAD-500886 MLS

This end unit villa is a bright and open space with an "A+" location. It is a unique opportunity for both golfers and/or beachers alike, within short walking distance to both the Sea Pines Beach Club and the acclaimed Heron Point and Atlantic Dunes golf courses. It is also an ideal location for anyone who prefers not to climb steps or wants simple access, due to its being first floor, one level residence. This villa has also proven to be an exceptional rental property, with a strong history of repeat guests who return year after year to enjoy the Sea Pines lifestyle. Currently grossing 39K. The interior was refreshed in November 2025 and offers the perfect blend of comfort, convenience, and Lowcountry charm. The spacious great room is sunlit and features an integrated Carolina Room off the living space enclosed with walls of glass that overlook a peaceful expanse of green space ideal for morning coffee. Both bedrooms are generously sized. Recent upgrades include a new HVAC system (2022). The outside features brand new pavers leading up to the front door as well as a new sodded lawn, updated drainage, and fresh landscaping which will be completed by Thanksgiving. Use as your own golf trip/beach trip destination, a lock-and-leave vacation escape, or as a proven income-producing property. With proximity to world-class golf, miles of pristine beaches, and the best of Hilton Heads dining, shopping, and recreation, it presents a rare opportunity to own your slice of paradise.

11 Lighthouse Road Unit 25, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club. Selling Office: Sea Pines Real Estate - Beach Club.

$289,000

2 Beds ⋅ 1 Baths ⋅ 725 SqFt. ⋅ HILTONHEAD-500809 MLS

Don't miss this fantastic opportunity to own a charming single-story, 2-bedroom, 1-bath brick villa located on the desirable South End of Hilton Head Island! This duplex-style home offers a spacious, fully fenced backyard complete with a fire pit and lounge area perfect for relaxing or entertaining. Just a short stroll to Palmetto Bay Marina where you'll find restaurants, shopping, water sports, and scenic nature trails. Conveniently located near the Cross Island Parkway for easy access to Mid-Island and the North End. Ideal as a primary residence or second home. Regime fee includes water/sewer, trash pickup, landscaping of common areas, pool maintenance, insurance, and building upkeep (excluding windows and doors).Don't let this wonderful South End opportunity pass you by!

6 Point Comfort Road Unit 1B, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: RE/MAX Island Realty.

$1,385,000

3 Beds ⋅ 3 Baths ⋅ 2,968 SqFt. ⋅ HILTONHEAD-500435 MLS

CLOSE PROXIMITY to the BEACH and the SEA PINES BEACH CLUB. Tucked away on a quiet cul-de-sac street sits this 3-bedroom + den/office and 3-bathroom home offering nearly 3,000sqft of space, privacy, and charm in the heart of Sea Pines. The great room features cathedral ceilings that bring in tons of natural light and seamless flow into the kitchen, ideal for everyday living and entertaining. Enjoy the Lowcountry lifestyle with lagoon views in the front and incredible golf views of the 13th fairway of Atlantic Dunes Golf Course from your screened in porch and private patio. A 2-car garage with additional storage completes the package. This central location gives you easy access to the Sea Pines Beach Club, South Beach, Salty Dog, Harbor Town and all of the world class amenities Sea Pines offers.

20 Woodbine Place, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty. Selling Office: Greenplate Group Brokered by eXp Realty.

$865,000

3 Beds ⋅ 2 Baths ⋅ 1,750 SqFt. ⋅ HILTONHEAD-500194 MLS

This 3-bedroom, 2.5-bath villa in close proximity to the beach has stunning views of the 11th fairway of the acclaimed Atlantic Dunes Golf Course. The current owners opened the kitchen by removing a wall, complete renovation of the kitchen with silestone countertops and premium appliances, and converted the screened porch area to what is now the Great room. This property features August 2025 HVAC, all tile/hardwood flooring, open floor plan, and the upper level houses 2 guest suites and 1 bath. This villa offers comfort, style, views, and incredible income potential with a gross rental projection of $54,900. Sea Pines offers world class amenities to include 2 beach clubs, restaurants, shopping, golf, tennis, pickleball, and 2 marinas.

15 Lighthouse Road Unit 32, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Sea Pines Real Estate - Beach Club.

$6,100,000

5 Beds ⋅ 5 Baths ⋅ 4,449 SqFt. ⋅ HILTONHEAD-500143 MLS

Welcome to 30 E Beach Lagoon, a stunningly remodeled Oceanfront home located on one of Sea Pines most prestigious streets. Rarely does a property blend luxury, charm, and location this seamlessly. Designed with timeless coastal elegance, this home offers an exceptional lifestyle, 5 bedrooms, 5 baths, and just steps from your private deeded beach access. Inside, soaring vaulted ceilings with exposed beams, a masonry brick fireplace, and wide-plank wood floors create a warm, inviting atmosphere. The kitchen features high-end natural wood cabinetry, sleek countertops, and stainless steel appliances ideal for entertaining or quiet mornings at home. The main house flows beautifully into a spacious living area filled with natural light, while the private, attached guest house offers flexibility for hosting friends or extended family. The primary suite features a private deck with peekaboo ocean views and easy access via the in-home elevator. Outside, enjoy your own private pool surrounded by lush, mature landscaping, creating a serene retreat that feels both secluded and coastal. The home also includes a two-car garage and has never been used as a rental, offering pristine condition and pride of ownership. Whether you're searching for a luxury second home or a high-performing short-term rental, 30 E Beach Lagoon delivers on all fronts location, design, and lifestyle all within the gates of Sea Pines Resort.

30 E Beach Lagoon Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$830,000

3 Beds ⋅ 2 Baths ⋅ 1,881 SqFt. ⋅ HILTONHEAD-454430 MLS

Discover this beautifully maintained 3-bedroom, 2-bath one-level home nestled in one of Hilton Head's most sought-after communities. Point Comfort captures the essence of early island living - quiet streets shaded by majestic live oaks, a private community boat ramp, and a day dock perfect for exploring Broad Creek and beyond. Step inside and be greeted by a bright, open living space that flows seamlessly to the fenced backyard - complete with a paver patio, lush natural surroundings, and room to add your dream pool. Enjoy cozy evenings by the fireplace in winter and stay cool in summer beneath custom retractable awnings. The open-concept kitchen features quartz countertops, counter seating, and smart storage with pull-out shelving. A butler's pantry and oversized garage add to the home's incredible functionality, while an insulated, air-conditioned bonus room offers endless possibilities - office, studio, fitness room, or workshop. Major updates since 2019 include a new roof, driveway, and appliances - move right in and start living the Hilton Head lifestyle you've always imagined. Homes in Point Comfort rarely come available - schedule your private showing today before this coastal gem is gone!

6 Sea Olive Road, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: Howard Hanna Allen Tate Hilton Head.

$2,850,000

4 Beds ⋅ 4 Baths ⋅ 2,958 SqFt. ⋅ HILTONHEAD-454319 MLS

Fully renovated in 2024 and located directly across from the beach path, this Sea Pines home offers an incredibly short walk to the ocean and sits on a rare 0.6+ acre lot. With 4 bedrooms, 3.5 baths, bonus spaces, and sold fully furnished, it sleeps 14 and features an open-concept layout with a brand-new kitchen ideal for entertaining. Outside, enjoy a private heated pool with splash-down spa, wrap-around deck, and putting green. Close to South Beach Marina, golf, tennis, and bike trails. Turnkey investment with excellent rental income and future bookings already in place. Coastal luxury at its finest!

4 South Beach Lane, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate. Selling Office: BESTNEST By Beverly Serral.

$905,000

3 Beds ⋅ 3 Baths ⋅ 1,275 SqFt. ⋅ HILTONHEAD-454120 MLS

RARE OFFERING IN SEA PINES! This ultra-charming 3BR villa is just a short, scenic stroll to the Beach Club and the Plantation Club! A remarkable setting with compelling golf and water views. Coastal and nautical touches blend seamlessly with recent interior updates. Featuring renovated baths, a stylish kitchen, updated appliances, smooth ceilings, and a custom floating staircase with cable rails. The most recent updates took place between 2020 and 2025! The sun-kissed Carolina Room is a wonderful contribution, making this villa ultra spacious. 1st floor primary suite and a rare laundry room shower for all kinds of creative uses! Pet-friendly.

2 Woodbine Place Unit 57, Hilton Head Island

Listing courtesy of Collins Group Realty. Selling Office: Sea Pines Real Estate - Beach Club.

$7,050,000

6 Beds ⋅ 9 Baths ⋅ 7,789 SqFt. ⋅ HILTONHEAD-453976 MLS

Unobstructed ocean views define this 1.16-acre Hilton Head Island estate cocooned in the privacy of a double lot. Designed for both quiet comfort and large-scale entertaining, noteworthy features include a temperature-controlled wine cellar for 1,000 bottles, an outdoor sports area with basketball, bocce, and shuffleboard, a beachfront putting green, a resort-style pool, and an outdoor kitchen. High ceilings and boundless windows allow for serene ocean vistas from the home's grand interiors, while coffered ceilings add to its timeless luxury. Complete with a temperature-controlled four-bay garage - this is the home for a true collector.

6 Overlook Pl, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Keller Williams Realty.

$1,900,000

4 Beds ⋅ 4 Baths ⋅ 2,985 SqFt. ⋅ HILTONHEAD-453221 MLS

A rare blend of timeless elegance and modern comfort in Sea Pines. This exquisitely reimagined single-level residence with beautiful finishes. The open-concept kitchen flows into a sunlit family room with custom built-ins and a tailored desk nook. New flooring, new lighting, new circular driveway. Offered beautifully furnished. Gracious entertaining spaces evoke refined coastal living. A private Savannah brick courtyard encloses a serene pool, waterside gazebo, and charming guest cottage. Wildlife oasis and entertainment paradise on a rambling private corner lot.

37 Woodbine Place, Hilton Head Island

Listing courtesy of Century 21 Diamond Realty. Selling Office: Hilton Head Properties.

$2,015,000

4 Beds ⋅ 3 Baths ⋅ 2,920 SqFt. ⋅ HILTONHEAD-452454 MLS

A PERFECT 4BR/3BA custom-crafted home on Baynard Cove Rd in Sea Pines! No detail overlooked in this captivating residence with gas lanterns, custom wrought iron gates, Tennessee flagstone courtyard, heated saltwater pool & waterfall spa, covered outdoor kitchen & fireplace. Very private fenced backyard borders Heritage Woods and is a 10-min walk to the beach. Crown molding, Australian Cypress wood floors, lit coffered and tongue & groove cathedral ceilings, 2 fireplaces, impact windows, sound system, hammered copper sinks, granite counters, stainless appliances, wet bar, chefs kitchen... A magical forever home or one-of-a-kind beach retreat!

44 Baynard Cove Road, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Blufft. Selling Office: Sea Pines Real Estate - The Cottage Group, LLC.

$1,550,000

3 Beds ⋅ 4 Baths ⋅ 3,285 SqFt. ⋅ HILTONHEAD-452520 MLS

Set on a lush 3/4-acre lot overlooking the 17th tee of Heron Point, this 3,285 SqFt Sea Pines home blends thoughtful updates with untapped potential. Enjoy a newer roof, HVAC, PEX plumbing, all new ductwork, and a refreshed kitchen. The heated saltwater pool and new circular drive add to the home's charm and curb appeal. Bathrooms and the primary suite offer a chance to add your personal touch. With space, privacy, and a strong framework, this home is perfect for a buyer with vision looking to create something special in one of Hilton Head's most desirable communities. Great proximity to Harbour Town and the Beach Club! Short-term rentals allowed. Seller offering a $20k buyer credit with an acceptable offer, providing flexibility for updates, aesthetic enhancements, or closing costs. A rare opportunity to tailor a Sea Pines property to your individual vision.

2 Red Maple Rd, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry. Selling Office: Sea Pines Real Estate - Beach Club.

$530,000

2 Beds ⋅ 3 Baths ⋅ 1,064 SqFt. ⋅ HILTONHEAD-452300 MLS

Rarely available, 2 bedroom, 2.5 bath Hilton Head Cabanas townhome style end villa location - no one above or below you and only one neighboring townhome to the side. Hilton Head Cabanas is ideally located across S. Forest Beach Dr. for beach access. Fresh inviting interior with tile flooring on main floor and LVP on stairway and bedrooms. Updated kitchen with quartz counters, modern white cabinetry and new stack style washer/dryer. Each bedroom has en suite bath and extra half bath on main floor. Secluded enlarged courtyard with easy access to community pool. Pet freindly and offered turn key to start enjoying the Hilton Head lifestyle.

32 S Forest Beach Drive Unit 48, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Real Life Brokered By EXP Realty LLC.

$1,625,000

6 Beds ⋅ 4 Baths ⋅ 3,052 SqFt. ⋅ HILTONHEAD-451958 MLS

Spacious 6BR Island getaway 5 rows from the Atlantic Ocean in beachy chic Folly Field Beach community! Refreshing heated pool with grill pavilion in private backyard with lots of space for your boat & extra vehicles on large lot situated close to Folly Field Beach Park - popular Islander Beach Park and Driessen Beach Park nearby. Lots of improvements including new roof in 2024, spray foam in attic in 2022, new Pella sliding patio door in 2023, all new modern kitchen in 2021, exterior & interior painting in 2021, first floor primary bath renovated in 2021, and smooth ceilings in 2020.

70 Folly Field Road, Hilton Head Island

Listing courtesy of Dunes Real Estate. Selling Office: Greenplate Group Brokered by eXp Realty.

$4,150,000

4 Beds ⋅ 6 Baths ⋅ 2,872 SqFt. ⋅ HILTONHEAD-450742 MLS

Iconic, 2nd row West Beach Lagoon estate on over 1+ acre - a rare and extraordinary offering in one of Hilton Head Island's most coveted ocean-oriented enclaves! This magnificent coastal property is framed by ancient, moss-draped live oak trees, some over 200 years old, creating an enchanting Lowcountry setting with privacy, beauty, and serenity. From nearly every room in this thoughtfully restored home, enjoy stunning vistas - golf course views to the side and rear, and ocean breezes just steps away across the quiet street. The timeless architecture and charming design details pay homage to Sea Pines' early history, blending the allure of "Old Hilton Head" with the comforts of today, thanks to extensive modern updates that preserve the home's character while enhancing its livability.The grounds are equally impressive, offering a private sanctuary to gather, entertain, and relax. A recently added resort-style pool with surrounding terrace transforms this estate into a personal retreat, creating the feel of your own private resort. Whether enjoying the expansive lawns, meandering among majestic oaks, or strolling just across the street to access nearly five miles of pristine white-sand Atlantic beach, this is island living at its finest.This is a property with many possibilities: ideal as a luxurious primary residence, a serene second home getaway, a lucrative vacation rental or even as a homesite to build their own custom home on. Currently, it enjoys immense popularity as a high-performing short-term rental, grossing approximately $200,000 annually, providing strong income potential for investors seeking both lifestyle and return. Homesites of this caliber, size, and location are nearly impossible to duplicate on Hilton Head Island, making this a rare opportunity for a discerning buyer who values privacy, proximity to the beach, natural beauty, and timeless appeal. A legacy estate in the truest sense - ready to be enjoyed today and cherished for generations to come.

34 W Beach Lagoon Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club. Selling Office: Keller Williams Realty.

$3,100,000

5 Beds ⋅ 5 Baths ⋅ 2,855 SqFt. ⋅ HILTONHEAD-451139 MLS

This rare 2nd-row property offers an unbeatable location just steps from the beach, combining coastal charm with modern comforts. This 5-bedroom, 5-bath home was thoughtfully expanded and upgraded in 2012, featuring an open-concept kitchen and family room, a private pool and spa surrounded by lush landscaping, and a fenced yard for added privacy. The upper level boasts a primary suite and two ensuite bedrooms, while the lower level provides additional living space, pool access, and two more bedrooms. This exceptional home in Sea Pines offers both relaxation and future development potential in one of the area’s most coveted locations!

13 Spotted Sandpiper Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Sea Pines Real Estate - Beach Club.

$650,000

4 Beds ⋅ 2 Baths ⋅ 1,576 SqFt. ⋅ HILTONHEAD-451198 MLS

Nestled in Hilton Head's Folly Field beach area, this home offers coastal living within walking distance to the beach. Inside find modern comfort with spacious living areas and a fully equipped kitchen. Retreat to the bedrooms and wake up to the gentle sea breeze on the private patio. Outside, lush grounds and a fenced yard await. Perfect for a short-term escape, indulge in the island's beauty and relaxation. This home is currently managed with Sea Turtle Vacation Rental as a short-term rental home. Recent updates include new roof, HVAC, water heater, flooring, doors, and more!

16 Oleander Street, Hilton Head Island

Listing courtesy of I Save Realty. Selling Office: Sea Pines Real Estate - The Cottage Group, LLC.

$4,250,000

6 Beds ⋅ 6 Baths ⋅ 6,000 SqFt. ⋅ HILTONHEAD-450230 MLS

Stunning deep-water residence in Sea Pines features a private, oversized dock with a boat lift, offering unparalleled waterfront access. Spanning nearly 6,000 square feet, the open floor plan showcases breathtaking, unobstructed water views. The entertainer’s dream kitchen boasts a 60” Viking gas range, double stainless steel refrigerator, walk-in pantry, and a striking 12-foot granite bar complete with a wine cooler and ice maker. The outdoor living space features a circular driveway with pervious pavers, a resort-style private pool and hot tub, and a fire pit—all set within over 3,000 square feet of beautifully designed patio space. OSCREA

25 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of DOT REAL ESTATE.

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