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$619,900
3 Beds ⋅ 2 Baths ⋅ 1,636 SqFt. ⋅ HILTONHEAD-512809 MLS
Nestled in the sought after Club Course neighborhood of Sea Pines, 21 Acorn Lane offers an exciting opportunity to create your ideal Lowcountry retreat. This 3 bedroom, 2 bath home features a cathedral ceiling that adds to its open and spacious feel, while the expansive deck provides the perfect setting for outdoor entertaining or peaceful mornings surrounded by mature Lowcountry landscaping. Ready for renovation and a new vision, the home offers a great foundation for a buyer looking to update and make it their own. Ideally located with convenient access to the Sea Pines leisure trails, restaurants, shopping, golf, beaches, Harbour Town, South Beach Marina, and all of the world class amenities Sea Pines has to offer. An incredible opportunity to bring your vision to life in one of Hilton Head Island's most desirable communities.

21 Acorn Lane, Hilton Head Island

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

$1,495,000
5 Beds ⋅ 3 Baths ⋅ 2,504 SqFt. ⋅ HILTONHEAD-512460 MLS
Some homes give you a place to stay in Sea Pines. 15 Dewberry gives you a reason to stay in. This five-bedroom home in Greenwood Forest pairs the Sea Pines lifestyle with the kind of amenities that make the house itself part of the vacation. And yes, the bikes come with the house. THE PUTTING GREEN: A professionally designed three-hole green spans 35 to 38 feet with an 11 stimp rating and real break, good for a morning warm-up or one more round after dinner. THE HANGOUT: A separate in-law suite with its own kitchenette turned wet bar, ice maker included. One of the home's five bedrooms currently serves as the suite's living room, and flexes just as easily into a bunk room when more sleeping space is needed. THE SPACE: Brazilian hardwood floors, a tongue and groove ceiling, quartz counters, and GE Cafe appliances run throughout the single story home, with new flooring added in the bedrooms. A Carolina room with a daybed and porch swing gives everyone one more place to land. THE NEIGHBORHOOD: Greenwood Forest is one of the few pockets of Sea Pines with its own community pool, tennis and pickleball, and a playground, a short distance from the Shops at Sea Pines and Beach Trolley access through a wooded community path. Easy distance to either HarbourTown or the Beach! Already an active vacation rental, the home has a confirmed booking of 91 nights for 2027 alone, worth more than $19,000, a sign of how much demand a house like this can hold.

15 Dewberry Lane, Hilton Head Island

Listing courtesy of Luxury Homes of Hilton Head.

$2,900,000
4 Beds ⋅ 4 Baths ⋅ 3,895 SqFt. ⋅ HILTONHEAD-511549 MLS
Filled with natural light and thoughtfully designed for comfortable living and entertaining, this exceptional home offers soaring ceilings, striking slate flooring, and an open, flowing floor plan. The spacious chef's kitchen seamlessly connects to the living room, dining area, family room, and breakfast nook, creating inviting spaces for gathering with family and friends. Offering four bedrooms and three-and-a-half baths, the home provides generous accommodations for both everyday living and hosting guests. Outside, enjoy a private fenced backyard complete with a sparkling pool, covered outdoor living area, and beautifully designed hardscape and mature landscaping-perfect for relaxing, grilling, and entertaining. Ideally located just moments from the iconic Harbour Town Golf Links, home of the annual RBC Heritage, this home places you in the heart of everything Sea Pines has to offer. Enjoy miles of leisure trails, pristine beaches, the Sea Pines Beach Club, Harbour Town Marina, South Beach Marina, Lawton Stables, world-class dining and shopping, and three championship golf courses. This is a rare opportunity to enjoy one of Hilton Head Island's most sought-after lifestyles.

75 Baynard Cove Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$879,000
3 Beds ⋅ 2 Baths ⋅ 1,882 SqFt. ⋅ HILTONHEAD-512297 MLS
Welcome to effortless Lowcountry living in the desirable Club Course neighborhood of world-famous Sea Pines Resort. This beautifully maintained 3-bedroom, 2-bath Hilton Head Island home is light, bright, and move-in ready, offering the perfect combination of comfort, location, and island lifestyle. Thoughtful updates include new LVP flooring, fresh paint, updated primary bathroom, Trex decking, and a 2025 Trane HVAC system. The spacious back deck is ideal for outdoor dining, entertaining, or relaxing, while the large backyard offers space for a pool and for creating a private oasis. Located near the main gate of Sea Pines, this home provides quick and convenient access to everything Hilton Head Island has to offer while still enjoying the privacy and amenities of one of the island's most iconic communities. Sea Pines is home to three renowned public golf courses, miles of pristine beaches, numerous restaurants, Harbour Town, private owner and guest beach access at Tower Beach, and the exciting redevelopment of South Beach. From biking beneath moss-draped live oaks to golf, boating, dining, and days spent on the beach, the Sea Pines lifestyle is truly hard to beat. Hilton Head Island has also been recognized as the #1 Island in the U.S. for nine consecutive years, further reinforcing why so many people choose to call this special place home. Whether you're searching for a primary residence in Sea Pines, a Hilton Head Island second home, or a short-term rental investment / coastal getaway, this turnkey property is ready for its next owner. Move in, unpack, and start enjoying the Hilton Head Island lifestyle from day one. Schedule your in-person or live video walkthrough today.

157 Otter Road, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$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.

$925,000
2 Beds ⋅ 3 Baths ⋅ 2,032 SqFt. ⋅ HILTONHEAD-511564 MLS
Beautifully renovated 2BR/2.5BA home in the heart of Sea Pines offering exceptional privacy on a corner lot backing to protected open space and an adjacent unbuildable lot. From the charming courtyard entry with privacy gate to the expansive outdoor living space, every detail has been designed for comfortable everyday living and effortless entertaining. Open kitchen, dining and living areas, separate den with fireplace and built-ins, smooth ceilings, parquet floors, renovated kitchen and owner's bath, spacious guest suite, expansive deck with covered pergola, 2016 roof and 2023 Lennox HVAC, and parking for 3 cars. Located in one of Sea Pines' most welcoming neighborhoods where neighbors truly know one another. Located within the world-renowned Sea Pines Resort, owners enjoy easy access to miles of leisure trails, championship golf, beaches, tennis, pickleball, Harbour Town, South Beach Marina, restaurants, shopping, and countless outdoor activities. Whether you're searching for a primary residence, second home, or Lowcountry getaway, 33 Oak Court delivers privacy, comfort, and timeless appeal in one of Hilton Head Island's most sought-after communities.

33 Oak Court, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,449,000
4 Beds ⋅ 3 Baths ⋅ 2,500 SqFt. ⋅ HILTONHEAD-510645 MLS
Experience the ease of the Sea Pines lifestyle in this beautifully updated Greenwood Forest retreat, where soaring ceilings, walls of glass, and a private wooded setting create a home that feels both spacious and serene. Tucked away on a quiet cul-de-sac, this light-filled 4-bedroom, 3-bath home offers exceptional indoor-outdoor living in one of Sea Pines' most convenient locations. Multiple gathering spaces flow seamlessly together, creating a layout equally suited for everyday living and entertaining. The heart of the home is the stunning kitchen, completely renovated in April 2026. Thoughtfully designed with expansive quartz countertops, abundant cabinetry, a large center island, stainless steel appliances, beverage cooler, and generous workspace, it balances style and function beautifully. Whether hosting friends or enjoying a quiet morning before a day at the beach, this is a space designed to bring people together. Just beyond, the spectacular sunroom serves as the home's signature gathering space. Framed by dramatic windows and vaulted ceilings, it captures peaceful views of the private backyard while flooding the interior with natural light. Morning coffee, afternoon reading, evening conversations-this is the space you'll find yourself drawn to again and again. Outdoor living is equally inviting. An expansive deck, hot tub, mature landscaping, and private wooded backdrop create a setting that feels worlds away while remaining remarkably convenient to everything Sea Pines has to offer. Greenwood Forest's central location is one of its greatest advantages. Residents enjoy access to the private community pool, miles of leisure trails, and a dedicated pathway to Sea Pines Center for coffee, lunch, shopping, and everyday conveniences. Harbour Town, golf, tennis, dining, and the beach are all just a short bike ride away. Whether you're searching for a primary residence, second home, or investment property, this thoughtfully updated home delivers the privacy, convenience, and lifestyle that make Sea Pines one of Hilton Head Island's most sought-after communities.

8 Pine Court, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$8,995,000
5 Beds ⋅ 6 Baths ⋅ 5,837 SqFt. ⋅ HILTONHEAD-510013 MLS
Positioned directly on the Atlantic Ocean within the prestigious Sea Pines Resort, 33 Ruddy Turnstone Road is an extraordinary 5-bedroom, 4.5-bath oceanfront estate where timeless coastal architecture, resort-style amenities, and uncompromising craftsmanship come together to create one of Hilton Head Island's premier waterfront residences. Spanning approximately 5,837 square feet, commercial-grade marble and hardwood floors set the tone throughout an interior designed for effortless coastal living. The chef's kitchen is equipped with Wolf appliances and a Sub-Zero refrigerator, seamlessly connecting the main living areas to the outdoor entertaining spaces. Just beyond, a stunning new 2026 pool and spa overlook a wide stretch of private beach and panoramic Atlantic views. A dramatic floating translucent staircase connects three thoughtfully designed levels, each curated for entertaining. The top-floor Sky Bar & Bedroom features folding glass walls opening to an expansive oceanfront terrace, complete with a wet bar, ice maker, and refrigerator. The ground-level sports bar offers the same indoor-outdoor experience through its folding glass wall, while the 1,800-bottle climate-controlled wine room with an eSommelier system creates an unforgettable centerpiece. A 20-zone Sonos sound system serves every room and outdoor living area, all controlled from your phone. Above the three-car garage, a fully finished, independent flex space offering 2 full bedrooms plus a punk loft with its own HVAC, water heater, and electrical system provides ideal accommodations for guests, extended family, a private office, or fitness studio. The garage itself is equally well-appointed with a second Sub-Zero refrigerator, sink, ice maker, and wine cooler. Additional highlights include a Tesla charger, 1,000-pound elevator, whole-house water filtration, tankless water heaters, highest-rated hurricane-impact windows and doors, outdoor bar & grill, a new 2024 roof, and professionally redesigned landscaping in 2026. Located within Sea Pines Resort, owners enjoy private beach access, 90 holes of championship golf including Harbour Town Golf Links, miles of leisure trails, world-class dining, boutique shopping, and the island's premier resort amenities. Whether you're seeking a primary residence, luxury vacation home, or an exceptional short-term rental investment, 33 Ruddy Turnstone Road offers an extraordinary opportunity to own one of Hilton Head Island's premier oceanfront properties.

33 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$2,100,000
5 Beds ⋅ 4 Baths ⋅ 3,214 SqFt. ⋅ HILTONHEAD-509680 MLS
GREAT NEW PRICE $2,100,000! Rare opportunity to own a 5-bedroom beach-oriented home in the coveted Sea Pines community, offering the perfect combination of coastal lifestyle, exceptional versatility, and outstanding investment potential. Located just a short walk to one of Hilton Head Island's most desirable stretches of beach, this spacious property is ideally suited as a primary residence, luxury second home, or high-demand vacation rental.Designed with an inverted floor plan to maximize natural light and privacy, the home offers exceptional sleeping capacity for large families and guests, making it especially attractive for those seeking strong rental income potential. The private fenced pool creates the ideal outdoor retreat for relaxing after a day at the beach, while an upper deck, a screened porch, and generous gathering spaces make entertaining effortless.Lovingly maintained by only its second owner, the home features spacious living areas, vaulted ceilings, skylights, built-ins, a fireplace, dumbwaiter, and a light-filled den that adds flexibility for additional living or work-from-home space.Positioned near the Sea Pines Ocean Gate for easy access in and out of the community, this location places you approximately one mile from Coligny Beach and one mile to the Sea Pines Beach Club - right in the heart of one of Hilton Head's strongest vacation rental corridors.

18 Canvasback Road, Hilton Head Island

Listing courtesy of Engel & Volkers.

$2,100,000
4 Beds ⋅ 5 Baths ⋅ 2,967 SqFt. ⋅ HILTONHEAD-505896 MLS
With four en-suite bedrooms and a tranquil lagoon backdrop, this home truly balances space and serenity. Brazilian oak hardwoods (2024) gleam throughout. The 2025 kitchen renovation and expansion create the perfect setting for both cooking and entertaining. New patio doors (2024) lead you out the expanded deck (2022) where you can relax and take in the beautiful views Sea Pines is so famous for providing. Truly, no stone was left unturned in maintaining and upgrading this home. A full list of upgrades/renovations as well as a pool rendering can be found in the home at your viewing or be made available upon request. Residents of Sea Pines enjoy natural beaches, championship golf courses, miles of bike paths, two marinas, an upscale beach club, shops and restaurants all in a gated community with 24/7 security. This is not an opportunity to miss! Virtually staged photos are meant to provide spatial information and decor inspiration. No structural modifications have been made.

46 Hearthwood Drive, Hilton Head Island

Listing courtesy of Collins Group Realty.

$3,875,000
7 Beds ⋅ 7 Baths ⋅ 4,400 SqFt. ⋅ HILTONHEAD-504560 MLS
7 Bedrooms | Brand New Construction | Close Proximity to the Beach | Sea Pines - Set along the fairways of Heron Point Golf Course in the heart of Sea Pines, 34 Tupelo is a newly constructed luxury residence designed for gracious living, gathering, and effortless Lowcountry style. With seven bedrooms and beautifully curated spaces throughout, this home offers both scale and intimacy. Inside, soaring ceilings and abundant natural light frame an open-concept layout that feels both elevated and welcoming. The chef's kitchen anchors the home with high-end appliances including a gas range, dual dishwashers and refrigerators, a butler's pantry, designed for entertaining with ease. Multiple living areas, including a recreation room, reading nook, and private in-law suite with its own staircase, provide flexibility and privacy for every lifestyle. A private pool overlooks the golf course, while the patio and built-in outdoor kitchen create an ideal setting for morning coffee, relaxed afternoons, or evenings spent under the stars. The home's location within Sea Pines Resort places you minutes from the beach, Harbour Town Marina, the iconic lighthouse, Lawton Stables, world-class golf and tennis, and miles of leisure trails. Whether biking to the beach, or exploring everything Sea Pines has to offer, the lifestyle here is both convenient and exceptional. 34 Tupelo is a rare opportunity to own a brand-new luxury home in one of Hilton Head Island's most sought-after resort communities. This is where refined design, thoughtful spaces, and an unmatched setting come together seamlessly.

34 Tupelo Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$9,495,000
4 Beds ⋅ 5 Baths ⋅ 4,025 SqFt. ⋅ HILTONHEAD-504472 MLS
A custom-built oceanfront home that is defined by exceptional craftsmanship and an enduring coastal presence located in the world-class Sea Pines community. Designed by architect Neil Gordon and built by Cambridge Builders, 52 Canvasback offers the best in oceanfront living. A welcoming entrance foyer with double height ceilings invites you to appreciate the coastal views and the beautifully-executed architectural details. The rich wood detailing, hardwood floors, extensive custom millwork, and two fireplaces complement the finely-crafted spaces. The open living, dining, and kitchen areas flow naturally for everyday living and entertaining, supported by a butler's pantry and separate laundry room. A first-floor primary suite and wood-paneled office offer privacy and convenience, while 3 oversized, en-suite bedrooms upstairs and an oceanfront balcony provide plenty of room for friends and family. An expansive oceanfront pool deck extends the living space outdoors, creating a natural backdrop for lasting memories in an idyllic setting. Beach access via a private beach walkway. Timeless design, thoughtful details, craftsmanship and a stunning oceanfront location make this home an exceptional opportunity. Bunk room plans for heated and conditioned storage room available in documents. All information in this listing is deemed reliable but is not guaranteed and should be verified by Purchaser.

52 Canvasback Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

$2,199,000
4 Beds ⋅ 4 Baths ⋅ 3,125 SqFt. ⋅ HILTONHEAD-500571 MLS
This sophisticated Marsh Island turn-key home offers a perfect floor plan and a gorgeous stunning marsh-wrapped view of the free-form pool with a large Stone Works designed surround. The numerous first-class updates in this home, its meticulous care, and only part-time occupancy by the owners add to its endless appeal. Enter into an atrium that opens to the great room and dining area with soaring ceiling, and the kitchen and breakfast area. This magazine-worthy kitchen offers extensive Poggen Pohl cabinets, SubZero refrigerator, Wolf Microwave and cook top, double ovens, Madagascar marble counters, and a laundry/pantry room with wine racks and a wine refrigerator. Also located on the first floor are a separate office and the primary suite. Over the garage is a large bonus room. Off the foyer soars a modern staircase and balcony with stainless handrails and balusters leading to the 3 guest rooms. There is a 220 volt EV charger in the garage. Enjoy the exclusive and coveted Marsh Island residential neighborhood, with close access to Sea Pines Country Club and all that Sea Pines offers.

2 Long Marsh Lane, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

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