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$799,000
6 Beds ⋅ 8 Baths ⋅ 4,407 SqFt. ⋅ HILTONHEAD-512129 MLS
Own one-eighth of this professionally managed, turnkey home by Pacaso. Bald Eagle sits on a quiet third-row lot on Hilton Head Island, just a short walk from the Atlantic through a private beachside community. The exterior has a covered front porch, classic columns and a shingled roofline that feels considered and unhurried against the island's natural landscape. Inside, the entry foyer has a custom curved staircase, ornate columns, coffered ceilings and light hardwood floors that run throughout the main level. The great room has box beam ceilings, a traditional fireplace with a modern tile surround and built-in storage, opening directly into the dining area with French doors to the backyard. The kitchen has dark stone countertops, a premium range hood, glass-front cabinetry, a quartz-topped island and a separate breakfast bar. The primary bedroom opens to the backyard patio and has a spa-caliber en suite bath with a freestanding soaking tub, tiled shower and dual vanities. Five additional bedrooms, each with private baths, and a bonus room with wet bar complete the layout across three floors connected by a four-stop elevator. The heated pool, overflowing hot tub and outdoor cooking area sit within mature landscaping that gives the backyard a private, enclosed quality. The beach is a short walk through the community's private beachside access. Harbour Town and its iconic lighthouse, the Quarterdeck's waterfront dining and the Sea Pines Resort's golf courses and trails are all within easy reach. Bald Eagle is professionally designed, appointed and managed by Pacaso. Owners arrive to find the home ready at every visit, with nothing left to coordinate before the stay begins.

8 Bald Eagle Road, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$7,399,500
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.

$1,650,000
4 Beds ⋅ 3 Baths ⋅ 2,015 SqFt. ⋅ HILTONHEAD-511511 MLS
Location is everything! This ocean-oriented, four-bedroom, three-and-one-half-bath condominium is just steps from the Atlantic Ocean and the shops, dining and entertainment of South Beach Marina Village in Sea Pines.Ideally positioned beside the new community pool, the residence offers a private rear deck as well as an upstairs deck off the primary suite. Enjoy convenient access to the beach, leisure trails, pickleball, restaurants, shopping and endless opportunities for recreation.Whether you are seeking a primary residence, vacation retreat or investment property, this is a wonderful opportunity to begin making lasting Hilton Head Island memories.

225 S Sea Pines Drive Unit 1401, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$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.

$2,100,000
4 Beds ⋅ 4 Baths ⋅ 3,531 SqFt. ⋅ HILTONHEAD-511413 MLS
Located in the heart of Harbour Town within Sea Pines, this beautifully appointed home offers the perfect blend of luxury, comfort and coastal charm. Enjoy easy access to iconic Harbour Town Yacht Basin, Lighthouse, shops, waterfront dining, renowned golf, miles of leisure trails and a short drive or shuttle to magnificent Hilton Head beaches. The home features 4 bedrooms and 4 bathrooms with expansive deck and pool. Ideal for entertaining, unwinding from a day at the beach or golf course. Whether you're seeking a full-time residence, vacation retreat or an investment property, this exceptional home captures the very best of the Sea Pines lifestyle.

8 Windjammer Court, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate.

$7,950,000
7 Beds ⋅ 5 Baths ⋅ 6,034 SqFt. ⋅ HILTONHEAD-510860 MLS
One of the finest oceanfront residences in Sea Pines, this custom-built home was thoughtfully designed for multi-generational living and showcases exceptional craftsmanship, timeless architecture, and views of the Atlantic Ocean. Offering an open-concept design filled with natural light, the home features multiple gathering spaces, four fireplaces, two entertainment rooms with full-service bars, a private office, and luxurious accommodations throughout. The chef's kitchen is a masterpiece of both form and function, appointed with premium Dacor, Wolf, Miele, and Sub-Zero appliances, custom cabinetry, striking green onyx countertops, and expansive preparation and dining areas designed for entertaining on any scale. From the moment you arrive, architectural details inspired by Frank Lloyd Wright set this home apart, beginning with a tranquil koi pond entrance. An oceanfront oasis awaits, featuring a large swimming pool, heated spa, private beach walkway, and white Italian marble framing the pool. Combining warmth, artistry, and unparalleled quality, this remarkable Sea Pines residence offers a rare opportunity to own one of Hilton Head Island's most distinguished oceanfront homes.

21 Red Cardinal Road, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate.

$9,375,000
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.

$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.

$5,295,000
5 Beds ⋅ 6 Baths ⋅ 4,965 SqFt. ⋅ HILTONHEAD-503477 MLS
A rare opportunity, nestled on over 2 acres in popular Sea Pines. This Lowcountry, custom estate features a private, detached multi-purpose cottage, quietly located in the rear of the property, accessed exclusively by a land bridge. A beautifully curated 5 bedroom compound, set among majestic live oaks and pines, offers a sanctuary with single level living on the main floor, a private lagoon, pool/spa along with multiple outdoor spaces, ideal for entertaining. Throughout the main living areas you'll find rich hardwood floors, beautiful trim details and walls finished in sophisticated, classic neutral tones-creamy whites and warm taupes. The kitchen sets the tone of the home with natural dolomite countertops, taupe perimeter and island cabinets with custom arched oak upper cabinets flanking the range, complete with pure brass hardware. The mix of traditional selections is balanced with a modern, linear light fixture over the island. The scullery kitchen provides ample prep space and storage in addition to a dedicated pantry. Enjoy mixing cocktails in the well appointed wet bar with floating shelves and knurled brass plumbing. Features in the bathrooms include timeless marble mosaics paired effortlessly with curated ceramics complete with custom cabinetry and classic hardware selections. This commitment to mixing the traditional with modern, high-end selections guarantees a home that will never go out of style. Experience working remotely in the study featuring custom built-in desks. Dramatic, cathedral ceilings make the home feel larger than life. A media room invites you to relax and linger. Details abound with ceilings trimmed in tongue and groove, shiplap walls, custom wood stained wall paneling, arched built-ins, custom built-in office. The versatile guest cottage welcomes friends and family, featuring a living room, wet bar, bedroom, full bathroom, and additional garage space for up to three vehicles. An expansive screened porch enhances the outdoor experience, making it perfect for gatherings such as oyster roasts or bourbon tastings, or simply relaxing while enjoying the picturesque natural surroundings. Experience a home that seamlessly integrates classic design with modern living amidst the scenic beauty rooted in Lowcountry heritage.This property offers a unique experience of residing on a secluded estate with world-class amenities including golf, tennis, stables, a nature preserve, restaurants and shops just a stroll away.

4 Plantation Drive, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$2,199,000
4 Beds ⋅ 4 Baths ⋅ 3,700 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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