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7 Genoa Court, Hilton Head Island
$1,990,000
6 Beds ⋅ 7 Baths ⋅ 2,786 SqFt. ⋅ HILTONHEAD-512306 MLS
Stepѕ away frοm thе famеd 18th grееn liеѕ a unique opportunіty іn the heart of Sea Pines' iconic Harbour Town. This turnkey furnished home boasts 6 en-suite bedrooms, perfect for family gatherings and countless vacation memories. Rows of sliders lead guests from the newly renovated kitchen and double-story living area to the freshly resurfaced swimming pool and spa. This unique home features a rooftop deck with views to Calibogue Sound and is walking distance to the famous lighthouse, Liberty Oak, and family friendly dining and retail. The Sea Pines trolley is a short stroll away with transportation to the Sea Pines Beach Club, Sea Pines Center and South Beach amenities. With an established rental history, premier location and sleeping space for 20 this home is truly an investor's dream.

7 Genoa Court, Hilton Head Island

Listing courtesy of The Hilton Head Agency.

157 Otter Road, Hilton Head Island
$876,000
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.

70 Lighthouse Road Unit 2885, Hilton Head Island
$2,300
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512178 MLS
Enjoy the relaxed sophistication of Hilton Head Island during deeded Week 20, ideally positioned in the late May when the island is at its springtime best. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most sought-after settings. This desirable villa overlooks a lush lagoon, providing peaceful views and a tranquil backdrop throughout your stay. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and a vibrant coastal arts and culture scene. Imagine beginning your mornings with refreshing ocean breezes and serene golf course vistas, then setting out to bike beneath towering live oaks along miles of shaded pathways. Spend your afternoons on award-winning fairways, relaxing on the beach, or exploring the island's natural beauty before unwinding with spectacular waterfront sunsets. May's comfortable temperatures and blooming landscapes create the perfect setting for beach walks, outdoor dining, dolphin cruises, and all that Sea Pines has to offer-without the crowds of peak summer. Whether you prefer championship golf, coastal adventures, or simply relaxing on your private balcony overlooking the greens, everything you need is right at your doorstep.

70 Lighthouse Road Unit 2885, Hilton Head Island

Listing courtesy of Lighthouse Realty.

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

34 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of Charter One Realty.

226 S Sea Pines Drive Unit 1588, Hilton Head Island
$950,000
2 Beds ⋅ 2 Baths ⋅ 1,086 SqFt. ⋅ HILTONHEAD-512086 MLS
Rare opportunity in Sea Pines Resort! This beautifully located 2-bedroom, 2-bath, single-level Lagoon Villa at 226 S Sea Pines Dr #1588 puts you less than 1/4 mile from the beach and just steps from the popular South Beach Marina Village on Hilton Head Island. Enjoy an unbeatable location near South Beach Marina, Harbour Town, dining, shopping, entertainment, bike trails, and the Atlantic Ocean-all within the world-renowned Sea Pines Resort.The villa features brand-new impact-rated windows and doors, vaulted ceilings, an open and spacious living area, and a private patio overlooking the tranquil lagoon. The one-floor layout makes this property especially appealing as a Hilton Head vacation home, second home, or investment property.While this villa has never been rented, other villas in this regime have demonstrated strong rental performance, making this an exciting opportunity for an owner looking to enter the highly sought-after Sea Pines vacation rental market. Use it as your own island retreat, generate rental income, or enjoy the flexibility of both. Location is everything on Hilton Head Island-and this one delivers: beach access, South Beach Marina Village, dining, recreation, and the amenities of Sea Pines are all exceptionally close. A rare combination of location, updates, lagoon views, and investment potential in one of Hilton Head Island's most desirable resort communities.Virtual enhancement has been used in some photographs.

226 S Sea Pines Drive Unit 1588, Hilton Head Island

Listing courtesy of Charter One Realty.

58 Planters Wood Drive, Hilton Head Island
$1,795,000
3 Beds ⋅ 3 Baths ⋅ 2,590 SqFt. ⋅ HILTONHEAD-511308 MLS
Don't miss this beautifully maintained, newer-style 3-bedroom, 3-bath home in a highly desirable Sea Pines location. Tucked away on a quiet cul-de-sac and private street just minutes from Harbour Town, this home offers the perfect combination of comfort, updates, and Lowcountry charm. Step inside to find beautiful new hardwood floors, smooth painted ceilings, and a spacious great room with soaring ceilings, a fireplace, and peaceful lagoon views. The updated kitchen features stainless steel appliances, granite countertops, a stylish backsplash, and opens seamlessly to the main living spaces. Additional features include a separate dining room and a wine bar, making this home ideal for entertaining. The first-floor primary suite offers a relaxing retreat with a spacious walk-in closet, double vanity, and walk-in shower. With two HVAC systems, a two-car garage, and abundant extra storage, this home is as functional as it is beautiful. Located in the heart of Sea Pines, enjoy convenient access to Harbour Town, beaches, leisure trails, golf, tennis, pickleball, dining, shopping, and all the incredible amenities Sea Pines has to offer.

58 Planters Wood Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

70 Lighthouse Road Unit 2871, Hilton Head Island
$1,800
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511928 MLS
Enjoy the laid-back elegance of Hilton Head Island during deeded Week 15 in late April, when the island is in full bloom and spring has settled in beautifully. Swallowtail at Sea Pines delivers a refined, low-maintenance vacation experience in an unbeatable setting. Perfectly positioned between Harbour Town's famous lighthouse and the sun-filled Beach Club, you're just a short stroll from top-tier golf courses, unspoiled beaches, waterfront restaurants, and a lively arts and culture scene. Imagine starting your days with gentle ocean breezes and warm spring sunshine, exploring miles of shaded bike paths beneath towering live oaks, or spending afternoons on award-winning fairways in ideal weather. However you like to unwind, it's all right at your doorstep, your spring getaway, tailored to you, with flexibility built in.

70 Lighthouse Road Unit 2871, Hilton Head Island

Listing courtesy of Lighthouse Realty.

70 Lighthouse Road Unit 2875, Hilton Head Island
$1,500
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511868 MLS
Owner is also selling Week 17 (Unit 2874) and is open to offering a discounted price if both weeks are purchased together-an excellent opportunity to enjoy two consecutive weeks in paradise! Enjoy the relaxed sophistication of Hilton Head Island during deeded Week 18, ideally positioned in the first week of May when the island is at its springtime best. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most sought-after settings. This desirable villa overlooks a lush lagoon, providing peaceful views and a tranquil backdrop throughout your stay. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and a vibrant coastal arts and culture scene. Imagine beginning your mornings with refreshing ocean breezes and serene golf course vistas, then setting out to bike beneath towering live oaks along miles of shaded pathways. Spend your afternoons on award-winning fairways, relaxing on the beach, or exploring the island's natural beauty before unwinding with spectacular waterfront sunsets. May's comfortable temperatures and blooming landscapes create the perfect setting for beach walks, outdoor dining, dolphin cruises, and all that Sea Pines has to offer-without the crowds of peak summer. Whether you prefer championship golf, coastal adventures, or simply relaxing on your private balcony overlooking the greens, everything you need is right at your doorstep. With the option to purchase the adjoining Week 17 at a discounted package price, this is a rare opportunity to enjoy two consecutive weeks in one of Hilton Head Island's premier vacation destinations.

70 Lighthouse Road Unit 2875, Hilton Head Island

Listing courtesy of Lighthouse Realty.

70 Lighthouse Road Unit 2874, Hilton Head Island
$1,500
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511798 MLS
Owner is also selling Week 18 (Unit 2875) and is open to offering a discounted price if both weeks are purchased together-an excellent opportunity to enjoy two consecutive weeks in paradise! Enjoy the relaxed sophistication of Hilton Head Island during deeded Week 17, ideally positioned in the first week of May when the island is at its springtime best. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most sought-after settings. This desirable villa overlooks a lush lagoon, providing peaceful views and a tranquil backdrop throughout your stay. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and a vibrant coastal arts and culture scene. Imagine beginning your mornings with refreshing ocean breezes and serene golf course vistas, then setting out to bike beneath towering live oaks along miles of shaded pathways. Spend your afternoons on award-winning fairways, relaxing on the beach, or exploring the island's natural beauty before unwinding with spectacular waterfront sunsets. May's comfortable temperatures and blooming landscapes create the perfect setting for beach walks, outdoor dining, dolphin cruises, and all that Sea Pines has to offer-without the crowds of peak summer. Whether you prefer championship golf, coastal adventures, or simply relaxing on your private balcony overlooking the greens, everything you need is right at your doorstep. With the option to purchase the adjoining Week 18 at a discounted package price, this is a rare opportunity to enjoy two consecutive weeks in one of Hilton Head Island's premier vacation destinations.

70 Lighthouse Road Unit 2874, Hilton Head Island

Listing courtesy of Lighthouse Realty.

33 Oak Court, Hilton Head Island
$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.

15 Green Wing Teal Road, Hilton Head Island
$7,875,000
HILTONHEAD-511653 MLS
An extraordinary opportunity to create a legacy oceanfront estate in one of Sea Pines most coveted locations. Offering an exceptional 100 feet of direct Atlantic Ocean frontage, this remarkable homesite is the first oceanfront lot to become available in this area in a long time. A rare opportunity. Tucked just off South Beach Lane, this premier property offers the chance to design and build a custom coastal retreat perfectly tailored to your vision. Wake to panoramic sunrises over the Atlantic, step directly onto the beach, and enjoy the privacy, prestige, and unmatched lifestyle that only true oceanfront ownership in Sea Pines can provide. Opportunities like this are extraordinarily scarce. If you've been waiting for the right oceanfront homesite to build your dream home, this is the moment.

15 Green Wing Teal Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

10 Bald Eagle Road, Hilton Head Island
$5,900,000
7 Beds ⋅ 8 Baths ⋅ 5,203 SqFt. ⋅ HILTONHEAD-511606 MLS
Properties of this caliber are increasingly difficult to find in Sea Pines. 7 Bedroom/6.5 Baths PLUS Pool Bath, 2022 construction, designer furnished and just a 3-minute walk to the beach. Set on an oversized nearly 1/3-acre 3rd row homesite, this is the rare combination discerning buyers wait years to find. Custom construction and incredibly designed for effortless coastal living, the home showcases sophisticated finishes, soaring ceilings, a gourmet kitchen with a separate prep kitchen, and seamless indoor-outdoor living centered around a covered porch with an outdoor fireplace, summer kitchen, heated pool, and spa. Seven beautifully appointed bedrooms-including a first-floor primary suite and four ensuite guest suites-provide exceptional comfort and privacy, while multiple gathering spaces make the home ideal for entertaining family and friends. Combining exceptional quality, an oversized homesite, beach proximity, and one of Sea Pines' most desirable locations, this is a true legacy property offering the very best of coastal living. Current rental projections of approximately $349,000 annually.

10 Bald Eagle Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

225 S Sea Pines Drive Unit 1401, Hilton Head Island
$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.

45 Night Heron Lane, Hilton Head Island
$815,000
3 Beds ⋅ 2 Baths ⋅ 928 SqFt. ⋅ HILTONHEAD-511473 MLS
Experience the charm of coastal living at 45 Night Heron, a beautifully positioned Sea Pines beach cottage just a five-minute stroll to Hilton Head Island's renowned beaches. This light-filled 3-bedroom, 2-bath retreat offers an open floor plan with soaring vaulted ceilings, creating an inviting space for gathering and relaxing. Ample enclosed storage beneath the home provides room for beach gear, bicycles, and more. Night Heron has its own private community pool. Harbour Town, South Beach, Sea Pines Beach Club, & the Plantation Golf Club are just moments away by way of 17 miles of picturesque leisure trails. Located near the Ocean Gate for easy island access and only minutes from the shopping, dining, and entertainment of Coligny Plaza, this property is perfectly suited as a primary residence, vacation home, or high-performing rental investment.

45 Night Heron Lane, Hilton Head Island

Listing courtesy of Lighthouse Realty.

37 Woodbine Place, Hilton Head Island
$2,499,000
4 Beds ⋅ 4 Baths ⋅ 2,982 SqFt. ⋅ HILTONHEAD-510784 MLS
One Lеvel Wonderful. Ꮮοcаtеd сloѕе to the beach in Sеa Ρines, this 4 bedroom home is a fantastic vacation home, short term rental(over $100k already in first year) or permanent residence. Bright and beautiful with big living spaces and fun outdoor spaces including gazebo, private pool and large yard. 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. The charming 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.

37 Woodbine Place, Hilton Head Island

Listing courtesy of Hilton Head Properties.

8 Windjammer Court, Hilton Head Island
$1,995,000
4 Beds ⋅ 4 Baths ⋅ 3,531 SqFt. ⋅ HILTONHEAD-511413 MLS
Locаted in the hеаrt of Ηаrbοur Tοwn wіthin Sea Pineѕ, thiѕ 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.

70 Lighthouse Road Unit 2896, Hilton Head Island
$2,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511359 MLS
Owner is also selling Week 17 (Unit 2900) and is open to offering a discounted price if both weeks are purchased together - an excellent opportunity to enjoy two consecutive weeks in paradise! Experience the relaxed sophistication of Hilton Head Island during deeded Week 16, ideally positioned in the last week of April, when spring is in full bloom and the island is at its most beautiful. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of Hilton Head's most sought-after communities. This desirable end-unit villa, located next to the pool, offers added privacy, extra natural light, and exceptional convenience. Overlooking the lush fairways of the golf course, it provides peaceful views and a tranquil backdrop throughout your stay. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and the vibrant coastal arts and culture that make Sea Pines so special. Imagine beginning your mornings with refreshing ocean breezes and serene golf course views before setting out to bike beneath towering live oaks along miles of shaded pathways. Spend your afternoons on award-winning fairways, relaxing on the beach, or exploring the island's natural beauty before unwinding with spectacular waterfront sunsets. Late April offers warm, comfortable temperatures, colorful spring blooms, and ideal conditions for beach walks, outdoor dining, dolphin cruises, tennis, and all that Sea Pines has to offer-before the peak summer crowds arrive. Whether you prefer championship golf, coastal adventures, or simply relaxing on your private balcony overlooking the greens, everything you need is right at your doorstep. With the option to purchase the adjoining Week 17 at a discounted package price, this is a rare opportunity to enjoy two consecutive weeks in one of Hilton Head Island's premier vacation destinations.

70 Lighthouse Road Unit 2896, Hilton Head Island

Listing courtesy of Lighthouse Realty.

70 Lighthouse Road Unit 2900, Hilton Head Island
$1,900
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511357 MLS
Owner is also selling Week 16 (Unit 2896) and is open to offering a discounted price if both weeks are purchased together-an excellent opportunity to enjoy two consecutive weeks in paradise! Enjoy the relaxed sophistication of Hilton Head Island during deeded Week 17, ideally positioned in the first week of May when the island is at its springtime best. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most sought-after settings. This desirable villa overlooks the lush fairways of the golf course, providing peaceful views and a tranquil backdrop throughout your stay. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and a vibrant coastal arts and culture scene. Imagine beginning your mornings with refreshing ocean breezes and serene golf course vistas, then setting out to bike beneath towering live oaks along miles of shaded pathways. Spend your afternoons on award-winning fairways, relaxing on the beach, or exploring the island's natural beauty before unwinding with spectacular waterfront sunsets. May's comfortable temperatures and blooming landscapes create the perfect setting for beach walks, outdoor dining, dolphin cruises, and all that Sea Pines has to offer-without the crowds of peak summer. Whether you prefer championship golf, coastal adventures, or simply relaxing on your private balcony overlooking the greens, everything you need is right at your doorstep. With the option to purchase the adjoining Week 17 at a discounted package price, this is a rare opportunity to enjoy two consecutive weeks in one of Hilton Head Island's premier vacation destinations.

70 Lighthouse Road Unit 2900, Hilton Head Island

Listing courtesy of Lighthouse Realty.

70 Lighthouse Road Unit 2875, Hilton Head Island
$1,350
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511051 MLS
Enjoy the peaceful elegance of Hilton Head Island during deeded Week 45, perfectly timed for the crisp beauty of late autumn and, in many years, the Thanksgiving holiday. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most coveted settings. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and the island's rich coastal arts and culture scene.Imagine beginning your mornings with cool ocean breezes and uncrowded beaches, biking beneath majestic live oaks draped in Spanish moss, or spending leisurely afternoons on award-winning fairways before gathering with family and friends for memorable holiday meals or spectacular waterfront sunsets. Whether you're seeking a relaxing seasonal escape, an active golf retreat, or a warm-weather destination for Thanksgiving celebrations, Week 45 offers the perfect blend of tranquility, natural beauty, and island charm; all with the flexibility and convenience of deeded ownership.

70 Lighthouse Road Unit 2875, Hilton Head Island

Listing courtesy of Lighthouse Realty.

125 Greenwood Drive Unit APT 3407, Hilton Head Island
$719,000
2 Beds ⋅ 3 Baths ⋅ 1,238 SqFt. ⋅ HILTONHEAD-510644 MLS
Come sеe this tοtаlly RΕΝΟVAΤΕD FEE SIMPLΕ homе Located in the exquisite Carolina Place community in the heart of the Low Country where you can live out your dreams of enjoying the island! This 2 bedroom 2 and 1/2 bath townhome has the ideal layout, location and VIEW! Complete privacy and serene view with wonderful wild life including deer, various Southern birds and so much more! Having been recently updated it is a turn-key opportunity to have a permanent primary, secondary or investment home in Sea Pines Plantation. The first floor is spacious and open with a HUGE screened-in back porch that runs the entire width of the townhome and is fully enclosed. It adds a welcome dimension to the living space and adds a variety of space for hosting friends and family. The view is peaceful and tranquil with the lagoon and the protected forest preserve backdrop behind it with only the natural wildlife as your neighbors. You can sit on your covered fully enclosed back porch and enjoy all the beauty that the Low Country has to offer! Both bedrooms are located upstairs and each have their own private updated bathrooms. This home is easy in and located in close proximity to the ample amenities that Carolina Place has to offer! It has a large swimming pool with on sight spa with tennis and pickle ball courts too! Sea Pines Plantation has so much to offer with biking trails that run throughout the area taking you throughout Sea Pines including Harbour Town, South Beach Marina or the Beach Club....there's also a private access beach for owners of Sea Pines Properties.....not to mention the 4 different golf courses, tennis, pickle ball, boating, shopping and all the water sports imaginable!! There's a reason this particular area has so many happy owners.....come see for yourself and become a Sea Pines Residential owner TODAY!!

125 Greenwood Drive Unit APT 3407, Hilton Head Island

Listing courtesy of Keller Williams Realty.

33 Ruddy Turnstone Road, Hilton Head Island
$8,995,000
5 Beds ⋅ 6 Baths ⋅ 5,837 SqFt. ⋅ HILTONHEAD-510013 MLS
Posіtioned dіrеctlу οn thе Atlаntіc Ocean within thе prеstigious 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.

19 Stoney Creek Road Unit 286, Hilton Head Island
$890,000
3 Beds ⋅ 4 Baths ⋅ 1,780 SqFt. ⋅ HILTONHEAD-509012 MLS
Luxury Updated 3 BR Stoney Creek Condo with great pool views. Only minutes to world famous Harbourtown Golf Links, Lighthouse, Shops and Restaurants this updated luxury condo can sleep 8 people. What a wonderful location to come and enjoy world class amenities for a family beach or golf vacation. Sea Pines has miles of bike paths, beach access and a trolley to run you around the Sea Pines Resort. Kitchen has granite counter tops, updated appliances, washer, dryer and fully stocked so you can prepare an afternoon snack or a full meal for the family or golfers. Living has large flat screen TV and half bath is just off the living room. Walk right out from the living room to enjoy a nice back patio with pool views. Pool is only steps from the back deck so you can take a dip and cool off after a long day on the beach or golf course. Master Bedroom has a king size bed with updated en suite bathroom. New vanity, new tile floors and tile shower with inlaid accents. Guest bedroom has new vanity, new tile, new shower and king size bed. Feels like a double master suite with all the updates and king size beds. The guest room has two double beds for kids or golfers. The luxury condo can sleep a total of eight people with plenty of room to spread out. Wonderful large townhome with private bedrooms and spectacular location near all the amenities in Sea Pines Resort

19 Stoney Creek Road Unit 286, Hilton Head Island

Listing courtesy of Hilton Head Luxury Homes, Inc.

70 Lighthouse Road Unit 2905, Hilton Head Island
$2,500
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-509812 MLS
Enjoy the relaxed sophistication of Hilton Head Island during deeded Week 28, ideally positioned in mid-to-late July when summer on the island is in full swing. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most sought-after settings. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and a vibrant coastal arts and culture scene. Imagine beginning your mornings with warm ocean breezes and long summer days, biking beneath towering live oaks along miles of shaded pathways, or spending afternoons on award-winning fairways before unwinding with waterfront sunsets and lively seasonal events across the island. Whether you prefer relaxing by the beach, exploring the island's natural beauty, or soaking in the easygoing energy of peak summer season, everything you need is right at your doorstep - your perfect midsummer getaway with flexibility built in.

70 Lighthouse Road Unit 2905, Hilton Head Island

Listing courtesy of Lighthouse Realty.

70 Lighthouse Road Unit 2873, Hilton Head Island
$1,450
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-508988 MLS
Enjoy the laid-back elegance of Hilton Head Island during deeded Week 15 in late April, when the island is in full bloom and spring has settled in beautifully. Swallowtail at Sea Pines delivers a refined, low-maintenance vacation experience in an unbeatable setting. Perfectly positioned between Harbour Town's famous lighthouse and the sun-filled Beach Club, you're just a short stroll from top-tier golf courses, unspoiled beaches, waterfront restaurants, and a lively arts and culture scene. Imagine starting your days with gentle ocean breezes and warm spring sunshine, exploring miles of shaded bike paths beneath towering live oaks, or spending afternoons on award-winning fairways in ideal weather. However you like to unwind, it's all right at your doorstep, your spring getaway, tailored to you, with flexibility built in.

70 Lighthouse Road Unit 2873, Hilton Head Island

Listing courtesy of Lighthouse Realty.

70 Lighthouse Road Unit 2895, Hilton Head Island
$1,300
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-508986 MLS
Enjoy the relaxed charm of Hilton Head Island during deeded Week 11 at Swallowtail at Sea Pines, the last week of March, when spring is in full swing and the island comes alive with mild temperatures, blooming landscapes, and sunny coastal days. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most desirable settings. Ideally located between Harbour Town Lighthouse and the beautiful Beach Club, this desirable end unit next to the pool places you just a short walk from championship golf, pristine beaches, waterfront dining, and the vibrant arts and culture that make Sea Pines so special. Picture starting your mornings with cool ocean breezes and golden spring sunshine, biking beneath moss-draped live oaks along miles of scenic pathways, or enjoying afternoons on award-winning golf courses during one of the island's most comfortable times of year. Whether you're seeking relaxation or adventure, everything you need is right at your doorstep: your perfect spring escape, with the flexibility to enjoy it your way.

70 Lighthouse Road Unit 2895, Hilton Head Island

Listing courtesy of Lighthouse Realty.

18 Lighthouse Road Unit 471, Hilton Head Island
$659,900
2 Beds ⋅ 2 Baths ⋅ 1,279 SqFt. ⋅ HILTONHEAD-508598 MLS
Easy walk to the Beach and Plantation Club from this second floor, furnished, golf view villa with 2 bedrooms and 2 bathrooms. The Plantation Club has two, private swimming pools. The Sea Pines Plantation Clubhouse has golf and a restaurant. The Sea Pines Beach Club has a bar and restaurants. The villa is a short ride from the Sea Pines Center with restaurants and shops. The villa is a short ride to Harbourtown. The villa has many upgrades: 2016, new HVAC. 2020, new microwave and 1st bedroom mattress/boxsprings. 2021, new dishwasher and bedroom television. 2022, new guest bedroom matresses. 2023, new patio furniture. 2024, new living room tables, primary bathroom tiled shower, new tile floors, all new interior paint, new living room television, new living room curtains, new window blinds, all new door casings and baseboards. 2025, new refrigerator, clothes washer and dryer, hot water tank. All linens are included with the sale.

18 Lighthouse Road Unit 471, Hilton Head Island

Listing courtesy of Go Gated Realty Inc.

70 Lighthouse Road Unit 2874, Hilton Head Island
$1,250
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-508472 MLS
Enjoy the relaxed coastal charm of Hilton Head Island during deeded Week 34, spanning the final days of August and welcoming the start of September, when summer lingers beautifully and the island begins to settle into a quieter rhythm. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in an unbeatable location. Ideally situated between Harbour Town's iconic lighthouse and the sun-soaked Beach Club, you're just a short walk from championship golf courses, pristine beaches, waterfront dining, and the vibrant arts and culture that make the island so special. Picture starting your mornings with warm ocean breezes and golden coastal sunrises, biking beneath majestic live oaks along miles of shaded paths, or spending afternoons on award-winning fairways while enjoying the tail end of summer. As the season transitions toward fall, the island's pace becomes even more relaxed, creating the perfect setting to unwind and recharge. However you choose to spend your time, it's all right at your doorstep, your late-summer escape, tailored to you, with flexibility built in.

70 Lighthouse Road Unit 2874, Hilton Head Island

Listing courtesy of Lighthouse Realty.

124 N Sea Pines Drive Unit 583, Hilton Head Island
$2,250
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-508006 MLS
TWO DEEDED WEEKS AT SPICEBUSH IN SEA PINES (WEEK 32 & 33)! Nestled in the heart of Hilton Head's iconic Sea Pines community, this is a rare opportunity to own two consecutive mid-August weeks in the same end unit; perfect for extended stays or flexible vacation planning. Just steps from the Sea Pines Beach Club and the Plantation Club Golf Course, you'll be right in the center of everything that makes the island special. Your Spicebush Weeks 32 & 33 place you here during one of the most vibrant times of the summer: when the island is alive with warm coastal breezes, long sun-filled days, and unforgettable evenings. Enjoy championship golf, sugar-soft beaches, waterfront dining, and all the seasonal energy Hilton Head is known for. Wake up to the sound of the ocean, spend your days exploring or unwinding, and linger over golden sunsets that stretch late into the evening. With effortless, low-maintenance ownership and the added value of two back-to-back weeks, your island retreat is always within reach-offering the perfect blend of relaxation, adventure, and lasting memories.

124 N Sea Pines Drive Unit 583, Hilton Head Island

Listing courtesy of Lighthouse Realty.

2065 Deer Island Road, Hilton Head Island
$1,055,000
1 Beds ⋅ 2 Baths ⋅ 816 SqFt. ⋅ HILTONHEAD-507877 MLS
Searсhing for a trulу рrivаtе Ѕeа Ρines retreat with unmаtchеd views just steps from Harbour Town? 2065 Deer Island Road offers a rare end-of-the-road setting in the coveted Sea Pines Resort, delivering breathtaking views of the marsh and out to the Calibogue Sound. Tucked away at the end of a quiet road, this unique home is surrounded by nature, where walls of windows flood the home with natural light and frame stunning water and wildlife views from every angle. Thoughtfully updated with luxurious finishes, the home features high-end appliances including a Sub-Zero refrigerator, JennAir range, and Bosch dishwasher and microwave, along with quartz countertops and an open-concept living space designed for relaxed coastal living. Heart pine floors upstairs and bamboo flooring on the lower level add warmth and character, while multiple decks provide the perfect setting to take in unforgettable sunsets over the water. The upstairs level of all Deer Island properties are similar and can be re-configured to accommodate various bedroom and bathroom layouts. This flexible layout lives beautifully as a second home or income-producing rental, offering a peaceful, private escape just a short walk or bike ride to the Harbour Town Lighthouse, the Quarterdeck Restaurant, and the shops, dining, and amenities of Harbour Town. A rare opportunity to own one of the most scenic and private homes in Sea Pines.

2065 Deer Island Road, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

70 Lighthouse Road Unit 2879, Hilton Head Island
$750
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-506994 MLS
Discover your perfect spring retreat at Swallowtail in Sea Pines with Week 10 ownership! Set in the heart of Hilton Head Island, this mid-March getaway offers a refreshing change of pace, with mild coastal weather, blooming scenery, and a more relaxed island vibe. Overlooking the 12th fairway of the Heron Point Golf Course, the property combines scenic golf views with easy access to everything that makes Sea Pines so special. You're just a short distance from the Harbour Town lighthouse, the Beach Club, and an array of dining, shopping, and outdoor experiences. Spend your days enjoying early rounds of golf, beach walks, or biking beneath moss-draped oaks, and your evenings unwinding in the charm of Harbour Town. With its low-maintenance ownership and prime location, Swallowtail offers an effortless way to enjoy Hilton Head year after year. Take advantage of this opportunity to claim your own slice of Sea Pines in one of the island's most inviting seasons-Week 10 is waiting.

70 Lighthouse Road Unit 2879, Hilton Head Island

Listing courtesy of Lighthouse Realty.

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