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31 N Calibogue Cay Road, Hilton Head Island

Set on one of Sea Pines' most prestigious streets, this exceptional waterfront estate offers breathtaking views, timeless architecture, and an unmatched Lowcountry lifestyle. Featuring 5 bedrooms, 5.5 baths, a spacious bonus room, and an oversized 2-car garage, this remarkable residence was thoughtfully designed for luxurious everyday living and effortless entertaining. Perfectly positioned to capture sweeping views of Calibogue Sound and the surrounding marshes, the home seamlessly blends elegant interiors with spectacular outdoor living. Expansive windows fill the home with natural light while framing picturesque water vistas. The well-designed floor plan offers generous gathering spaces, private guest accommodations, and exceptional flow for both everyday living and entertaining. Step outside to your own private retreat featuring a sparkling pool, beautifully landscaped grounds, and a charming gazebo overlooking the water. The private deep-water dock provides direct access for boating, fishing, kayaking, and unforgettable sunset views over Calibogue Sound. With five spacious bedroom suites, a large bonus room offering flexible living space, and an oversized two-car garage, this home combines luxury, comfort, and functionality in one extraordinary package. Located within the gates of Sea Pines, residents enjoy world-class amenities including miles of pristine beaches, Harbour Town, the Sea Pines Beach Club, championship golf, tennis, leisure trails, equestrian facilities, marinas, dining, shopping, and one of the most sought-after lifestyles on Hilton Head Island. A rare opportunity to own a premier waterfront estate on one of Sea Pines' most coveted streets.

5 Beds ⋅ 6 Baths ⋅ 5,206 SqFt. ⋅ HILTONHEAD-511968 MLS

Set on one of Sea Pines' most prestigious streets, this exceptional waterfront estate offers breathtaking views, timeless architecture, and an unmatched Lowcountry lifestyle. Featuring 5 bedrooms, 5.5 baths, a spacious bonus room, and an oversized 2-car garage, this remarkable residence was thoughtfully designed for luxurious everyday living and effortless entertaining. Perfectly positioned to capture sweeping views of Calibogue Sound and the surrounding marshes, the home seamlessly blends elegant interiors with spectacular outdoor living. Expansive windows fill the home with natural light while framing picturesque water vistas. The well-designed floor plan offers generous gathering spaces, private guest accommodations, and exceptional flow for both everyday living and entertaining. Step outside to your own private retreat featuring a sparkling pool, beautifully landscaped grounds, and a charming gazebo overlooking the water. The private deep-water dock provides direct access for boating, fishing, kayaking, and unforgettable sunset views over Calibogue Sound. With five spacious bedroom suites, a large bonus room offering flexible living space, and an oversized two-car garage, this home combines luxury, comfort, and functionality in one extraordinary package. Located within the gates of Sea Pines, residents enjoy world-class amenities including miles of pristine beaches, Harbour Town, the Sea Pines Beach Club, championship golf, tennis, leisure trails, equestrian facilities, marinas, dining, shopping, and one of the most sought-after lifestyles on Hilton Head Island. A rare opportunity to own a premier waterfront estate on one of Sea Pines' most coveted streets.

31 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Charter One Realty.

25 N Calibogue Cay Road, Hilton Head Island

$4,200,000

Stunning deеp-watеr rеsіdеnсe іn Ѕea Pines feаtureѕ 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

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

Stunning deеp-watеr rеsіdеnсe іn Ѕea Pines feаtureѕ 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.

$1,325,000

Exceptional Harbour Town location in the heart of Sea Pines! 18 Spinnaker Court is a spacious 3-bedroom, 3.5-bath townhome offering more than 2,300 square feet, multiple outdoor living areas, and distant views of the 18th fairway of Harbour Town Golf Links and Calibogue Sound. A paver driveway leads to the 1-car garage, while inside, the floor plan offers generous living and dining spaces with high ceilings, hardwood floors, granite countertops, a wet bar, and a fireplace. The galley-style kitchen is efficient and functional, and the primary suite is located upstairs along with additional guest accommodations. Sold furnished, this property is especially appealing as a turnkey rental opportunity, second home, or full-time residence. Multiple decks provide additional space to relax, entertain, and take in the surrounding Harbour Town setting. Enjoy all that Sea Pines has to offer, including miles of leisure trails, beautiful beaches, Harbour Town Marina, South Beach Marina, world-class golf, tennis and pickleball, dining, shopping, and easy access to the Harbour Town Golf Links, home of the PGA TOUR's RBC Heritage Presented by Boeing. With its size, furnished offering, garage, outdoor living spaces, and prime Harbour Town setting, 18 Spinnaker Court presents an outstanding opportunity to own in one of Hilton Head Island's most iconic communities.

3 Beds ⋅ 4 Baths ⋅ 2,343 SqFt. ⋅ HILTONHEAD-512807 MLS

Exceptional Harbour Town location in the heart of Sea Pines! 18 Spinnaker Court is a spacious 3-bedroom, 3.5-bath townhome offering more than 2,300 square feet, multiple outdoor living areas, and distant views of the 18th fairway of Harbour Town Golf Links and Calibogue Sound. A paver driveway leads to the 1-car garage, while inside, the floor plan offers generous living and dining spaces with high ceilings, hardwood floors, granite countertops, a wet bar, and a fireplace. The galley-style kitchen is efficient and functional, and the primary suite is located upstairs along with additional guest accommodations. Sold furnished, this property is especially appealing as a turnkey rental opportunity, second home, or full-time residence. Multiple decks provide additional space to relax, entertain, and take in the surrounding Harbour Town setting. Enjoy all that Sea Pines has to offer, including miles of leisure trails, beautiful beaches, Harbour Town Marina, South Beach Marina, world-class golf, tennis and pickleball, dining, shopping, and easy access to the Harbour Town Golf Links, home of the PGA TOUR's RBC Heritage Presented by Boeing. With its size, furnished offering, garage, outdoor living spaces, and prime Harbour Town setting, 18 Spinnaker Court presents an outstanding opportunity to own in one of Hilton Head Island's most iconic communities.

18 Spinnaker Court, Hilton Head Island

Listing courtesy of Charter One Realty.

41 Stoney Creek Road, Hilton Head Island

$1,249,000

It's a great house!

3 Beds ⋅ 2 Baths ⋅ 2,156 SqFt. ⋅ HILTONHEAD-512887 MLS

It's a great house!

41 Stoney Creek Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

150 Lighthouse Road Unit A-711, Hilton Head Island

$1,195,000

The first thing is the water. Calibogue Sound opens off the back of this villa, framed by a broad lawn and a great live oak, a private green for owners alone. Sailboats cross all afternoon. The patio faces west, so the day ends out here, the Sound turning gold as the last boats slide home. On the Fourth of July, walk to the seawall and watch fireworks rise over the water. That view held the same owners for 34 years. lnside, the water cornes with you, from the couch, from the primary suite. A 2-bed, 2.5-bath townhouse villa, 1,441 square feet, renovated in 2013 and true turnkey, sold furnished. Three new impact-resistant sliding glass doors and one impact-resistant window have just been installed on the sound facing side. The regime has approved a third floor, already built a few doors down, taking the plan to 3 bedrooms and 3.5 baths with unobstructed Sound views from the primary suite, subject to Sea Pines ARB and town approval. Villas on this water almost never come up. This one finally has.

2 Beds ⋅ 3 Baths ⋅ 1,441 SqFt. ⋅ HILTONHEAD-512422 MLS

The first thing is the water. Calibogue Sound opens off the back of this villa, framed by a broad lawn and a great live oak, a private green for owners alone. Sailboats cross all afternoon. The patio faces west, so the day ends out here, the Sound turning gold as the last boats slide home. On the Fourth of July, walk to the seawall and watch fireworks rise over the water. That view held the same owners for 34 years. lnside, the water cornes with you, from the couch, from the primary suite. A 2-bed, 2.5-bath townhouse villa, 1,441 square feet, renovated in 2013 and true turnkey, sold furnished. Three new impact-resistant sliding glass doors and one impact-resistant window have just been installed on the sound facing side. The regime has approved a third floor, already built a few doors down, taking the plan to 3 bedrooms and 3.5 baths with unobstructed Sound views from the primary suite, subject to Sea Pines ARB and town approval. Villas on this water almost never come up. This one finally has.

150 Lighthouse Road Unit A-711, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

107 Lighthouse Road Unit 2284, Hilton Head Island

$1,040,000

Refined coastal living in Sea Pines! Beautifully updated and fully furnished, this exceptional 3BR/3BA Heritage Villa enjoys a coveted setting overlooking the 1st and 9th holes of the Harbour Town Golf Links. Thoughtfully renovated with a sophisticated aesthetic, this villa features all new appliances, fresh paint, new doors, carpet, lighting, updated baths and coastal shiplap detailing throughout the vaulted living and dining areas. The well-appointed floor plan offers a main-level bedroom and full bath, plus two spacious upstairs bedrooms with private en-suite baths. The open living and dining areas create an inviting setting for entertaining, while the expansive back deck provides a tranquil vantage point overlooking the golf course and mature live oaks.Ideally positioned within easy walking distance of the Harbour Town Clubhouse, this turnkey property offers exceptional convenience within Sea Pines. Enjoy nearby Harbour Town Marina, dining, shopping, world-class golf, tennis, miles of leisure trails, and the Sea Pines Beach Club, less than two miles away with trolley access. A rare opportunity to own a beautifully appointed retreat in one of Sea Pines' most desirable locations.

3 Beds ⋅ 3 Baths ⋅ 1,750 SqFt. ⋅ HILTONHEAD-512911 MLS

Refined coastal living in Sea Pines! Beautifully updated and fully furnished, this exceptional 3BR/3BA Heritage Villa enjoys a coveted setting overlooking the 1st and 9th holes of the Harbour Town Golf Links. Thoughtfully renovated with a sophisticated aesthetic, this villa features all new appliances, fresh paint, new doors, carpet, lighting, updated baths and coastal shiplap detailing throughout the vaulted living and dining areas. The well-appointed floor plan offers a main-level bedroom and full bath, plus two spacious upstairs bedrooms with private en-suite baths. The open living and dining areas create an inviting setting for entertaining, while the expansive back deck provides a tranquil vantage point overlooking the golf course and mature live oaks.Ideally positioned within easy walking distance of the Harbour Town Clubhouse, this turnkey property offers exceptional convenience within Sea Pines. Enjoy nearby Harbour Town Marina, dining, shopping, world-class golf, tennis, miles of leisure trails, and the Sea Pines Beach Club, less than two miles away with trolley access. A rare opportunity to own a beautifully appointed retreat in one of Sea Pines' most desirable locations.

107 Lighthouse Road Unit 2284, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

19 Stoney Creek Road Unit 286, Hilton Head Island

$890,000

Luxury Uрdated 3 BR Ѕtοneу Crееk Condο wіth great pool viewѕ. Onlу 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

3 Beds ⋅ 4 Baths ⋅ 1,780 SqFt. ⋅ HILTONHEAD-509012 MLS

Luxury Uрdated 3 BR Ѕtοneу Crееk Condο wіth great pool viewѕ. Onlу 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.

11 Lighthouse Road Unit 24, Hilton Head Island

$845,000

Located in a great spot in Sea Pines, this 2 BD, 2 BA Lighthouse Road Villa is an end unit, providing extra privacy and a more open feel. One of the highlights is the large Carolina Room overlooking the peaceful landscape setting, giving you plenty of additional living space to enjoy year round. Inside, you'll find wood floors, a spacious great room with fireplace, and a kitchen with mostly new stainless steel appliances. Recent improvements also include a new washer and dryer, and HVAC system. Just a short walk or bike ride to Sea Pines Beach Club, Harbour Town, and Fraser's Tavern, the villa is being sold turn-key with a strong rental history.

2 Beds ⋅ 2 Baths ⋅ 1,600 SqFt. ⋅ HILTONHEAD-512238 MLS

Located in a great spot in Sea Pines, this 2 BD, 2 BA Lighthouse Road Villa is an end unit, providing extra privacy and a more open feel. One of the highlights is the large Carolina Room overlooking the peaceful landscape setting, giving you plenty of additional living space to enjoy year round. Inside, you'll find wood floors, a spacious great room with fireplace, and a kitchen with mostly new stainless steel appliances. Recent improvements also include a new washer and dryer, and HVAC system. Just a short walk or bike ride to Sea Pines Beach Club, Harbour Town, and Fraser's Tavern, the villa is being sold turn-key with a strong rental history.

11 Lighthouse Road Unit 24, Hilton Head Island

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

6 Lighthouse Lane Unit 946, Hilton Head Island

$825,000

Wake up to one of the most iconic views on Hilton Head Island. This third-floor end-unit Cutter Court villa overlooks Harbour Town, the Calibogue Sound, and the legendary Harbour Town Lighthouse. Featuring two bedrooms and two full baths, the villa offers a bright, open living area where the living room slider and kitchen windows perfectly frame the marina and famous lighthouse. Just moments from your door are Harbour Town's boutique shopping, waterfront dining, world-class golf, and full-service marina. Relax on your private balcony as sailboats and yachts glide across the Sound. Whether you're here for a weekend getaway or an extended stay, everything you need is within easy reach. Miles of leisure trails connect you to the Sea Pines Beach Club, South Beach Marina, Lawton Stables, beautiful beaches, and countless opportunities to explore.

2 Beds ⋅ 2 Baths ⋅ 1,200 SqFt. ⋅ HILTONHEAD-511429 MLS

Wake up to one of the most iconic views on Hilton Head Island. This third-floor end-unit Cutter Court villa overlooks Harbour Town, the Calibogue Sound, and the legendary Harbour Town Lighthouse. Featuring two bedrooms and two full baths, the villa offers a bright, open living area where the living room slider and kitchen windows perfectly frame the marina and famous lighthouse. Just moments from your door are Harbour Town's boutique shopping, waterfront dining, world-class golf, and full-service marina. Relax on your private balcony as sailboats and yachts glide across the Sound. Whether you're here for a weekend getaway or an extended stay, everything you need is within easy reach. Miles of leisure trails connect you to the Sea Pines Beach Club, South Beach Marina, Lawton Stables, beautiful beaches, and countless opportunities to explore.

6 Lighthouse Lane Unit 946, Hilton Head Island

Listing courtesy of Keller Williams Realty.

107 Lighthouse Road Unit 2289, Hilton Head Island

$735,000

Enjoу the best οf thе Sеа Ρinеѕ lifestyle from thiѕ beаutifully updated and nicely furnished 2-bedroom Heritage Villa, ideally located just minutes from Harbour Town. The light and inviting interior features stylish LVP flooring, comfortable living spaces, and thoughtful updates throughout, making this villa truly move-in ready. Enjoy a pleasant view of the community pickleball courts and easy access to all that Sea Pines has to offer. An excellent vacation rental opportunity, the villa has generated $29,264 in gross rental income year-to-date. Whether you're looking for a full-time residence, vacation getaway, or income-producing investment, this villa offers exceptional convenience to Harbour Town, world-class golf, dining, shopping, biking trails, and more. Offered furnished and ready to enjoy!

2 Beds ⋅ 3 Baths ⋅ 1,600 SqFt. ⋅ HILTONHEAD-513104 MLS

Enjoу the best οf thе Sеа Ρinеѕ lifestyle from thiѕ beаutifully updated and nicely furnished 2-bedroom Heritage Villa, ideally located just minutes from Harbour Town. The light and inviting interior features stylish LVP flooring, comfortable living spaces, and thoughtful updates throughout, making this villa truly move-in ready. Enjoy a pleasant view of the community pickleball courts and easy access to all that Sea Pines has to offer. An excellent vacation rental opportunity, the villa has generated $29,264 in gross rental income year-to-date. Whether you're looking for a full-time residence, vacation getaway, or income-producing investment, this villa offers exceptional convenience to Harbour Town, world-class golf, dining, shopping, biking trails, and more. Offered furnished and ready to enjoy!

107 Lighthouse Road Unit 2289, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

150 Lighthouse Road Unit E-728, Hilton Head Island

$550,000

Discover timeless Lowcountry charm and waterfront views from this charming end-unit efficiency villa in the heart of Harbour Town. Overlooking the tranquil Calibogue Sound, this rare Schooner Court gem has been freshly painted and tastefully decorated, offering an inviting coastal retreat steps from the iconic Harbour Town Lighthouse, marina, shops, and dining. The open-concept living and dining areas feature sliding doors that lead to a spacious, fully fenced courtyard perfect for enjoying morning coffee or evening cocktails. The efficiency-style layout includes a convenient first-floor laundry utility closet, while the upstairs loft serves as a cozy sleeping space. Surrounded by lush landscaping and ample private parking, this villa captures the essence of island living. Ideal as a personal getaway or an exceptional investment property with strong rental potential, this is a truly special opportunity to own your slice of paradise in the beautiful community of Sea Pines on Hilton Head Island.

1 Beds ⋅ 1 Baths ⋅ 720 SqFt. ⋅ HILTONHEAD-501995 MLS

Discover timeless Lowcountry charm and waterfront views from this charming end-unit efficiency villa in the heart of Harbour Town. Overlooking the tranquil Calibogue Sound, this rare Schooner Court gem has been freshly painted and tastefully decorated, offering an inviting coastal retreat steps from the iconic Harbour Town Lighthouse, marina, shops, and dining. The open-concept living and dining areas feature sliding doors that lead to a spacious, fully fenced courtyard perfect for enjoying morning coffee or evening cocktails. The efficiency-style layout includes a convenient first-floor laundry utility closet, while the upstairs loft serves as a cozy sleeping space. Surrounded by lush landscaping and ample private parking, this villa captures the essence of island living. Ideal as a personal getaway or an exceptional investment property with strong rental potential, this is a truly special opportunity to own your slice of paradise in the beautiful community of Sea Pines on Hilton Head Island.

150 Lighthouse Road Unit E-728, Hilton Head Island

Listing courtesy of Keller Williams Realty.

81 Harbour Town Yacht Basin, Hilton Head Island

$325,000

Perfectly positioned across from the iconic 18th green of Harbour Town Golf Links-host course of the prestigious RBC Heritage-this exceptional offering places you at the center of one of the Lowcountry's most celebrated destinations.Enjoy access to an unmatched array of amenities, including membership to the Harbour Town Yacht Club, featuring elegant lodging, waterfront dining, conference facilities, concierge services, and a newly enhanced veranda lounge with sweeping harbor views. Just a short stroll away, you'll find the Harbour Town Golf Clubhouse, pool, and the renowned Smith Stearns Tennis Academy.The vibrant Harbour Town area offers something for everyone, from live concerts and a waterfront playground to boutique shopping and an array of restaurants. Set along a well-protected harbor on the Intracoastal Waterway and Calibogue Sound, this location is ideal for boating enthusiasts-and with the ability for owners to rent their slips, it also presents an excellent income opportunity.

HILTONHEAD-506978 MLS

Perfectly positioned across from the iconic 18th green of Harbour Town Golf Links-host course of the prestigious RBC Heritage-this exceptional offering places you at the center of one of the Lowcountry's most celebrated destinations.Enjoy access to an unmatched array of amenities, including membership to the Harbour Town Yacht Club, featuring elegant lodging, waterfront dining, conference facilities, concierge services, and a newly enhanced veranda lounge with sweeping harbor views. Just a short stroll away, you'll find the Harbour Town Golf Clubhouse, pool, and the renowned Smith Stearns Tennis Academy.The vibrant Harbour Town area offers something for everyone, from live concerts and a waterfront playground to boutique shopping and an array of restaurants. Set along a well-protected harbor on the Intracoastal Waterway and Calibogue Sound, this location is ideal for boating enthusiasts-and with the ability for owners to rent their slips, it also presents an excellent income opportunity.

81 Harbour Town Yacht Basin, Hilton Head Island

Listing courtesy of ERA Wilder Realty, Inc.

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