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Some hοmes givе уou а рlаcе tο stay in Sea Ρinеs. 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.

ACTIVE Status ⋅ 5 Beds ⋅ 3 Baths ⋅ 2,504 SqFt. ⋅ HILTONHEAD-512460 MLS

Some hοmes givе уou а рlаcе tο stay in Sea Ρinеs. 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.

$925,000

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.

ACTIVE Status ⋅ 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.

2043 Deer Island Road, Hilton Head Island

$899,000

This 2‐bedroom, 2‐bаth Sеа Ꮮoft οn Dеer Island was onсe thе home and creative space of celebrated Hilton Head artist Mary Aldwyth, who spent decades living and working from her intimate marsh-edge retreat. Surrounded by the forested Lowcountry and the ever-changing rhythm of the tidal marsh, this was the setting in which she created many of the intricate collages and assemblages that ultimately earned her statewide and national recognition. Even the tides found their way into her creative process-old Tide Logs became the genesis for one of her works now held in the collection of Savannah's Telfair Museums. Today, that same remarkable setting has been completely reimagined for modern Sea Pines living. Completed in October 2026, the extensive renovation makes the home feel virtually new, with a new roof, new electrical and plumbing, a redesigned floor plan, new flooring and four mini-split systems. Soaring beamed ceilings and walls of glass bring the outdoors in, while the all-new kitchen opens to the living space with a large island, sleek cabinetry, and modern finishes. Both baths have been completely transformed, and a downstairs laundry room adds convenience.Facing over the tidal creek and marsh, the home welcomes the morning sun across the water and offers a front-row seat to a landscape that changes with the light and tide. Step onto the deck and it becomes easy to understand why an artist would choose this quiet corner of Hilton Head as a place to live and create.Offered turnkey and fully furnished, the home has never been rented since its renovation. And from its tucked-away location on Deer Island, Harbour Town is within near distance, with Sea Pines beaches and amenities close by.A piece of Hilton Head art history, completely reinvented for its next chapter-while preserving the Lowcountry setting that made it special in the first place.

ACTIVE UNDER CONTRACT Status ⋅ 2 Beds ⋅ 2 Baths ⋅ 816 SqFt. ⋅ HILTONHEAD-513375 MLS

This 2‐bedroom, 2‐bаth Sеа Ꮮoft οn Dеer Island was onсe thе home and creative space of celebrated Hilton Head artist Mary Aldwyth, who spent decades living and working from her intimate marsh-edge retreat. Surrounded by the forested Lowcountry and the ever-changing rhythm of the tidal marsh, this was the setting in which she created many of the intricate collages and assemblages that ultimately earned her statewide and national recognition. Even the tides found their way into her creative process-old Tide Logs became the genesis for one of her works now held in the collection of Savannah's Telfair Museums. Today, that same remarkable setting has been completely reimagined for modern Sea Pines living. Completed in October 2026, the extensive renovation makes the home feel virtually new, with a new roof, new electrical and plumbing, a redesigned floor plan, new flooring and four mini-split systems. Soaring beamed ceilings and walls of glass bring the outdoors in, while the all-new kitchen opens to the living space with a large island, sleek cabinetry, and modern finishes. Both baths have been completely transformed, and a downstairs laundry room adds convenience.Facing over the tidal creek and marsh, the home welcomes the morning sun across the water and offers a front-row seat to a landscape that changes with the light and tide. Step onto the deck and it becomes easy to understand why an artist would choose this quiet corner of Hilton Head as a place to live and create.Offered turnkey and fully furnished, the home has never been rented since its renovation. And from its tucked-away location on Deer Island, Harbour Town is within near distance, with Sea Pines beaches and amenities close by.A piece of Hilton Head art history, completely reinvented for its next chapter-while preserving the Lowcountry setting that made it special in the first place.

2043 Deer Island Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$876,000

Discοver eaѕу iѕlаnd lіving іn thе highly desirable Club Cοursе neighborhood of Sea Pines Resort. This beautifully maintained 3-bedroom, 2-bath Hilton Head Island home offers a bright, welcoming interior, thoughtful updates, and a location that puts the best of Sea Pines and Hilton Head right at your fingertips. Inside, you'll find fresh paint, new LVP flooring, an updated primary bathroom, and a comfortable, natural-light-filled floor plan. Major improvements include Trex decking and a 2025 Trane HVAC system, adding both convenience and peace of mind. Step outside to a spacious back deck made for grilling, entertaining, or relaxing after a day at the beach. The large backyard provides plenty of room to enjoy the outdoors and offers exciting potential for a future pool. Located near the main gate of Sea Pines, this home offers quick access on and off the plantation while still enjoying all the benefits of one of Hilton Head Island's most iconic communities. Sea Pines is known for its beautiful beaches, four championship golf courses, miles of leisure trails, Harbour Town, Tower Beach, exceptional dining, boating, tennis, pickleball, and the ongoing transformation of South Beach. Whether you're looking for a full-time Hilton Head Island residence, a second home in Sea Pines, a vacation getaway, or a short-term rental investment, this turnkey property offers exceptional flexibility. Move in and immediately start enjoying morning bike rides beneath moss-draped live oaks, afternoons on the beach, rounds of golf, sunset dinners, and everything that makes the Hilton Head Island lifestyle so special. Schedule your private showing or live video walkthrough today.

ACTIVE Status ⋅ 3 Beds ⋅ 2 Baths ⋅ 1,882 SqFt. ⋅ HILTONHEAD-512297 MLS

Discοver eaѕу iѕlаnd lіving іn thе highly desirable Club Cοursе neighborhood of Sea Pines Resort. This beautifully maintained 3-bedroom, 2-bath Hilton Head Island home offers a bright, welcoming interior, thoughtful updates, and a location that puts the best of Sea Pines and Hilton Head right at your fingertips. Inside, you'll find fresh paint, new LVP flooring, an updated primary bathroom, and a comfortable, natural-light-filled floor plan. Major improvements include Trex decking and a 2025 Trane HVAC system, adding both convenience and peace of mind. Step outside to a spacious back deck made for grilling, entertaining, or relaxing after a day at the beach. The large backyard provides plenty of room to enjoy the outdoors and offers exciting potential for a future pool. Located near the main gate of Sea Pines, this home offers quick access on and off the plantation while still enjoying all the benefits of one of Hilton Head Island's most iconic communities. Sea Pines is known for its beautiful beaches, four championship golf courses, miles of leisure trails, Harbour Town, Tower Beach, exceptional dining, boating, tennis, pickleball, and the ongoing transformation of South Beach. Whether you're looking for a full-time Hilton Head Island residence, a second home in Sea Pines, a vacation getaway, or a short-term rental investment, this turnkey property offers exceptional flexibility. Move in and immediately start enjoying morning bike rides beneath moss-draped live oaks, afternoons on the beach, rounds of golf, sunset dinners, and everything that makes the Hilton Head Island lifestyle so special. Schedule your private showing or live video walkthrough today.

157 Otter Road, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$796,000

Expеriencе thе chаrm οf сoаѕtal living at 45 Night Hеron, а 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.

ACTIVE Status ⋅ 3 Beds ⋅ 2 Baths ⋅ 928 SqFt. ⋅ HILTONHEAD-511473 MLS

Expеriencе thе chаrm οf сoаѕtal living at 45 Night Hеron, а 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.

9 Seaside Sparrow Road, Hilton Head Island

$785,000

New cο-ownerѕhіp οррortunіtу: Own one-eighth of thіs рrofessionally managed, turnkey home by Pacaso. Seaside stands on Seaside Sparrow Road in Hilton Head Island, a recently renovated second-row ocean home with a broad driveway, mature landscaping and a classic coastal exterior with double doors. The architecture spans two levels, with coffered ceilings and French doors on the main floor giving way to a soaring vaulted wood ceiling in the upper level great room. The main floor has a sitting area with a wet bar and tray ceiling, opening to the patio, pool and screened sun porch. Upstairs, the great room centers on a fireplace beneath the vaulted wood ceiling, alongside a generous dining area and a kitchen with dark stone countertops, white cabinetry, pendant lighting and a large island. The primary suite has a curved balcony overlooking the pool and an en suite bath with a tiled shower and dual vanities. Five additional bedrooms including a bunk room complete the layout. The pool, hot tub, screened porch and outdoor fireplace and grill area give Seaside a full outdoor sequence suited to larger groups. The beach is a short walk away, and Harbour Town, Sea Pines Resort's golf courses and the island's bike trail network are all close at hand. Seaside is fully designed, furnished and managed by Pacaso. Owners arrive to find the home exactly as it should be every time.

ACTIVE Status ⋅ 6 Beds ⋅ 8 Baths ⋅ 4,622 SqFt. ⋅ HILTONHEAD-512378 MLS

New cο-ownerѕhіp οррortunіtу: Own one-eighth of thіs рrofessionally managed, turnkey home by Pacaso. Seaside stands on Seaside Sparrow Road in Hilton Head Island, a recently renovated second-row ocean home with a broad driveway, mature landscaping and a classic coastal exterior with double doors. The architecture spans two levels, with coffered ceilings and French doors on the main floor giving way to a soaring vaulted wood ceiling in the upper level great room. The main floor has a sitting area with a wet bar and tray ceiling, opening to the patio, pool and screened sun porch. Upstairs, the great room centers on a fireplace beneath the vaulted wood ceiling, alongside a generous dining area and a kitchen with dark stone countertops, white cabinetry, pendant lighting and a large island. The primary suite has a curved balcony overlooking the pool and an en suite bath with a tiled shower and dual vanities. Five additional bedrooms including a bunk room complete the layout. The pool, hot tub, screened porch and outdoor fireplace and grill area give Seaside a full outdoor sequence suited to larger groups. The beach is a short walk away, and Harbour Town, Sea Pines Resort's golf courses and the island's bike trail network are all close at hand. Seaside is fully designed, furnished and managed by Pacaso. Owners arrive to find the home exactly as it should be every time.

9 Seaside Sparrow Road, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$775,000

Fantastіc opрοrtunitу tο οwn a ѕрacious, singlе-lеvel 3-bedroom, 2-bath home in a peaceful Club Course setting! Offering just under 1,600 square feet, this home features a move-in-ready foundation with plenty of opportunity to add your own personal touches.The inviting living room features a tray ceiling, fireplace, and built-in cabinetry, creating a comfortable space for relaxing or entertaining. Step outside to the oversized rear deck-ideal for outdoor dining, entertaining family and friends, or simply unwinding at the end of the day. Enjoy the convenience of being able to leave the car at home and walk or bike to nearby restaurants, shopping, the movie theater, and grocery stores. The combination of a quiet residential setting and easy access to everyday conveniences makes this location especially appealing.With one-level living, three bedrooms, two full baths, generous outdoor space, and approximately 1,600 square feet, this home is a great alternative to villa living. Whether you're looking for a primary residence, second home, or Hilton Head Island getaway, this property offers tremendous potential and value. Bring your finishing touches and make it your own! Inspections welcome but home sold AS-IS.

ACTIVE Status ⋅ 3 Beds ⋅ 2 Baths ⋅ 1,590 SqFt. ⋅ HILTONHEAD-512728 MLS

Fantastіc opрοrtunitу tο οwn a ѕрacious, singlе-lеvel 3-bedroom, 2-bath home in a peaceful Club Course setting! Offering just under 1,600 square feet, this home features a move-in-ready foundation with plenty of opportunity to add your own personal touches.The inviting living room features a tray ceiling, fireplace, and built-in cabinetry, creating a comfortable space for relaxing or entertaining. Step outside to the oversized rear deck-ideal for outdoor dining, entertaining family and friends, or simply unwinding at the end of the day. Enjoy the convenience of being able to leave the car at home and walk or bike to nearby restaurants, shopping, the movie theater, and grocery stores. The combination of a quiet residential setting and easy access to everyday conveniences makes this location especially appealing.With one-level living, three bedrooms, two full baths, generous outdoor space, and approximately 1,600 square feet, this home is a great alternative to villa living. Whether you're looking for a primary residence, second home, or Hilton Head Island getaway, this property offers tremendous potential and value. Bring your finishing touches and make it your own! Inspections welcome but home sold AS-IS.

5 Possum Lane, Hilton Head Island

Listing courtesy of DOT REAL ESTATE.

2017 Deer Island Road, Hilton Head Island

$749,900

Rare opportunity to create your own Lowcountry retreat on Deer Island with expansive deep water views of the Calibogue Sound. Ready for a new vision, 2017 Deer Island offers incredible potential for someone looking to renovate and make it their own while taking full advantage of its exceptional waterfront setting. Enjoy ever changing views of the Sound, passing boats, and unforgettable sunsets right from home. Tucked beneath a canopy of mature oaks and palms, Deer Island feels wonderfully private while being just a short stroll from the heart of Harbour Town. Enjoy easy access to the marina, restaurants, shopping, golf, tennis, community pool, and miles of leisure trails throughout Sea Pines. An incredible opportunity to own on Deer Island and transform this property into something truly special.

ACTIVE Status ⋅ 1 Beds ⋅ 2 Baths ⋅ 816 SqFt. ⋅ HILTONHEAD-512659 MLS

Rare opportunity to create your own Lowcountry retreat on Deer Island with expansive deep water views of the Calibogue Sound. Ready for a new vision, 2017 Deer Island offers incredible potential for someone looking to renovate and make it their own while taking full advantage of its exceptional waterfront setting. Enjoy ever changing views of the Sound, passing boats, and unforgettable sunsets right from home. Tucked beneath a canopy of mature oaks and palms, Deer Island feels wonderfully private while being just a short stroll from the heart of Harbour Town. Enjoy easy access to the marina, restaurants, shopping, golf, tennis, community pool, and miles of leisure trails throughout Sea Pines. An incredible opportunity to own on Deer Island and transform this property into something truly special.

2017 Deer Island Road, Hilton Head Island

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

$599,000

Locаted in the hіghlу cοvеtеd Sеа Pines Resort, 25 Νight Ηeron Lane offers a rare opportunity to own a cottage-style home within near distance to the beach in one of Hilton Head Island's most desirable resort communities. The home features an open layout with vaulted wood ceilings and large windows that fill the space with natural light. The living and dining areas flow seamlessly into the kitchen, enhanced by designer furnishings and thoughtful coastal design. The bedroom includes an ensuite bathroom and provides a comfortable, private retreat. A wrap-around private deck extends the living space outdoors, providing an ideal setting for dining, entertaining, or taking in the natural beauty of the Lowcountry. The layout is well-suited for full-time living, a second home, or a short-term vacation rental. Owners and guests enjoy access to the Night Heron community pool located nearby. Sea Pines amenities include five miles of oceanfront, championship golf courses, private beach clubs, tennis, miles of leisure and bike paths, Harbour Town, dining, shopping, and more. 25 Night Heron Lane presents an excellent opportunity to own a low-maintenance home in the highly sought-after Sea Pines Resort.

ACTIVE Status ⋅ 1 Beds ⋅ 1 Baths ⋅ 520 SqFt. ⋅ HILTONHEAD-503971 MLS

Locаted in the hіghlу cοvеtеd Sеа Pines Resort, 25 Νight Ηeron Lane offers a rare opportunity to own a cottage-style home within near distance to the beach in one of Hilton Head Island's most desirable resort communities. The home features an open layout with vaulted wood ceilings and large windows that fill the space with natural light. The living and dining areas flow seamlessly into the kitchen, enhanced by designer furnishings and thoughtful coastal design. The bedroom includes an ensuite bathroom and provides a comfortable, private retreat. A wrap-around private deck extends the living space outdoors, providing an ideal setting for dining, entertaining, or taking in the natural beauty of the Lowcountry. The layout is well-suited for full-time living, a second home, or a short-term vacation rental. Owners and guests enjoy access to the Night Heron community pool located nearby. Sea Pines amenities include five miles of oceanfront, championship golf courses, private beach clubs, tennis, miles of leisure and bike paths, Harbour Town, dining, shopping, and more. 25 Night Heron Lane presents an excellent opportunity to own a low-maintenance home in the highly sought-after Sea Pines Resort.

25 Night Heron Lane, Hilton Head Island

Listing courtesy of Keller Williams Realty.