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$7,399,500

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.

5 Beds ⋅ 6 Baths ⋅ 5,278 SqFt. ⋅ HILTONHEAD-511871 MLS

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

34 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,300,000

First time on the market! Come see this bright, elegant home with high smooth ceilings, skylights, and glass on nearly every wall. This 4 bedroom (or 3-bed + bonus), 3-bath home includes a large bonus room with full bath over the garage that could be the 4th bedroom, or a studio, office, den, lounge, or workout space, along with a 2-car garage & under-house storage. The living room was designed for cozy movie nights & entertaining, with built-ins flanking the never-used wood fireplace. Bull-nosed corners soften the space. Out back is private & protected, with lagoon & Forest Preserve views that mean your morning coffee comes with egrets, herons, and turtles. An easy bike or walk to the restaurants & shops outside the main gate, or ride through the Forest Preserve to the beach, garden, or Harbour Town. Enjoy all the amenities Sea Pines and Carolina Place have to offer. Carolina Place fees include pool, pickleball, tennis, steam room, sauna, lawn & landscape maintenance, pest control, and trash. The owner had this home built & has never rented it, which is easy to see once you walk through the front door. It is spotlessly clean & updated. New roof in 2018. Replaced subflooring in 2020 through much of the main level, topped with 5-inch ebonized oak plank hardwood & a UV sealer coat to protect it. KitchenAid appliances. The primary bath was redone with new flooring, a new shower, and Kohler fixtures & hardware throughout, and the other two baths have new toilets. Both front bedrooms have hurricane-resistant pop-out windows. Gutters & gutter guards in 2020, skylights re-tightened, the entire exterior painted, and about 70 percent of the interior. New garage door system & front door hardware in 2026, along with new upstairs shower fixtures & paint. The HVAC compressor & furnace fan motor were replaced in 2025 on one of the two maintained 2016 systems, and the kitchen faucet & disposal are new as well. Underneath, a vapor barrier & foam insulation were added in 2020, and the perimeter is fenced with secured access gates. Outside, six large trees were cleared to open up the lot, with new sod, fresh landscaping, and a 2021 Rainbird irrigation system. Termite bond has been in place since 2020 with annual inspections & no issues. If you're looking for a home that's ready to move into, this is it. Some photos are virtually staged to show what the space can do. This home would be excellent as a primary, secondary, or rental home. Homes like this do not come up often.

4 Beds ⋅ 3 Baths ⋅ 2,673 SqFt. ⋅ HILTONHEAD-511956 MLS

First time on the market! Come see this bright, elegant home with high smooth ceilings, skylights, and glass on nearly every wall. This 4 bedroom (or 3-bed + bonus), 3-bath home includes a large bonus room with full bath over the garage that could be the 4th bedroom, or a studio, office, den, lounge, or workout space, along with a 2-car garage & under-house storage. The living room was designed for cozy movie nights & entertaining, with built-ins flanking the never-used wood fireplace. Bull-nosed corners soften the space. Out back is private & protected, with lagoon & Forest Preserve views that mean your morning coffee comes with egrets, herons, and turtles. An easy bike or walk to the restaurants & shops outside the main gate, or ride through the Forest Preserve to the beach, garden, or Harbour Town. Enjoy all the amenities Sea Pines and Carolina Place have to offer. Carolina Place fees include pool, pickleball, tennis, steam room, sauna, lawn & landscape maintenance, pest control, and trash. The owner had this home built & has never rented it, which is easy to see once you walk through the front door. It is spotlessly clean & updated. New roof in 2018. Replaced subflooring in 2020 through much of the main level, topped with 5-inch ebonized oak plank hardwood & a UV sealer coat to protect it. KitchenAid appliances. The primary bath was redone with new flooring, a new shower, and Kohler fixtures & hardware throughout, and the other two baths have new toilets. Both front bedrooms have hurricane-resistant pop-out windows. Gutters & gutter guards in 2020, skylights re-tightened, the entire exterior painted, and about 70 percent of the interior. New garage door system & front door hardware in 2026, along with new upstairs shower fixtures & paint. The HVAC compressor & furnace fan motor were replaced in 2025 on one of the two maintained 2016 systems, and the kitchen faucet & disposal are new as well. Underneath, a vapor barrier & foam insulation were added in 2020, and the perimeter is fenced with secured access gates. Outside, six large trees were cleared to open up the lot, with new sod, fresh landscaping, and a 2021 Rainbird irrigation system. Termite bond has been in place since 2020 with annual inspections & no issues. If you're looking for a home that's ready to move into, this is it. Some photos are virtually staged to show what the space can do. This home would be excellent as a primary, secondary, or rental home. Homes like this do not come up often.

64 Shell Ring Road, Hilton Head Island

Listing courtesy of Southern Lifestyle Properties of SC LLC.

$1,985,000

An absolute standout in Sea Pines. This exceptional home was worth the wait... but is not expected to last long! Relaxed and comfortable meets modern and sophisticated. Prepare to be captivated by this exceptionally cool, single-level stunner! A private (gated) front courtyard enhances the arrival experience, while the private backyard setting is unmatched. Inside you will find an open-concept interior that is complimented by numerous design enhancements. The design-forward, chef-style kitchen will reignite your love of both cooking and entertaining, boasting quartz counters, impressive cabinetry, designer lighting, updated appliances, gas cooking, beverage refrigerator, pantry, and an expansive flat-top island. The home naturally flows out to an inviting screened porch, extending comfortable living space outdoors. The spacious owner's suite enjoys tranquil water views and a spa-like bath, while the two private guest rooms offer beautifully remodeled en-suite baths as well. Embrace a year-round outside lifestyle with a refreshing (heated) saltwater pool, firepit area, peaceful lagoon and private backyard lawn. The property features a durable TPO roofing system, valued for its energy efficiency, longevity, and low-maintenance performance. Set on nearly a half-acre with open space on two sides, this high-elevation property stands apart! Ideally positioned in Sea Pines on a quiet street almost directly between the Sea Pines Beach Club and the Harbourtown Yacht Basin! Tastefully furnished for immediate gratification!

3 Beds ⋅ 4 Baths ⋅ 2,722 SqFt. ⋅ HILTONHEAD-511813 MLS

An absolute standout in Sea Pines. This exceptional home was worth the wait... but is not expected to last long! Relaxed and comfortable meets modern and sophisticated. Prepare to be captivated by this exceptionally cool, single-level stunner! A private (gated) front courtyard enhances the arrival experience, while the private backyard setting is unmatched. Inside you will find an open-concept interior that is complimented by numerous design enhancements. The design-forward, chef-style kitchen will reignite your love of both cooking and entertaining, boasting quartz counters, impressive cabinetry, designer lighting, updated appliances, gas cooking, beverage refrigerator, pantry, and an expansive flat-top island. The home naturally flows out to an inviting screened porch, extending comfortable living space outdoors. The spacious owner's suite enjoys tranquil water views and a spa-like bath, while the two private guest rooms offer beautifully remodeled en-suite baths as well. Embrace a year-round outside lifestyle with a refreshing (heated) saltwater pool, firepit area, peaceful lagoon and private backyard lawn. The property features a durable TPO roofing system, valued for its energy efficiency, longevity, and low-maintenance performance. Set on nearly a half-acre with open space on two sides, this high-elevation property stands apart! Ideally positioned in Sea Pines on a quiet street almost directly between the Sea Pines Beach Club and the Harbourtown Yacht Basin! Tastefully furnished for immediate gratification!

41 Willow Oak W Road, Hilton Head Island

Listing courtesy of Collins Group Realty.

$975,000

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.

2 Beds ⋅ 3 Baths ⋅ 2,032 SqFt. ⋅ HILTONHEAD-511564 MLS

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

33 Oak Court, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,449,000

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

4 Beds ⋅ 3 Baths ⋅ 2,500 SqFt. ⋅ HILTONHEAD-510645 MLS

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

8 Pine Court, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$2,625,000

Welcome to 5 Heritage Court! This beautifully designed newer-style home offers an exceptional blend of space, comfort, and privacy in the highly sought-after Heritage Woods community within Sea Pines.Featuring 5 spacious bedrooms and 5 full bathrooms, the home is thoughtfully designed with multiple gathering areas, making it ideal for hosting family and friends. Nestled on a quiet cul-de-sac, the property enjoys a private setting backing to Sea Pines open space, providing a peaceful natural backdrop.Just two doors from the leisure trail, you'll enjoy a convenient bike ride or stroll directly to the beach. Whether you're looking for a primary residence, second home, or investment property, this home checks every box.Outdoor living is enhanced by a recently resurfaced pool and the addition of a relaxing spa, creating the perfect setting for entertaining or unwinding after a day on the island. With its desirable location, spacious floor plan, and excellent rental potential, 5 Heritage Court offers a rare opportunity to enjoy the best of Hilton Head Island living.

5 Beds ⋅ 5 Baths ⋅ 3,872 SqFt. ⋅ HILTONHEAD-510379 MLS

Welcome to 5 Heritage Court! This beautifully designed newer-style home offers an exceptional blend of space, comfort, and privacy in the highly sought-after Heritage Woods community within Sea Pines.Featuring 5 spacious bedrooms and 5 full bathrooms, the home is thoughtfully designed with multiple gathering areas, making it ideal for hosting family and friends. Nestled on a quiet cul-de-sac, the property enjoys a private setting backing to Sea Pines open space, providing a peaceful natural backdrop.Just two doors from the leisure trail, you'll enjoy a convenient bike ride or stroll directly to the beach. Whether you're looking for a primary residence, second home, or investment property, this home checks every box.Outdoor living is enhanced by a recently resurfaced pool and the addition of a relaxing spa, creating the perfect setting for entertaining or unwinding after a day on the island. With its desirable location, spacious floor plan, and excellent rental potential, 5 Heritage Court offers a rare opportunity to enjoy the best of Hilton Head Island living.

5 Heritage Court, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$9,375,000

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

5 Beds ⋅ 6 Baths ⋅ 5,837 SqFt. ⋅ HILTONHEAD-510013 MLS

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

33 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$2,250,000

GREAT NEW PRICE $2,225,000! Rare opportunity to own a 5-bedroom beach-oriented home in the coveted Sea Pines community, offering the perfect combination of coastal lifestyle, exceptional versatility, and outstanding investment potential. Located just a short walk to one of Hilton Head Island's most desirable stretches of beach, this spacious property is ideally suited as a primary residence, luxury second home, or high-demand vacation rental.Designed with an inverted floor plan to maximize natural light and privacy, the home offers exceptional sleeping capacity for large families and guests, making it especially attractive for those seeking strong rental income potential. The private fenced pool creates the ideal outdoor retreat for relaxing after a day at the beach, while an upper deck, a screened porch, and generous gathering spaces make entertaining effortless.Lovingly maintained by only its second owner, the home features spacious living areas, vaulted ceilings, skylights, built-ins, a fireplace, dumbwaiter, and a light-filled den that adds flexibility for additional living or work-from-home space.Positioned near the Sea Pines Ocean Gate for easy access in and out of the community, this location places you approximately one mile from Coligny Beach and one mile to the Sea Pines Beach Club - right in the heart of one of Hilton Head's strongest vacation rental corridors.

5 Beds ⋅ 4 Baths ⋅ 3,214 SqFt. ⋅ HILTONHEAD-509680 MLS

GREAT NEW PRICE $2,225,000! Rare opportunity to own a 5-bedroom beach-oriented home in the coveted Sea Pines community, offering the perfect combination of coastal lifestyle, exceptional versatility, and outstanding investment potential. Located just a short walk to one of Hilton Head Island's most desirable stretches of beach, this spacious property is ideally suited as a primary residence, luxury second home, or high-demand vacation rental.Designed with an inverted floor plan to maximize natural light and privacy, the home offers exceptional sleeping capacity for large families and guests, making it especially attractive for those seeking strong rental income potential. The private fenced pool creates the ideal outdoor retreat for relaxing after a day at the beach, while an upper deck, a screened porch, and generous gathering spaces make entertaining effortless.Lovingly maintained by only its second owner, the home features spacious living areas, vaulted ceilings, skylights, built-ins, a fireplace, dumbwaiter, and a light-filled den that adds flexibility for additional living or work-from-home space.Positioned near the Sea Pines Ocean Gate for easy access in and out of the community, this location places you approximately one mile from Coligny Beach and one mile to the Sea Pines Beach Club - right in the heart of one of Hilton Head's strongest vacation rental corridors.

18 Canvasback Road, Hilton Head Island

Listing courtesy of Engel & Volkers.

$899,000

You're invited to my Open House at my Sea Pines listing in Greenwood Forrest Sunday and Friday from 1-330. I look forward to seeing you there! This charming two-bedroom, two-bathroom home is nestled in the desirable Greenwood Forest community, right in the heart of Sea Pines. Surrounded by mature landscaping, the property offers a private backyard retreat-perfect for enjoying a quiet, relaxed Lowcountry setting. Whether as a primary residence, second home, or investment opportunity, this home presents a wonderful chance to own in one of Hilton Head Island's most sought-after communities. Sweet jasmine and azaleas bloom on the property during the Heritage Golf Tournament each spring, adding to the Lowcountry charm of this special setting. Just steps from the shared Greenwood Forest amenities, a wooded trail leads directly behind The Shops at Sea Pines Center. Grab a morning coffee, pick up a pizza, enjoy breakfast at Lowcountry Produce, or settle in for a fine-dining dinner at Truffles-all just about a three-minute walk from the property. The beach is approximately 0.8 miles away, with Harbour Town approximately 1.5 miles from the property. Not all locations inside the gates of Sea Pines are the same, and this is truly one of its best central locations. Sit on your back patio beneath the Lowcountry's umbrella of protected live oaks and hear the distant sound of the ocean through the trees. Experience the lifestyle that makes Sea Pines so special-and make your move today!

2 Beds ⋅ 2 Baths ⋅ 1,516 SqFt. ⋅ HILTONHEAD-507616 MLS

You're invited to my Open House at my Sea Pines listing in Greenwood Forrest Sunday and Friday from 1-330. I look forward to seeing you there! This charming two-bedroom, two-bathroom home is nestled in the desirable Greenwood Forest community, right in the heart of Sea Pines. Surrounded by mature landscaping, the property offers a private backyard retreat-perfect for enjoying a quiet, relaxed Lowcountry setting. Whether as a primary residence, second home, or investment opportunity, this home presents a wonderful chance to own in one of Hilton Head Island's most sought-after communities. Sweet jasmine and azaleas bloom on the property during the Heritage Golf Tournament each spring, adding to the Lowcountry charm of this special setting. Just steps from the shared Greenwood Forest amenities, a wooded trail leads directly behind The Shops at Sea Pines Center. Grab a morning coffee, pick up a pizza, enjoy breakfast at Lowcountry Produce, or settle in for a fine-dining dinner at Truffles-all just about a three-minute walk from the property. The beach is approximately 0.8 miles away, with Harbour Town approximately 1.5 miles from the property. Not all locations inside the gates of Sea Pines are the same, and this is truly one of its best central locations. Sit on your back patio beneath the Lowcountry's umbrella of protected live oaks and hear the distant sound of the ocean through the trees. Experience the lifestyle that makes Sea Pines so special-and make your move today!

10 Hollyberry Lane, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$2,100,000

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

4 Beds ⋅ 5 Baths ⋅ 2,967 SqFt. ⋅ HILTONHEAD-505896 MLS

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

46 Hearthwood Drive, Hilton Head Island

Listing courtesy of Collins Group Realty.

$3,875,000

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

7 Beds ⋅ 7 Baths ⋅ 4,400 SqFt. ⋅ HILTONHEAD-504560 MLS

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

34 Tupelo Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$9,495,000

A custom-built oceanfront home that is defined by exceptional craftsmanship and an enduring coastal presence located in the world-class Sea Pines community. Designed by architect Neil Gordon and built by Cambridge Builders, 52 Canvasback offers the best in oceanfront living. A welcoming entrance foyer with double height ceilings invites you to appreciate the coastal views and the beautifully-executed architectural details. The rich wood detailing, hardwood floors, extensive custom millwork, and two fireplaces complement the finely-crafted spaces. The open living, dining, and kitchen areas flow naturally for everyday living and entertaining, supported by a butler's pantry and separate laundry room. A first-floor primary suite and wood-paneled office offer privacy and convenience, while 3 oversized, en-suite bedrooms upstairs and an oceanfront balcony provide plenty of room for friends and family. An expansive oceanfront pool deck extends the living space outdoors, creating a natural backdrop for lasting memories in an idyllic setting. Beach access via a private beach walkway. Timeless design, thoughtful details, craftsmanship and a stunning oceanfront location make this home an exceptional opportunity.

4 Beds ⋅ 5 Baths ⋅ 4,025 SqFt. ⋅ HILTONHEAD-504472 MLS

A custom-built oceanfront home that is defined by exceptional craftsmanship and an enduring coastal presence located in the world-class Sea Pines community. Designed by architect Neil Gordon and built by Cambridge Builders, 52 Canvasback offers the best in oceanfront living. A welcoming entrance foyer with double height ceilings invites you to appreciate the coastal views and the beautifully-executed architectural details. The rich wood detailing, hardwood floors, extensive custom millwork, and two fireplaces complement the finely-crafted spaces. The open living, dining, and kitchen areas flow naturally for everyday living and entertaining, supported by a butler's pantry and separate laundry room. A first-floor primary suite and wood-paneled office offer privacy and convenience, while 3 oversized, en-suite bedrooms upstairs and an oceanfront balcony provide plenty of room for friends and family. An expansive oceanfront pool deck extends the living space outdoors, creating a natural backdrop for lasting memories in an idyllic setting. Beach access via a private beach walkway. Timeless design, thoughtful details, craftsmanship and a stunning oceanfront location make this home an exceptional opportunity.

52 Canvasback Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

$2,199,000

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

4 Beds ⋅ 4 Baths ⋅ 3,700 SqFt. ⋅ HILTONHEAD-500571 MLS

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

2 Long Marsh Lane, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.