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$799,000

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

6 Beds ⋅ 8 Baths ⋅ 4,407 SqFt. ⋅ HILTONHEAD-512129 MLS

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

8 Bald Eagle Road, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$7,399,500

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.

$1,985,000

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.

$7,950,000

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

HILTONHEAD-511653 MLS

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

15 Green Wing Teal Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$5,900,000

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

7 Beds ⋅ 8 Baths ⋅ 5,203 SqFt. ⋅ HILTONHEAD-511606 MLS

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

10 Bald Eagle Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$815,000

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

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

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

45 Night Heron Lane, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$2,499,000

Welcome to this 4 bedroom Sea Pines getaway! Lagoon and majestic live oaks in the backyard with private pool, gazebo and beautiful guest cottage. This updated single-level home offers the relaxed coastal lifestyle that makes Sea Pines one of Hilton Head Island's most sought-after destinations. Thoughtfully renovated and offered beautifully furnished, the home blends timeless Lowcountry charm with modern updates, making it ready to enjoy from day one.Inside, the open-concept floor plan is designed for gathering. The updated kitchen flows seamlessly into a bright and inviting family room with custom built-ins and a convenient desk nook for remote work or vacation planning. New flooring, updated lighting, and stylish finishes create a fresh, welcoming atmosphere throughout.The main house features three spacious bedrooms, while a separate guest cottage provides additional space for extended family, friends, or vacation guests. The flexible layout is ideal for second-home owners looking to maximize both enjoyment and rental potential.Step outside and discover the true magic of this property. A private Savannah brick courtyard surrounds the sparkling pool, creating an intimate outdoor retreat perfect for entertaining, relaxing, and making memories. Beyond the pool, a picturesque lagoon meanders through the backyard beneath a canopy of live oaks, providing a beautiful natural backdrop filled with Lowcountry wildlife and year-round scenery. A charming waterside gazebo offers the perfect spot for morning coffee, afternoon reading, or evening cocktails as the sun filters through the trees.Located in the heart of Sea Pines, owners and guests enjoy easy access to beaches, championship golf, miles of leisure trails, Harbour Town, South Beach Marina, shopping, dining, and all the amenities that have made Hilton Head Island a premier vacation destination for generations.Whether you're searching for a family retreat, a second home, or an investment property with proven vacation rental appeal, this exceptional Sea Pines residence delivers the best of island living.

4 Beds ⋅ 4 Baths ⋅ 2,982 SqFt. ⋅ HILTONHEAD-510784 MLS

Welcome to this 4 bedroom Sea Pines getaway! Lagoon and majestic live oaks in the backyard with private pool, gazebo and beautiful guest cottage. This updated single-level home offers the relaxed coastal lifestyle that makes Sea Pines one of Hilton Head Island's most sought-after destinations. Thoughtfully renovated and offered beautifully furnished, the home blends timeless Lowcountry charm with modern updates, making it ready to enjoy from day one.Inside, the open-concept floor plan is designed for gathering. The updated kitchen flows seamlessly into a bright and inviting family room with custom built-ins and a convenient desk nook for remote work or vacation planning. New flooring, updated lighting, and stylish finishes create a fresh, welcoming atmosphere throughout.The main house features three spacious bedrooms, while a separate guest cottage provides additional space for extended family, friends, or vacation guests. The flexible layout is ideal for second-home owners looking to maximize both enjoyment and rental potential.Step outside and discover the true magic of this property. A private Savannah brick courtyard surrounds the sparkling pool, creating an intimate outdoor retreat perfect for entertaining, relaxing, and making memories. Beyond the pool, a picturesque lagoon meanders through the backyard beneath a canopy of live oaks, providing a beautiful natural backdrop filled with Lowcountry wildlife and year-round scenery. A charming waterside gazebo offers the perfect spot for morning coffee, afternoon reading, or evening cocktails as the sun filters through the trees.Located in the heart of Sea Pines, owners and guests enjoy easy access to beaches, championship golf, miles of leisure trails, Harbour Town, South Beach Marina, shopping, dining, and all the amenities that have made Hilton Head Island a premier vacation destination for generations.Whether you're searching for a family retreat, a second home, or an investment property with proven vacation rental appeal, this exceptional Sea Pines residence delivers the best of island living.

37 Woodbine Place, Hilton Head Island

Listing courtesy of Hilton Head Properties.

$7,950,000

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

7 Beds ⋅ 5 Baths ⋅ 6,034 SqFt. ⋅ HILTONHEAD-510860 MLS

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

21 Red Cardinal Road, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate.

$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.

$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.

$4,200,000

This exceptional second-row ocean home in Sea Pines offers a compelling blend of location, scale, and long-term flexibility. Just steps to the beach, expansive first- and second-level balconies capture ocean views and coastal breezes, while a private pool creates an ideal setting for outdoor living and entertaining. Inside, nearly 3,000 square feet of light-filled living space showcases an open-concept design with oversized windows and skylights. The thoughtfully designed floor plan includes 4 bedrooms plus a bunk room and 3.5 baths, providing flexible accommodations for family, guests, or rental demand. The first level features a secondary primary suite, while additional bedrooms are connected by a Jack and Jill bath, creating functional and private guest spaces. Upstairs, the primary suite serves as a quiet retreat. A fully equipped kitchen, garage parking, washer and dryer, gas grill, and electric vehicle charger enhance everyday functionality. Enjoy easy access to the beach and a short walk to South Beach Marina, offering premier tennis and pickleball facilities, or relax and dine at the iconic The Salty Dog Cafe. Whether positioned as a legacy coastal retreat or a high-performing investment property, this home represents a rare opportunity in one of Hilton Head Island's most desirable ocean-oriented communities.

4 Beds ⋅ 4 Baths ⋅ 2,918 SqFt. ⋅ HILTONHEAD-504969 MLS

This exceptional second-row ocean home in Sea Pines offers a compelling blend of location, scale, and long-term flexibility. Just steps to the beach, expansive first- and second-level balconies capture ocean views and coastal breezes, while a private pool creates an ideal setting for outdoor living and entertaining. Inside, nearly 3,000 square feet of light-filled living space showcases an open-concept design with oversized windows and skylights. The thoughtfully designed floor plan includes 4 bedrooms plus a bunk room and 3.5 baths, providing flexible accommodations for family, guests, or rental demand. The first level features a secondary primary suite, while additional bedrooms are connected by a Jack and Jill bath, creating functional and private guest spaces. Upstairs, the primary suite serves as a quiet retreat. A fully equipped kitchen, garage parking, washer and dryer, gas grill, and electric vehicle charger enhance everyday functionality. Enjoy easy access to the beach and a short walk to South Beach Marina, offering premier tennis and pickleball facilities, or relax and dine at the iconic The Salty Dog Cafe. Whether positioned as a legacy coastal retreat or a high-performing investment property, this home represents a rare opportunity in one of Hilton Head Island's most desirable ocean-oriented communities.

1 Brown Pelican Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

$2,995,000

Welcome to 13 Beach Lagoon, a classic 2nd-row home in the coveted "Gold Coast" area of Sea Pines offering an exceptional location just steps to the beach and outstanding investment potential. Situated on a large lot with generous backyard space, this property provides rare room to expand, redesign, or create your ideal outdoor oasis. The fenced yard and expansive outdoor areas add both privacy and versatility. The home features a spacious floor plan with vaulted ceilings, multiple living areas, and abundant natural light, along with wonderful architectural charm throughout. Generous bedrooms are thoughtfully separated for privacy, creating an ideal layout for family and guests. An elevator shaft is already in place, offering future convenience and accessibility. Expansive decking and porch areas overlook the sizable backyard, including one of the largest screened porches you'll find in Sea Pines - an incredible space for relaxing or entertaining. There is ample room to add enhancements such as a pool while still maintaining substantial outdoor living space. Additional highlights include a 2-car side-entry garage and a flexible layout ready for your updates and vision. This is a rare opportunity to renovate and truly make it your own. Whether you're looking to create a custom coastal retreat or invest in a high-demand rental location, the setting, lot size, and layout make this property especially appealing. Enjoy access to Sea Pines' beaches, bike trails, golf, marina, and dining - all from this prime 2nd-row location. 13 Beach Lagoon offers location, space, character, and unlimited potential.

6 Beds ⋅ 8 Baths ⋅ 4,685 SqFt. ⋅ HILTONHEAD-504849 MLS

Welcome to 13 Beach Lagoon, a classic 2nd-row home in the coveted "Gold Coast" area of Sea Pines offering an exceptional location just steps to the beach and outstanding investment potential. Situated on a large lot with generous backyard space, this property provides rare room to expand, redesign, or create your ideal outdoor oasis. The fenced yard and expansive outdoor areas add both privacy and versatility. The home features a spacious floor plan with vaulted ceilings, multiple living areas, and abundant natural light, along with wonderful architectural charm throughout. Generous bedrooms are thoughtfully separated for privacy, creating an ideal layout for family and guests. An elevator shaft is already in place, offering future convenience and accessibility. Expansive decking and porch areas overlook the sizable backyard, including one of the largest screened porches you'll find in Sea Pines - an incredible space for relaxing or entertaining. There is ample room to add enhancements such as a pool while still maintaining substantial outdoor living space. Additional highlights include a 2-car side-entry garage and a flexible layout ready for your updates and vision. This is a rare opportunity to renovate and truly make it your own. Whether you're looking to create a custom coastal retreat or invest in a high-demand rental location, the setting, lot size, and layout make this property especially appealing. Enjoy access to Sea Pines' beaches, bike trails, golf, marina, and dining - all from this prime 2nd-row location. 13 Beach Lagoon offers location, space, character, and unlimited potential.

13 Beach Lagoon Road, Hilton Head Island

Listing courtesy of Charter One 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.

$4,250,000

Stunning deep-water residence in Sea Pines features 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 deep-water residence in Sea Pines features 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.

$4,600,000

This one-of-a-kind property is privately sited on almost an acre lot with panoramic marsh and water views providing the perfect backdrop for spectacular sunsets. Kermit Huggins, renowned architect, designed this property with 2 structures that harmoniously co-exist with their natural surroundings. Special features include new metal roof, hardwood flooring, pella windows/doors, renovated kitchen,& interior paint. The main house boasts an upper level luxurious owner suite & guest house has 2 en-suite bedrooms plus kitchenette. Incredible outdoor living with heated/chilled saltwater pool, expansive deck, and private dock. Waterfront Perfection!

4 Beds ⋅ 6 Baths ⋅ 6,042 SqFt. ⋅ HILTONHEAD-447864 MLS

This one-of-a-kind property is privately sited on almost an acre lot with panoramic marsh and water views providing the perfect backdrop for spectacular sunsets. Kermit Huggins, renowned architect, designed this property with 2 structures that harmoniously co-exist with their natural surroundings. Special features include new metal roof, hardwood flooring, pella windows/doors, renovated kitchen,& interior paint. The main house boasts an upper level luxurious owner suite & guest house has 2 en-suite bedrooms plus kitchenette. Incredible outdoor living with heated/chilled saltwater pool, expansive deck, and private dock. Waterfront Perfection!

29 Baynard Park Road, Hilton Head Island

Listing courtesy of Charter One Realty.