SP Ocean Side Homes with Two Story Style

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Newest SP Ocean Side Homes with Two Story Style

$7,399,500

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.

$5,900,000

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

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

10 Bald Eagle Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$7,950,000

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.

$2,250,000

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.

$4,190,000

5 Beds ⋅ 6 Baths ⋅ 3,880 SqFt. ⋅ HILTONHEAD-504388 MLS

Welcome to a remarkable coastal retreat ideally positioned just steps from the sand in the heart of Sea Pines. This exceptional second-row ocean home offers the perfect blend of refined craftsmanship, spacious design, and effortless island living, all within one of Hilton Head Island's most coveted communities. Just moments from the beach, the property captures the essence of relaxed luxury with inviting indoor and outdoor living spaces designed for both everyday comfort and memorable gatherings. Spanning approximately 3,800 square feet, this beautifully furnished residence features five spacious bedrooms, each with its own en-suite bath, creating a private and comfortable experience for owners and guests alike. Multiple primary suites provide flexibility and convenience, while expansive living areas offer an ideal setting for entertaining or unwinding after a day on the water. Soaring ceilings, custom built-ins, and rich natural materials such as heart pine flooring enhance the home's warm coastal character, while Saturnia stone baths and thoughtfully selected finishes reflect quality throughout. At the heart of the home, the kitchen is equipped for both casual meals and entertaining, featuring granite countertops, stainless steel appliances, and generous workspace. Adjacent dining and living areas flow seamlessly to outdoor spaces, where a heated pool and spa create a private resort-style setting perfect for year-round enjoyment. Covered porches and balconies provide additional spaces to relax, dine al fresco, or enjoy the ocean-oriented setting and coastal breezes. Beyond the property, residents enjoy access to the world-class amenities of Sea Pines, including pristine beaches, championship golf, tennis and pickleball, marinas, miles of leisure trails, dining, shopping, and the iconic Harbour Town. Whether used as a primary residence, second home, or investment opportunity with strong rental appeal, this coastal haven offers an exceptional lifestyle in one of Hilton Head Island's most celebrated communities.

30 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of Maxey Blackstream Christie's International Real Estate.

$2,995,000

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.

$9,495,000

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.

$6,999,000

5 Beds ⋅ 6 Baths ⋅ 3,669 SqFt. ⋅ HILTONHEAD-500303 MLS

Welcome to your coastal sanctuary in Sea Pines Resort-an exquisite 2ND ROW new-construction home designed for luxury living and / or exceptional rental potential. This 5-bedroom, 5.5-bath masterpiece offers approximately 3,669 heated square feet of finely crafted space, perfectly positioned on a 2nd-row homesite with STRONG OCEAN VIEWS and effortless access to the wide white sand beaches of Hilton Head Island.From the moment you enter, a private elevator and light-filled foyer set the tone for a home that blends coastal elegance with modern comfort. The open-concept main level showcases a chef's kitchen with premium appliances, custom cabinetry, and a large island that flows seamlessly into the dining and living areas-ideal for entertaining large groups or enjoying intimate family gatherings. Expansive windows and glass doors draw your eye outward to the ocean and to the resort-style outdoor living spaces.Step outside to your private oasis: an infinity-edge pool and spa that appear to melt into the horizon, framed by a spacious covered lanai and multiple porches. Enjoy al fresco dining, lounging, or watching the sunset by the outdoor fireplace-this home was designed to embrace indoor-outdoor living at its finest. Just steps away, a convenient beach path delivers you onto one of Hilton Head's most beautiful stretches of sand.Each of the six bedrooms is thoughtfully appointed with its own en-suite bath, offering comfort and privacy for owners and guests alike. Multiple primary suites, generous bunk or guest rooms, and carefully planned bath layouts make this home ideal for multi-generational living or high-occupancy vacation rentals. The half bath is perfectly positioned for pool and common-area use.Every detail was considered for both luxury and durability: high-end finishes, impact-rated windows and doors, designer lighting, and a floor plan optimized for today's coastal lifestyle. Ample storage, a ground-level drop zone for beach gear, and flexible gathering spaces ensure that the home is as functional as it is beautiful.

18 Oyster Catcher Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$6,100,000

5 Beds ⋅ 5 Baths ⋅ 4,449 SqFt. ⋅ HILTONHEAD-500143 MLS

Welcome to 30 E Beach Lagoon, a stunningly remodeled Oceanfront home located on one of Sea Pines most prestigious streets. Rarely does a property blend luxury, charm, and location this seamlessly. Designed with timeless coastal elegance, this home offers an exceptional lifestyle, 5 bedrooms, 5 baths, and just steps from your private deeded beach access. Inside, soaring vaulted ceilings with exposed beams, a masonry brick fireplace, and wide-plank wood floors create a warm, inviting atmosphere. The kitchen features high-end natural wood cabinetry, sleek countertops, and stainless steel appliances ideal for entertaining or quiet mornings at home. The main house flows beautifully into a spacious living area filled with natural light, while the private, attached guest house offers flexibility for hosting friends or extended family. The primary suite features a private deck with peekaboo ocean views and easy access via the in-home elevator. Outside, enjoy your own private pool surrounded by lush, mature landscaping, creating a serene retreat that feels both secluded and coastal. The home also includes a two-car garage and has never been used as a rental, offering pristine condition and pride of ownership. Whether you're searching for a luxury second home or a high-performing short-term rental, 30 E Beach Lagoon delivers on all fronts location, design, and lifestyle all within the gates of Sea Pines Resort.

30 E Beach Lagoon Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$3,390,000

4 Beds ⋅ 5 Baths ⋅ 3,100 SqFt. ⋅ HILTONHEAD-452729 MLS

SECOND ROW OCEANFRONT HOME IN THE SOUTH BEACH AREA OF SEA PINES PLANTATION is available to make your dreams come true!!! LOCATION! LOCATION! LOCATION! Living life in the Low Country only MINUTES away from our nationally recognized beach is now a REALITY! This custom built 2nd ROW OCEAN beauty has very close proximity to the beach & to the South Beach Marina area where your ultimate island experiences await. There are soooooo many direct views of the ocean from the multiple levels and balconies! All newly renovated coastal bathrooms give this home a current vibe! Fun local activities include biking, boating, dining, shopping, kayaking, dolphin watching, tennis, pickle ball & MORE! The cathedral ceilings in the living area, travertine floors & open concept living w/outside wrap-around balconies towards the ocean complement the Low Country lifestyle! The kitchen has a Viking stove, newer refrigerator, floating shelves, Italian imported marble countertops & a huge pantry! The entire lowest floor has as much space as you can imagine to store all your beach/pool/bikes and MORE!! During high season you can take the trolley anywhere in Sea Pines so you can park your car and never have to drive while you are visiting. The gorgeous pool has a spa with a water fountain and the pool also has had a heater added to it so you can swim in the pool year round! If you are looking for the perfect house in the PERFECT easy location....you have just found it!

4 Gadwall Road, Hilton Head Island

Listing courtesy of Keller Williams Realty.

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