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$3,300,000
4 Beds ⋅ 4 Baths ⋅ 5,034 SqFt. ⋅ HILTONHEAD-505597 MLS
Rare opportunity to own a spectacular Lowcountry marshfront deepwater estate on nearly an acre along one of Sea Pines' most coveted streets. This fully reimagined 5,034-square-foot residence blends luxury, privacy, and breathtaking coastal scenery. The home features a first-floor primary suite, three guest retreats, den, elevator, and a chef's kitchen appointed with GE Monogram appliances. An expansive enclosed heated pool and recreation area, outdoor grilling space, and private dock with direct access to the Atlantic Ocean create an exceptional waterfront lifestyle. Rebuilt from the studs, the residence offers all new electrical, plumbing, HVAC, and spray-foam insulation, along with bamboo flooring, designer lighting, and walls of glass that fill the home with natural light. Open living spaces flow seamlessly to the pool enclosure and waterfront dock-perfectly designed for effortless entertaining and unforgettable Lowcountry living. Your coastal life begins here!

50 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: RE/MAX Island Realty.

$3,750,000
3 Beds ⋅ 3 Baths ⋅ 2,549 SqFt. ⋅ HILTONHEAD-504606 MLS
Located in Sea Pines, this one-level 3 bed 2 1/2 bath waterfront home offers a deep-water dock and a private, oak-framed setting with serene water views. Vaulted, beamed ceilings, warm wood paneling, and hardwood floors create a timeless Lowcountry feel. The home features a built-in wet bar, kitchen with breakfast area, formal dining room with adjacent flex space, and a spacious primary suite with access to outdoor living. Recently remodeled with new Pella doors and expansive windows, the raised Old Savannah brick patio overlooks a lush, manicured lawn. This property sits close to the popular Harbour Town as well as beaches, golf, and leisure trails.

21 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: ELEVE PROPERTIES Brokered by EXP Realty.

$4,200,000
4 Beds ⋅ 6 Baths ⋅ 4,469 SqFt. ⋅ HILTONHEAD-452346 MLS
On Calibogue Cay's tree lined road, the classic southern features of 38 beckon, with wraparound porches, double stair entry and deep eaves. Heritage live oaks and brick elements enhance the elegant façade. Water laps against the boat dock as sunlight dances on the tidal creek and private pool, tracing its east-west path over the property. Inside, custom lighting highlights warm European oak floors, complemented by bespoke cabinetry and millwork, elevating everyday existence into a luxury experience. This exceptional home offers 4 BD suites, 2 levels of indoor+out entertaining, 3 fireplaces, 3-stop elevator, 4+-car garage, ample storage.

38 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: William Raveis - Carolina LLC.

$4,250,000
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.

$3,315,000
4 Beds ⋅ 6 Baths ⋅ 3,718 SqFt. ⋅ HILTONHEAD-449981 MLS
Located on one of the most sought-after streets in Sea Pines, Calibogue Cay, this exceptional 4-bedroom + bunkroom 5.5-bath home sits on a rare 0.74-acre lot with 150 feet of marsh and creek frontage, offering unmatched privacy and breathtaking views. The open-concept interior is designed for endless entertaining featuring multiple living and dining spaces that blend elegance and comfort.  Framed by majestic live oaks, enjoy the spectacular setting of a covered porch, swimming pool, fire pit, and private dock with 16,000lb boat lift. Embrace the Lowcountry lifestyle, where fishing, boating, and forever marsh views are everyday occurrences!

8 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Keller Williams Realty.

$6,000,000
4 Beds ⋅ 7 Baths ⋅ 5,300 SqFt. ⋅ HILTONHEAD-448072 MLS
SEA PINES RESORT AWARD-WINNING HOME. EXPERIENCE DEEP WATER VIEWS AND BREATHTAKING SUNSETS FROM YOUR PRIVATE DOCK AND HOME OVERLOOKING CALIBOGUE SOUND. This home is nestled on .77 acres on one of the most sought-after streets in Sea Pines Resort. Built new in 2017 by Graves Construction with well-known architect, Neil Gordon, assisting in all aspects of design. Spacious floor plan w/soaring ceilings highlight the main living area w/large custom designed kitchen for entertaining. The 5300 s/f home boasts 4BR/5BA/2 Half BA/Office with option for 5th BR, 3 Fireplaces, Elevator, Generator and MORE! Expansive lawn to design your dream pool/spa.

63 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club. Selling Office: Collins Group Realty.

$6,500,000
5 Beds ⋅ 7 Baths ⋅ 5,775 SqFt. ⋅ HILTONHEAD-442910 MLS
Waterfront excellence on coveted Calibogue Cay! Serenity and breathtaking water views of Calibogue Sound align with architectural grandeur, infused with premium hardwoods, stone, elevated craftsmanship standards, incredible attention to detail, the finest of materials, Wolf appliances, elevator, impact glass, foam insulation, and (3) tankless water heaters. Professionally maintained (inside & out)! One of the most compelling, deep-water experiences you will find in all of Sea Pines! This exquisite home enjoyed an exhaustive and complete transformation in 2009, yielding a fully reimagined and curated style, layout, and appearance. Spectacular!

51 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Collins Group Realty. Selling Office: Charter One Realty.

$5,480,000
5 Beds ⋅ 7 Baths ⋅ 6,473 SqFt. ⋅ HILTONHEAD-441743 MLS
This spectacular 5-bedroom, 5.5-bathroom waterfront home offers unparalleled, deep water views of the Calibogue Sound, situated in the highly coveted location of Calibogue Cay within Sea Pines. Boasting 100 feet of private waterfront and built by Cambridge Builders in 2010, the home showcases exquisite craftsmanship and attention to detail, making it a premier choice for those seeking the epitome of luxury living.

11 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Keller Williams Realty.

$2,900,000
4 Beds ⋅ 4 Baths ⋅ 4,015 SqFt. ⋅ HILTONHEAD-441473 MLS
This classic residence, on a street of waterfront homes, reflects the sophisticated taste and warm family vibes of its owners. Curated is the best way to describe the spacious interiors, with high ceilings, traditional details and contemporary design. The functional interiors include 4 bedrooms, a screened porch with fireplace, sleek kitchen, formal living/dining rooms, a spacious gathering room, hidden office and wet bar, expansive outdoor living room & patio. The creative design of this home is the result of a total re-build in 2002. This home lives big, yet a cozy home for two as well as a flowing residence for family & guests.

40 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Collins Group Realty.

$7,900,000
4 Beds ⋅ 5 Baths ⋅ 6,243 SqFt. ⋅ HILTONHEAD-439249 MLS
This impeccable estate behind the gates of Sea Pines Resort is the apex of coastal luxury. Nestled on Hilton Head Island, a beautiful barrier island off South Carolina coast, you will be transcended to a world of serene beauty and ever-changing scenery. One-of-a-kind Calibogue lot, it spans over 1.2 acres just around the corner from Sea Pines’ famed Harbour Town. This magnificent, tailor-made residence boasts 6,240 elevated sqft of an architectural design that seamlessly combines practicality and grace. Take a seat by the water’s edge or enjoy the beauty in the pool/spa. This property must be seen on both land and sea to truly be appreciated.

69 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Dunes Real Estate. Selling Office: Sea Pines Real Estate - Beach Club.

$3,335,000
5 Beds ⋅ 5 Baths ⋅ 3,530 SqFt. ⋅ HILTONHEAD-438914 MLS
The epitome of waterfront luxury. A remarkable Sea Pines home, boasting a private dock, waterside pool, & a relaxing hot tub. With 5 spacious bedrooms and 4.5 bathrooms, this home provides ample space for your family & guests. Step into a brand-new gourmet chef's kitchen, equipped with state of the art stainless steel appliances, exquisite wood floors, granite countertops, and modern lighting fixtures. Home features 2 primary bedroom suites, offering breathtaking water views. Ranch-style home features a wide-open great room with a two-sided cozy fireplace, a perfect setting to savor the stunning sunsets and all that Sea Pines has to offer.

16 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Weichert Realtors Coastal Properties. Selling Office: Weichert Realtors Coastal Properties.

$5,300,000
HILTONHEAD-436658 MLS
Sweeping views across the Calibogue Sound define this once-in-a-lifetime homesite in Hilton Head Island's coveted Sea Pines community. Encompassing 1.76 acres, this estate lot is the only buildable land opportunity available on South Calibogue Cay Road, an enviable 11-home neighborhood quietly tucked away along the water. Lush foliage creates a cocoon of seclusion around the homesite, extending to the lot's private beach. Enjoy unobstructed sunsets over your future deepwater dock. Sea Pines has long been the gold standard for planned communities, offering world-class amenities in a pristine Lowcountry setting.

6 S Calibogue Cay Rd, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Hilton Head Properties.

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