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63 N Calibogue Cay Road, Hilton Head Island
$6,000,000
CLOSED Status ⋅ 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.

18 Plumbridge Lane, Hilton Head Island
$3,250,000
CLOSED Status ⋅ 5 Beds ⋅ 6 Baths ⋅ 6,010 SqFt. ⋅ HILTONHEAD-448037 MLS
Experience luxury living at its finest in this breathtaking harborfront home in Wexford. Boasting over 6,000 sq ft of meticulously designed space, this estate features a resort-style raised pool and a private dock for waterfront enjoyment. The main floor offers a great room with direct pool access, perfect for entertaining, a chef's kitchen, formal living and dining rooms, and an expansive primary suite. Upstairs, you'll find four generously sized ensuite bedrooms. With ample storage and a 5+ car garage, this home is as practical as it is opulent. High-end finishes and smart home technology elevate every aspect of this remarkable residence.

18 Plumbridge Lane, Hilton Head Island

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

16 Castlebridge Court, Hilton Head Island
$3,800,000
CLOSED Status ⋅ 4 Beds ⋅ 8 Baths ⋅ 6,362 SqFt. ⋅ HILTONHEAD-447818 MLS
Introducing an impressively beautiful, 6,362 sq ft, Spanish modern design home in highly desirable Wexford w/ direct access to the harbour that blends comfort, contemporary style & tons of natural light. Features include 4 BR/4 Full BA /4 Half BA, state of the art kitchen, magnificent LR w/soaring ceilings & walls of windows overlooking the private 70’ dock & pool w outdoor kitchen, 2 lanais w/motorized screens, conservatory, wine cellar, library, media & workout room. Every detail is designed to provide an unparalleled living experience: 5 stop elevator, air purification system, heated floors, 2 laundry rooms, 3+ car garage & much more!

16 Castlebridge Court, Hilton Head Island

Listing courtesy of Weichert Realtors Coastal Properties. Selling Office: Charter One Realty.

206 N Sea Pines Drive, Hilton Head Island
$5,000,000
CLOSED Status ⋅ 7 Beds ⋅ 8 Baths ⋅ 8,560 SqFt. ⋅ HILTONHEAD-446822 MLS
This fully renovated 8,650 sqft estate on over 2 acres, just steps from the beach, is one of Hilton Head's finest. Ideal for gatherings, it features a chef’s kitchen with two islands, a large resurfaced pool, brand new and spacious pool deck, and a screened porch with fireplace. Enjoy a fantastic movie/entertainment room, a 4-car garage, an elevator, and two separate guest spaces. The primary suite features a sitting area, fireplace, and luxurious soaking tub. The private beach access is the cherry on top! This property is perfect for families or as a high-performing short-term rental. Don’t miss this rare opportunity in Sea Pines!

206 N Sea Pines Drive, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Sea Pines Real Estate - Beach Club.

1 Seaside Sparrow Road, Hilton Head Island
$3,900,000
CLOSED Status ⋅ 7 Beds ⋅ 7 Baths ⋅ 5,022 SqFt. ⋅ HILTONHEAD-446927 MLS
Welcome to this classic Sea Pines beach home located just 4 rows from the beach on a larger gorgeous lot with tranquil views over Sprunt Pond. Designed to be a great rental home or retreat for your large family. Recently dramatically updated kitchen, bathrooms, furnishings & many special touches. Light & bright w/ plenty of windows & beautiful flooring. Do not miss this 7 BR/7 ensuite BAs w/plenty of closet space, two large living areas inside & spacious pool area. Fenced yard that adds privacy and is pet/child friendly plus a screened-in porch. Located off South Beach Lane & close to south-end activities at the South Beach Marina.

1 Seaside Sparrow Road, Hilton Head Island

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

28 Oyster Shell Lane, Hilton Head Island
$5,000,000
CLOSED Status ⋅ 4 Beds ⋅ 6 Baths ⋅ 6,171 SqFt. ⋅ HILTONHEAD-446411 MLS
Timeless Nantucket Coastal design situated on a high bluff overlooking spectacular views of Port Royal Sound. Voted Best Overall & Best Exterior by HHI Home Builders Association, 1st floor features furniture grade Amish craftsman-built cabinetry; 9” oak wood floors; and custom milled clear poplar millwork. Kitchen w/ quartz counters, granite surface island, Subzero, Wolf 48” double oven range, and fully equipped back Kitchen. Spacious Primary Suite w/ His & Her Baths & double walk-in closets. 2nd floor features 3 ensuite Guest BR, Media/Family Room & Gym/Office. Exterior includes Pool & Spa, 4-season porch, and beautifully landscaped grounds.

28 Oyster Shell Lane, Hilton Head Island

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

52 Wicklow Drive, Hilton Head Island
$2,100,000
CLOSED Status ⋅ 4 Beds ⋅ 6 Baths ⋅ 6,311 SqFt. ⋅ HILTONHEAD-446264 MLS
No compromises at 52 Wicklow Drive! This custom home in Wexford is situated on an elegant cul-de-sac. Recent transformations include interior fresh paint throughout, epoxied garage floors, sanded and sealed wood floors and more! 4 bedrooms, 4 full 2 half baths, home office/optional 5th BR, living and dining rooms, open kitchen, upstairs sitting area, bonus/craft room and 3-stop elevator. Plus a drive-through 3400 sq ft 5 car garage and cart bay. Private pool, verandah and views of the 4th green. To build new, this home would cost a minimum of $3.8M. If you're looking for an incredible home, lifestyle and a great opportunity...look no further.

52 Wicklow Drive, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Blufft. Selling Office: Keller Williams Realty.

23 Bridgetown Road, Hilton Head Island
$2,775,000
CLOSED Status ⋅ 5 Beds ⋅ 6 Baths ⋅ 5,276 SqFt. ⋅ HILTONHEAD-445632 MLS
Experience unparalleled stately elegance in this Wexford harbor-front home. Perfect for entertaining, it features a great room, gourmet kitchen with custom cabinetry, top-of-the-line appliances, and a full wet bar. Enjoy master suites on both floors and ensuite guest bedrooms. Includes an elevated pool, private 65’ dock, drive-through 7+ car garage with ample storage, and an elevator. The Harbour provides access to Broad Creek and Intracoastal Waterway through a lock system. Enjoy Wexford’s Arnold Palmer Signature golf course, tennis, pickleball, croquet, walking trails, clubhouse with fine dining and a range of social activities and events.

23 Bridgetown Road, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Engel & Volkers.

36 Plumbridge Circle, Hilton Head Island
$3,200,000
CLOSED Status ⋅ 5 Beds ⋅ 9 Baths ⋅ 6,389 SqFt. ⋅ HILTONHEAD-445452 MLS
This Wexford waterfront retreat is a MUST-SEE to truly appreciate. Overlooking the harbor, the home has fresh interior/exterior paint, wool carpet, new lighting, new cabinet faces, water softener & filtration, new pool equipment, etc. The custom millwork is unmatched! 1st floor primary bedroom has his & hers closets, two showers, infinity jetted tub, two toilets, fireplace & screened porch off sitting area. 5 bedrooms, 6 full baths & 3 half baths. 8+car garage. Incredible outdoor living with a waterfall pool, raised hot tub, outdoor kitchen, multiple covered areas and your private 70' boat dock. OSCREA:Home is owned by real estate agent

36 Plumbridge Circle, Hilton Head Island

Listing courtesy of EXP Realty LLC. Selling Office: Weichert Realtors Coastal Properties.

95 S Port Royal Drive, Hilton Head Island
$3,900,000
CLOSED Status ⋅ 5 Beds ⋅ 6 Baths ⋅ 5,900 SqFt. ⋅ HILTONHEAD-444541 MLS
A rare find in the private Port Royal community on Hilton Head. Enjoy coastal living at its finest in this 2017 custom-built 2nd row home with partial ocean views & private beach access. A perfectly designed multi-generational home combining luxury & comfort. Enjoy seamless indoor & outdoor living with a game room, study, media room, & expansive screened lanai. The gourmet kitchen with high-end appliances & screened-in outdoor kitchen is perfect for the chef or entertainer. Beautifully landscaped grounds feature a private pool & spa. High ceilings, custom finishes, elevator, & designer fixtures enhance this unparalleled living experience.

95 S Port Royal Drive, Hilton Head Island

Listing courtesy of EXP Realty LLC. Selling Office: Daniel Ravenel Sotheby's International Realty.

3 Armada, Hilton Head Island
$3,600,000
CLOSED Status ⋅ 5 Beds ⋅ 7 Baths ⋅ 5,418 SqFt. ⋅ HILTONHEAD-444778 MLS
It's all about the beach.This outstanding 5-bed, 6.5-bath second-row Lowcountry home sits directly across from the beach walkway on Armada Street-just a short stroll to the sand and to the pathways leading to all resort amenities. Designed with a reverse floor plan, the home captures maximum sunlight and refreshing breezes from three miles of award-winning beach. Parking is easy, with both a front street-side driveway and rear parking with access to the garage and 3-stop elevator-perfect for unloading groceries.Level 1 offers entrance and guest-level access through handsome wooden doors, and up one flight of stairs to the oceanside, outdoor entertainment area with a private pool, outdoor kitchen, and dining space ideal for gatherings. Inside, this floor features a spacious family room with a cleverly hidden bunk bed behind a paneled wall, a pool bath, a bar area, a separate kitchenette with bar seating, a laundry room, and four guest bedrooms with full baths.A beautiful circular staircase leads to Level 2, the primary living level. Here you'll find a generous master ensuite with a steam shower, a powder room, an open dining area, and a large kitchen complete with an island, bar seating, and table seating. The family room includes a cozy fireplace, perfect for cooler evenings. Step outside to a substantial wraparound deck with multiple seating and dining area ideal for enjoying ocean breezes and year-round outdoor living.This home is a rare opportunity to own a beautifully designed beach retreat in an unbeatable location-your next unforgettable coastal retreat awaits.

3 Armada, Hilton Head Island

Listing courtesy of Schembra Real Estate Group. Selling Office: Schembra Real Estate Group.

83 Peninsula Drive, Hilton Head Island
$1,300,000
CLOSED Status ⋅ 5 Beds ⋅ 4 Baths ⋅ 5,055 SqFt. ⋅ HILTONHEAD-444376 MLS
Superb value on expansive lifestyle home with private pool/spa & 180+ degree tidal marsh views on the Peninsula in amenity rich Moss Creek. Features include extensive custom millwork & built-ins, granite counters, custom cabinetry, bamboo & LVP flooring, smooth ceilings, spray foam insulation, wine cellar, indoor/outdoor fireplaces, etc. Floor plan offers 6BR or 5BR + office, Island Kitchen open to FR, DR, Great Rm/Media rm with 7 seat bar, huge bonus suite, Flex & Carolina Rm, workshop & max storage space. All with 2 covered front porches, 2 rear decks, outdoor bar & grilling station, huge back yard, spectacular live oaks & circular drive.

83 Peninsula Drive, Hilton Head Island

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

26 Gull Point Road, Hilton Head Island
$3,300,000
CLOSED Status ⋅ 5 Beds ⋅ 7 Baths ⋅ 5,699 SqFt. ⋅ HILTONHEAD-444111 MLS
Nestled within the prestigious Gull Point community in Sea Pines, this exceptional 5BR home offers an extraordinary lifestyle amidst stunning marsh views, short distance to beach, and a boater’s dream with a slip at the Gull Point marina. Designed by Neil Gordon, every detail has been meticulously crafted to include exquisite trim work, soaring ceilings, a library, office, multiple living/dining areas, 1st floor owner suite, 4 guest ensuites, and amazing outdoor space with swimming pool & marsh views. Gull Point is a family friendly neighborhood with marina, tennis, playground,& kayak storage. Perfect property to create a lifetime of memories

26 Gull Point Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Peirce Group Brokered by EXP Realty LLC.

13 Angel Wing Drive, Hilton Head Island
$2,500,000
CLOSED Status ⋅ 5 Beds ⋅ 5 Baths ⋅ 6,169 SqFt. ⋅ HILTONHEAD-443608 MLS
Experience the epitome of Lowcountry living in this stunning 6100 sq ft estate located in Dolphin Head. 5 bed 5 bath family home offers expansive water views of Port Royal Sound. Direct access to bluff walking path & Dolphin Head Park. The grand foyer leads to a light-filled great room w/ floor to ceiling windows overlooking the private swimming pool and Intracoastal Waterway. The open kitchen features Brazilian marble countertops & connects seamlessly to the living & dining areas. Primary suites on both floors and an in-law suite over the three-car garage. The master offers direct pool access w/ water views, dual closets, & spacious bath.

13 Angel Wing Drive, Hilton Head Island

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

36 Wicklow Drive, Hilton Head Island
$1,800,000
CLOSED Status ⋅ 5 Beds ⋅ 6 Baths ⋅ 5,226 SqFt. ⋅ HILTONHEAD-444064 MLS
Hot Property Alert! Back on the Market due to Buyer Financing—Best Value in Wexford! A Second Chance to Make It Yours! This luxurious custom golf course home boasts a screened porch, heated pool, hot tub, and outdoor fireplace. Inside, a grand two-story foyer, Santos mahogany floors, and a cozy family room set the tone. The open gourmet kitchen features top-tier appliances, while the main-level primary suite and four additional ensuites—one with a kitchenette—offer flexibility. Climate-controlled 3-car garage. Built in 2006 by Randy Jeffcoat Builders. Exceptional craftsmanship and timeless elegance throughout.

36 Wicklow Drive, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Sea Pines Real Estate - The Cottage Group, LLC.

19 Burkes Beach Rd, Hilton Head Island
$1,800,000
CLOSED Status ⋅ 6 Beds ⋅ 8 Baths ⋅ 5,491 SqFt. ⋅ HILTONHEAD-443498 MLS
Just down the street from one of Hilton Head Island's best beaches, this Charleston style home is perfectly located and has strong rental income projections. Offering reclaimed wood floors, stained glass windows, 12' ceilings featuring crown molding, & a kitchen perfect for entertaining! Home boasts an oversized living space, theatre room, elevator & private, heated pool/spa perfect for you or guests to relax & enjoy the southern summers. Chaplin Park is across the street offering a dog park, tennis, basketball & playground. The wonderful beaches of HHI are so close you can smell the salt air! Gross rentals projected at $180,000-don't miss!

19 Burkes Beach Rd, Hilton Head Island

Listing courtesy of Century 21 Diamond Realty. Selling Office: The Hilton Head Agency.

40 Widewater Road, Hilton Head Island
$4,395,000
CLOSED Status ⋅ 6 Beds ⋅ 7 Baths ⋅ 5,702 SqFt. ⋅ HILTONHEAD-443645 MLS
Luxury, like new furnished waterfront home on Broad Creek-private dock, boat lift & deep-water access. Extensively renovated 2023 inside & out, 6 BR, 6.5 BA, primary suite on 1st floor. Brand new chef’s kitchen opens to breakfast area, separate bar & great room with high ceilings & fireplace, with views of the water. Formal dining room & living room w/fireplace. Primary suite offers his & her walk-in closets, brand new bathroom w/soaking tub, shower & double vanities. Outdoor living area-pool, covered cabana area, multiple fans, grill, fridge, ice maker & tv. Separate carriage house w/fridge, microwave, sink, W/D. 3.5 car garage. Smart Home!

40 Widewater Road, Hilton Head Island

Listing courtesy of Hilton Head Real Estate Partners. Selling Office: Keller Williams Realty.

20 Pelican Watch Way, Hilton Head Island
$2,850,000
CLOSED Status ⋅ 4 Beds ⋅ 4 Baths ⋅ 5,074 SqFt. ⋅ HILTONHEAD-443623 MLS
Embrace waterfront luxury in this unparalleled masterpiece, nestled on the most private waterfront lot on Hilton Head. Located on a 1.2-acre parcel, with 15 acres of town-owned land to the right offering unrivaled privacy. This newer-style 2005-built home boasts 4 bedrooms, with the primary suite on the 1st floor. This two-story residence is equipped with an elevator. Drive-through garage accommodates up to 8 cars, leaving no detail overlooked. Hardwood floors throughout the home and an expansive deck to savor the views. Flooded with natural light, the interior is inviting & bright. Acquire the lot next door for a complete 1.7-acre package.

20 Pelican Watch Way, Hilton Head Island

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

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