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$4,150,000
4 Beds 6 Baths 6,084 SqFt. HILTONHEAD-454296 MLS
A distinguished residence set on a rare estate-sized lot showcases exceptional craftsmanship. The home features impressive ceiling heights on both levels, complemented by transom windows and wide plank flooring. Striking impact windows frame majestic oak trees, providing elegant shade, with the lush greenery of Heron Point visible in the distance. The kitchen is designed for both form and function, enhanced by a butler's pantry for added convenience. 4 spacious bedroom suites, with multiple options for a fifth bedroom, ensure comfort for all. Conveniently close to Harbour Town, beaches, tennis, restaurants, shops, and the forest preserve.

5 Twin Pines Road, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: Sea Pines Real Estate - Beach Club.

$1,800,000
6 Beds 6 Baths 5,163 SqFt. HILTONHEAD-454293 MLS
Tucked away on a private, oversized lot in Shipyard, this classic Lowcountry home offers timeless charm and coastal comfort. Heart pine flooring adds warmth, while a wide wraparound porch welcomes you, and the screened-in rear porch and spacious deck invite outdoor living. Inside, large bedrooms, elevator access and ample living space provide flexibility and comfort. The garage apartment is ideal for guests. New roof installed in 2026! Surrounded by lush landscaping on a quiet street and just moments from the beach, golf, and bike trails, this well-maintained home is the perfect second home or short term rental property, in one of Hilton Head's most beloved communities.

4 Saint Johns Place, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Keller Williams Realty.

$7,050,000
6 Beds 9 Baths 7,789 SqFt. HILTONHEAD-453976 MLS
Unobstructed ocean views define this 1.16-acre Hilton Head Island estate cocooned in the privacy of a double lot. Designed for both quiet comfort and large-scale entertaining, noteworthy features include a temperature-controlled wine cellar for 1,000 bottles, an outdoor sports area with basketball, bocce, and shuffleboard, a beachfront putting green, a resort-style pool, and an outdoor kitchen. High ceilings and boundless windows allow for serene ocean vistas from the home's grand interiors, while coffered ceilings add to its timeless luxury. Complete with a temperature-controlled four-bay garage - this is the home for a true collector.

6 Overlook Pl, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Keller Williams Realty.

$5,050,000
5 Beds 7 Baths 5,560 SqFt. HILTONHEAD-453496 MLS
Live the ultimate Hilton Head lifestyle in this elegant lagoon-front estate, just minutes from the beach. Crafted for relaxed luxury, this home invites you to unwind, entertain, and savor every moment—whether dining al fresco, lounging by the pool or fireplaces, or enjoying tranquil water views from your screened living areas or private dock. Highest quality finishes and furnishings throughout offer coastal comfort with inviting spaces curated for connection and calm. Every detail, from the chef’s kitchen to the serene primary suite, enhances the experience of effortless island living. Offered fully furnished with designer touches throughout.

3 Port Tack, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: Alliance Group Realty/Howard Hanna Tate.

$2,600,000
7 Beds 7 Baths 6,180 SqFt. HILTONHEAD-453048 MLS
Castle by the Sea! Income-generating 7BR home with 6 ensuite baths, custom closets, and multiple living spaces in a solid concrete build. Includes a 8th non-conforming bedroom as an owner’s lockout. Fully remodeled with newer geothermal systems, fresh paint, updated kitchen and baths, furnishings, and a pool heater. 12 foot ceilings throughout, heated and cooled floors with wood inlays, custom cabinetry and huge playroom. Four garages for multiple vehicles. Southern-facing views of the 11-mile lagoon. Private beach access close by. Located in Palmetto Dunes—Hilton Head’s top resort with 3 golf courses, pickleball, marina, dining, and shops.

25 Starboard Tack, Hilton Head Island

Listing courtesy of Hilton Head Properties. Selling Office: Coldwell Banker Access Realty.

$6,000,000
5 Beds 7 Baths 9,287 SqFt. HILTONHEAD-452750 MLS
Stately, Sound front home with Ocean views. 199 ft of Waterfront. Water views from every room to include Ocean, Sound, Lagoon and #6 Oyster Reef Golf green. The home boasts man-made and natural elements that make it Dazzle. Designed for Cooking and Entertaining with large open concept spaces surrounded by glass. Well designed Chefs Kitchen to include Sub zero refrigerators, Wolf cooktop and Miele appliances. Formal living spaces include Cypress ceilings, Rosewood inlays, White Oak flooring, Teak inlays and 2-story Stone and Copper clad Fireplace. Expansive Resort style Pool with Spa, Wading area, new decking and Pool House. 4 Car Garage with quiet lift door mechanisms. Glass door Elevator, Wine Room, Den, Game & Theater rooms.

16 Oyster Shell Lane, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$7,300,000
5 Beds 7 Baths 5,386 SqFt. HILTONHEAD-452596 MLS
Own this architecturally custom-crafted 5BD/6.5BA, 1st row, oceanfront masterpiece in the world-class Sea Pines community on Hilton Head Island. Dramatic ocean views, substantial woodwork, custom beams, solid 8’ doors & skylights that bathe the space in natural light & beauty. Large gathering spaces including expansive great room, screened porch, multiple outdoor decks, study, oversized bdrms & massive bonus/rec room. Private walkway to beach + pool. Primary, vacation home, or a coveted short-term rental. The home is set back on a large lot w/ pines, live oaks & a natural landscape yet the ocean waves & sandy beach still take center stage.

36 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: Sea Pines Real Estate - Beach Club.

$10,995,000
7 Beds 9 Baths 6,200 SqFt. HILTONHEAD-452384 MLS
An oceanfront masterpiece designed for elevated coastal living and exceptional entertaining. The open great room - anchored by a coffered ceiling and fireplace-flows seamlessly into an expansive chef's kitchen with a generous center island and an ocean-view dining area. On the main level, the primary suite enjoys serene pool-to-ocean vistas, while a private study with sleeper sofa and adjacent full bath offers flexible accommodations. Upstairs, four guest suites capture sweeping ocean views, complemented by two bunk rooms-each with its own full bath-creating an ideal retreat for multi-generational gatherings. Outdoors, a resort-caliber setting awaits: a large private pool with heated spa and separate children's pool, plus an exclusive boardwalk leading directly to the beach. A covered patio with outdoor kitchen, spacious dining area, and TV lounge completes the experience-perfect from sunrise coffee to evening cocktails. Solar panels support efficient heating and cooling. Proven rental performance exceeds $500,000 in 2024 and 2025. For the discerning oceanfront buyer, this is a must-see.

15 Grey Widgeon Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach (505).

$6,750,000
6 Beds 8 Baths 7,037 SqFt. HILTONHEAD-452018 MLS
Absolutely stunning Spanish Wells deep waterfront estate situated perfectly on a 1.5 acre gorgeously landscaped property. Custom designed and exquisitely built for current owners inspired by their previous Richmond, VA home. 6 bedrooms & 6 baths plus 2 half baths, perfect in-law suite with full kitchen, majestic entry foyer with grand staircase, walnut paneled den/office, open & well-appointed kitchen to warm and inviting family room, first floor master suite all with amazing sunset views out to the dock on the Calibogue sound. Don't miss the incredible climate-controlled wine room, full home generator, elevator and so much more. Interior 7037SF + 1339 SF of additional covered space and a 550 SF Garage. One of the finest custom homes on Hilton Head!!

34 Brams Point Road, Hilton Head Island

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

$3,700,000
5 Beds 6 Baths 5,722 SqFt. HILTONHEAD-451501 MLS
This stunning home offers unparalleled, unobstructed views of the sound w/ the ocean in the backdrop & beautifully designed backyard. Spanning nearly 6,000 sq ft, this exceptional residence w/impressive curb appeal features 5 spacious ensuite BR, plus powder room. The 2nd floor office area has sweeping views of both the sound & backyard pool. Along with a brand-new designer kitchen the home offers the perfect space for entertaining & relaxation. Recent additions include a new whole home generator. Located in sought after amenity rich Hilton Head Plantation this property offers access to world-class golf facilities & picturesque nature trails.

14 Herring Gull Lane, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry. Selling Office: Howard Hanna Allen Tate Lowcountry.

$9,995,000
5 Beds 7 Baths 8,025 SqFt. HILTONHEAD-451687 MLS
Introducing a distinguished waterfront estate located within an ultra-private five-lot, gated deep-water enclave on Hilton Head. This exceptional offering is the only residence in the community comprised of two separate lots, conveyed together to create an unparalleled opportunity for privacy and long-term flexibility. The primary residence is positioned on 1.2 acres, complemented by an additional 0.58-acre parcel. The secondary lot allows for the construction of a second luxury residence for multi-generational living or guest accommodations, or the creation of a private amenity setting featuring tennis/pickleball courts, a chipping/putting green or boat storage. The home was custom built by H2 Builders, with architectural design by Woods Dendy Architects and interiors curated by J. Banks Design, resulting in a residence of exceptional craftsmanship and architectural integrity. Reclaimed wood beams, bespoke millwork, refined stone and wood finishes, and hurricane-grade windows and doors define the home's elevated aesthetic. Interior amenities include a chef's kitchen, a 600+ bottle climate-controlled wine cellar, theater, golf simulator, fitness studio, garden, and a 7.5-car garage providing exceptional storage and flexibility. The residence is equipped with whole-home Control4 automation, seamlessly integrating lighting, climate, audio, security, and entertainment systems. Outdoor living is anchored by a resort-style environment featuring an infinity-edge pool heated and cooled for year-round enjoyment, outdoor kitchen, fireplace, and multiple gathering areas designed for entertaining. A private deep-water dock with boat lift provides effortless access to Broad Creek, allowing owners to boat locally to areas like Harbour Town and Palmetto Bluff or up and down the intercoastal. This legacy waterfront estate is located moments from premier private golf and tennis clubs - allowing you to fully enjoy the lowcountry lifestyle.

90 Tidewater Manor, Hilton Head Island

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

$3,499,000
9 Beds 11 Baths 5,300 SqFt. HILTONHEAD-448624 MLS
Brand New Home Just Completed! 5,300 heated sq. ft. 9 BR's 10 1/2 baths. Private Infinity Edge Pool. Amazing ocean and marsh views from this ideal location. Finest finishes, details, trim, fixtures, appliances. Parking garage for 6+ cars, plus 4 on the driveway. Elevator. Penthouse gathering room with beamed ceilings, kitchen open to huge dining area and great room. Best views in the home are on this level, with a large covered porch to admire the sunshine, breathe in the salt air, gaze over the marsh and ocean, listen to the shore birds calling and celebrating another gift of a day! Brand new homes all around, resort style atmosphere. Just a short distance to the beach. Additionally, the open space to the side and rear of this home create a uniquely open feeling! New on the rental market, already a favorite, expected to generate significant income.

13 Bradley Circle, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$2,999,000
5 Beds 5 Baths 5,080 SqFt. HILTONHEAD-451467 MLS
A modern masterpiece in Leamington, this brand-new 2024 home offers luxury living just a short golf cart ride to the private beach club. Overlooking the Arthur Hills Golf Course and lagoon, it blends sleek design with functionality, featuring a floating stair system, custom lighting, and a gourmet kitchen. Double wraparound balconies capture the breathtaking views. The outdoor oasis boasts a heated/cooled pool with a sun ledge, marble pavers, multiple fire features, a grilling station, and a lounge/bar area. With 10,000 sq ft under roof, ample parking, an elevator, and hurricane-grade windows/doors, this stunning retreat has it all.

50 Leamington Lane, Hilton Head Island

Listing courtesy of Maxey Blackstream Christie's International Real Estate. Selling Office: Premier Properties of Hilton Head Island.

$1,825,000
5 Beds 5 Baths 5,047 SqFt. HILTONHEAD-451783 MLS
Investor Alert! Palmetto Dunes retreat generated $172,000 in short-term rental income in 2024! Designed for entertaining & relaxation, this home sits on a large corner lot with golf course views & features heated pool, firepit, patio & multiple outdoor spaces. Inside, the freshly painted open floor plan offers seamless flow, with primary suites on both levels, a game room & a well-appointed kitchen.Thoughtfully designed for comfort & convenience, this home is moments from world-class beaches, championship golf, and premier dining. Whether you're seeking a high-performing investment or a private coastal retreat, this turnkey opportunity is it!

2 High Water, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Century 21 Diamond Realty.

$6,125,000
4 Beds 6 Baths 7,183 SqFt. HILTONHEAD-451285 MLS
There is nothing quite like this home on Hilton Head Island. This modern architectural masterpiece offers unparalleled waterfront living w/ breathtaking dual water views of Broad Creek to the East and the shimmering Calibogue Sound to the West. Inside, 4 spacious ensuite bedrooms, custom Italian glass doors & a German-made gourmet kitchen elevate the art of living. Enjoy the Living Room w/ soaring 21-foot ceilings & natural light throughout. Step outside to discover a private oasis: a negative-edge upper pool cascades into 75' lap pool, a generously sized covered deck w/ space for future outdoor kitchen & separate 600 sqft Studio/Pool House.

73 Brams Point Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - The Cottage Group, LLC. Selling Office: Premier Properties of Hilton Head Island.

$4,750,000
6 Beds 8 Baths 6,741 SqFt. HILTONHEAD-451281 MLS
The ultimate home, perfect for entertaining! Spacious 2nd-row, 6 BR | 6 BA | 2 HB home on Armada in Palmetto Dunes just steps from 3 miles of award-winning beach. Freshly painted with coastal-chic décor, this home has a spectacular 1st floor featuring a chef's eat-in kitchen, dining room, living room, wet bar off the leisure room, powder room & sunroom. Offers a 3-stop elevator & three primary suites on the 2nd-floor. Outdoor entertainment area offers an idyllic wooded view, a covered lounging & dining area with a wet bar and grill, & a large pool with a spa. Ample parking with a large driveway & garage. Guests and owners have access to all the amenities in Palmetto Dunes: golf, tennis, pickleball, an 11-mile lagoon, golf at the Arthur Hills Golf Course in Leamington, and much more. Short walk or bike ride to the heart of Palmetto Dunes. Seasonal Dunes Buggy is available throughout Palmetto Dunes and the Shelter Cove area. Short walk or bike ride to resort amenities!

9 Armada Street, Hilton Head Island

Listing courtesy of Schembra Real Estate Group.

$15,000,000
6 Beds 9 Baths 7,000 SqFt. HILTONHEAD-450301 MLS
The most sensational & remarkable home is under construction! Brand New masterpiece in World-Class Sea Pines Resort. Magnificent Oceanfront parcel, in the sought after South Beach Area. Finest finishes, trim, accessories, appliances, cabinets, flooring & fixtures. In addition to 6 ensuite bedrooms (3 master suites) there's an office, a sitting/wine tasting room, Butler's Pantry, huge 2nd floor recreation room w/wetbar opens up to a sprawling upper deck. Amazing pool, spa & outdoor areas. Main floor Master Suite suitable for Royalty; steam shower, free standing tub, double entry curb-less shower. Under parking for up to 8 vehicles. Elevator. Please see the extensive description in documents.

9 Brown Pelican Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$6,350,000
5 Beds 7 Baths 6,346 SqFt. HILTONHEAD-450493 MLS
This rare oceanfront opportunity sits in one of Hilton Head’s premier gated communities, offering direct access to the island’s finest beaches. Surrounded by pristine dunes and open space, the home features a private path leading directly to the sand. Designed with exquisite woodwork and fine craftsmanship, the home’s expansive interior has been lightly used as a secondary residence, ensuring exceptional condition. Enjoy breathtaking ocean views and stunning sunrises, embracing a coastal lifestyle. This property provides an unparalleled opportunity to own a refined oceanfront escape in one of Hilton Head’s most exclusive enclaves.

28 Planters Row, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Maxey Blackstream Christie's International Real Estate.

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