315 listings, but only 250 max can be displayed.
Sort by
$3,400,000
5 Beds 6 Baths 4,566 SqFt. HILTONHEAD-450788 MLS
Experience the ultimate Lowcountry lifestyle at this stunning harbor-view retreat nestled in the Wexford community. Located on a private cul-de-sac, this 5-BR, 4 BA, 2 1/2 BA home offers an exquisite blend of luxury, comfort, and breathtaking waterfront living. The private heated pool, hot tub, outdoor fireplace, and built-in grill are perfect for year-round entertaining. A private dock provides direct access to Wexford’s exclusive harbor, making boating effortless. The spacious floor plan includes a bonus room, spacious kitchen, 2 fireplaces, 3-car garage + golf cart bay. Amenities include golf, tennis, pickleball, & private marina.

20 Castlebridge Court, Hilton Head Island

Listing courtesy of RE/MAX Island Realty. Selling Office: Daniel Ravenel Sotheby's International Realty.

$1,350,000
5 Beds 4 Baths 2,720 SqFt. HILTONHEAD-450365 MLS
Offered at $1,499,999, this stunning ocean-oriented home, built in 2019, sits less than 300 yards from the beach in the exclusive gated Sandcastle community. Designed for relaxation, rental performance, and effortless entertaining, it delivers an exceptional blend of luxury and coastal convenience. Featuring 5 bedrooms and 4 baths, the spacious open-concept layout provides plenty of room for family and guests. Multiple oversized decks and balconies showcase serene long lagoon views, while the private heated pool offers year-round enjoyment and strong rental appeal. A proven income producer, this home has generated over $100K annually for the past three years, even with heavy owner use, and already has $65K+ booked for 2025. Sold fully furnished and able to sleep up to 18, the property also includes a 4-stop elevator-a rare, high-value feature that enhances comfort and accessibility. Turn-key and rental-ready, this property is ideal as a high-performing investment, a luxurious vacation retreat, or both.

42 Sandcastle Court, Hilton Head Island

Listing courtesy of RE/MAX Island Realty. Selling Office: Real Broker, LLC.

$5,900,000
5 Beds 6 Baths 4,226 SqFt. HILTONHEAD-450403 MLS
Prime "Beach Lagoon" location, 2nd row in Sea Pines! BEAUTIFUL home, high-quality custom built in 2017, set on nearly 3/4 of an acre. Spacious & open floor plan. Tall, beamed ceilings, 4 beds/4.5 baths on the main floor & newly added bunkroom/bath/loft up. Flooded with natural light. Wonderful bedroom separation for comfortable living. Huge backyard entertaining area with pool & separate spa overlooking the Atlantic Dunes golf course. Close enough to hear the waves crashing but set back enough for blissful privacy. Quick & Easy beach access. Use as your primary home or as a luxury investment. $248K gross 2024 w/ $221K already booked for 2025

30 W Beach Lagoon Road, Hilton Head Island

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

$1,920,000
5 Beds 6 Baths 4,076 SqFt. HILTONHEAD-450278 MLS
This home has been remodeled and expanded on a double .77 acre lot surrounded on three sides by marsh & saltwater creek. Dock permit approved. All new glass dorrs & windows, except master with insulated Anderson doors. Large swimming pool overlooks marsh. Wood floors, wood plank & beamed ceilings, 3 fireplaces. Main house features 4 BR, 4 BA and an office. Bunk room added to guest room. Standing seam metal roof. Two 2-car garages with guest suite above (currently used as a gym). Beautifully landscaped with pierced brick walls, two pergolas, mature oaks. Stunning & unique contemporary beautifully contstructed & remodeled.

10 Wild Turkey Run, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - The Cottage Group, LLC. Selling Office: Sea Pines Real Estate - The Cottage Group, LLC.

$5,150,000
5 Beds 7 Baths 4,803 SqFt. HILTONHEAD-449020 MLS
Brand New Construction-3rd row in PD! Spectacular home, professionally furnished/decorated, boasts the finest details in construction. Expansive chef's kitchen w/Thermador appliances & 2 islands opens to coffered ceiling GR & screened porch with FP & ocean glimpse. Private office, 2 master suites & 3 guest BR's, all w/ensuite BA's. Upper den has wet bar & built-in daybeds. Private outdoor oasis w/large pool/spa, travertine deck, o/d kitchen, living area & pool BA. With a tankless hot water sys, 4-car garage, 3-stop elevator & sound sys throughout, this is the perfect island home or invest. prop. w/over $321K in proj. rentals. Owner is SCREA.

116 Mooring Buoy, Hilton Head Island

Listing courtesy of Alliance Group Realty/Howard Hanna Tate. Selling Office: Charter One Realty.

$2,995,000
5 Beds 6 Baths 3,860 SqFt. HILTONHEAD-448993 MLS
Location-Location Location! Experience Lowcountry living in this awesome 3rd-row ocean, 5 BR | 5.5 BA home in Palmetto Dunes on the beautiful, unique 11-mile lagoon system! Walkway to the beach across the street to 3 miles of newly nourished, award-winning beach. Southern charm curb appeal-beautiful columns, expansive verandas on front and back of the home, window shutters & brick accents. Offers idyllic outdoor enjoyment with a pool, a large deck, a lagoon dock, and a great covered entertainment deck for dining and lounging. Huge garage, 3- stop elevator. LVL 1: The dining room can easily convert to a 2nd private separate tv room/den/office/sleeping area, plus living room, eat-in kitchen table and bar area, powder room, laundry room, and Mstr BR #1. LVL 2: Mstr BR #2 and 3 BR | 3 BA. Huge basement area suitable for a game room. A short bike ride or walk to all the resort amenities in Palmetto Dunes. Stroll down to the Dunes House, Hilton Oceanfront and Omni Oceanfront Resort Hotel for lunch or dinner. Seasonal Dunes Buggy available throughout Palmetto Dunes and Shelter Cove area. Great location for rentals and personal usage!

155 Mooring Buoy, Hilton Head Island

Listing courtesy of Schembra Real Estate Group.

$3,000,000
5 Beds 5 Baths 3,500 SqFt. HILTONHEAD-448856 MLS
3rd row OCEAN home w/ private heated pool ON BEACH PATH to Island’s BEST beach! New renovation 2023 w/ winning floorplan showcasing 5BR/5BA. DUAL masters w/ sitting rooms & 3rd BR on main & 2 upper en-suite BR with study. Sunlit Greatroom has cathedral ceilings, fireplace and screened porch for family enjoyment. All areas open to wrap-around pool deck making it an entertainers dream. A rental favorite with $150k+ in proven rentals! This special Beach Bungalow is a smart investment for the 2025 rental season, a fabulous vacation home or your very own ocean oriented sanctuary! Location, location, location on Mariners side of exclusive Palmetto Dunes Resort offers summer buggy transportation to Shelter Cove restaurants, arts & shopping. Walking distance to best pickleball/tennis facility on the Island.

84 Mooring Buoy, Hilton Head Island

Listing courtesy of RE/MAX Island Realty. Selling Office: Sea Pines Real Estate - Beach Club.

$1,525,000
5 Beds 7 Baths 5,634 SqFt. HILTONHEAD-448823 MLS
Overlooking Long Cove’s 1st and 9th greens with sweeping views over water and fairways. Situated along one of the best Championship-style Golf Courses in all of Hilton Head... an unrivaled setting. Nestled at the end of a serene cul-de-sac, with ultra-convenient access to both the Sports Complex and Clubhouse. The home’s grandeur is apparent in its seamless fusion of size, design, and livability. Highlights include a spacious owner’s suite, luxurious (en-suite) bathrooms, soaring ceilings, custom millwork, Wolf appliances, formal & casual dining spaces, a screen porch, a Carolina (grilling) porch, a large garage, and elevated brick sun deck.

6 Otranto Court, Hilton Head Island

Listing courtesy of Collins Group Realty. Selling Office: Keller Williams Realty.

$1,650,000
5 Beds 5 Baths 2,666 SqFt. HILTONHEAD-448377 MLS
Charming Lowcountry style home featuring classic Charleston-style porch, paver driveway, 5 bedrooms, expansive fenced-in backyard, minutes to beach. Inviting bright kitchen features island, black stainless steel appliances, warming drawer, quartz countertops & shiplap. Open family room w/fireplace. Dining area overlooks spacious deck & huge fenced-in private backyard. Primary suite on 1st floor w/cozy sitting room, double vanity & large tub. Upstairs offers 4 bedrooms, 3 full baths & add'l living room. Loads of outdoor living space for entertaining & room for pool addition. Prime Sea Pines location, ideal primary/second home or rental home.

19 Tupelo Road, Hilton Head Island

Listing courtesy of Alliance Group Realty/Howard Hanna Tate. Selling Office: Greenplate Group Brokered by eXp Realty.

board logo

We do not attempt to independently verify the currency, completeness, accuracy or authenticity of the data contained herein. It may be subject to transcription and transmission errors. Accordingly, the data is provided on an “as is” “as available” basis only and may not reflect all real estate activity in the market. © 2026 REsides, Inc. All rights reserved. Certain information contained herein is derived from information, which is the licensed property of, and copyrighted by, REsides, Inc.