Refine Search
Sort by
$5,499,800
5 Beds 5 Baths 4,563 SqFt. HILTONHEAD-508634 MLS
Designed for those who love to entertain with purpose and elegance, this custom-built seaside home on a rare 0.77-acre lot offers an unmatched relaxed lifestyle both inside and out. Purposely designed by philanthropic owners, the home's open layout including dual sided fireplace effortlessly accommodates private gatherings and charitable galas for 50+ seated guests-flowing smoothly from indoor living spaces to the expansive, light-filled rear veranda. At the heart of the home, a chef's kitchen features a custom wenge wood-top island flanked by durable finished upper tier cabinetry and a massive butler's pantry built to handle full-service catering or intimate family dinners with equal ease. The outdoor sanctuary continues the theme of year-round hospitality, featuring a screened porch with a cozy fireplace, a custom boardwalk, and a climate-controlled heated and chilled pool for seasonal comfort. Two primary ensuites-conveniently situated on both the main and second levels-provide ultimate privacy and flexibility for hosting overnight guests or multi-generational family living. From grand philanthropic events beneath the veranda to quiet mornings on the shoreline, this home embodies the very best of Port Royal coastal living. Click the video link to view interior and drone exterior footage.

3 Wagener Place, Hilton Head Island

Listing courtesy of Charter One Realty.

$605,000
1 Beds 1 Baths 756 SqFt. HILTONHEAD-508317 MLS
This beautiful villa is not only just steps from the beach, but also offers stunning views of Braddock Cove and the charming South Beach Marina. Imagine beginning and ending your day with the sliders open, enjoying a warm sea breeze as boats glide into the marina and egrets and herons wander along the marsh. Located on the top floor, this villa was completely renovated in 2019 with no detail overlooked. The redesigned kitchen features stainless steel appliances, quartz countertops, and custom cabinetry. Additional upgrades include smooth ceilings with crown molding and baseboards, luxury vinyl flooring, updated lighting and ceiling fans, and all-new plumbing fixtures. Major systems have also been replaced, including the HVAC, water heater, and washer and dryer. The home is further enhanced by impact-resistant patio doors, new interior doors, and updated furnishings and décor throughout. Enjoy all the amenities South Beach has to offer right outside your door, including shopping, dining, tennis, pickleball, and a variety of water activities. Never rented and only lightly used by the owners, this villa has been lovingly maintained as their perfect beach getaway.

8 Braddock Bluff Drive Unit 1813, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$745,900
2 Beds 3 Baths 1,647 SqFt. HILTONHEAD-508214 MLS
This beautifully updated 2-bedroom, 2.5-bath Harbourside II villa on the 4th floor puts you at the heart of Shelter Cove Marina. A unique additional window frames stunning marina views from your living room, while the expansive balcony delivers the premier vantage point for Shelter Cove's beloved fireworks and live concert series. Both bedrooms feature en suite baths; a half bath serves the main living area. Interior updates include smooth ceilings, crown moulding and baseboards, an additional bar area, freshly painted, new furnishings, and more! With shops, restaurants, and waterfront walking paths steps away, this villa offers the Lowcountry waterfront lifestyle in one of Hilton Head Island's most sought-after communities.

13 Harbourside Lane Unit 7164, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

$8,700,000
5 Beds 6 Baths 5,580 SqFt. HILTONHEAD-508090 MLS
Quite simply, one of the finest homes to come on the market in Sea Pines in many years. This luxury custom home, completed in 2022 by Esposito Builders and masterfully designed by architect Terry Rosser, is set along the highly coveted Calibogue Cay, an address reserved for a select few. Sweeping marsh vistas and extraordinary sunsets create a setting that is both serene and unforgettable. Dramatic 20+ ft ceilings span the living room, kitchen, and breakfast nook, filling the space with natural light and drawing your eye straight to the marsh beyond. The kitchen is beautifully executed and opens to a refined entertaining space with a wet bar, glass-front cabinetry, and a well-appointed butler's pantry. Just off the main living area, the screened porch with fireplace offers a comfortable, private retreat you will enjoy year round. The outdoor setting is equally impressive. A generous saltwater pool, private dock, and boat lift are perfectly positioned to capture long marsh views and remarkable sunsets. The primary suite is a true retreat, with expansive his-and-her walk-in closets, separate vanities, and a convenient Primary Laundry Room. Five bedrooms, along with a private executive office overlooking the marsh and sound, provide both scale and flexibility. Additional features include a 3-stop elevator, whole-house generator, and an oversized 2+ car garage with climate-controlled storage. Opportunities like this are few and far between. This is Calibogue Cay at its absolute best.

59 N Calibogue Cay Road, Hilton Head Island

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

$2,165,000
5 Beds 5 Baths 3,738 SqFt. HILTONHEAD-507876 MLS
Experience elevated harbor front living in one of Hilton Head Island's most exclusive gated waterfront communities. Perfectly positioned in Windmill Harbour, 58 Sparwheel Lane offers sweeping marina views, timeless architecture, and an extensively renovated home designed for effortless coastal living. Reimagined in 2017, this exceptional residence showcases custom craftsmanship, refined interior design, and high-end finishes throughout, blending classic elegance with modern comfort. (Architectural Plans showing before and after floor plans and elevation changes and scope of work are in the MLS Docs folder). Expansive lanais overlook a picturesque backdrop of sailboats and yachts, creating an ever-changing waterfront setting for morning coffee, sunset cocktails, or entertaining family and friends. The luxurious primary suite features a private lanai and fireplace, while four ensuite guest bedrooms provide exceptional comfort and privacy. A chef's kitchen, inviting living room with fireplace, lower-level family room, two laundry areas, and a 2-car garage offer the functionality today's buyers desire. Furniture is negotiable. The Seller owns and will sell Dock I-36, a 48' slip visible from the Townhouse. Boating enthusiasts will appreciate Windmill Harbour's renowned lock-controlled marina, one of only three private lock systems on the East Coast, providing protected deep-water access to the Intracoastal Waterway regardless of the tides. Residents also enjoy a community pool, and optional membership to the South Carolina Yacht Club with dining, tennis, pickleball, fitness, and social amenities. Whether you're searching for a luxury primary residence or an exceptional second home, this is a rare opportunity to own one of Windmill Harbour's premier marina front properties.

58 Sparwheel Lane, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$1,055,000
1 Beds 2 Baths 816 SqFt. HILTONHEAD-507877 MLS
Searching for a truly private Sea Pines retreat with unmatched views just steps from Harbour Town? 2065 Deer Island Road offers a rare end-of-the-road setting in the coveted Sea Pines Resort, delivering breathtaking views of the marsh and out to the Calibogue Sound. Tucked away at the end of a quiet road, this unique home is surrounded by nature, where walls of windows flood the home with natural light and frame stunning water and wildlife views from every angle. Thoughtfully updated with luxurious finishes, the home features high-end appliances including a Sub-Zero refrigerator, JennAir range, and Bosch dishwasher and microwave, along with quartz countertops and an open-concept living space designed for relaxed coastal living. Heart pine floors upstairs and bamboo flooring on the lower level add warmth and character, while multiple decks provide the perfect setting to take in unforgettable sunsets over the water. The upstairs level of all Deer Island properties are similar and can be re-configured to accommodate various bedroom and bathroom layouts. This flexible layout lives beautifully as a second home or income-producing rental, offering a peaceful, private escape just a short walk or bike ride to the Harbour Town Lighthouse, the Quarterdeck Restaurant, and the shops, dining, and amenities of Harbour Town. A rare opportunity to own one of the most scenic and private homes in Sea Pines.

2065 Deer Island Road, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$414,000
2 Beds 2 Baths 917 SqFt. HILTONHEAD-507802 MLS
Experience coastal living at its finest in 2-bedroom, 2-bathroom villa offering breathtaking sound views and tranquil lagoon views. Whether you're seeking a primary residence, a second home, or a rental investment, this property delivers the perfect blend of comfort and resort level amenities. Step inside to find a bright, open layout enhanced by white cabinetry, granite countertops, tile flooring and engineered wood flooring. The kitchen flows seamlessly into the main living area, creating an inviting space for relaxing or entertaining. The amazing standout feature of this villa is the enclosed all year-round balcony, offering additional living space with stunning water views. Enjoy morning coffee overlooking the lagoon, unwind with evening sunsets looking at the sound, or simply relax in your private balcony no matter what the season. Both bedrooms are nicely sized, making the villa comfortable for owners and guests alike. The layout provides privacy while still maintaining an easy flow throughout space. This community is packed with amenities designed to elevate your lifestyle. Residents and guests can enjoy access to two outdoor pools, an indoor pool, tennis courts, a basketball court, playground, fitness room, hot tub, sauna, and multiple grilling areas perfect for gatherings with friends and family. Whether you prefer active recreation or peaceful relaxation, there's something here for everyone. With its unbeatable combination of water views and resort style amenities, this villa stands out as a rare opportunity on Hilton Head Island. Its flexibility makes it ideal for full time living, a vacation getaway, or a rental property. Don't miss your chance to own a piece of island paradise, this one checks all the boxes.

239 Beach City Road Unit 1215, Hilton Head Island

Listing courtesy of Hilton Head Isl Realty.

$3,295,000
5 Beds 6 Baths 5,200 SqFt. HILTONHEAD-507766 MLS
This exceptional NEW CONSTRUCTION end-unit semi-detached residence offers an unparalleled blend of luxury, space, and breathtaking panoramic marina views stretching out to the Intracoastal Waterway. Boasting 5 bedrooms, 5.5 baths, and over 5,200 heated square feet, this home is thoughtfully designed for both refined living and effortless entertaining. Inside, the main living areas are anchored by stunning 7-inch white oak flooring, creating a warm and sophisticated backdrop. A beautifully appointed interior fireplace enhances the inviting atmosphere, while expansive windows frame serene waterfront vistas. The chef's kitchen is a true showpiece, featuring custom inset cabinetry with fully integrated paneled appliances, sleek stainless appliances, and meticulous craftsmanship throughout. Adjacent, a well-equipped wet bar and scullery with a striking wine tower provide both functionality and elegance for hosting. A dedicated office offers a quiet retreat for work or study, while the home's four-stop elevator ensures seamless access to every level. The primary suite is a private sanctuary, highlighted by a spa-inspired bathroom featuring a luxurious wet room clad in floor-to-ceiling Italian marble. Every bathroom in the home showcases Italian marble flooring, reinforcing the property's elevated design. The expansive bonus room is ideal for entertaining, complete with its own wet bar and beverage center, making it perfect for gatherings or relaxed evenings at home. Outdoor living is equally impressive, with three spacious marble-floored patios that overlook the marina and provide sweeping views out to the ICW-perfect for enjoying coastal breezes and unforgettable sunsets. An additional exterior fireplace creates a cozy ambiance for year-round enjoyment. Located within the prestigious Windmill Harbor community, residents enjoy access to a 15.5-acre lock-controlled marina with immediate Intracoastal Waterway access. Amenities include an Olympic-size pool, tennis courts, a fitness center, and proximity to the South Carolina Yacht Club, offering a truly elevated coastal lifestyle. This remarkable property seamlessly combines timeless design, modern luxury, and an unbeatable waterfront setting.

54 Sparwheel Lane, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$2,945,000
5 Beds 7 Baths 6,384 SqFt. HILTONHEAD-507058 MLS
Four levels of harbour living distinguish this substantial Windmill Harbour residence, offering 6,384 sq. ft., elevator access throughout, protected harbour and Intracoastal views, and exceptional flexibility for boating, guests, work and recreation. The ground level is designed as a private Harbour Club, with an oversized tandem 2-car garage plus separate 1-car garage, leisure room with wet bar, utility room, guest suite with ensuite bath, covered patio and direct access to the waterfront setting. Additional conditioned rooms may serve as fitness, studio, workshop, storage or guest spaces. Conceptual renderings are in pictures. The main living level is centered around a chef's kitchen and includes a formal dining room, parlor, office, great room, half bath, rich wood flooring, extensive millwork and a broad balcony overlooking the harbour. One level above, the expansive owner's suite features two walk-in closets, a private bath and balcony access, accompanied by three additional ensuite bedrooms, a laundry room, secondary kitchenette and another generous harbour-facing balcony. The top floor creates an additional entertainment destination with a large family or media room, two flexible rooms, a shared bath and elevator access- well suited for a private theatre, game lounge, office or extended-stay accommodations. Windmill Harbour is one of Hilton Head Island's most distinctive private communities, built around a protected inland harbour and lock-controlled marina with direct access to the Intracoastal Waterway. The South Carolina Yacht Club offers dining, fitness, swimming, tennis, pickleball, yachting events and an active social calendar. Rarely does a home combine this scale, guest capacity, storage, garage space and harbour lifestyle in one residence.

144 Harbour Passage, Hilton Head Island

Listing courtesy of Coldwell Banker Access Realty.

$2,250,000
3 Beds 4 Baths 3,589 SqFt. HILTONHEAD-507275 MLS
Harbourfront elegance in Windmill Harbour. Positioned on two lots in one of Hilton Head Island's most exclusive private communities, 1 Sailwing Lane is a residence of uncommon quality, privacy, and architectural distinction. Designed with true flair, the home captures the beauty of its harbourfront setting while offering a warm, sophisticated interior made for both everyday living and gracious entertaining.The gourmet kitchen anchors the home with style and function, while the primary suite is a retreat of its own-complete with a fireplace and a spa-inspired bath featuring a large soaking tub. An open den/loft adds flexibility and character, and every space reflects the craftsmanship and thoughtful design found throughout the home. Outside, the setting is just as impressive, with beautifully kept grounds, and the rare advantage of a 45-foot boat slip that conveys with the sale-making this an exceptional opportunity for boating enthusiasts and those seeking the full Windmill Harbour lifestyle. A truly special harbourfront offering in one of Hilton Head Island's most coveted private communities.

1 Sailwing Lane, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$1,739,000
6 Beds 6 Baths 3,662 SqFt. HILTONHEAD-506891 MLS
Welcome to this exceptional coastal retreat in the private, gated community of Fish Haul on Hilton Head Island. Built in 2020, this stunning 6-bedroom, 5 full and 1 half bath home offers the perfect blend of luxury, comfort, and investment potential. Ideally located just moments from Fish Haul Beach, the property features beautiful Port Royal Sound views and is designed to accommodate large gatherings with ease. The spacious, thoughtfully designed layout includes expansive living areas, multiple porches and decks, and seamless indoor-outdoor living throughout. The chef's kitchen is equipped with high-end appliances, ample storage, and an open flow ideal for entertaining. The inviting living room provides the perfect setting for relaxing evenings, while the adjoining outdoor spaces offer plenty of seating and a grill for hosting. Step outside to your private backyard oasis featuring a heated saltwater pool, putting green, and lush landscaping. Multiple porches-some with charming swings-create peaceful spots to unwind and enjoy the coastal breeze. With upscale finishes, strong rental potential, and the ability to comfortably sleep large groups, this home is an outstanding investment opportunity or personal getaway. A rare offering in one of Hilton Head's most serene and sought-after neighborhoods. Strong Short Term rental numbers for 2026: over $160,000!! Fast walk to the beach with a brand-new board walk, grab your beach chair and be there in 3 minutes!

2 Talon Court, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$325,000
HILTONHEAD-506978 MLS
Perfectly positioned across from the iconic 18th green of Harbour Town Golf Links-host course of the prestigious RBC Heritage-this exceptional offering places you at the center of one of the Lowcountry's most celebrated destinations.Enjoy access to an unmatched array of amenities, including membership to the Harbour Town Yacht Club, featuring elegant lodging, waterfront dining, conference facilities, concierge services, and a newly enhanced veranda lounge with sweeping harbor views. Just a short stroll away, you'll find the Harbour Town Golf Clubhouse, pool, and the renowned Smith Stearns Tennis Academy.The vibrant Harbour Town area offers something for everyone, from live concerts and a waterfront playground to boutique shopping and an array of restaurants. Set along a well-protected harbor on the Intracoastal Waterway and Calibogue Sound, this location is ideal for boating enthusiasts-and with the ability for owners to rent their slips, it also presents an excellent income opportunity.

81 Harbour Town Yacht Basin, Hilton Head Island

Listing courtesy of ERA Wilder Realty, Inc.

$360,000
2 Beds 2 Baths 917 SqFt. HILTONHEAD-505734 MLS
Discover one of the best values on Hilton Head Island at The Spa on Port Royal Sound. This beautifully updated top floor 2-bedroom, 2-bath villa offers sweeping ocean views and comes fully furnished, making it a true turnkey short-term rental or effortless coastal retreat. Inside, you'll find stylish LVP flooring throughout, stainless steel appliances, and an inviting coffee bar. Relax on the screened-in porch with expansive ocean and pool views, along with resort-style amenities including an onsite fitness center, tennis courts, and indoor and outdoor pools, all just steps from the beach. With a proven short-term rental history, this move-in-ready villa is an exceptional opportunity for investors, second-home buyers, or anyone seeking the ultimate island getaway.

239 Beach City Road Unit 1317, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$984,900
2 Beds 2 Baths 1,240 SqFt. HILTONHEAD-504832 MLS
Experience elevated coastal living with panoramic marina views - all from the top floor overlooking the beautiful Shelter Cove Harbour & Marina. This beautifully renovated residence captures sweeping views and unforgettable sunsets. As a penthouse, you will enjoy added privacy, elevated ceilings, and an abundance of natural light. No detail has been overlooked in this renovation. Modern finishes, updated flooring, a redesigned kitchen with contemporary cabinetry, and premium countertops - all complement the relaxed coastal setting. The bathrooms have been stylishly remodeled with Carrara tile, creating a spa-like retreat. The open concept living flows seamlessly to a private balcony overlooking the marina - ideal for morning coffee, evening cocktails, and front row views of Shelter Cove's year-round activity.

7 Shelter Cove Lane Unit 7556, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$990,000
2 Beds 3 Baths 1,890 SqFt. HILTONHEAD-504820 MLS
Shelter Cove Harbour community's most deluxe residence -- spacious & bright 2BR/2.5BA Main Sail Villa overlooking Shelter Cove Harbour & deepwater Broad Creek. Rarely listed Main Sail is Shelter Cove's newest & most well-appointed waterfront property with private gate access, outside & under-building parking along with convenient private storage room. Beautifully updated villa with quality Travertine tile throughout, smart Ethan Allen furniture package, large mounted Smart televisions in living room & each bedroom, ensuite bathrooms with walk-in closets, custom showers, electric commodes, & soaker tub. Excellent bedroom separation with open floorplan, lots of sunlight, large windows and sliders leading to screened balcony overlooking the harbour and 2nd balcony with casual pool/spa view. 2022 improvements include redesigned custom closets, new furnishings, new washer/dryer, plus new range with induction cooktop. Stroll to the harbour & marina to enjoy shops, restaurants, and the sunset over the Broad Creek. You'll enjoy the sense of privacy and elegance at Main Sail each time you enter the gate!

9 Shelter Cove Lane Unit 106, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$285,000
HILTONHEAD-502032 MLS
What an opportunity to build your perfect townhome in the exclusive enclave of Windmill Harbour! With views overlooking a marsh toward the intercoastal, your build can include all the features you have ever wanted in a home with none of the hassle and inconvenience of remodeling. You would immediately become a member of the Windmill Harbour community and have access to the community pool, community dock, dog park, and walking paths. There is no required time to build! This lot is situated on the quiet end of Harbour Passage, close to the lock and marina dock/office. You may choose to become a member of the South Carolina Yacht Club and enhance your Windmill Harbour lifestyle with access to the Sports Center Pool, Gym, Tennis and Pickleball Facilities, Sailing Fleet and beautiful club house and restaurant. SCYC special events abound and you will quickly find yourself a member of a thriving and exciting coastal coterie. A 2025 Survey and Geo-technical Evaluation was performed and is available to prospective buyers so you can head right to your architect and builder to get started. This could be your chance to begin your dream and at a fantastic price to boot!

141 Harbour Passage, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

$4,750,000
4 Beds 5 Baths 2,216 SqFt. HILTONHEAD-500657 MLS
Incredible development opportunity on Hilton Head Island with the potential for 8 UNITS AN ACRE, featuring marsh and sound views with a designated beach walk easement. Four combined parcels span over four acres, offering rare potential for a private estate, multi-home enclave or workforce housing. The property adjoins historic Mitchellville Freedom Park, providing a unique setting rich in natural beauty and heritage. A gracious 2200 SF home with additional SF in separate barn and apartment (6000+ total finished SF on the property) already on-site can serve as a primary residence, creating a sprawling private compound, or function as a clubhouse for future residences. Whether envisioned as a legacy property or an investment in a premier coastal destination, this offering presents unmatched possibilities in one of Hilton Heads most desirable locations.

170 Dillon Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$1,299,000
3 Beds 2 Baths 1,400 SqFt. HILTONHEAD-500129 MLS
This highly sought-after Cutter Court Penthouse in the heart of Sea Pines, with its jaw-dropping direct views of the iconic Harbour Town Lighthouse, world-famous Harbour Town Marina, and the shimmering Calibogue Sound, is fully furnished and move-in ready. These penthouses rarely hit the market and sell quickly. This 3BR/2BA retreat has been completely updated and offers the perfect blend of style, comfort, and convenience, along with a strong short-term rental history. The spacious open layout includes a modern kitchen with granite countertops, stainless steel appliances, a dinette, and a bright living area. Relax and take in unforgettable sunsets from the main balcony, showcasing postcard-perfect views of the Lighthouse, Yacht Basin, and Calibogue Sound. The king master suite boasts its own private balcony, while two additional queen bedrooms offer comfort for family or guests. The two bathrooms each feature a walk-in shower, and the many windows throughout the Penthouse provide awesome views and abundant natural light. Its prime location puts you just steps from the Harbour Town Golf Links & Clubhouse, the Sea Pines Racquet Club, waterfront dining at the Quarterdeck and other popular restaurants, as well as charming shops, boutiques, art galleries, and the iconic Lighthouse itself. Enjoy world-class golfing in Sea Pines at the the three championship courses: Harbour Town Golf Links, Heron Point by Pete Dye and Atlantic Dunes by Davis Love III. Additional amenities include tennis and pickleball, Lawton Stables, Sea Pines Forest Preserve, Sea Pines Beach Club with private beach access, South Beach Marina, miles of bike trails, Sea Pines Center, and the free seasonal trolley service. Harbour Town is the vibrant heart of Hilton Head Island, alive with festivals, live music, shops, dining, and endless water activities all year long. Whether you're seeking a high-income short-term rental, a luxurious second home, or a permanent retreat, this Penthouse delivers it all - a prime location, top-floor privacy, as well as designer finishes and low-maintenance living in one of the Islands most prestigious addresses. Don't miss this chance to own a true Harbour Town gem where every day feels like a vacation.

6 Lighthouse Lane Unit 953, Hilton Head Island

Listing courtesy of Premier Properties of Hilton Head Island.

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.