Hilton Head Island, SC Two Story Homes For Sale

5 Beds ⋅ 6 Baths ⋅ 5,278 SqFt. ⋅ HILTONHEAD-511871 MLS

Welcome to 34 Ruddy Turnstone - a classic custom-built oceanfront home in Sea Pines designed by renowned Hilton Head architect Jakie Lee. Perfectly positioned on a large private homesite, this timeless residence showcases the charm, craftsmanship, and thoughtful design that define the finest Sea Pines properties. Exceptional quality is evident throughout with wide stairways, custom woodworking, soaring ceilings, and solid-core doors, all blending to create an atmosphere of relaxed yet refined coastal living. Designed for both comfort and entertainment, the home offers generous indoor and outdoor living spaces, including a heated pool and spa surrounded by lush privacy. The second level features the private Primary Suite with a sitting area, a spacious Great Room, Dining Room, and Eat-In Kitchen - all opening to an expansive IPE wood deck with elevated views overlooking the pool and the Atlantic Ocean. The entry level welcomes guests through a covered entrance into a dramatic foyer with high ceilings and access to the large Family Room complete with built-in beverage coolers and bar area. From here, enjoy seamless access to the covered porch, pool/spa and private beach path. Three Guest Bedrooms, each with their own Ensuite Bath, are also located on this level, along with an additional full bath and Laundry Room for added convenience. A fourth Guest Bedroom and full-size private Office with balcony occupy the mid-level, providing additional flexibility for family and guests. A newly installed elevator with service to all four levels, ensuring effortless enjoyment throughout the home. Thoughtfully designed and meticulously maintained by its original owners as a cherished second home, this exceptional oceanfront retreat offers the rare opportunity to enjoy a classic Sea Pines residence exactly as it is today - or reimagine and personalize it over time to create your own coastal legacy.

34 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,290,000

4 Beds ⋅ 4 Baths ⋅ 3,286 SqFt. ⋅ HILTONHEAD-511550 MLS

Set on more than 0.4 acres along a quiet private street in Hilton Head Plantation, this beautifully maintained 4-bedroom, 3.5-bath home offers a spacious floor plan, abundant natural light, and exceptional indoor-outdoor living. The welcoming foyer opens to generous living and dining areas, where large windows overlook the screened lanai and pool. The kitchen flows seamlessly into the family room and breakfast area, creating a comfortable gathering space for everyday living and entertaining. The spacious primary suite features a beautifully appointed bath with dual vanities, a walk-in shower, separate soaking tub, and a large walk-in closet. Two additional guest bedrooms provide privacy and comfort for family and visitors. A standout feature of the home is the expansive bonus room, complete with a wet bar, custom built-ins, and a full bath. Currently used as a bonus room, this flexible space serves as the home's fourth bedroom and is ideal for guests, a media room, or a private retreat. Step outside to the impressive screened lanai featuring a sparkling pool and generous covered seating area-the perfect place to relax, entertain, or enjoy Hilton Head's year-round outdoor lifestyle. The backyard offers a peaceful and private setting. Additional highlights include an oversized three-car garage, abundant storage, and a functional layout that is equally suited for a primary residence or second home. Located within the gates of Hilton Head Plantation, residents enjoy an outstanding array of amenities, including four championship golf courses, the Country Club of Hilton Head, Spring Lake Recreation Area, Dolphin Head Recreation Area, a full-service marina, tennis and pickleball courts, miles of leisure trails, a community pool, and 24-hour security-all just minutes from Hilton Head Island's beaches, shopping, and dining.

5 Royal James Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,275,000

4 Beds ⋅ 4 Baths ⋅ 4,138 SqFt. ⋅ HILTONHEAD-512009 MLS

Beautifully designed and filled with natural light, this spacious 4-bedroom, 4-bath residence offers an exceptional floor plan in the prestigious Long Cove community. Thoughtfully designed for both comfortable everyday living and effortless entertaining, the home features expansive living spaces, quality craftsmanship, and peaceful lagoon views from two sides of the property. The open-concept kitchen flows seamlessly into the great room while remaining connected to the formal dining and living rooms, creating the perfect layout for entertaining family and friends. Soaring smooth ceilings, abundant windows, custom built-ins, and two fireplaces add warmth, character, and timeless appeal throughout the home. The first-floor primary suite provides a private retreat complete with a spacious en-suite bath featuring dual vanities, a large walk-in shower, separate soaking tub, and two generous walk-in closets. The fourth bedroom is currently configured as a home office, while two additional guest suites are located on the second floor, providing privacy and comfort for family and visitors. Designed with comfort and efficiency in mind, the home features three HVAC systems, two water heaters, and spray foam insulation. A side-entry two-car garage provides ample storage, while the beautifully landscaped lot offers exceptional privacy. Step outside to enjoy the expansive rear patio and second-floor balcony overlooking tranquil lagoon views, creating the perfect setting for morning coffee or evening relaxation. Surrounded by lagoons on two sides, the property offers a rare sense of privacy and a picturesque natural setting. Ideally located on one of Long Cove's most desirable streets, this home combines a fantastic location with timeless design and an outstanding floor plan. Residents of Long Cove Club enjoy an exceptional lifestyle with a championship Pete Dye golf course, deep-water marina, tennis and pickleball, a fitness center, clubhouse, and all of the world-class amenities that make Long Cove one of Hilton Head Island's premier private communities.

10 Strawberry Hill Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$807,899

3 Beds ⋅ 3 Baths ⋅ 2,544 SqFt. ⋅ HILTONHEAD-512070 MLS

Welcome to The Tybee currently under construction, a beautifully designed 3 bedroom, 2.5 bath coastal retreat. This stunning elevated home offers the perfect blend of style and functionality with a gorgeous marsh view. Providing a spacious drive-under garage and charming front porch, it showcases exceptional curb appeal. Upon entering the main floor, you will be greeted by a bright and open living space designed for comfort and entertaining. The open-concept kitchen, great room, and dining area create the perfect gathering space for family and friends. The gourmet kitchen is a chef's delight, featuring a large island, ample cabinetry, and modern finishes throughout. Photos are not the actual home, but representations of the models.

126 Sandy Oaks Drive, Hilton Head Island

Listing courtesy of K. Hovnanian Homes.

$665,000

3 Beds ⋅ 3 Baths ⋅ 1,595 SqFt. ⋅ HILTONHEAD-511940 MLS

Welcome to this beautifully reimagined 3-bedroom, 2.5-bath home in the desirable Tansyleaf community, where timeless Craftsman architecture meets today's modern comforts. Originally built in 2018 with an open-concept floor plan, this home has been extensively upgraded with high-end finishes, custom millwork, smart home features, and exceptional attention to detail throughout. The heart of the home is a stunning designer kitchen featuring quartz countertops, gray shaker cabinetry, a custom island with decorative millwork, stainless farmhouse sink, subway tile backsplash, pantry, breakfast bar, and an upgraded LG ThinQ smart appliance package. The kitchen flows seamlessly into the spacious dining and living areas, creating an ideal space for entertaining or everyday living. The inviting great room showcases a contemporary linear fireplace and an impressive custom floor-to-ceiling wine wall capable of storing more than 300 bottles, creating a true focal point for entertaining. Luxury vinyl plank flooring, fresh paint, updated lighting, custom window treatments, built-in shelving, and designer finishes continue throughout the home, providing a sophisticated yet comfortable coastal aesthetic. Step outside to enjoy the screened lanai complete with composite flooring and retractable solar/privacy shades overlooking a fully fenced backyard featuring a decorative paver patio, mature landscaping, privacy trellises, and inviting outdoor living spaces. Upstairs, the spacious primary suite offers a tray ceiling, walk-in closet with custom organization, luxury vinyl flooring, and an updated ensuite bath with dual vanities and framed mirrors. Two additional bedrooms, an upgraded guest bath, and a Samsung Smart laundry suite complete the second level. Additional upgrades include custom closet systems, hurricane shutters, fresh interior paint, luxury vinyl flooring throughout much of the home, updated lighting and ceiling fans, and meticulous documentation of warranties, finishes, and materials that will transfer to the next owner. This exceptional property offers the perfect blend of style, comfort, functionality, and lifestyle-just minutes from Hilton Head Island's beaches, golf, dining, shopping, and all the Lowcountry has to offer.

18 Tansyleaf Drive, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$4,250,000

3 Beds ⋅ 3 Baths ⋅ 2,733 SqFt. ⋅ HILTONHEAD-511980 MLS

Reimagine oceanfront living on one of Hilton Head Island's most exceptional beachfront properties. Set beneath magnificent live oaks and surrounded by mature natural landscaping, this private retreat offers sweeping ocean views, ample room for expansion, and the rare opportunity to renovate, enhance, or create a new coastal estate tailored to your vision. Ideally positioned in the most coveted section of Port Royal Plantation, the property enjoys a peaceful setting away from the island's resort corridor while remaining minutes from renowned dining, golf, shopping, and amenities. The expansive rear deck is perfectly suited for entertaining, oyster roasts, or simply enjoying the ocean breeze and breathtaking coastal views. The existing residence offers 3 bedrooms and 2.5 baths, with the half bath easily converted back to its original full-bath configuration. Wide-plank pine floors, a beautifully renovated chef's kitchen, and walls of glass create warm, inviting interiors that connect seamlessly with the surrounding landscape. Adding to the property's distinction is its remarkable architectural history. Designed by internationally acclaimed architect Dean Winesett, whose work has appeared in *Architectural Digest* and *Southern Living*, the home was also featured in *Southern Living* and reflects his signature Lowcountry style and craftsmanship. Port Royal Plantation prohibits short-term rentals, preserving the privacy, tranquility, and exceptional quality of life that define this exclusive oceanfront community. Private amenities reserved for property owners and their guests include an oceanfront Beach House and swimming pool overlooking the Atlantic, tennis and pickleball courts, community gardens, leisure trails, and an array of recreational and social offerings. An irreplaceable beachfront setting, celebrated architectural legacy, exceptional private amenities, and endless possibilities combine to create one of the most compelling oceanfront opportunities currently available on Hilton Head Island.

4 Middleton Place, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS III brokered eXp Realty.

$828,900

3 Beds ⋅ 3 Baths ⋅ 2,544 SqFt. ⋅ HILTONHEAD-511971 MLS

Welcome to The Tybee currently under construction, a beautifully designed 3 bedroom, 2.5 bath coastal retreat. This stunning elevated home offers the perfect blend of style and functionality. With a spacious drive-under garage and charming front porch, it showcases exceptional curb appeal. Upon entering the main floor, you will be greeted by a bright and open living space designed for comfort and entertaining. The open-concept kitchen, great room, and dining area create the perfect gathering space for family and friends. The gourmet kitchen is a chef's delight, featuring a large island, ample cabinetry, and modern finishes throughout. Photos are not the actual home, but representations of the models.

131 Sandy Oaks Drive, Hilton Head Island

Listing courtesy of K. Hovnanian Homes.

$4,800,000

5 Beds ⋅ 6 Baths ⋅ 5,206 SqFt. ⋅ HILTONHEAD-511968 MLS

Set on one of Sea Pines' most prestigious streets, this exceptional waterfront estate offers breathtaking views, timeless architecture, and an unmatched Lowcountry lifestyle. Featuring 5 bedrooms, 5.5 baths, a spacious bonus room, and an oversized 2-car garage, this remarkable residence was thoughtfully designed for luxurious everyday living and effortless entertaining. Perfectly positioned to capture sweeping views of Calibogue Sound and the surrounding marshes, the home seamlessly blends elegant interiors with spectacular outdoor living. Expansive windows fill the home with natural light while framing picturesque water vistas. The well-designed floor plan offers generous gathering spaces, private guest accommodations, and exceptional flow for both everyday living and entertaining. Step outside to your own private retreat featuring a sparkling pool, beautifully landscaped grounds, and a charming gazebo overlooking the water. The private deep-water dock provides direct access for boating, fishing, kayaking, and unforgettable sunset views over Calibogue Sound. With five spacious bedroom suites, a large bonus room offering flexible living space, and an oversized two-car garage, this home combines luxury, comfort, and functionality in one extraordinary package. Located within the gates of Sea Pines, residents enjoy world-class amenities including miles of pristine beaches, Harbour Town, the Sea Pines Beach Club, championship golf, tennis, leisure trails, equestrian facilities, marinas, dining, shopping, and one of the most sought-after lifestyles on Hilton Head Island. A rare opportunity to own a premier waterfront estate on one of Sea Pines' most coveted streets.

31 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$2,500,000

4 Beds ⋅ 5 Baths ⋅ 3,508 SqFt. ⋅ HILTONHEAD-511633 MLS

Beautiful Ocean Views from Multiple Rooms. This exceptional 3rd-row Port Royal home offers an inviting blend of coastal elegance, spacious living, and an unbeatable location. Soaring ceilings and a thoughtfully designed floor plan create an open, airy atmosphere with excellent separation of living spaces. Features include an eat-in kitchen, spacious family room, formal living and dining rooms, and a conditioned Carolina room for year-round enjoyment.Just steps from the Port Royal Beach Club, oceanfront pool, and beach access, this home offers the convenience of premier community amenities without the maintenance of a private pool. Port Royal is one of Hilton Head Island's most sought-after private oceanfront communities, featuring gated security, beach access, pickleball and tennis courts, and scenic leisure trails and more. Optional membership to the Port Royal Golf Club provides access to championship golf, tennis & dining. To preserve the community's peaceful residential character, short-term rentals are not permitted.

14 Salt Spray Lane, Hilton Head Island

Listing courtesy of Charter One Realty.

$999,000

4 Beds ⋅ 4 Baths ⋅ 3,567 SqFt. ⋅ HILTONHEAD-511502 MLS

This wonderful family home offers an abundance of space tailored to meet every modern need. Featuring 4 bedrooms, 3.5 baths, a private office, a sun-drenched Carolina room, and a versatile loft, this property is designed for both comfort and functionality. As you enter, you are greeted by a beautiful grand staircase and an open concept with vaulted and tray ceilings throughout the main living areas. Other features include a large eat-in kitchen with stainless appliances, solid surface flooring, wainscoting panels, gas fireplace, 2-car garage and golf-cart bay, covered front porch, back deck, firepit, and views of the 11th hole of the Hills course. This property provides the perfect framework for a vibrant family lifestyle, combining an exceptional design with highly functional living spaces. Residents of Palmetto Hall enjoy 2 championship golf courses, tennis/pickleball courts, a swimming pool, and a beautiful southern styled clubhouse offering dining and social events. Seller is offering a $15,000 painting credit at closing. Seller is a SC licensed Real Estate Agent.

6 Tucker Ridge Court, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$619,000

4 Beds ⋅ 4 Baths ⋅ 2,625 SqFt. ⋅ HILTONHEAD-511634 MLS

Welcome to Peregrine Pointe, a quiet enclave on Hilton Head Island's convenient north end. Offering 2,625 square feet of living space, this well-designed home presents an exceptional opportunity for buyers seeking the space and privacy of a single-family home at an attainable price point.The ground level features a private-entry guest suite with its own living area and full bath, providing flexible space for extended family, guests, a home office, or multi-generational living.The elevated main living level is bright and inviting, offering an eat-in kitchen, spacious living room with fireplace, powder room, laundry closet, and a versatile den or flex room. A large covered screened porch extends the living space outdoors, creating the perfect spot to relax, entertain, or enjoy the coastal breeze year-round.Upstairs, the generous primary suite includes a walk-in shower, soaking tub, double vanity, and ample closet space. Two additional guest bedrooms share a Jack-and-Jill bath, creating a functional layout for family or visitors.Tucked away in a peaceful neighborhood just off Marshland Road, you'll enjoy convenient access to beaches, shopping, dining, schools, and everything Hilton Head Island has to offer. Whether you're searching for a primary residence, second home, or investment opportunity, this home delivers exceptional space, flexibility, and value in today's market. New roof 2026!

26 Peregrine Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,650,000

3 Beds ⋅ 3 Baths ⋅ 3,442 SqFt. ⋅ HILTONHEAD-511482 MLS

Perfectly positioned on a spacious corner lot overlooking a tranquil lagoon in Hilton Head Island's prestigious Windmill Harbour, this exceptional Lowcountry home has been completely reimagined into a turnkey coastal retreat where timeless design meets effortless luxury. A welcoming front porch and classic French doors open to beautifully curated interiors where white oak hardwood flooring flows throughout the home. Just off the foyer, the first-floor guest suite, currently used as an office, is complemented by a stunning marble bath with a custom vanity and convenient access from both the bedroom and main living space. Designed to impress, the chef's kitchen features custom cabinetry, GE Café appliances, an oversized porcelain farmhouse sink, illuminated cabinetry, a large island, and custom brass-accented shelving. Across the hall, the dining room is anchored by a striking oyster shell chandelier and designer grasscloth wallpaper, while the spacious living room showcases custom built-ins, detailed millwork, a gas fireplace with quartz surround, and walls of windows that flood the home with natural light. A custom back pantry with additional cabinetry, glass shelving, and a beverage refrigerator provides exceptional storage and entertaining space.Upstairs, the thoughtfully designed split floor plan offers privacy for family and guests. The oversized guest suite features custom closets, a beautifully updated bath, and a separate flex room ideal as a home office, fitness room, or private retreat. The primary suite overlooks the lagoon and features exposed wood beam ceilings, dual custom walk-in closets, and a spa-inspired bath complete with a freestanding soaking tub, oversized shower, and expansive dual vanity. An upstairs laundry room and additional built-in storage add everyday convenience. Designer lighting, custom window treatments, automatic blinds, and bespoke built-ins elevate every space, while the outdoor living areas are equally impressive. A tabby shell paver patio overlooks the lagoon, and a charming brick courtyard illuminated by café lights creates the perfect setting for outdoor entertaining. A covered breezeway seamlessly connects the home to the detached two-car garage, completing its classic Lowcountry charm. Located within Windmill Harbour, home to the South Carolina Yacht Club and one of the East Coast's premier private marinas, this golf-cart-friendly community offers one of Hilton Head Island's most desirable coastal lifestyles.

55 Crosstree Drive, Hilton Head Island

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

$629,000

5 Beds ⋅ 3 Baths ⋅ 2,363 SqFt. ⋅ HILTONHEAD-511641 MLS

Need 5 bedrooms? Take another look! This light and bright Hilton Head Island home offers 4 bedrooms plus wonderfully flexible space that can easily evolve with you-think optional 5th bedroom, home office, TV den, or even two separate work-from-home spaces. There's also room to add a shower to the downstairs bath, creating even more possibilities. With NO HOA fees, this is an exciting option for a primary residence, second home, or investor exploring long- or short-term rental potential. Inside, you'll find an easy-flowing floor plan with a welcoming foyer, dining room, spacious great room, eat-in kitchen, LVP flooring, abundant storage, and attached 2-car garage. Outside, the private wooded backyard brings the vacation vibes with a large deck, Tiki hut, and fire pit. All of this in a convenient north-end location close to schools, the Rec Center, bike paths, Main Street, Skull Creek, Islanders Beach, shopping, Bluffton, and Cross Island access. HVAC 2022. A home with space to live, work, play-and plenty of possibilities for what's next.

20 Hanahan Lane, Hilton Head Island

Listing courtesy of The Cobb Group brokered by eXp Realty.

$5,900,000

7 Beds ⋅ 8 Baths ⋅ 5,203 SqFt. ⋅ HILTONHEAD-511606 MLS

Properties of this caliber are increasingly difficult to find in Sea Pines. 7 Bedroom/6.5 Baths PLUS Pool Bath, 2022 construction, designer furnished and just a 3-minute walk to the beach. Set on an oversized nearly 1/3-acre 3rd row homesite, this is the rare combination discerning buyers wait years to find. Custom construction and incredibly designed for effortless coastal living, the home showcases sophisticated finishes, soaring ceilings, a gourmet kitchen with a separate prep kitchen, and seamless indoor-outdoor living centered around a covered porch with an outdoor fireplace, summer kitchen, heated pool, and spa. Seven beautifully appointed bedrooms-including a first-floor primary suite and four ensuite guest suites-provide exceptional comfort and privacy, while multiple gathering spaces make the home ideal for entertaining family and friends. Combining exceptional quality, an oversized homesite, beach proximity, and one of Sea Pines' most desirable locations, this is a true legacy property offering the very best of coastal living. Current rental projections of approximately $349,000 annually.

10 Bald Eagle Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$5,500,000

4 Beds ⋅ 5 Baths ⋅ 3,590 SqFt. ⋅ HILTONHEAD-511537 MLS

Oceanfront Luxury in a Private Gated Community on Hilton Head Island. Experience the ultimate in coastal living with this exceptional oceanfront residence, perfectly positioned within one of Hilton Head Island's most private gated communities. Offering breathtaking Atlantic Ocean views, direct beach access, and thoughtfully designed living spaces, this remarkable home is the perfect blend of elegance, comfort, and Lowcountry charm. Designed for both everyday living and effortless entertaining, the home features four spacious bedrooms, including two luxurious primary suites, five full bathrooms, and two separate living areas, providing exceptional flexibility for family and guests. The light-filled main living area showcases soaring vaulted ceilings, expansive windows, a fireplace, and walls of glass that frame spectacular ocean views. Enjoy relaxing on the upstairs deck allowing you to enjoy the sights and sounds of the Atlantic from nearly every angle. The generous primary suites offer private retreats complete with spa-inspired baths and tranquil coastal vistas. The first floor living area also offers a fireplace. Stroll outside to a private pool, expansive patio, lush tropical landscaping, and a private walk leading directly to one of Hilton Head Island's most pristine beaches create an unparalleled outdoor experience. Towering live oaks provide timeless Lowcountry character while preserving privacy and natural beauty. Whether you're seeking a luxurious primary residence, a second home, or an extraordinary oceanfront retreat, this exceptional property delivers the rare combination of privacy, sophistication, and direct beachfront living in one of Hilton Head Island's most coveted locations.

21 Barnacle Road, Hilton Head Island

Listing courtesy of Hilton Head Real Estate Partners.

$1,750,000

4 Beds ⋅ 4 Baths ⋅ 3,218 SqFt. ⋅ HILTONHEAD-511500 MLS

Experience the best of Hilton Head living in this beautifully designed home within the highly sought-after Port Royal Community. Perfectly positioned directly across from the residents' beach path, the Atlantic Ocean is less than 0.3 miles away, making beach days part of everyday life.Thoughtfully designed with exceptional bedroom separation, this predominantly single-story home offers 4 bedrooms and 4 baths, including a guest suite above the garage that can be closed off from the main home offering comfortable space for extended family or homeowners. The welcoming floor plan features a gracious foyer, formal dining room, spacious living room with a fireplace, and an inviting kitchen with counter seating, a sun-filled breakfast nook, and an adjoining great room with a second fireplace. The screened porch and expansive deck overlook the 11th fairway of the Barony Course, creating a peaceful backdrop for relaxing or entertaining.The spacious primary suite offers a calm and restful setting with a walk-in closet, dual vanities, a soaking tub, a separate shower, and a water closet. Two additional ensuite guest rooms are privately situated in their own wing.Set on a generous 0.636-acre homesite with room for a pool, this 3,218-square-foot home is part of one of Hilton Head Island's premier residential communities, where short-term rentals are prohibited. Residents enjoy private beach access, an oceanfront beach house, leisure trails, tennis, pickleball, gardens, 24-hour security, and optional membership to the Port Royal Golf Club.

108 S Port Royal Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$2,800,000

3 Beds ⋅ 3 Baths ⋅ 2,467 SqFt. ⋅ HILTONHEAD-511327 MLS

Imagine beginning each day with a short walk to one of Hilton Head Island's most beautiful beaches - just 200 steps from your door to the sand. Set in a coveted third-row location directly on the beach path, beneath a canopy of mature live oaks and palms, 8 Marsh Wren Road offers effortless access to Sea Pines' five miles of pristine Atlantic coastline, where morning walks, sunrise swims, and salt air become part of everyday life. The generous 106' x 120' lot is the true value here - a rare, buildable homesite in one of the Island's most sought-after beach communities, offering room for a pool, expansive outdoor living, and a residence designed exactly to your vision. For the ambitious buyer, the existing home presents an opportunity to undertake a transformative renovation and bring fresh life to this beachside setting. Whether you're drawn to the sunrises and salt air, the ease of beach access with the path just off the property, or the ability to bring your own luxury coastal vision to life in Sea Pines, 8 Marsh Wren Road presents a rare opportunity. Whether the goal is an ambitious renovation or a new coastal residence, 8 Marsh Wren Road presents a compelling opportunity to invest in the location, lot, and lifestyle that make Sea Pines beach-life so desirable.

8 Marsh Wren Road, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$650,000

3 Beds ⋅ 3 Baths ⋅ 1,481 SqFt. ⋅ HILTONHEAD-511467 MLS

Opportunity awaits on Hilton Head's highly desirable South End! Priced to sell, this is currently the least expensive single-family home available on the South End, making it an exceptional value and the perfect opportunity to update and personalize to your own style. Situated on a large corner lot with peaceful lagoon views, this charming 3-bedroom, 2.5-bath home offers a wonderful floor plan with the primary suite conveniently located on the first floor. The primary bedroom features a walk-in closet and an en-suite bath with a double vanity, soaking tub, and separate walk-in shower. Upstairs, two guest bedrooms share a Jack-and-Jill bath, and a large walk-in attic provides abundant storage. The kitchen features granite countertops, counter-height bar seating, and a dining area. The home offers an abundance of windows that fill the living spaces with natural light, creating a warm and inviting atmosphere. Enjoy outdoor living from the welcoming covered front porch or the back deck overlooking the fenced backyard and tranquil lagoon views. An oversized garage provides plenty of room for vehicles, golf carts, and additional storage. The roof is approximately 9 years old, the HVAC approximately 7 years old, and the water heater approximately 7 years old. With cosmetic updates needed, this is a wonderful opportunity to bring your vision to life and create a home that reflects your personal style. Located in a gated community with outstanding amenities including a community pool, tennis and pickleball courts, basketball court, and playground. Just minutes from the beach, Cross Island Parkway, the Bristol Sports Arena, public boat landing, restaurants, shopping, and Hilton Head's extensive leisure trails, you'll enjoy the very best of Lowcountry living in one of Hilton Head's most desirable locations.

65 Ashton Cove Drive, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$2,100,000

4 Beds ⋅ 4 Baths ⋅ 3,531 SqFt. ⋅ HILTONHEAD-511413 MLS

Located in the heart of Harbour Town within Sea Pines, this beautifully appointed home offers the perfect blend of luxury, comfort and coastal charm. Enjoy easy access to iconic Harbour Town Yacht Basin, Lighthouse, shops, waterfront dining, renowned golf, miles of leisure trails and a short drive or shuttle to magnificent Hilton Head beaches. The home features 4 bedrooms and 4 bathrooms with expansive deck and pool. Ideal for entertaining, unwinding from a day at the beach or golf course. Whether you're seeking a full-time residence, vacation retreat or an investment property, this exceptional home captures the very best of the Sea Pines lifestyle.

8 Windjammer Court, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate.

$2,100,000

4 Beds ⋅ 5 Baths ⋅ 4,175 SqFt. ⋅ HILTONHEAD-511369 MLS

Welcome to Lakeside Luxury at 5 Stonewall Circle on Hilton Head Island. A custom two-toned paver U-shaped driveway sets the stage for this meticulously maintained and updated home, where elegant finishes meet a relaxed lakeside setting overlooking the 18th hole of the Cupp Course in Palmetto Hall. Offering 4 bedrooms, 4.5 bathrooms, an office, and a versatile loft that can serve as a fifth bedroom, this home provides exceptional flexibility. Multiple primary suites with professionally designed custom closets deliver comfort, privacy, and abundant storage.The beautifully updated kitchen anchors the home with solid cherry wood cabinetry, quartz countertops, stainless-steel sink, satin nickel faucet, and designer pendant lighting. Elegant white swirled ceramic tile flows throughout the main level, while premium COREtec flooring enhances the upper level.Thoughtfully renovated for style and peace of mind, the home features a new roof (2024), two newer HVAC systems (2025), 19 Andersen windows, new gutters, solar attic fans, all-new LED lighting and ceiling fans, automatic exterior landscape lighting and professionally painted interior and three-car garage.Outdoor living is designed for entertaining with a one-of-a-kind pool cabana featuring leathered black granite countertops, abundant cabinetry, a refrigerator, wet bar, and exterior speakers. The resort-style pool includes new tile, built-in benches and steps, a new chlorine generator, and gas heater. A spacious hot tub, outdoor shower, and paver conversation area overlooking the lake, create the perfect private retreat.Located in the highly desirable, gated Palmetto Hall community, residents enjoy two championship golf courses, a clubhouse, playground, tennis and pickleball courts, a community pool, on site restaurant and a vibrant lifestyle just minutes from Hilton Head Island's beaches, dining, shopping, and entertainment. Meticulously maintained and move-in ready, this exceptional home offers luxury Lowcountry living at its finest. SCREB owned.

5 Stonewall Circle, Hilton Head Island

Listing courtesy of Family Tides Real Estate LLC.

Hilton Head Island, SC Two Story Homes for Sale

Two Story Homes for sale in Hilton Head Island, SC