Hilton Head Island Homes with Two Story Style

Hilton Head Island Homes with Two Story Style

Welcome to Hilton Head Island, South Carolina—a coastal gem nestled in Beaufort County, renowned for its breathtaking beaches, lush landscapes, and vibrant community spirit. This idyllic island, spanning over 12 miles of pristine shoreline, offers a perfect blend of natural beauty and modern conveniences, making it an ideal destination for both vacationers and those seeking a permanent residence.

One of the most charming residential options on the island is the two-story home. These properties not only provide ample living space but also offer stunning views of the surrounding scenery. Imagine waking up to the sound of waves lapping against the shore, with your morning coffee enjoyed on a private balcony overlooking the ocean or marshlands. Many of the two-story homes in Hilton Head Island feature open-concept designs, allowing for seamless flow between the living, dining, and kitchen areas—perfect for hosting family gatherings or entertaining friends.

The architecture of these homes often reflects the island's coastal character, with features such as expansive windows, spacious decks, and inviting outdoor spaces that encourage a relaxed lifestyle. Whether you’re looking for a cozy retreat or a luxurious family abode, Hilton Head’s two-story homes cater to a variety of tastes and preferences.

Beyond the stunning properties, Hilton Head Island boasts a wealth of recreational activities, from world-class golf courses and tennis clubs to scenic bike trails and nature preserves. With its warm climate, friendly community, and rich cultural offerings, Hilton Head Island is more than just a place to live—it's a lifestyle waiting to be embraced. Discover your dream two-story home on this enchanting island today!

Newest Hilton Head Island Homes with Two Story Style

$1,245,000
3 Beds ⋅ 3 Baths ⋅ 3,544 SqFt. ⋅ HILTONHEAD-513054 MLS
More to come including professional photos.

1 Shaftsbury Lane, Hilton Head Island

Listing courtesy of Charter One Realty.

$649,000
2 Beds ⋅ 3 Baths ⋅ 1,647 SqFt. ⋅ HILTONHEAD-513045 MLS
Enjoy beautiful marina views from this exceptional 4th-floor, two-story villa in the heart of Shelter Cove Harbour & Marina. This spacious 2-bedroom, 2.5 bath villa features an inviting living and dining area, well-appointed kitchen, powder room, and a large private balcony overlooking the harbour - the perfect place to relax and take in the views. Upstairs the owner's suite features a Jacuzzi tub and separate walk-in shower, while a supplemental A/C unit provides added comfort. Additional features include a Wi-Fi controlled thermostat and convenient elevator access located directly across from the villa. Step outside to waterfront dining, boutique shopping, live entertainment, seasonal events, and all the activity of the marina. Owners and guests also enjoy access to the Harbourside I pool and Palmetto Dunes Resort amenities, including beach access via the seasonal Dunes Buggy, golf, tennis, pickleball, and miles of leisure trails. A wonderful opportunity to enjoy the Shelter Cove lifestyle and the very best of Hilton Head Island.

13 Harbourside Lane Unit 7170, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$899,000
3 Beds ⋅ 3 Baths ⋅ 1,576 SqFt. ⋅ HILTONHEAD-513137 MLS
Beautifully updated 3-bedroom, 3-bath villa in Turnberry Village, ideally situated along the George Fazio Golf Course in the heart of Palmetto Dunes. This light-filled villa offers an open and inviting floor plan with a beautifully updated kitchen featuring quartz countertops, stainless steel appliances, generous cabinet space, and a large peninsula with bar seating overlooking the dining and living areas. The spacious living room opens to a large private Trex deck with sweeping golf course views, creating the perfect setting for relaxing or entertaining. The first-floor primary suite offers convenient main-level living with a private bath, while upstairs you'll find two additional spacious bedrooms, each with access to its own full bath. Turnberry Village offers a community pool and playground and is conveniently located less than a mile from the beach, with easy access by bike or the seasonal Dunes Buggy. Enjoy all that Palmetto Dunes has to offer, including world-class golf, tennis and pickleball, dining, shopping, miles of leisure trails, and beautiful beaches. Whether you're looking for a second home or investment property, this is a wonderful opportunity to own in one of Hilton Head Island's most desirable resort communities.

59 Carnoustie Road Unit 279, Hilton Head Island

Listing courtesy of Charter One Realty.

$775,000
4 Beds ⋅ 3 Baths ⋅ 2,322 SqFt. ⋅ HILTONHEAD-513132 MLS
Welcome to 14 Marblehead Road, a beautifully renovated Hilton Head Island retreat located just minutes from Folly Field Beach and everything this incredible area has to offer. This stunning 4-bedroom, 3-bath home offers the perfect combination of coastal style, comfort, and investment potential. Inside, you'll find a thoughtfully renovated interior with spacious living areas, a beautiful kitchen, and plenty of room for family, friends, or vacation guests. Step outside and discover your own private backyard pool oasis, creating the perfect setting for relaxing after a day at the beach, entertaining guests, or enjoying the laid-back Hilton Head lifestyle. The spacious outdoor area adds another layer of appeal for vacation rental guests and makes this home feel like a true private resort. The location is hard to beat. You'll be just minutes from Folly Field Beach, with easy access to the island's beaches, restaurants, shopping, golf, biking, and outdoor activities. Whether you're spending the day on the sand, exploring Hilton Head by bike, or enjoying the pool at home, everything you need for the perfect island getaway is close by. For investors, the property offers rental projections currently up to $86,000 annually as is, garage and sunroom conversion to 6 bedrooms and maximizing rental income, creating the potential for an exceptional income-producing vacation property while still providing an incredible personal retreat. Whether you're looking for a high-performing short-term rental, second home, or full-time Hilton Head residence, 14 Marblehead delivers an exceptional combination of renovation, location, privacy, pool oasis, and investment potential. This is Hilton Head Island living with a fantastic investment opportunity already built in!

14 Marblehead Road, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$2,849,000
4 Beds ⋅ 5 Baths ⋅ 3,925 SqFt. ⋅ HILTONHEAD-512812 MLS
Fully remodeled and beautifully appointed, this exceptional harbourfront home in Wexford offers a relaxed Lowcountry lifestyle with harbour views, private pool, 3,925 square feet of living space, and a private dock that can accommodate a 70' vessel. The home features 4 bedrooms, 4 full and 1 half baths, and 2-car plus golf cart garage. Wexford's private marina and harbour provide direct access to the Broad Creek and the Intracoastal Waterway through its 24/7 lock system, one of only three on the East Coast. Upon entering, the formal living room makes an immediate impression with soaring ceilings, exposed beams, a propane fireplace, and expansive windows that fill the space with natural light. Doors open directly to the pool deck, creating an effortless connection between indoor and outdoor living. The inviting family room features high ceilings, floor-to-ceiling windows, an electric fireplace, and direct access to the pool deck. At the heart of the home is a stunning, fully remodeled kitchen with a bright, open design, double islands, top-of-the-line appliances, quartz countertops, and a walk-in pantry. The spacious first-floor primary suite features a beautifully remodeled bath with a zero-entry shower, a soaking tub, and a generous walk-in closet. A first-floor laundry room adds everyday convenience. Three guest rooms with fully remodeled ensuite baths provide flexibility and room for guests. The outdoor living spaces have been thoughtfully enhanced with a brand-new covered area overlooking the pool and harbour, creating an inviting space for relaxing and entertaining. The newly plastered pool and resurfaced pool deck provide a refreshed outdoor retreat. This home also has a built in generator for added piece of mind. The generous lot offers plenty of room and privacy, while the 2-car plus golf cart garage provides storage and convenience. Wexford members enjoy a premier private club lifestyle, including an Arnold Palmer Signature golf course, tennis, pickleball, croquet, pool complex, private harbour, fire pit, and newly opened Clubhouse and Harbour Center. Combined with a vibrant social calendar and Wexford's unique marina lifestyle, this is an exceptional opportunity to enjoy the best of private club living on Hilton Head Island.

44 Wexford Club Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$4,400,000
6 Beds ⋅ 6 Baths ⋅ 4,796 SqFt. ⋅ HILTONHEAD-513002 MLS
Like NEW, this State of the Art Lowcountry 6BR/5.5BA Beach Home approx 8000+ sq ft under roof offering 2 living rooms, 2 screened porches, huge garage, workshop and large private pool was designed for the way you actually want to live on Hilton Head Island. Open, comfortable, private, premium finishes, with perfectly designed outdoor spaces, all just moments from the residents only private beach . Hardwood floors, custom millwork, built-ins and walls of windows carry throughout the home. The kitchen is a showstopper, with an oversized island, custom cabinetry, high-end appliances and a true walk-in pantry. The primary suite is equally impressive withhis & her bathrooms w/freestanding soaking tub, oversized tiled shower and custom his & hers walk-in closets. Outside is where this home really separates itself. Two screened porches create an incredible amount of year-round living space, including an upper porch with fireplace, built-in grill and dining area. Downstairs, another oversized screened living area opens to the private pool, hot tub and beautifully landscaped backyard. Add an elevator, dedicated office, game area, workshop and more storage than you expect to find in an island home, and there's very little this house leaves you wanting. One of the finest homes ever offered for sale in Port Royal situated on a premium oversized extremely private lot in close proximity to the Residents Private Beach & Beach Club. The private gated community of Port Royal on Hilton Head is an Outdoor Enthusiast Dream offering Tennis. Golf. Pickle Ball. Bike Paths. Swimming. Gardening. Beach Activities

51 Scarborough Head Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$309,000
1 Beds ⋅ 1 Baths ⋅ 540 SqFt. ⋅ HILTONHEAD-513107 MLS
Turnkey and renovated in 2024, C217 offers Lowcountry marsh and wooded views with convenient beach access. Used exclusively as the owners' private retreat, the villa has been carefully maintained and is located in a building with an elevator. The open kitchen and living area feature quartz countertops, new cabinetry and stainless steel appliances, LVP flooring and a built-in sound system. A new HVAC system was installed in 2026. The villa is offered fully furnished and includes fresh paint in a coastal color and a custom designed bedroom closet. The redesigned bathroom features a white quartz-topped vanity and a tiled walk-in shower with a glass enclosure. Expansive living room windows bring natural light into the living area and frame the private marsh and wooded surroundings. The balcony offers sunrise views overlooking the marsh and trees where birds are frequently seen and heard. Shaded from direct afternoon sun, it creates a great place to relax after a day at the beach. Hilton Head Beach and Tennis Resort amenities include tennis and pickleball courts, swimming pools, on-site dining, a fitness center, playground, laundry facilities and 24-hour security. This villa can easily be used as a primary residence, vacation home or investment property.

40 Folly Field Road Unit C217, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$735,000
2 Beds ⋅ 3 Baths ⋅ 1,600 SqFt. ⋅ HILTONHEAD-513104 MLS
Enjoy the best of the Sea Pines lifestyle from this beautifully updated and nicely furnished 2-bedroom Heritage Villa, ideally located just minutes from Harbour Town. The light and inviting interior features stylish LVP flooring, comfortable living spaces, and thoughtful updates throughout, making this villa truly move-in ready. Enjoy a pleasant view of the community pickleball courts and easy access to all that Sea Pines has to offer. An excellent vacation rental opportunity, the villa has generated $29,264 in gross rental income year-to-date. Whether you're looking for a full-time residence, vacation getaway, or income-producing investment, this villa offers exceptional convenience to Harbour Town, world-class golf, dining, shopping, biking trails, and more. Offered furnished and ready to enjoy!

107 Lighthouse Road Unit 2289, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$629,990
4 Beds ⋅ 4 Baths ⋅ 2,092 SqFt. ⋅ HILTONHEAD-513099 MLS
Welcome to 64 E Morgan Court inside Middleton Place, a beautifully established neighborhood ideally located on the island. Middleton Place homes are in high demand and do not come available often! This home comes in immaculate condition inside and out. This exceptional home combines exterior charm on a cul de sac with sophisticated interior design, offering a seamless blend of comfort and style for the discerning buyer. Upon entering, you are greeted by an inviting open-concept layout that promotes an effortless lifestyle. The soaring ceilings draw your eyes toward the spacious great room, where an abundance of natural light filters in throughout the day. To your left, a beautifully updated kitchen provides the perfect space for either entertaining guests or enjoying happy, home-cooked meals with family. The main-level primary suite serves as a peaceful retreat, while three additional bedrooms upstairs offer ideal privacy and comfort for family or guests. Step outside to the screened porch overlooking a private backyard-a perfect setting for relaxing as the sun sets. Convenience meets coastal living here. After a day in the sun, park in your private garage, grab your flip-flops, and walk to Broad Creek Marina for a boating adventure, or head to waterfront dining and a spectacular sunset. Whether you are looking for your first island home, an island upgrade for more space, or a dream vacation retreat, this property truly has it all. Middleton Place HOA fee is only $500.00 per year.

64 E Morgan Court, Hilton Head Island

Listing courtesy of Hilton Head Properties.

$399,000
2 Beds ⋅ 1 Baths ⋅ 960 SqFt. ⋅ HILTONHEAD-513044 MLS
The location of this villa truly cannot be beat. Completely renovated from top to bottom, this turnkey, second-floor Dunes Villa is the ultimate coastal retreat. Situated just steps from the ocean, this property offers a seamless island lifestyle whether you are looking to generate immediate rental income as an investment, relax in your own second home, or settle into a low-maintenance primary residence. Every detail of this turn-key two-bedroom, one-bath home was thoughtfully designed for maximum style and comfort. The light and bright kitchen features renovated cabinetry and modern appliances, while the updated bathroom provides a crisp, contemporary space to rinse off after a day in the sun. What sets this property apart is its unbeatable combination of location, community amenities, and low regime fee. Just steps away you can feel the ocean breeze, or walk down the block to dine at one of the nearby restaurants. A quick five minute stroll takes you straight to the Lowcountry Celebration Park and Coligny Plaza. Hilton Head's Coligny area is a vibrant downtown area where you will find over 20 restaurants, local shopping, and lively entertainment. Dunes Villas offers hassle-free parking, the rare island luxury of a year-round swimming pool, and is pet-friendly exclusively for owners. An opportunity to own a completely updated villa this close to the beach and Coligny Plaza rarely presents itself. Claim your piece of Hilton Head's paradise today.

6 Woodward Avenue Unit C3, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$1,475,000
3 Beds ⋅ 3 Baths ⋅ 1,167 SqFt. ⋅ HILTONHEAD-512579 MLS
Exquisitely reimagined, remodeled, and renovated, this stunning 3-bedroom, 3-full-bath villa is an exceptional Sea Pines opportunity - just SIX homes from the beach! Beautifully furnished and impeccably decorated, this bright and airy villa offers the perfect combination of luxury, location, and income-producing potential. A gorgeous rear wall of windows fills the living space with natural light and brings the beautiful outdoor setting right inside. And then there's the location...Perfectly positioned just a short distance inside the Sea Pines Ocean Gate, you can walk out your front door and cross the street to the beach path - putting the beach practically at your doorstep. Prefer to explore by bike? Take a leisurely ride to Coligny, the Plantation Club, or Sea Pines Center for shopping, dining, and entertainment. Golfers will love the private putting green exclusive to Fairway Lane Villas - and even non-golfers will appreciate having a little extra fun right outside their door. Best of all, you'll have the incredible amenities and attractions of Sea Pines right at your fingertips: three golf courses, including Harbour Town Golf Links, home of the RBC Heritage; Lawton Stables; the Sea Pines Forest Preserve; the iconic Harbour Town Lighthouse; and the shops, restaurants, and waterfront charm of Harbour Town and South Beach - including the beloved Salty Dog Cafe. Whether you're looking for a dream beach retreat, a memorable family getaway, or a vacation property with rental income potential, this villa checks all the boxes. Beautifully updated. Perfectly located. Ready to enjoy. This just might be the one you've been waiting for. Don't miss it!

13 Lawton Drive Unit 94, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

$385,000
1 Beds ⋅ 2 Baths ⋅ 1,217 SqFt. ⋅ HILTONHEAD-512916 MLS
12 Devils Elbow is one of Moss Creek's distinctive Golf Cottages, part of the community's original architectural vision dating to the 1970s. The Golf Cottages were designed by the same architectural firm responsible for Moss Creek's award-winning original golf clubhouse, with the cottages, clubhouse, cart bridges and rain shelters conceived together to create architectural continuity throughout the golf setting. These distinctive cottages are designed to complement their natural surroundings rather than compete with them. That thoughtful design is especially evident at 12 Devils Elbow. High ceilings and generous windows fill the home with natural light, while the Carolina room draws your eye across the marsh to distant golf course and pond views. As an end unit, the home enjoys an especially appealing connection to its surroundings-a wonderfully comfortable, easy-to-maintain Lowcountry retreat with architectural character rarely found in today's condominium construction. Couple that with Moss Creek's generous amenities and the Golf Cottages location within near distance to the recently renovated Clubhouse, golf and tennis facilities, 12 Devils Elbow makes an ideal place for full time living or a welcoming second-home.

12 Devils Elbow Lane Unit 12, Hilton Head Island

Listing courtesy of Dunes Real Estate.

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