Hilton Head Island Homes with Three Story Style

Welcome to Hilton Head Island, South Carolina—a breathtaking coastal paradise nestled in Beaufort County. Renowned for its stunning beaches, world-class golf courses, and vibrant maritime forests, Hilton Head Island offers a unique blend of relaxation and adventure. With its rich history and commitment to environmental preservation, this charming island is not just a destination; it's a lifestyle.

Imagine waking up to the gentle sound of waves lapping at the shore, with the sun rising over the Atlantic Ocean. This idyllic setting is complemented by a diverse range of properties, including exquisite three-story homes that epitomize luxury and coastal living. These architectural gems often feature expansive open floor plans, large windows that flood the interiors with natural light, and spacious balconies that provide panoramic views of the lush landscapes and shimmering waters.

Three-story homes in Hilton Head Island are designed for both comfort and elegance, making them perfect for families or those seeking a second home. Many of these residences come equipped with modern amenities, gourmet kitchens, and private outdoor spaces ideal for entertaining or simply unwinding after a day of exploring the island’s many attractions.

Whether you’re an avid golfer, a beach lover, or someone who appreciates the arts and culture, Hilton Head Island has something for everyone. With its friendly community and plethora of recreational activities, you’ll find yourself immersed in a lifestyle that celebrates both relaxation and adventure. Discover your dream home on this enchanting island, where every day feels like a vacation.

Newest Hilton Head Island Homes with Three Story Style

$675,000

3 Beds ⋅ 3 Baths ⋅ 1,941 SqFt. ⋅ HILTONHEAD-512886 MLS

Welcome to 137 Cordillo Parkway, Suite 6002, a beautifully furnished 3-bedroom, 2.5-bath Hilton Head Island retreat offered at $675,000.Whether you are searching for your own beach getaway or an investment opportunity, this property offers the perfect combination of comfort, convenience, and island lifestyle. The spacious floor plan comfortably sleeps up to eight guests and comes fully furnished, making it easy to begin enjoying the property from day one.One of the highlights of the home is the relaxing back patio and porch area-the perfect place to unwind after a day at the beach. Community amenities include three swimming pools, convenient elevator access, and a private walkway providing direct access toward the beach.Enjoy an approximately eight-minute scenic walk along the shaded pathway to the sand, with convenient access to a wonderful beachfront restaurant along the way. Whether spending the day by the pool, relaxing on the beach, enjoying nearby dining, or simply taking in the laid-back Hilton Head atmosphere, this property offers an exceptional coastal experience.Ideal for an owner-occupant, second-home buyer, or investor seeking rental potential. Forecasted rental projections are available upon request.Schedule your private showing today and come experience everything this Hilton Head Island property has to offer.

137 Cordillo Parkway Unit 6002, Hilton Head Island

Listing courtesy of Douglas Lane Real Estate Group.

$1,325,000

3 Beds ⋅ 4 Baths ⋅ 2,343 SqFt. ⋅ HILTONHEAD-512807 MLS

Exceptional Harbour Town location in the heart of Sea Pines! 18 Spinnaker Court is a spacious 3-bedroom, 3.5-bath townhome offering more than 2,300 square feet, multiple outdoor living areas, and distant views of the 18th fairway of Harbour Town Golf Links and Calibogue Sound. A paver driveway leads to the 1-car garage, while inside, the floor plan offers generous living and dining spaces with high ceilings, hardwood floors, granite countertops, a wet bar, and a fireplace. The galley-style kitchen is efficient and functional, and the primary suite is located upstairs along with additional guest accommodations. Sold furnished, this property is especially appealing as a turnkey rental opportunity, second home, or full-time residence. Multiple decks provide additional space to relax, entertain, and take in the surrounding Harbour Town setting. Enjoy all that Sea Pines has to offer, including miles of leisure trails, beautiful beaches, Harbour Town Marina, South Beach Marina, world-class golf, tennis and pickleball, dining, shopping, and easy access to the Harbour Town Golf Links, home of the PGA TOUR's RBC Heritage Presented by Boeing. With its size, furnished offering, garage, outdoor living spaces, and prime Harbour Town setting, 18 Spinnaker Court presents an outstanding opportunity to own in one of Hilton Head Island's most iconic communities.

18 Spinnaker Court, Hilton Head Island

Listing courtesy of Charter One Realty.

$2,195,000

4 Beds ⋅ 5 Baths ⋅ 2,930 SqFt. ⋅ HILTONHEAD-512616 MLS

Just 100 yards from the Atlantic Ocean, this 4-bedroom, 4.5-bath Singleton Beach home offers an exceptional combination of beach proximity, beautiful marsh views, and relaxed coastal living. With 2,930 sq. ft., the home features a private pool, elevator, two-car garage, and multiple balconies designed to take advantage of the surrounding island scenery and coastal breezes. Each bedroom offers its own en-suite bath, while the primary suite enjoys a private balcony overlooking the marsh. The versatile layout is ideal as a primary residence, second home, or vacation rental investment. Enjoy an easy walk to the beach along with convenient access to Chaplin Park, bike paths, pickleball, shopping, dining, and Coco's on the Beach. Ideally positioned in the heart of Hilton Head Island, this Singleton Beach property delivers the sought-after combination of ocean access, marsh views, private outdoor living, and strong rental potential. Rental projection available.

91 Singleton Beach Road, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$325,000

2 Beds ⋅ 2 Baths ⋅ 917 SqFt. ⋅ HILTONHEAD-512515 MLS

Turnkey Short-Term Rental Opportunity on Hilton Head Island! This fully furnished 2-bedroom, 2-bath villa at The Spa on Port Royal Sound offers an excellent opportunity for those seeking an investment property, vacation rental, or island getaway with rental potential. Located in Building A near the tennis courts, this villa is ready to enjoy or rent, with furnishings already in place and a comfortable two-bedroom floor plan. Features include stainless steel appliances and a convenient stackable washer/dryer. The Spa on Port Royal Sound is a gated waterfront community with direct access to the beautiful shoreline of Port Royal Sound and an array of amenities designed for both relaxation and recreation. Enjoy multiple pools, tennis courts, a fitness facility, and the laid-back Lowcountry lifestyle Hilton Head Island is known for. Whether you're looking for a vacation retreat, a second home, or a property with income-producing potential, this villa offers flexibility and convenience. Use it for your own island escapes and take advantage of short-term rental opportunities when you're away. A great way to own a piece of Hilton Head Island with amenities and waterfront access right outside your door!

239 Beach City Road Unit 3230, Hilton Head Island

Listing courtesy of Charter One Realty.

$299,000

2 Beds ⋅ 2 Baths ⋅ 917 SqFt. ⋅ HILTONHEAD-512186 MLS

Enjoy effortless coastal living in this beautifully updated top-floor, 2-bedroom, 2-bathroom villa directly on Hilton Head Island's Port Royal Sound. The bright interior features smooth ceilings, durable laminate flooring, and brand-new furnishings throughout the living areas. Highlights include a custom coffee bar and a fully stocked kitchen with a brand-new garbage disposal. Essential upgrades include a brand-new HVAC system and freshly applied protective and aesthetic coatings on all shower surfaces. This villa is truly turn-key, with new bedding and linens, as well as a restocked activity closet featuring games and beach essentials. Unwind on your private screened porch and enjoy the refreshing ocean breeze, or step outside to take advantage of The Spa's gated amenities, including three pools, tennis and basketball courts, a fitness center, and direct beach access!

239 Beach City Road Unit 3323, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$650,000

4 Beds ⋅ 4 Baths ⋅ 1,939 SqFt. ⋅ HILTONHEAD-512286 MLS

Welcome to this charming Charleston-style 4-bedroom, 3.5-bath home overlooking the lagoon in the gated community of Victoria Square. Designed across three levels, the home offers a flexible floor plan with a true fourth bedroom and full bath on the first floor-ideal for giving guests a private space of their own-along with direct access to a spacious screened patio. The beautifully updated kitchen features crisp white cabinetry, stone countertops, a tile backsplash, and generous workspace, opening to a bright dining area surrounded by windows. The comfortable living room offers space to relax, a nook for your special piece of furniture or a convenient placement for a desk and flows onto an oversized screened porch, creating an inviting space for relaxing or entertaining while enjoying the lagoon setting. The third-floor primary suite opens to its own private balcony, while three distinct levels of outdoor living provide plenty of ways to enjoy Hilton Head's coastal climate. Additional features include a welcoming front porch, abundant storage, and a spacious tandem garage offering plenty of room for parking, a workshop, bikes, beach gear, and more. Centrally located on Hilton Head Island, Victoria Square offers low HOA fees and desirable amenities, including a community pool, playground, leisure trails, a two-acre lagoon, security gate, and convenient boat and RV storage. Shopping, waterfront dining, parks, and everyday conveniences are easily accessible...and the beach is a short ride away. This is an excellent opportunity to enjoy a spacious island home, flexible guest accommodations, and relaxed Lowcountry living in a convenient mid-island location.

65 Victoria Square Drive, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$489,000

4 Beds ⋅ 4 Baths ⋅ 2,022 SqFt. ⋅ HILTONHEAD-512139 MLS

Offering a level of space and flexibility rarely found in townhome living, this four-bedroom, 3.5-bath Allenwood residence pairs a versatile multi-level floor plan with peaceful lagoon views and multiple outdoor living spaces. Front and rear balconies extend from the main living level, creating natural places to enjoy the Lowcountry setting.A defining feature of the home is the private fourth-bedroom suite located off the garage, complete with a full bath, walk-in closet, and its own waterfront porch. Separated from the primary living areas, this space creates exceptional flexibility for guests, extended family, a home office, or additional living space.Inside, generous living areas accommodate both everyday life and entertaining, while the oversized one-car garage provides valuable parking and storage. Offered partially furnished and move-in ready, the home is well suited for a primary residence, second home, or investment property.Allenwood is a gated Hilton Head Island community offering a neighborhood pool and a convenient location near beaches, dining, shopping, recreation, leisure trails, and the Hilton Head Island school campus. With four bedrooms, abundant outdoor living, water views, and a floor plan that offers genuine versatility, this residence brings together space, privacy, and the ease of island living. Some images have been virtually enhanced with conceptual furnishings.

315 Ceasar Place, Hilton Head Island

Listing courtesy of Engel & Volkers.

$329,900

2 Beds ⋅ 2 Baths ⋅ 888 SqFt. ⋅ HILTONHEAD-512362 MLS

Fully furnished and turn-key, this updated 2BR/2BA end-unit Tennis Villa is the perfect coastal retreat or Short Term Rentalinvestment. Sleeps 6 comfortably with a private balcony overlooking the tennis courts. Features include 2021 renovation LVPflooring, furnishings, refrigerator, located in Hilton Head Beach & Tennis, an oceanfront resort offering 24/7 gated security,direct beach access, oceanfront pool with food service + kids' pool, lighted tennis & pickleball, fitness center, beach bar &dining, grilling areas, and seasonal bike rentals, on-site rental services. HOA includes insurance and TV/Wifi included inregime fee. beachside getaway! Gross 2024 Revenue 36,816.40. Gross 2025 Revenue $26,166.42.

40 Folly Field Road Unit E17, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$365,000

1 Beds ⋅ 1 Baths ⋅ 588 SqFt. ⋅ HILTONHEAD-512279 MLS

INVESTMENT ALERT! This beautiful gem consistently generates impressive rental income; $52,000 in 2025, and on tract to do the same for 2026, $48,500 in 2024, $42,000 in 2023 and $42,800 in 2022. DIRECT SOUNDFRONT, a Proven rental machine at The Spa on Port Royal Sound. This 1BR/1BA villa offers sweeping sound views from the private balcony, along with a comfortable coastal interior featuring a king-size bedroom, en-suite bath with walk-in shower, well-equipped kitchen. The oceanfront community offers natural beach access, an observation pier, two outdoor pools, indoor pool, hot tub, dry sauna, fitness center, tennis and basketball courts, and multiple grilling and picnic areas. Enjoy beautiful sandy beaches and stunning sunrises just outside your door. With a strong rental history and an exceptional oceanfront setting, this is a turnkey opportunity for a second home or investment property on Hilton Head Island.

239 Beach City Road Unit 1203, Hilton Head Island

Listing courtesy of Coastal Luxury Real Estate.

$295,000

2 Beds ⋅ 2 Baths ⋅ 831 SqFt. ⋅ HILTONHEAD-512265 MLS

Brand new HVAC and HW Heater! Welcome to this amazing unit in building 4, sold fully furnished and fully equipped with everything you need to start vacationing or renting. 2BD/2BA condo, ideally located just steps away from the beaches of Hilton Head. Top-floor unit complete with LVP floors and a spacious open-concept, making it an ideal residence or rental opportunity. Great rental history with a perfect set up for family vacations. Enjoy an array of incredible amenities, including indoor and outdoor pools, convenient beach access, tennis/pickleball courts, and a tropical beach bar. Additionally, numerous restaurants and shops are conveniently located nearby, ensuring the convenience and entertainment of island life. Don't miss the chance to see this exceptional condo today.

663 William Hilton Parkway Unit 4427, Hilton Head Island

Listing courtesy of Lowcountry Live Oak Realty.

$3,995,000

5 Beds ⋅ 7 Baths ⋅ 4,566 SqFt. ⋅ HILTONHEAD-512060 MLS

Waterfront living in Wexford doesn't get much better than this and 20 Castlebridge Court offers the ONLY harborfront setting currently available in the community. Set directly on the harbor at the end of a private cul-de-sac, this five-bedroom residence combines exceptional outdoor living with one of the neighborhood's most desirable settings. A heated pool and spa, outdoor fire pit, built-in grilling station, and private dock make the most of life on the water. The spacious floor plan features a grand living room upon entry, adjacent dining room, a generous kitchen enhanced by Sub zero and Viking appliances, two stately gas fireplaces, bonus room, bunk room, three-car garage, and dedicated golf cart bay. The quality of construction does not go unnoticed with solid wood doors, plantation shutters, wide-planked hardwood floors, elevated lighting, and built-in features throughout. Then there is Wexford itself. Boasting a newly redesigned clubhouse with indoor/outdoor dining, community pool, exceptional Arnold Palmer Signature golf, active tennis community, pickle ball, a private marina, and the signature lock-controlled 37 acre inland harbour. The community truly is unlike anything else on Hilton Head Island and for someone looking for harborfront living within Wexford, there is only ONE.

20 Castlebridge Court, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$575,000

3 Beds ⋅ 2 Baths ⋅ 1,600 SqFt. ⋅ HILTONHEAD-512034 MLS

Ready for the beach? This beautifully updated 3-bedroom, 2-bath Seascape Villa offers the space, location, and easy coastal lifestyle that make South Forest Beach such a favorite. The bright main level features an open living and dining area with updated flooring and beadboard ceilings, a renovated kitchen with crisp quartz counters, coastal cabinetry and backsplash as well as SS appliances. A private deck with personal grill makes for perfect outdoor dining or relaxing. Upstairs, three bedrooms provide plenty of room for family and guests, including a spacious primary bedroom with sliding doors opening to its own covered balcony overlooking the palms. Both baths have been nicely updated, and the villa is offered fully furnished with attractive coastal furnishings and décor. Recent improvements make ownership even easier, including a new HVAC (2025), hot water heater and refrigerator (2024), plus a brand-new dishwasher, washing machine, dryer, and grill. Best of all, Hilton Head's beautiful beaches are just across the street, with Seascape's cabana making beach days especially easy. The community also offers two swimming pools tucked among the trees, plus Celebration Park just a short walk/ bike rise away as well as Coligny's restaurants, shopping, entertainment, and miles of leisure paths nearby. 3031 Seascape is ready to enjoy from day one-whether as a Hilton Head getaway, second home, or vacation rental investment.

42 S Forest Beach Drive Unit 3031, Hilton Head Island

Listing courtesy of Keller Williams Realty.

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