Hilton Head Island Homes with Two Story Style

Welcome to Hilton Head Island, South Carolina, a stunning coastal paradise nestled in Beaufort County. Renowned for its pristine beaches, lush landscapes, and vibrant community, Hilton Head is the perfect blend of relaxation and adventure. With over 12 miles of sandy shores, this island is a haven for sun-seekers, nature enthusiasts, and golf aficionados alike. The area boasts an impressive array of outdoor activities, from world-class golfing at renowned courses to kayaking through serene marshes, ensuring that there’s something for everyone.

One of the appealing aspects of Hilton Head Island is its diverse real estate market, particularly the charming two-story homes that dot the landscape. These residences often feature spacious floor plans, allowing for both comfort and functionality. With high ceilings and large windows, many two-story homes offer breathtaking views of the surrounding scenery, from lush gardens to picturesque golf courses. Whether you’re looking for a family retreat or a vacation getaway, these homes provide ample space for entertaining guests or simply enjoying the tranquil island lifestyle.

Living in Hilton Head Island means embracing a vibrant community culture, with delightful dining options, boutique shopping, and year-round events that celebrate the island’s rich heritage. The warm, welcoming atmosphere coupled with the beauty of the natural surroundings makes Hilton Head Island not just a place to live, but a lifestyle to cherish. Explore the charm of two-story homes in this idyllic coastal haven, where every day feels like a vacation.

Newest Hilton Head Island Homes with Two Story Style

$1,039,000

3 Beds ⋅ 2 Baths ⋅ 1,822 SqFt. ⋅ HILTONHEAD-512792 MLS

Experience breathtaking sunsets, panoramic marsh and deepwater views, and exceptional outdoor living from this one-of-a-kind custom home in Cedar Woods. The moment you take in the drop-dead gorgeous 180-degree views of the marsh and Broad Creek, you'll understand what makes this property truly special.Completely renovated by the architect/owner in 2013 and bathrooms recently renovated, the home was thoughtfully redesigned to maximize both comfort and its incredible Lowcountry setting. Beautiful heart pine floors add warmth and character throughout, while the renovation included an inviting sunroom, expanded primary suite with large walk in closet system.Step outside and enjoy your own private Lowcountry retreat, launch a kayak and explore the surrounding waterways, watch local wildlife from your backyard, or simply settle in for spectacular sunsets over the marsh and Broad Creek. For the hobbyist or craftsman, the property also features a woodworker's dream workshop in addition to a two-car garage.Cedar Woods is one of Hilton Head Island's hidden gems, offering a peaceful setting while keeping you remarkably close to everything the island has to offer. Coligny Beach, shopping, groceries, pharmacies, favorite local restaurants, and convenient access to the Cross Island Parkway are all approximately five minutes away.

16 Song Sparrow Lane, Hilton Head Island

Listing courtesy of Better Homes and Gardens Real Estate Paracle.

$3,890,000

5 Beds ⋅ 5 Baths ⋅ 4,796 SqFt. ⋅ HILTONHEAD-512833 MLS

Welcome to 14 Castlebridge Court, a spectacular waterfront residence transformed into a modern masterpiece. Recently remodeled with exceptional craftsmanship and designer finishes throughout, this stunning 5-bedroom, 4 full and 1 half bath home offers sophisticated Lowcountry living with breathtaking harbour views and a private dock.A dramatic contemporary entry opens to an expansive great room featuring soaring ceilings, designer lighting, a stunning statement electric fireplace, walls of glass, and oversized sliding doors that seamlessly blend indoor and outdoor living. The open-concept design flows effortlessly into the gourmet kitchen, formal dining room, and casual dining area, all perfectly positioned to take full advantage of the picturesque waterfront setting.The luxurious first-floor primary suite is a private retreat, complete with a spa-inspired bath featuring a soaking tub, oversized shower, dual walk-in closets, and a private laundry room. A spacious home office and powder room complete the main level.Upstairs, four generously sized guest suites provide exceptional accommodations. Two bedrooms share a beautifully appointed bath, while the remaining two enjoy private ensuite baths. All feature generous closets and designer finishes, with two guest suites opening onto private decks overlooking the harbour. An open loft overlooks the great room below while showcasing stunning waterfront views.The lower level offers incredible flexibility, with space for three cars and a golf cart, and currently serves as an impressive home gym and bonus recreation room. A convenient three-stop elevator provides effortless access to every level.Designed for both entertaining and relaxation, the outdoor living spaces are equally impressive, featuring waterfront decks, a pool, a private dock, and spectacular harbour views. Wexford offers a truly exceptional private club lifestyle, with an Arnold Palmer Signature golf course, tennis, pickleball, croquet, pool complex, private harbour, fire pit, and the newly opened Clubhouse and Harbour Center. With a vibrant social calendar and one of Hilton Head Island's most distinctive marina settings, Wexford provides an unparalleled combination of recreation, community, and waterfront living.

14 Castlebridge Court, Hilton Head Island

Listing courtesy of Charter One Realty.

$2,200,000

4 Beds ⋅ 3 Baths ⋅ 2,484 SqFt. ⋅ HILTONHEAD-512850 MLS

Beautifully renovated and fully updated 4 bed/3 bath home just minutes from the beach! This stunning property has been thoughtfully transformed from top to bottom, offering stylish finishes, modern upgrades, and all new furnishings inside and out. The freshly painted interior features new doors & hardware, ceiling fans, lighting, and fixtures throughout. The completely renovated kitchen showcases new cabinetry and appliances, while all three bathrooms have been beautifully updated, including a reconfigured primary bath designed for improved functionality and style. Major improvements include new plumbing, ductwork, roof, and gutter systems, providing peace of mind for years to come. Outside, enjoy a serene private pool area overlooking a lagoon, with updated landscaping and pool surrounds creating the perfect setting for relaxing or entertaining. With its exceptional location near the beach and extensive renovations inside and out, this turnkey home is ready to be enjoyed!

15 Wagon Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

$1,249,000

4 Beds ⋅ 5 Baths ⋅ 3,048 SqFt. ⋅ HILTONHEAD-512841 MLS

Set right along the 18th fairway of the Country Club of Hilton Head, 55 Santa Maria Drive delivers the double fairway view that makes a golf course home worth having. The Raintree floor plan gives each of its four bedrooms real separation, with en-suite baths throughout.Inside, tall vaulted ceilings and walls of windows pull the fairway view into the living room, where a fireplace anchors the space without competing with the light. A separate family room, with a fireplace of its own, opens to the kitchen and breakfast nook, distinct from the formal living area. The fourth bedroom sits over the garage, set apart enough to work well as a guest suite, and the garage below leaves room for a dedicated work area alongside the vehicles.Outside, a fenced pool sits behind a nicely grassed backyard, screened by privacy vegetation from everything but the fairway. The outdoor grill and patio make the space livable, not just decorative.The Country Club of Hilton Head is a short stroll away. Whether that means a quick nine or lunch at the clubhouse, the walk is part of what makes this address work.

55 Santa Maria Drive, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$770,000

3 Beds ⋅ 3 Baths ⋅ 2,020 SqFt. ⋅ HILTONHEAD-512727 MLS

Welcome to Point Comfort Woods, a desirable neighborhood for the boating enthusiast! Conveniently located near Palmetto Bay Marina and the Cross Island Parkway, this 3-bedroom, 3-bath home offers an oversized driveway with room to park a boat and trailer plus there are no HOA fees! The flexible floor plan provides plenty of space to enjoy the Lowcountry lifestyle. The living room features a brick, wood-burning fireplace, while the kitchen opens to the dining room and overlooks an additional living area, creating a welcoming space for everyday living and entertaining. The primary bedroom with ensuite bath and an additional full bath are located on the main floor. Upstairs are two bedrooms, one with a balcony overlooking the backyard, and a shared full bath. Recent updates include the kitchen and bathrooms, new tile in the laundry room, a large rear deck, LVP flooring and subfloor throughout, new chandeliers, new attic fan, new HVAC ducts under the house, new joists, and a new concrete footer. Additional storage is conveniently located under the stairs. With its boat-friendly features, thoughtful updates, and convenient location near the Cross Island Parkway, this home is ready to welcome you to the Lowcountry!

16 Kingbird Lane, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$674,000

2 Beds ⋅ 3 Baths ⋅ 1,432 SqFt. ⋅ HILTONHEAD-512810 MLS

Welcome to this beautifully furnished 2-bedroom, 2-bath villa in the highly sought-after Evian community of Shipyard Plantation. Offering 1,431 square feet of stylish living space, this beautifully updated villa features an open-concept floor plan enhanced by a dramatic skylight that fills the home with natural light. Luxury vinyl plank flooring flows throughout, and the updated bathrooms provide a fresh, modern touch. Enjoy serene golf course views from the private patio--an ideal setting for morning coffee or evening relaxation. Sold beautifully furnished, this turnkey property is ready for you to enjoy immediately or begin generating rental income. Private Beach access at Sonesta 1/2 mile via car or Bicycle Path.

70 Shipyard Drive Unit 109, Hilton Head Island

Listing courtesy of Chosen Realty LLC.

$522,500

2 Beds ⋅ 3 Baths ⋅ 980 SqFt. ⋅ HILTONHEAD-512795 MLS

Charming and low-maintenance, this 2-bedroom, 2.5-bath villa offers 980 square feet of comfortable coastal living just a 5-minute walk to the beach. Ideal as a primary residence, second home, or turnkey rental investment, this well-appointed unit combines convenience with island lifestyle.Enjoy easy access to a community pool right on-site, perfect for relaxing between beach days. The location can't be beat, just minutes from Coligny Plaza's shops, dining, and entertainment, and close to Celebration Park's green space, and community events. Whether you're heading to the sand, grabbing dinner out, or enjoying a quiet evening at home, everything you need is within easy reach.With two spacious bedrooms and 2.5 updated bathrooms, this layout works well for families, couples, or investors looking to capitalize on Hilton Head's strong vacation rental demand. Don't miss this opportunity to own a slice of island living in one of Hilton Head's most walkable, amenity-rich locations.

5 Tanglewood Drive Unit 604, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$729,000

4 Beds ⋅ 3 Baths ⋅ 2,065 SqFt. ⋅ HILTONHEAD-512779 MLS

A GEM! Fabulous, spacious and wonderfully upgraded with such a clever use of space! Four bedrooms OR 3 with study/office, delightful kitchen with a WOW (who knew) butler's pantry, super laundry and drop zone, spacious bedrooms with updated bathrooms, and large, open and light living areas with views onto a serene natural lagoon from screened in porch and deck! This home is a treat!!! On a quiet cul-de-sac in stunningly beautiful Moss Creek with outstanding amenities and a newly renovated Club House/restaurant, its a MUST SEE! PHOTOS COMING SOON!

42 Wax Myrtle Court, Hilton Head Island

Listing courtesy of Renew Realty, LLC.

$490,000

2 Beds ⋅ 2 Baths ⋅ 1,281 SqFt. ⋅ HILTONHEAD-512155 MLS

Enjoy easy island living in this 2BR/2BA second-floor residence in the gated community of The Preserve at Indigo Run. With no neighbors above, this home offers an added level of privacy and a quiet setting. The interior features wood flooring, updated appliances, a convenient coffee bar, pantry storage, and finished closets. Recent improvements include brand new carpet in the bedrooms, an updated main bathroom in 2025 and a screened-in porch completed the same year, creating a comfortable outdoor living space to enjoy throughout the seasons. Residents of The Preserve have access to a community pool, fitness center, tennis courts, and clubhouse. Located on Hilton Head's desirable North End, you're convenient to the beach, restaurants, shopping, and other island amenities. Short-term rentals are not permitted, making this an appealing option for a primary home, second residence, or long-term rental property.

4 Indigo Run Drive Unit 3810, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$545,000

2 Beds ⋅ 2 Baths ⋅ 1,177 SqFt. ⋅ HILTONHEAD-512749 MLS

Schedule a showing today to view 1859 St Andrew Commons Villa! Bright and sunny, fully furnished 2BD/2BA second-floor townhouse, located within Palmetto Dunes. The villa features vaulted ceilings, abundant natural light, a split-bedroom floor plan, and a spacious sunken living room. The updated kitchen provides ample cabinet and counter space. Sold furnished with a full-size washer/dryer, refrigerator, stovetop, window treatments, and ceiling fans. Private balcony and generous storage for beach gear, bicycles, golf clubs, and seasonal items. Community pool and entertainment area are conveniently located nearby. Palmetto Dunes offers beach access, bike paths, golf, tennis, pickleball, kayaking, and dining. Excellent option for a primary residence, second home, or investment property.

20 Queens Folly Road Unit 1859, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$950,000

4 Beds ⋅ 3 Baths ⋅ 2,201 SqFt. ⋅ HILTONHEAD-512744 MLS

Don't miss this rare 4-bedroom home in the quiet Club Course section of Sea Pines, ideally positioned along the par-5 2nd hole of the Sea Pines Country Club golf course. Renovated in 2021, this turnkey property offers an updated, easy-living floor plan with beautiful finishes throughout.The kitchen was fully remodeled with updated cabinetry, countertops, and appliances, while the bathrooms were also refreshed and the hardwood flooring refinished throughout. The open floor plan connects the living area to the dining space and Carolina room, with a classic brick fireplace anchoring the main living room.Step outside to a spacious back deck overlooking the golf course, creating a peaceful setting for relaxing or entertaining. Additional updates include a newer HVAC system replaced in 2021.Whether you're looking for a fantastic rental property, second home, or low-maintenance full-time residence, this 4-bedroom Sea Pines home offers a rare combination of space, location, and thoughtful updates. Enjoy all that Sea Pines has to offer, including miles of leisure trails, beautiful beaches, world-class golf, tennis and pickleball, Harbour Town, South Beach Marina, dining, shopping, and endless opportunities to enjoy the Lowcountry lifestyle.

150 Otter Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$975,000

3 Beds ⋅ 3 Baths ⋅ 2,443 SqFt. ⋅ HILTONHEAD-512730 MLS

Discover coastal luxury and investment potential in this former model home! With 3 bedrooms, 2.5 baths, and 2,443 sqft of refined living space, plus over 1,200 sqft of unfinished garage space, this home is perfect for entertaining. Highlights include an open-concept kitchen/dining/living, two large screened-in decks, backyard w/ fire pit - ready for a pool. The owner's suite offers a spa-like bath and custom walk-in closet, while the 3-stop elevator adds convenience. Short-term rentals allowed. Just a short walk to Fish Haul Beach! New community boardwalk direct to the beach just opened in July! Don't miss this one! Seller related to SCREA.

178 Mitchellville Road, Hilton Head Island

Listing courtesy of EXP Realty LLC.

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