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

$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.

26 Peregrine Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$829,000

2 Beds ⋅ 2 Baths ⋅ 1,473 SqFt. ⋅ HILTONHEAD-511551 MLS

Move right into this beautifully furnished townhome featuring soaring ceilings, expansive windows, and picturesque golf course views. The spacious floor plan offers two bedrooms, two bathrooms, and a versatile loft that's perfect for a home office, media room, or additional guest accommodations. Located within the highly sought-after Palmetto Dunes Oceanfront Resort, you'll enjoy convenient access to the community pool, Fazio Golf Course Clubhouse, beach, tennis and pickleball facilities, kayak and bike rentals, restaurants, and the General Store. Whether you're searching for a primary residence, vacation retreat, or investment property, this turnkey villa offers outstanding short-term rental potential in one of Hilton Head Island's premier resort communities, making it an excellent opportunity to generate rental income while enjoying the Lowcountry lifestyle.

59 Carnoustie Road Unit 273, Hilton Head Island

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

$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.

$659,000

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

Don't miss this spacious 5-bedroom Hilton Head Island home with NO HOA fees and a private wooded backyard oasis. Ideally located on the island's desirable north end, you'll enjoy easy access to shopping, Skull Creek waterfront restaurants, Cross Island Parkway, Bluffton, the south end of Hilton Head, and can walk to the school complex and Hilton Head Island Recreation Center. The flexible floor plan features a first-floor bedroom, four additional bedrooms upstairs, plus a dedicated office. Welcoming foyer, formal dining room, expansive great room, eat-in kitchen (newer appliances), abundant storage, luxury vinyl plank flooring throughout, and an attached 2-car garage. Relax or entertain on the large deck overlooking the peaceful backyard complete with a Tiki hut and fire pit. New HVAC (2022). A rare combination of space, location, privacy, and freedom without HOA restrictions.

20 Hanahan Lane, Hilton Head Island

Listing courtesy of The Cobb Group brokered by eXp Realty.

$299,999

2 Beds ⋅ 3 Baths ⋅ 1,025 SqFt. ⋅ HILTONHEAD-511726 MLS

Welcome to this beautifully renovated 2-bedroom, 2.5-bath villa in Woodlake on Hilton Head Island. Peacefully tucked away with a serene lagoon view, this move-in-ready condo has been completely updated with a fresh, modern feel and thoughtful finishes throughout. The renovated kitchen and bathrooms complement the bright and inviting living spaces, creating a comfortable setting to relax or entertain. Both bedrooms offer comfortable private retreats, making this villa a great fit for a full-time residence, second home, or investment property. Enjoy the peaceful setting while still being just minutes from Hilton Head's beaches, restaurants, shopping, and everything the island has to offer. With its peaceful setting, extensive renovations, and convenient island location, this Woodlake villa is one you won't want to miss.

96 Mathews Drive Unit 142, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$1,695,000

4 Beds ⋅ 4 Baths ⋅ 3,374 SqFt. ⋅ HILTONHEAD-511697 MLS

Extremely rare opportunity! No expense spared in this 100% remodeled luxury penthouse villa with sweeping Skull Creek & ICW views. Top of the line, curated finishes by award winning design team throughout including wide plank maple flooring, soaring smooth ceilings, built-ins & millwork by master craftsmen, walls of windows & private terraces to view, high end designer fixtures, hardware, window treatments, wall & door coverings (MDF panels, polished stainless steel, leathered, etc.), lighting (crystal waterfall & raindrop chandeliers, sconces, pendant, niche, accent, recessed LED), stainless steel & glass staircase railings, dramatic floor to ceiling fireplace w/ herringbone tile surround, ultra custom cabinetry, limestone & quartz counters, acid etched mirrored backsplash, 800 series Bosch & Fisher-Paykel appliances, dual Fagor wine coolers, tankless water heater, floating vanities, glass & tile surround showers, wall-mounted fixtures, integrated Alexa system & built-in speakers, etc. Thoughtfully designed floor plan for living and entertaining includes first floor Chef's peninsula kitchen & breakfast bar open to spacious dining area, handsome den w/wet bar, awe-inspiring great room & water view sitting area, lavish primary suite with stunning bath, guest BR & bath + laundry room. 2nd floor offers game area, media area, office nook, ensuite BR's 3 & 4 with well-appointed baths + storage & mechanical access. A stunning transformation with a breathtaking locale... All with covered parking, large storage unit & private complex pool and cabana. And just down the street from CCHH, waterfront dining & entertainment + Spring Lake pool complex, Dolphin Head Recreational Area & recently renourished Pine Island Beach Park.

4 Village North Drive Unit 43, Hilton Head Island

Listing courtesy of Charter One Realty.

$420,000

2 Beds ⋅ 2 Baths ⋅ 1,022 SqFt. ⋅ HILTONHEAD-511716 MLS

This rarely available and family owned, never rented Stones Throw villa is tucked beneath a canopy of gorgeous live oak trees. The property has been well maintained and features tile flooring on the main level, an updated kitchen including granite countertops and smooth ceilings. Upstairs offers 2 spacious bedrooms and a recently updated bathroom with walk -in shower. Owners and guests can relax under the shade of the trees at the community pool or take a quick 5 minute walk to Folly Field Beach. This move in ready coastal retreat, sold fully furnished, makes everyday feel like a vacation!

43 Folly Field Road Unit 42, Hilton Head Island

Listing courtesy of Meybohm Real Estate.

$125,000

1 Baths ⋅ 260 SqFt. ⋅ HILTONHEAD-511686 MLS

This south end studio is in the woodhaven complex that has a great pool, and very easy to bike or walk to the beach. Woodhaven complex is installing brand new metal siding and roofs confirm with office manager.

101 Woodhaven Drive Unit 33, Hilton Head Island

Listing courtesy of Realty One Group - Lowcountry.

$665,000

2 Beds ⋅ 2 Baths ⋅ 1,279 SqFt. ⋅ HILTONHEAD-511624 MLS

RARE OPPORTUNITY! Upgrades Upgrades Upgrades This villa is the perfect luxurious second home from penthouse perch across the street from the beach and Tiki Hut with Celebration Park literally next door! Forest Beach Villa first class amenities include pool, tennis, pickleball, turtle filled lagoons and garage parking. Monthly fee is $541 and includes water, cable, pest, trash and maintenance. Annual exterior insurance is $2184. Take advantage of voluntary POA fee of $125 annually! This property is known for it's lower fees and great location to the beach This is a RARE and Best low risk rental winner! Ask agent for income details. Proforma at $53,000. Low regime fees, close to the beach. It doesn't get any better in this price range! This is a home run investment! Motivated Sellers! Don't miss out and Don't Feed the Alligators!

10 S Forest Beach Drive Unit 412, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS 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.

$1,195,000

3 Beds ⋅ 4 Baths ⋅ 2,772 SqFt. ⋅ HILTONHEAD-511567 MLS

Welcome to Windmill Harbour, one of Hilton Head Island's premier gated waterfront communities. This beautifully maintained 3-bedroom, 3.5-bath home offers the perfect blend of Lowcountry charm, comfort, and functionality. The thoughtfully designed floor plan features spacious living areas filled with natural light, creating an inviting atmosphere for both everyday living and entertaining. Enjoy multiple outdoor living spaces, including front and rear balconies and a private deck, all perfectly positioned to take in breathtaking Intracoastal Waterway and serene marsh views. Whether you're enjoying your morning coffee or unwinding at sunset, the picturesque Lowcountry scenery provides an ever-changing backdrop. Each bedroom offers privacy and comfort, making the home ideal for family and guests alike. Residents of Windmill Harbour enjoy access to the world-renowned lock-controlled marina, the South Carolina Yacht Club, scenic walking paths, and beautifully landscaped grounds. Conveniently located just minutes from Hilton Head's beaches, championship golf, dining, and shopping, this exceptional property offers the perfect combination of waterfront beauty, luxury, and the unmatched Lowcountry lifestyle.

135 Harbour Passage, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,700,000

4 Beds ⋅ 3 Baths ⋅ 2,015 SqFt. ⋅ HILTONHEAD-511511 MLS

Location is everything! This ocean-oriented, four-bedroom, 3.5-bath condominium is just steps from the Atlantic Ocean and all the amenities of South Beach Marina Village in Sea Pines. Ideally located beside the new community pool, the residence features a private rear deck and an upstairs deck off the primary bedroom. Enjoy easy access to the beach, bike paths, pickleball, shops, restaurants, and entertainment. Start making your Hilton Head memories today!

225 S Sea Pines Drive Unit 1401, Hilton Head Island

Listing courtesy of Keller Williams Realty.

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