Hilton Head Island Homes with Two Story Style

Welcome to the enchanting Hilton Head Island, a jewel nestled in Beaufort County, South Carolina. Known for its stunning beaches, lush landscapes, and a vibrant community, Hilton Head Island offers a lifestyle that seamlessly blends relaxation with adventure. With its temperate climate, residents enjoy year-round outdoor activities, from golfing on world-class courses to biking along scenic paths and indulging in water sports on the Atlantic Ocean.

One of the most appealing aspects of living on Hilton Head Island is the diverse array of housing options available, particularly the charming two-story homes that grace its neighborhoods. These residences are designed to provide ample space and comfort, making them ideal for families, retirees, or anyone seeking a bit more room to breathe. With their elegant architecture and thoughtful layouts, two-story homes often feature expansive living areas, gourmet kitchens, and serene master suites, allowing for both entertaining and relaxation.

Imagine waking up to the gentle sound of waves and enjoying your morning coffee on a spacious balcony. Many two-story homes here offer stunning views of the island's natural beauty, from serene marshlands to picturesque golf courses. The vibrant community surrounding these homes is filled with friendly neighbors, local shops, and delightful dining options, ensuring that you’ll always feel at home.

Whether you’re looking for a permanent residence or a vacation getaway, Hilton Head Island’s two-story homes provide the perfect blend of comfort, style, and coastal charm. Embrace the island lifestyle and discover your dream home in this idyllic paradise!

Newest Hilton Head Island Homes with Two Story Style

$759,900

2 Beds ⋅ 3 Baths ⋅ 1,289 SqFt. ⋅ HILTONHEAD-512915 MLS

This beautifully updated Water Oaks villa delivers the perfect blend of coastal comfort, modern finishes, and unbeatable walkability to the beach. Located in the heart of Palmetto Dunes, this 2BD retreat offers a bright, open layout, refreshed interiors, and easy access to world-class amenities - all just a short stroll from the beach and Dunes house. The main living area features abundant natural light, updated flooring, and a seamless flow to the dining space and renovated kitchen. Master bedroom located on the first floor and is generously sized. Beautiful golf view from your back patio. Water Oaks is known for peaceful lagoons, winding bike paths, and a community pool. With walk-to-the-beach convenience, strong rental history, and modern updates throughout, this villa is an ideal choice for personal use, investment, or a lock-and-leave coastal getaway. Over $32,000 rental income on the books for 2026. Over $22,000 rental income already for 2027, includes snowbirds!

21 Haul Away Unit 24, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$1,100,000

3 Beds ⋅ 4 Baths ⋅ 3,204 SqFt. ⋅ HILTONHEAD-512855 MLS

This 3BR + office, 3.5BA home has the space and flexibility you are looking for, with tons of natural light and a floor plan that gives everyone room to spread out. Cathedral ceilings, exposed beams, custom built-ins, and smooth ceilings bring character to the main living spaces, while LVP flooring throughout keeps everyday living easy. The eat-in kitchen features newer stainless-steel appliances and plenty of room to gather, with both a living room and separate family room offering options for entertaining, relaxing, or simply finding a quiet space of your own. A dedicated office makes working from home easy without sacrificing a bedroom. Out back, a large deck overlooks the golf course, the perfect spot for morning coffee, dinner outside, or simply enjoying the view. Add a two-car garage, a great location, and a new roof in 2026, and many of the things buyers are asking for are already here.

13 Pheasant Run, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$1,040,000

3 Beds ⋅ 3 Baths ⋅ 1,750 SqFt. ⋅ HILTONHEAD-512911 MLS

Refined coastal living in Sea Pines! Beautifully updated and fully furnished, this exceptional 3BR/3BA Heritage Villa enjoys a coveted setting overlooking the 1st and 9th holes of the Harbour Town Golf Links. Thoughtfully renovated with a sophisticated aesthetic, this villa features all new appliances, fresh paint, new doors, carpet, lighting, updated baths and coastal shiplap detailing throughout the vaulted living and dining areas. The well-appointed floor plan offers a main-level bedroom and full bath, plus two spacious upstairs bedrooms with private en-suite baths. The open living and dining areas create an inviting setting for entertaining, while the expansive back deck provides a tranquil vantage point overlooking the golf course and mature live oaks.Ideally positioned within easy walking distance of the Harbour Town Clubhouse, this turnkey property offers exceptional convenience within Sea Pines. Enjoy nearby Harbour Town Marina, dining, shopping, world-class golf, tennis, miles of leisure trails, and the Sea Pines Beach Club, less than two miles away with trolley access. A rare opportunity to own a beautifully appointed retreat in one of Sea Pines' most desirable locations.

107 Lighthouse Road Unit 2284, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$515,000

2 Beds ⋅ 2 Baths ⋅ 980 SqFt. ⋅ HILTONHEAD-512748 MLS

FULLY FURNISHED and tucked into the Tanglewood Villas building closest to the beach path, this beautifully updated 2-bedroom townhouse captures the easygoing Forest Beach lifestyle from the moment you arrive ... Step inside to a bright, relaxed coastal interior where an OPEN KITCHEN DESIGN creates a natural gathering space, complemented by elegant MARBLE surfaces, rich HARDWOOD FLOORS, crisp SHIPLAP walls, and SMOOTH CEILINGS that give the home a clean, finished feel ... Just beyond the living space, the private deck overlooks the community pool, framed by mature live oaks and lush Lowcountry landscaping - the perfect setting for morning coffee, an afternoon break after the beach, or a quiet evening under the trees ... Thoughtful updates continue throughout with a Trane HVAC system, Rheem water heater, full-size washer and dryer, generous floored attic storage, and custom storage tucked beneath the stairs ... Outside, Tanglewood Villas offers a gated community pool, grilling areas, towering live oaks, palmettos, and tropical landscaping that gives the entire setting a true island feel ... Best of all, you can leave the car behind and stroll to the BEACH, Coligny Plaza, Lowcountry Celebration Park, the Tiki Hut, Pool Bar Jim's, restaurants, shops, walking paths, playgrounds, entertainment, and some of the most loved spots in South Forest Beach ... Offered in pristine, TURNKEY condition, this is the kind of Hilton Head property that works equally well as a SECOND HOME, VACATION RETREAT, or SHORT-TERM RENTAL - a comfortable coastal escape where the beach, pool, dining, and entertainment are all right outside your door.

1 Tanglewood Drive Unit 504, Hilton Head Island

Listing courtesy of Real Broker, LLC.

$1,299,000

3 Beds ⋅ 3 Baths ⋅ 1,652 SqFt. ⋅ HILTONHEAD-512787 MLS

A sophisticated top-floor retreat in the heart of Harbour Town, where direct marina, lighthouse, and Calibogue Sound views define every level. This 3-bedroom, 3-bath, two-story penthouse offers a rare vantage point above Sea Pines' most storied address - steps from the shops, restaurants, and marina energy of Harbour Town, yet elevated well above it. The two-story layout gives the living space real scale and separation while keeping the lighthouse and sound as the constant backdrop. Move-in ready as a personal getaway, or well-suited as a short-term rental - direct marina and lighthouse views like this are consistently the strongest driver of rental demand and rate in Harbour Town. This villa is sold furnished. A location, elevation, and view combination that rarely comes to market. Schedule a private showing.

18 Lighthouse Lane Unit 1043, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$599,000

2 Beds ⋅ 2 Baths ⋅ 1,203 SqFt. ⋅ HILTONHEAD-512893 MLS

Welcome to Sarah's Cottage at Bryant Park Cottages, a beautifully maintained detached home nestled in the heart of Mid-Island Hilton Head. Inspired by the renowned Ross Chapin neighborhood design, this charming community embraces "front porch" living, creating a warm and welcoming sense of connection. From the inviting front porch, enjoy tranquil views across the expansive community courtyard toward the community pool. Garden trails wind throughout the neighborhood, adding to the peaceful, walkable setting and inviting residents to slow down and enjoy the outdoors.Inside, thoughtful design and recent updates make this cottage truly move-in ready. The primary suite is conveniently located on the main level, while vaulted cathedral ceilings and skylights fill the living spaces with natural light. A gas fireplace creates a cozy focal point, complemented by built-in shelving that adds both character and functionality. The updated kitchen features all-new stainless steel appliances, while LVP flooring extends throughout the home. The entire interior has also been recently painted, offering a fresh, cohesive feel.The private detached garage provides secure parking and valuable additional storage, with convenient pull-down attic stairs leading to the attic space. A new HVAC system adds to the home's comfort and peace of mind.Bryant Park Cottages offers a unique blend of neighborhood charm, community amenities, and low-maintenance island living. With its inviting architecture, generous courtyard, pool, garden trails, and welcoming front-porch lifestyle, this is a special place to call home. Conveniently located near the Cross Island Parkway, Sarah's Cottage provides easy access to both sides of Hilton Head Island, making trips to the beaches, shopping, dining, golf, and other island amenities a breeze. Come experience the charm of cottage living in one of Mid-Island's most distinctive communities.

625 Spanish Wells Road Unit Unit 6, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$1,425,000

5 Beds ⋅ 3 Baths ⋅ 3,235 SqFt. ⋅ HILTONHEAD-512885 MLS

Experience the ultimate Lowcountry lifestyle in this impeccably maintained home located in the sought-after Hilton Head Plantation. This stunning residence offers tranquil golf and lagoon views, providing a peaceful backdrop for both everyday living and entertaining. The gourmet kitchen features quartz countertops, a large center island, a spacious pantry, and premium stainless steel appliances, all flowing seamlessly into the formal dining room and a grand living area defined by soaring cathedral ceilings and a cozy gas fireplace. A bright, airy Carolina room extends the living space, leading out to a private paver patio and a heated saltwater pool. The main-level primary suite is a true retreat, boasting a spa-like ensuite bath, two oversized walk-in closets, and direct access to a private screened porch. There are also two additional spacious bedrooms on the first floor. Upstairs, a versatile loft serves as an ideal home office or media area, accompanied by two spacious guest bedrooms that share a full bath and ample storage. Additional highlights include professional landscaping, a generous driveway, and an unbeatable location just a three-minute stroll from the Port Royal Sound or a five-minute bike ride to Dolphin Head Beach. Residents of Hilton Head Plantation enjoy world-class gated amenities, including private beach access, a marina, tennis and pickleball courts, leisure trails, bocce courts and a resort-style community pool with a lazy river. This home perfectly balances comfort, privacy, and the quintessential Hilton Head Island experience.

24 Angel Wing Drive, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$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.

$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.

$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

Beautifully remodeled and furnished 2BR/2.5BA Evian villa in Shipyard with exceptional views and updates throughout. Enjoy direct views of Shipyard Golf Club's Brigantine #1 from the rear and the main Evian lagoon with picturesque gazebo just across the street. Features include LVP flooring, remodeled kitchen cabinetry, smooth ceilings, updated baths, open-concept living, vaulted ceilings, skylight, abundant natural light and a built-in electric fireplace with flexibility for future conversion. Relax on the private patio and enjoy Evian's pool, tennis and pickleball courts, scenic lagoon and gazebo. Just 0.7 miles to Sonesta Resort and Shipyard's private beach access, plus convenient biking paths, golf, dining and shopping. Move-in ready as a primary home, second home or vacation retreat.

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.

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