Hilton Head Island Homes with Two Story Architectural Style

Welcome to Hilton Head Island, South Carolina, a stunning coastal gem nestled in Beaufort County. Renowned for its pristine beaches, lush landscapes, and vibrant community, Hilton Head Island offers an idyllic lifestyle that perfectly blends relaxation and recreation. With its mild climate, residents enjoy year-round outdoor activities, from world-class golf courses and tennis facilities to scenic bike trails and nature reserves.

One of the architectural styles that beautifully complements the island's charm is the two-story home. These residences not only provide ample living space but also capture the essence of coastal living with their open layouts and expansive views. Imagine waking up in a spacious master suite on the upper level, where you can sip your morning coffee while gazing out at the shimmering Atlantic Ocean or the lush greenery of your backyard. The two-story design allows for a seamless flow between indoor and outdoor living, perfect for entertaining friends and family or simply enjoying the serene surroundings.

In Hilton Head, two-story homes often feature expansive decks and balconies, ideal for soaking up the sun or hosting evening gatherings under the stars. With many properties located just a stone's throw from the beach, residents can easily access the island's stunning shores, making every day feel like a vacation.

Whether you’re seeking a permanent residence or a vacation retreat, Hilton Head Island's two-story homes offer the perfect blend of luxury, comfort, and coastal charm. Discover your dream home in this enchanting paradise today!

Newest Hilton Head Island Homes with Two Story Architectural Style

$289,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512188 MLS

Turnkey and move-in ready, this beautifully renovated top-floor villa was fully updated and furnished in 2023, with fresh contemporary finishes throughout. Every surface, fixture, and furnishing is new, making this an effortless purchase for a primary residence, vacation retreat, or investment property. Just steps from Coligny Beach Park, the Children's Museum, and Celebration Park, with Coligny Plaza's restaurants, shops, and bike rentals around the corner. The Bank Beer Garden is one block away. Resort-style pool and tennis/pickleball courts are right outside your door. Unlike many units in this community, #D7 features an in-unit washer and dryer - a rare and highly practical convenience that adds real value for owners and renters alike. Add in the top-floor privacy, elevated light, and no upstairs neighbors, and this villa stands apart from everything else in the building. Whether you're looking for a personal escape or a high-performing short-term rental, this one checks every box.

104 Cordillo Parkway Unit D7, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$899,000

4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-512036 MLS

This stunning four-bedroom home located on a cul-de-sac street sits on a great lot with views of the Oyster Reef Golf Course. Even better, it's just around the corner from the access point for the Dolphin Head Bluff Path. This home boasts an incredible floor plan with two primary bedroom suites, one downstairs and one upstairs. You will enjoy the renovated kitchen with stainless steel appliances, custom cabinets, all open to the main living areas. There is so much natural light throughout and tons of storage space. This home has beautiful crown moldings and great ceiling height throughout.Living in the Low Country means outdoor living space is a must, and this has an incredible back yard/patio with exceptional golf views of #8 of the Oyster Reef Course. Updated bathrooms recently painted and the roof was replaced a year ago, you can move in worry free. Hilton Head Plantation has low fees and incredible amenities: Golfers have four championship 18-hole courses within the community (Bear Creek, Dolphin Head, Oyster Reef and the Country Club of Hilton Head). Private beach lovers enjoy a private shoreline along the Port Royal Sound in Dolphin Head Park. HHP has a resort-style zero-entry pool with lazy river and splash pad anchors Spring Lake Recreation Area. There's even a Marina just inside the community and for garden lovers, Seabrook Farms is a place where residents can rent beds to grow vegetables, fruits, and flowers.

16 Yellow Rail Lane, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$899,000

4 Beds ⋅ 5 Baths ⋅ HILTONHEAD-511354 MLS

Experience spacious island living in this beautifully updated home, ideally situated within a sought-after gated golf community. Overlooking the tranquil 12th green of the Arthur Hills course, the backyard offers a peaceful setting to relax, entertain, or simply enjoy the view. Inside, soaring two-story ceilings and an inviting fireplace create a warm yet dramatic first impression, while the open-concept floor plan provides effortless flow for everyday living and gatherings. The highly desirable layout features the primary suite on the main level, an additional bedroom on the first floor which has versatile use, and two other bedrooms upstairs, all generously sized, all with ensuite. With recent exterior paint, a newer roof, HVAC, and other significant updates, this home is move-in ready and designed for years of worry-free enjoyment. Offering one of the largest sq ft four-bedrooms currently available on the island under $1 million, this is a rare opportunity to own exceptional space, value, and lifestyle in one remarkable property.

17 Tucker Ridge Court, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$673,500

3 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511997 MLS

Opportunity to own a beautifully updated 3-bedroom townhouse in Hilton Head Plantation for under $700,000. This is one of those homes you truly have to see to appreciate. Stunning renovated kitchen from top to bottom has it all, while the great room features a custom wood-trim ceiling that adds warmth and character. LVP extends throughout the first floor. The bathrooms have been thoughtfully updated with today's finishes. The versatile floor plan includes a 1st floor bedroom or den along with two 2nd floor bedrooms. Outside, you'll find a generously sized fenced front service yard that can also be used as a dog run. The expansive private rear stone patio, complete with a fire pit, creates a peaceful retreat for relaxing alone or with family and friends. Storage is another feature, with 2 separate storage areas--one is exceptionally large and could be a workshop. New Anderson sliding doors add both beauty and energy efficiency. This townhome checks all the boxes, making it a great property for a primary residence, 2nd home, starter home, or long-term rental. It is a low-maintenance lifestyle home, allowing you to enjoy all Hilton Head has to offer. As the saying goes, "Don't judge a book by its cover." This home has been transformed with remarkable updates and is one you won't want to miss.

4 Honeysuckle Court, Hilton Head Island

Listing courtesy of Charter One Realty.

$7,399,500

5 Beds ⋅ 6 Baths ⋅ HILTONHEAD-511871 MLS

Welcome to 34 Ruddy Turnstone - a classic custom-built oceanfront home in Sea Pines designed by renowned Hilton Head architect Jakie Lee. Perfectly positioned on a large private homesite, this timeless residence showcases the charm, craftsmanship, and thoughtful design that define the finest Sea Pines properties. Exceptional quality is evident throughout with wide stairways, custom woodworking, soaring ceilings, and solid-core doors, all blending to create an atmosphere of relaxed yet refined coastal living. Designed for both comfort and entertainment, the home offers generous indoor and outdoor living spaces, including a heated pool and spa surrounded by lush privacy. The second level features the private Primary Suite with a sitting area, a spacious Great Room, Dining Room, and Eat-In Kitchen - all opening to an expansive IPE wood deck with elevated views overlooking the pool and the Atlantic Ocean. The entry level welcomes guests through a covered entrance into a dramatic foyer with high ceilings and access to the large Family Room complete with built-in beverage coolers and bar area. From here, enjoy seamless access to the covered porch, pool/spa and private beach path. Three Guest Bedrooms, each with their own Ensuite Bath, are also located on this level, along with an additional full bath and Laundry Room for added convenience. A fourth Guest Bedroom and full-size private Office with balcony occupy the mid-level, providing additional flexibility for family and guests. A newly installed elevator with service to all four levels, ensuring effortless enjoyment throughout the home. Thoughtfully designed and meticulously maintained by its original owners as a cherished second home, this exceptional oceanfront retreat offers the rare opportunity to enjoy a classic Sea Pines residence exactly as it is today - or reimagine and personalize it over time to create your own coastal legacy.

34 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$315,000

2 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512010 MLS

Located in the desirable Yacht Cove community, this beautifully updated villa offers peaceful lagoon views and a bright, open floor plan designed for comfortable island living. The updated kitchen features granite countertops, stainless steel appliances, and flows seamlessly into the dining and living areas, while second-floor laundry and thoughtful updates throughout make the home move-in ready. Residents enjoy access to a community pool and an exceptional mid-island location just minutes from Shelter Cove Harbour & Marina, offering waterfront dining, boutique shopping, kayaking, live entertainment, and summer fireworks. With Hilton Head Island's beaches, golf, tennis, and bike paths all just a short drive or ride away, this villa is an ideal primary residence or vacation retreat.

50 Yacht Cove Drive Unit 326, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$1,325,000

4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-511550 MLS

Set on more than 0.4 acres along a quiet private street in Hilton Head Plantation, this beautifully maintained 4-bedroom, 3.5-bath home offers a spacious floor plan, abundant natural light, and exceptional indoor-outdoor living. The welcoming foyer opens to generous living and dining areas, where large windows overlook the screened lanai and pool. The kitchen flows seamlessly into the family room and breakfast area, creating a comfortable gathering space for everyday living and entertaining. The spacious primary suite features a beautifully appointed bath with dual vanities, a walk-in shower, separate soaking tub, and a large walk-in closet. Two additional guest bedrooms provide privacy and comfort for family and visitors. A standout feature of the home is the expansive bonus room, complete with a wet bar, custom built-ins, and a full bath. Currently used as a bonus room, this flexible space serves as the home's fourth bedroom and is ideal for guests, a media room, or a private retreat. Step outside to the impressive screened lanai featuring a sparkling pool and generous covered seating area-the perfect place to relax, entertain, or enjoy Hilton Head's year-round outdoor lifestyle. The backyard offers a peaceful and private setting. Additional highlights include an oversized three-car garage, abundant storage, and a functional layout that is equally suited for a primary residence or second home. Located within the gates of Hilton Head Plantation, residents enjoy an outstanding array of amenities, including four championship golf courses, the Country Club of Hilton Head, Spring Lake Recreation Area, Dolphin Head Recreation Area, a full-service marina, tennis and pickleball courts, miles of leisure trails, a community pool, and 24-hour security-all just minutes from Hilton Head Island's beaches, shopping, and dining.

5 Royal James Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$609,000

2 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511985 MLS

Here's your opportunity to own a meticulously maintained villa in the heart of Shipyard that has been totally renovated and is TURN-KEY! Do not miss this chance to see this well cared for villa unit that has been used as a second home by current owner! There have been over 37k in recent renovations to bring in a nicely appointed kitchen with all new cabinets with quart countertops, sink/faucet and new microwave. This open galley kitchen is perfectly appointed and uses every inch wisely. Brand new pavers have been installed on both the oversized front porch entrance/service area and the spacious back patio! The bedrooms upstairs have cathedral ceilings and both bathrooms have been updated and are coastal chic! Each bedroom has a patio as another area to sit and relax and enjoy the beauty that Hilton Head has to offer. The primary bedroom has an oversized sliding glass door that provides a beautiful view of the Galleon golf course. The downstairs is an open concept and incorporates neutral 16 inch tiles throughout for easy wear.....the kitchen is also open to the living area and it's easy to stay connected to the visitors while the cook is in the kitchen. There is a full laundry room with extra space for well needed storage. Shipyard is a thriving and excellent plantation to enjoy all that is offered on Hilton Head Island. There are 3 nine hole golf courses, a restaurant and golf pro shoppe, Van Der Meer tennis facility and a newer beach club that offers storage underneath for those that are interested! The Shipmaster complex provides a spacious pool and tennis courts that are included in your regime fee. Shipyard has two separate entrances including one off of Highway 278 and the other on Pope Avenue which offers easy access to Coligny Plaza....considered by many to be the 'downtown' of HHI! This villa can be used as a primary, secondary or a rental property so it is very flexible...and animals are welcome for owners! Come see this villa TODAY! It won't last long!

63 Shipyard Drive Unit 704, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$665,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511940 MLS

Welcome to this beautifully reimagined 3-bedroom, 2.5-bath home in the desirable Tansyleaf community, where timeless Craftsman architecture meets today's modern comforts. Originally built in 2018 with an open-concept floor plan, this home has been extensively upgraded with high-end finishes, custom millwork, smart home features, and exceptional attention to detail throughout. The heart of the home is a stunning designer kitchen featuring quartz countertops, gray shaker cabinetry, a custom island with decorative millwork, stainless farmhouse sink, subway tile backsplash, pantry, breakfast bar, and an upgraded LG ThinQ smart appliance package. The kitchen flows seamlessly into the spacious dining and living areas, creating an ideal space for entertaining or everyday living. The inviting great room showcases a contemporary linear fireplace and an impressive custom floor-to-ceiling wine wall capable of storing more than 300 bottles, creating a true focal point for entertaining. Luxury vinyl plank flooring, fresh paint, updated lighting, custom window treatments, built-in shelving, and designer finishes continue throughout the home, providing a sophisticated yet comfortable coastal aesthetic. Step outside to enjoy the screened lanai complete with composite flooring and retractable solar/privacy shades overlooking a fully fenced backyard featuring a decorative paver patio, mature landscaping, privacy trellises, and inviting outdoor living spaces. Upstairs, the spacious primary suite offers a tray ceiling, walk-in closet with custom organization, luxury vinyl flooring, and an updated ensuite bath with dual vanities and framed mirrors. Two additional bedrooms, an upgraded guest bath, and a Samsung Smart laundry suite complete the second level. Additional upgrades include custom closet systems, hurricane shutters, fresh interior paint, luxury vinyl flooring throughout much of the home, updated lighting and ceiling fans, and meticulous documentation of warranties, finishes, and materials that will transfer to the next owner. This exceptional property offers the perfect blend of style, comfort, functionality, and lifestyle-just minutes from Hilton Head Island's beaches, golf, dining, shopping, and all the Lowcountry has to offer.

18 Tansyleaf Drive, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$379,790

1 Beds ⋅ 1 Baths ⋅ HILTONHEAD-512030 MLS

Fun and eclectic desirable end-unit boasts an extra side window, balcony, privacy and a full-on frontal view of the Marina and Broad Creek. Custom Art Deco black and white checkered floors compliment the bedroom with gorgeous new ceramic tile floors in the fitchen highlighted by a new contemporary light fixture and quartz countertops. Custom Shiplap adds to the nautical coastal feel as you overlook deepwater, and the yachts floating outside of your doors. Palmetto Bay Club gym on-site. This villa is in the hub of some of the Island's most popular shopping, restaurants and bars, but remains private and quiet nestled in the exclusive Palmetto Bay Club. Long-term rental projection of $2500/month. Owner is SCRA.

100 Helmsman Way Unit 212, Hilton Head Island

Listing courtesy of Hilton Head Properties.

$395,000

2 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511966 MLS

Completely renovated 2bd/2.5 bath townhome on slab foundation with wood burning fireplace. This condo has been completely remodeled to include LVP flooring, PEX plumbing and water heater moved to storage closet on front porch, new kitchen with quartz countertops, new carpet, new bathrooms and much more! This condo is located near the community pool, tennis courts, gym and playground - and getting off the island is a breeze as it is close to the HHI bridge.

5 Gumtree Road Unit D3, Hilton Head Island

Listing courtesy of Coastal Realty Group.

$275,000

1 Beds ⋅ 1 Baths ⋅ HILTONHEAD-512004 MLS

Beautifully updated 1-bedroom villa in desirable Building A at Hilton Head Beach & Tennis Resort! This second-floor villa offers a glimpse of the ocean from the private balcony and is a very short stroll from one of Hilton Head Island's most beautiful beaches. Thoughtfully updated with shaker-style cabinetry, granite countertops, a tile backsplash, and luxury vinyl plank flooring, this turnkey villa is offered tastefully furnished and rental-ready! The efficient floorplan features a private queen bedroom, built-in hallway bunk beds for additional guests, plus a sleeper sofa to comfortably accommodate even more guests. The bright, open living area that flows seamlessly to the private balcony. Hilton Head Beach & Tennis Resort features direct beach access, one of the island's largest oceanfront pools, tennis and pickleball courts, on-site dining, a playground, a fitness center, bike rentals, and 24-hour gated security. Whether you are looking for a vacation retreat, investment property, or both, this coastal retreat checks all the boxes.

40 Folly Field Road Unit A234, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

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