Hilton Head Island Homes with Courtyard Exterior features

Welcome to Hilton Head Island, South Carolina – a coastal paradise renowned for its pristine beaches, lush landscapes, and vibrant community spirit. Nestled in Beaufort County, this charming island is a haven for nature lovers, golf enthusiasts, and anyone seeking a relaxed, upscale lifestyle. With its mild climate, Hilton Head boasts year-round outdoor activities, from world-class golfing on its acclaimed courses to biking along scenic trails or enjoying sun-soaked days on the sandy shores.

One of the most captivating features of homes in Hilton Head is their stunning courtyard exteriors. These architectural gems are designed to create an inviting atmosphere, offering a perfect blend of privacy and open-air charm. Imagine stepping through your front door into a beautifully landscaped courtyard, an oasis where you can unwind, entertain friends, or enjoy a quiet evening under the stars. The design not only enhances aesthetic appeal but also promotes a seamless indoor-outdoor living experience that embodies the coastal lifestyle.

Whether you’re looking for a cozy retreat or a spacious family home, properties with courtyard features provide a unique touch that sets them apart. The lush greenery, tranquil water features, and inviting seating areas create a serene environment, making these homes a perfect choice for relaxation and entertainment alike.

Discover the magic of Hilton Head Island, where every day feels like a vacation, and let the allure of courtyard homes welcome you to your next chapter in paradise!

Newest Hilton Head Island Homes with Courtyard Exterior features

$715,000

2 Beds ⋅ 3 Baths ⋅ 1,380 SqFt. ⋅ HILTONHEAD-512876 MLS

Carefree Island living - Fairway Views and close to the Beach. This fully renovated 1,380 sq ft villa in Shipyard Plantation is the vacation home that makes everything easy. Two bedrooms, two and a half baths, and an open, light-filled layout built for both entertaining and quiet downtime - with golf course fairways views right outside and the beach just a short walk away. Sold fully furnished and truly turnkey - arrive with your suitcase and nothing else. Rent it when you're away, keep it just for you, or do both. Either way, this home is ready the moment you are. Shipyard Plantation adds resort-style amenities to the mix: golf, tennis, beach club, and gated privacy, all close to shops, dining, and more! Easy to show - schedule your appointment now.

113 Shipyard Drive Unit 109, 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.

$259,000

1 Beds ⋅ 1 Baths ⋅ 540 SqFt. ⋅ HILTONHEAD-512890 MLS

BEST VALUE FOR A 1BR OCEANFRONT VILLA AT HILTON HEAD BEACH & TENNIS!**- SELLER MOTIVATED!** Ready to own your own piece of Hilton Head Island? This turnkey, oceanfront 1BR/1BA villa at Hilton Head Beach & Tennis Resort is priced with a quick sale in mind, and all reasonable offers will be considered! The seller has simply reached a point where they are no longer enjoying their beach trips, creating an opportunity for the next owner to make this renovated villa their own Hilton Head getaway, second home, or short-term rental investment. Located on the first floor with peak a boo ocean views, this fully furnished villa is ready to enjoy or rent. The updated kitchen, renovated in 2022-2023, features stainless steel appliances, while luxury vinyl plank flooring and thoughtful updates create a comfortable coastal feel. Built-in bunk beds with mounted TVs are a fantastic bonus for families and guests, allowing the villa to comfortably sleep up to six. Step outside to your private balcony and take in the ocean views-or head downstairs and enjoy one of Hilton Head's most amenity-rich beachfront resorts. Resort amenities include direct beach access, one of the largest oceanfront pools on Hilton Head Island, two outdoor pools, tiki bar, on-site restaurant and sports bar, tennis courts, pickleball courts, fitness center, bike rentals, outdoor grilling areas, playground, 24/7 gated security, and cable and internet included. The villa also features a brand-new HVAC system installed June 2025, adding peace of mind for both owners and guests. Whether you're looking for a beachfront second home, a turnkey vacation rental, or an affordable way to own on Hilton Head Island, this is an opportunity worth seeing. **Seller is motivated, priced for a quick sale, and will consider all offers. Bring your offer and make this oceanfront Hilton Head retreat yours!**

40 Folly Field Road Unit A134, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$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.

$1,600,000

4 Beds ⋅ 5 Baths ⋅ 3,505 SqFt. ⋅ HILTONHEAD-512875 MLS

Welcome home to 21 Ribaut Dr. on Hilton Head Plantations prestigious Ribaut Island in a private gate with 63 homesites. Take advantage and enjoy the private amenities of a community pool, dock and tennis/pickleball courts. Sitting on just under a half an acre lot, this wonderful, updated floor plan has 4 bedrooms, & 4.5 bathrooms. The office is just off the primary suite. Enjoy the open updated kitchen/family room and cooking on your propane stove and oven while entertaining friends and family. The Primary bath has been renovated with large soaking tub. There are wood floors in the living areas and carpet in the bedrooms. The home is equipped with an extended 2 car garage with workshop space and a large storage closet. Storage galore with many closets and a walk-in floored attic. 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.

21 Ribaut Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$610,000

2 Beds ⋅ 2 Baths ⋅ 1,371 SqFt. ⋅ HILTONHEAD-512852 MLS

Completely updated inside and out, this charming coastal cottage with golf view at 52 Stable Gate offers move-in-ready, single-story living in sought-after Moss Creek. More than a surface renovation, major improvements include a new roof (2021), HVAC and ductwork (2024), updated electrical and smoke detectors, plus new Anderson kitchen window and two sliders with a 20-year warranty.Enjoy an updated kitchen and baths, automatic primary bedroom window treatments, a wraparound patio and private screened courtyard. The newly sodded yard features irrigation and an invisible fence, plus exterior storage.Just minutes from Hilton Head Island, Moss Creek offers an exceptional Lowcountry lifestyle with deep-water boat slips, launch and storage, waterfront pool, full-featured fitness center, golf, tennis, pickleball and countless other recreational and social amenities.

52 Stable Gate Road, Hilton Head Island

Listing courtesy of ERA Wilder Realty, Inc - Bluffton.

$4,795,000

4 Beds ⋅ 5 Baths ⋅ 4,386 SqFt. ⋅ HILTONHEAD-512195 MLS

Oceanfront Living, Elevated. Set directly along the Atlantic Ocean within Leamington, Palmetto Dunes, 136 South Shore Drive offers an exceptional combination of oceanfront living, privacy, and refined coastal comfort. Tasteful interiors and a spacious floor plan create an inviting setting for both everyday living and entertaining. Just beyond the residence, owners can enjoy the beach, pool, and the natural beauty of Hilton Head Island's coastline. South Shore's intimate setting provides a distinctive advantage. With no short-term rentals, the community maintains a quieter, more private residential atmosphere while remaining conveniently close to the golf, tennis, pickleball, dining, biking, and recreational amenities of Palmetto Dunes.136 South Shore Drive is a rare opportunity to enjoy a beautiful oceanfront residence in one of Hilton Head Island's most desirable and private coastal settings.

136 S Shore Drive, Hilton Head Island

Listing courtesy of Keller Williams 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.

$389,000

2 Beds ⋅ 2 Baths ⋅ 917 SqFt. ⋅ HILTONHEAD-512708 MLS

When money matter...this one has done over $43,000 with 3 months more left of rental income. Move-in ready and beautifully updated, this 2-bedroom, 2-bath villa sits in one of the best locations at Spa Villas at Port Royal Sound - the second closest unit to the water, with sound views right from your private balcony.Every inch of this villa has been tastefully renovated. The open-concept living area features a stunning kitchen with white shaker cabinets, granite counters, subway tile backsplash, and stainless steel appliances, flowing into a spacious living room with a large sectional and a live-edge wood coffee table. Both full baths have been updated with marble-look vanities, modern lighting, and glass-enclosed tub/showers. The primary bedroom is a showstopper, with a bold paneled accent wall, en-suite bath, and walk-in closet with plantation shutters.Sold fully furnished and equipped as a successful short-term rental, this villa is turnkey for an owner-investor or the perfect low-maintenance island retreat. Step out onto the balcony to towering pines, the multiple pools, bbq, hammocks, indoor pool, walking track, dry sauna, pickleball, and adjacent bike paths and sound views beyond. Just minutes to Hilton Head's beaches, dining, shopping, and golf.Rare combination of prime water-adjacent location, high-end finishes, and proven rental income - schedule your showing today!

239 Beach City Road Unit 1210, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$1,495,000

5 Beds ⋅ 3 Baths ⋅ 2,504 SqFt. ⋅ HILTONHEAD-512460 MLS

Some homes give you a place to stay in Sea Pines. 15 Dewberry gives you a reason to stay in. This five-bedroom home in Greenwood Forest pairs the Sea Pines lifestyle with the kind of amenities that make the house itself part of the vacation. And yes, the bikes come with the house. THE PUTTING GREEN: A professionally designed three-hole green spans 35 to 38 feet with an 11 stimp rating and real break, good for a morning warm-up or one more round after dinner. THE HANGOUT: A separate in-law suite with its own kitchenette turned wet bar, ice maker included. One of the home's five bedrooms currently serves as the suite's living room, and flexes just as easily into a bunk room when more sleeping space is needed. THE SPACE: Brazilian hardwood floors, a tongue and groove ceiling, quartz counters, and GE Cafe appliances run throughout the single story home, with new flooring added in the bedrooms. A Carolina room with a daybed and porch swing gives everyone one more place to land. THE NEIGHBORHOOD: Greenwood Forest is one of the few pockets of Sea Pines with its own community pool, tennis and pickleball, and a playground, a short distance from the Shops at Sea Pines and Beach Trolley access through a wooded community path. Easy distance to either HarbourTown or the Beach! Already an active vacation rental, the home has a confirmed booking of 91 nights for 2027 alone, worth more than $19,000, a sign of how much demand a house like this can hold.

15 Dewberry Lane, Hilton Head Island

Listing courtesy of Luxury Homes of Hilton Head.

$2,195,000

4 Beds ⋅ 5 Baths ⋅ 4,199 SqFt. ⋅ HILTONHEAD-512563 MLS

Rarely does a home combine views this dramatic with privacy this complete. Set on an oversized, beautifully landscaped homesite at the end of a quiet cul-de-sac, 70 Deerfield Road enjoys captivating marsh and Port Royal Sound views, with the newly renourished sands of Pine Island Beach at Dolphin Head visible from multiple rooms and accessible just steps away via the beach path. Comprehensively refreshed in 2025-2026, this custom residence offers effortless Lowcountry living with every bedroom featuring an ensuite bath, a separate dining room, and a richly wood-paneled den with pocket doors. The primary retreat occupies a private pod all its own; hidden behind a discreet door off the living room, it reveals what may be the most spectacular sunrise view from bed you will ever experience. Outdoor spaces include a private courtyard, screened patio, expansive deck, sunken hot tub, propane-fed grill station, and zero-step ramp access, while a large folding living-room door invites the outdoors in. The well-appointed kitchen features a spacious island with seating, dual ovens-one convection-a five-burner cooktop, generous pantry storage, and an adjacent wet bar. Significant improvements include crawlspace encapsulation, extensive spray-foam insulation, refreshed skylights, three geothermal HVAC systems, a metal roof, PSD water, and well-fed irrigation. With extraordinary privacy, exceptional indoor-outdoor living, beach access, and one of Hilton Head Plantation's most remarkable marsh-to-Sound settings, this is more than a beautiful home-it is a truly special retreat. Select photos are virtually staged. Listing Broker is the Seller and is licensed in South Carolina, Georgia, and Wisconsin.

70 Deerfield Road, Hilton Head Island

Listing courtesy of AIM Real Estate Sales.

$1,899,000

3 Beds ⋅ 3 Baths ⋅ 2,643 SqFt. ⋅ HILTONHEAD-512472 MLS

MASSIVE RENOVATION-EVERY DETAIL REIMAGINED. This is not simply an updated home-it is the result of a complete transformation by a retired luxury homebuilder who purchased the property new in 1986 and, after moving in full-time in 2018, meticulously reimagined virtually every inch of this 3BR+Office home and grounds. The craftsmanship, quality, and attention to detail are evident at every turn. Highlights include a resort-style heated and chilled saltwater pool with waterfall, bubbler, and paver surround; Estate wire-brushed alder hardwood flooring and tile throughout; Sub-Zero and Wolf appliances; Cambria quartz countertops in the kitchen; granite countertops in every bath; extensive custom cabinetry and built-ins; Delta plumbing fixtures; solid-core doors; 5-inch crown molding; vaulted tongue-and-groove ceilings in the living room and screened porch; and a coffered ceiling in the office. Major system improvements include Jeld-Wen Low-E impact-rated windows and doors, HVAC systems, asphalt roof, stairway to large attic over garage, foam attic insulation, garage doors, epoxy garage flooring, paver driveway, and professionally designed landscaping by The Greenery. Perhaps the greatest luxury of all is the lifestyle. Enjoy your own private resort on a picturesque lake, then stroll just ten minutes to one of Hilton Head Island's pristine Atlantic beaches. This is a home where nothing has been overlooked and every day feels like a vacation.

7 Off Shore, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

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