Hilton Head Plantation Homes with Guard Association amenities

Welcome to Hilton Head Plantation, a gem nestled on the picturesque Hilton Head Island in Beaufort County, South Carolina. This exclusive community is not just a place to live; it’s a lifestyle that combines natural beauty with a wealth of amenities designed for relaxation and recreation.

Hilton Head Plantation is known for its stunning landscapes, featuring lush greenery, scenic marshlands, and breathtaking waterfront views. The area is a paradise for outdoor enthusiasts, offering miles of walking and biking trails, access to pristine beaches, and world-class golf courses. Residents can enjoy the tranquility of nature while being just a stone’s throw away from the vibrant cultural and culinary scene that Hilton Head Island is famous for.

One of the standout features of Hilton Head Plantation is its Guard Association, which provides an added layer of security and peace of mind for residents. This gated community is committed to ensuring a safe and welcoming environment, allowing you to enjoy your home and surroundings without worry.

Within the plantation, you’ll find a variety of homes that cater to different lifestyles and preferences, from charming cottages to luxurious waterfront estates. Each home is thoughtfully designed to harmonize with the natural beauty of the area, offering a perfect sanctuary for families and individuals alike.

With its combination of stunning scenery, top-notch amenities, and a strong sense of community, Hilton Head Plantation is more than just a place to live; it’s a place to thrive. Come discover your dream home in this idyllic setting and experience the best of coastal living in South Carolina!

Newest Hilton Head Plantation Homes with Guard Association amenities

$925,000

4 Beds ⋅ 3 Baths ⋅ 2,211 SqFt. ⋅ HILTONHEAD-512782 MLS

Privately situated at the end of a quiet cul-de-sac, this 4-bedroom, 2.5-bath home offers a wonderful setting with wide expansive lagoon view. Built in 1994, the home features a great floor plan with light and bright living spaces and plenty of room for family and guests. A two-car garage provides added storage and convenience. Enjoy the privacy of the cul-de-sac location while taking in the scenic Lowcountry views from your own backyard. A great opportunity to make this well-located home your own!

8 Trails End Road, Hilton Head Island

Listing courtesy of Collins Group Realty.

$950,000

5 Beds ⋅ 4 Baths ⋅ 3,190 SqFt. ⋅ HILTONHEAD-512873 MLS

Opportunity awaits at 2 Deerfield Road in desirable Hilton Head Plantation. Situated on a large homesite near Dolphin Head, this spacious property offers a peaceful Lowcountry setting with golf course views framed by mature trees. The home provides a great canvas for a buyer looking to renovate, personalize, and add value over time, plus an apartment over the garage offering additional flexible living space. Enjoy the privacy and natural beauty of the generous lot, with convenient access to Dolphin Head Recreation Area and the beach just minutes away. With its desirable location, golf views, substantial homesite, apartment over the garage, and renovation potential, 2 Deerfield Road offers an exciting opportunity to create something special on Hilton Head Island. *Some photos have been virtually staged and/or digitally decluttered to showcase the home's potential.*

2 Deerfield Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$1,699,000

4 Beds ⋅ 4 Baths ⋅ 3,458 SqFt. ⋅ HILTONHEAD-512898 MLS

Wake to sunrise over shimmering water and sun-kissed marsh grasses, with views stretching to Dolphin Head Beach and the Port Royal Sound. From its Bayley Point setting, this 4-bedroom, 3.5-bath home enjoys one of the most stunning Lowcountry views in Hilton Head Plantation and a landscape that changes with the tides, light, and sky throughout the day. Designed to embrace its setting, soaring ceilings and expansive windows bring the outdoors into the main living spaces. Newly updated windows surround the fireplace in the great room, beautifully framing the sweeping landscape, while the dining area offers an equally memorable setting overlooking the water. Step outside to the large deck and pergola for coffee at sunrise, evenings under the stars, or simply watching the tides move through the marsh. The adjacent lot is designated open space to add another layer of privacy and protect the expansive water and marsh views from future development. Mature landscaping, an inviting entry courtyard, and circular drive complete the setting. With approximately 3,458 square feet, the thoughtfully designed floor plan provides space and separation for everyone. The spacious kitchen features a large center island, gas cooking, extensive cabinetry and updated finishes, opening naturally to the casual living areas. Hardwood floors, built-ins and architectural details add warmth and character. The first-floor owner's suite looks out to the water, while a separate main-level office provides dedicated work-from-home space without sacrificing a bedroom. Upstairs, two additional bedrooms with exceptional water views offer privacy for family or guests, plus a separate bonus-room getaway with its own full bath-ideal for guests, a media room, or additional living space. All within Hilton Head Plantation, this is a home that offers room to gather, room to retreat, and a setting that is difficult to duplicate. The view may be what first captures your attention, but the way this home lives is what makes it special.

16 Bayley Point Lane, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$1,175,000

3 Beds ⋅ 2 Baths ⋅ 2,090 SqFt. ⋅ HILTONHEAD-512948 MLS

Rare Opportunity! 7 years young, 3rd row Port Royal Sound, custom-built residence by award-winning H2 Builders in popular Hilton Head Plantation. Features in this pristine property include 10' wood/glass front door system, volume ceilings, wood flooring, millwork & built-ins by master craftsmen (crown molding, tall baseboards, custom closets, shelving, cabinets, pantry, hutch, etc.), honed/leathered granite counters, high end appliance package (Wolf double ovens & gas range, etc.), designer fixtures/hardware/lighting, plantation shutters, glass front gas fireplace, and energy-saving spray foam insulation. Very livable floor plan offers Chef's dream kitchen (island w/4 seat breakfast bar, herringbone pattern tile backsplash, walk-in pantry) open to spacious dining area, expansive great room and sliding glass doors to "must have" vaulted ceiling screened porch, superbly appointed & private primary suite with luxe bath, 2 ample guest BR's & bath, oversize laundry room with Flex Space (craft/office nook/workout), huge walk up/floored conditioned attic space and coveted 2.5+ car garage. Exterior offers charming curb appeal, durable/attractive hard coat stucco w/ Hardie shake accents, mature plantings & lawn, irrigation system, specimen trees, rear patio (stubbed for gas grill) and maximum privacy. All with much desired high elevation, "Shell Street" locale just a short stroll to waterfront leisure path + nearby Dolphin Head Recreational Area, Pine Island Beach Park, Spring Lake Pool Complex, Whooping Crane Conservancy, 4 golf courses, Country Club of HH & Spring Lake Racquet Club! What's not to love about 16 Wing Shell Lane & HHP!

16 Wing Shell Lane, Hilton Head Island

Listing courtesy of Charter One 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. Additional features like a two-car garage, a great location, and a new roof in 2026, check a lot of boxes for many buyers.

13 Pheasant Run, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$749,000

3 Beds ⋅ 2 Baths ⋅ 1,635 SqFt. ⋅ HILTONHEAD-512909 MLS

Beautiful golf course views and easy one-level living await at 62 Cypress Marsh Drive in Hilton Head Plantation. This inviting 3-bedroom, 2-bath home is filled with natural light and features a spacious kitchen with newer cabinetry, LVP flooring throughout, vaulted ceilings in the living room, and a comfortable, functional floor plan. Enjoy peaceful views of Bear Creek Golf Course from the screened porch or paved patio, perfect for morning coffee, outdoor dining, or simply relaxing. Additional highlights include an oversized 2-car garage and a newer HVAC system. Well maintained and move-in ready, this home also offers access to Hilton Head Plantation's exceptional amenities, including community pool, a lazy river, miles of leisure trails, beach access, golf, and more.

62 Cypress Marsh Drive, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International 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.

$1,600,000

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.

$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.

$674,900

4 Beds ⋅ 3 Baths ⋅ 1,846 SqFt. ⋅ HILTONHEAD-512599 MLS

Welcome to this great island home in Hickory Forest, located in HIlton Head Plantation, one of Hilton Head Island's most desirable residential communities. This house is located at the end of a private road & has a well designed floor plan offering a primary suite on the main level plus three additional bedrooms and a spacious loft upstairs, providing plenty of room for family, guests, or a home office. The home offers a newer HVAC (25), newer roof (22) & newer plank flooring. The updated kitchen features granite countertops, a new backsplash, updated lighting, newer appliances, a pantry, & a convenient breakfast/dining area. The inviting great room features a wood burning fireplace, cathedral ceiling & sliding glass doors overlooking a large two-tiered deck. The spacious primary suite offers a dual sink vanity, large walk-in closet & additional storage closet. Upstairs, you will find 3 additional bedrooms plus a versatile loft area. A private backyard retreat, perfect for relaxing, entertaining, or enjoying the Lowcountry lifestyle. Residents enjoy access to a wide range of amenities & outdoor activities, including beautiful leisure & biking trails, community pools, tennis & pickleball, golf & convenient access to the island's beaches, Broad Creek, shipping, dining & everyday services Tandem 2 car garage.

25 Honey Locust Circle, Hilton Head Island

Listing courtesy of ERA Wilder Realty, Inc.

$864,958

3 Beds ⋅ 3 Baths ⋅ 2,588 SqFt. ⋅ HILTONHEAD-512467 MLS

Situated on a quiet cul-de-sac with a peninsula-like setting and beautiful long lagoon views, this custom home offers an exceptional opportunity to create something truly special. With three bedrooms, two and a half baths, an office, a family room open to the kitchen, and a separate living room featuring a dramatic wall of glass overlooking the spectacular view, the home offers a wonderful floor plan and an abundance of potential. Ahead of its time in both design and layout, the home features a very large two-car garage with generous perimeter space-ideal for a workshop, storage, or additional workspace. The home is ready for someone to bring their own vision, personalize the finishes, and elevate it to the level of the beautiful homes surrounding it. The location is equally impressive. Enjoy a short walk to Spring Lake, the community's activity center featuring tennis, pickleball, a new pool, multiple gathering areas, and the Plantation House. Just a two-minute drive away is the newly enhanced Dolphin Head Park and beach, with beautifully updated amenities and one of the many outstanding recreational areas within this amenity-rich community. With low POA fees and an unmatched combination of amenities, natural beauty, and location, Hilton Head Plantation remains one of Hilton Head Island's most desirable gated residential communities. The property is approximately 15 minutes from Hilton Head Island Airport, seven minutes from shopping, and 15 minutes from the Atlantic Ocean beaches. Historic Savannah and Savannah/Hilton Head International Airport are approximately an hour away. A special setting, custom design, spectacular views, and tremendous potential make this an opportunity not to be missed. Grass has been enhanced in some photos.

8 Cougar Run, Hilton Head Island

Listing courtesy of Charter One Realty.

$499,900

3 Beds ⋅ 2 Baths ⋅ 1,462 SqFt. ⋅ HILTONHEAD-512479 MLS

Beautiful & updated coastal townhome for under $500,000 in highly desired Hilton Head Plantation! This stunning 3BD/2BA lock and leave townhome is perfect for anyone looking for maintenance free living. With a newer roof and a short walk to Spring Lake Pavillion where all your world class amenities are, this location is ideal. Spacious floor plan with large living area, one bedroom and full bathroom on the first floor. Find two additional bedrooms and one full bathroom upstairs. Step outside to a generous deck and patio area surrounded by natural foliage-ideal for morning coffee, evening gatherings, or simply enjoying the quiet Lowcountry setting. With its cul-de-sac location, proximity to Dolphin Head, miles of leisure trails, and the Plantation's signature amenities, this home delivers both privacy and convenience. Maintenance free living with regime covering trash, pest control and landscaping. Come enjoy everything Hilton Head Plantation has to offer with their high-end amenities and beautiful nature that surrounds the community!

7 Windflower Court, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

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