Hilton Head Island Homes with Playground Association amenities

Welcome to Hilton Head Island, South Carolina, a stunning coastal paradise nestled in Beaufort County. Known for its pristine beaches, lush landscapes, and vibrant culture, this idyllic island is a haven for both relaxation and adventure. With a rich history dating back to the early 18th century, Hilton Head boasts a charming blend of Southern hospitality and modern amenities, making it a sought-after destination for families, retirees, and vacationers alike.

The island is renowned for its extensive recreational opportunities, from world-class golf courses to scenic bike trails, and of course, the breathtaking Atlantic Ocean just steps away. Whether you’re strolling along the sandy shores or enjoying a sunset cruise, Hilton Head Island offers a lifestyle that embodies the essence of coastal living.

For families seeking a community with exceptional amenities, homes within the Playground Association on Hilton Head Island are a perfect choice. These residences not only provide comfortable living spaces but also grant access to a range of family-friendly facilities. Imagine your children playing in well-maintained playgrounds, where laughter fills the air and friendships blossom. The Playground Association fosters a sense of community, ensuring that families can come together for events, activities, and shared experiences.

Living in Hilton Head Island means embracing a lifestyle rich in nature, leisure, and community spirit. With homes that offer the perfect blend of comfort and convenience, you can create lasting memories in this beautiful corner of South Carolina. Come discover your dream home in Hilton Head Island today, and let the island’s charm captivate your heart!

Newest Hilton Head Island Homes with Playground Association amenities

$219,000

HILTONHEAD-513084 MLS

Welcome to beautiful RV site #231. This lot has a stamped concrete pad and can accommodate coaches up to 45' and a vehicle. This lot comes complete with irrigation, landscape lighting, dining table with 4 chairs, 2 high-top adirondack style chairs. Conveniently located just steps away from the clubhouse, pool and entrance/exit in the resort that makes this the perfect oasis for your enjoyment in Paradise! Head Island Motorcoach Resort is located in the heart of Hilton Head Island and is a luxury RV resort designed for the conveniences and enjoyment of class A, C and Super C Motorcoaches only. The resort consists of 50 acres of woodland and lush landscape setting accented with live oaks dripping with Spanish Moss, palms trees, ferns and flowering shrubs. The resorts amendities include tennis courts, pickle ball, shuffleboard, swimming pool, hot tub, clubhouse, laundry facilities, fitness center, basketball courts, playground, dog park, Wi-Fi, cable, daily trash pickup, lawn maintenance, water & sewer. Hilton Head Island Motorcoach Resort is a short bike ride to Coligny Beach, restaurants and island shopping.

133 Arrow Road Unit 231, Hilton Head Island

Listing courtesy of View Properties.

$659,000

HILTONHEAD-512982 MLS

Build your dream home in Sea Pines Resort on this full-size, empty corner homesite in the desirable Club Course area of Sea Pines! Presently undeveloped and measuring .367-acres with green space on two sides, the property boasts the privacy and security of 5,000-acre Sea Pines Resort while affording close proximity to the front gate. It's located just minutes to the 500-acre Sea Pines Forest Preserve, Sea Pines Country Club, 8-acre Sea Pines Heritage Community Farms and kid-friendly Lawton Stables. World-class golf, tennis, 5 miles of Atlantic beach and the many attractions of Harbour Town are just a bike ride away. Lot lines run roughly 110' x 150', and the parcel is located in the 500-year X Zone - no flood insurance is needed for most federally insured mortgages. The Club Course section of Sea Pines - peaceful with a true neighborhood feel - was intentionally designed to be a premier residential neighborhood within a world-class oceanfront resort. The superior location - both close to resort amenities, the beach and within easy access to the shopping, dining and everyday services right outside the front gates - provides the ideal blend of accessibility and resort living. A wonderful opportunity to create a custom full-time residence, a second home beach retreat or a long-awaited pre-retirement/retirement home in Hilton Head's most sought after community.

2 Club Course Drive, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

$925,000

3 Beds ⋅ 2 Baths ⋅ 2,016 SqFt. ⋅ HILTONHEAD-512538 MLS

Exceptional curb appeal, beautiful updates, and a private natural setting make this 3BR/2BA home in Hilton Head Plantation truly special. Open, bright, and beautifully updated throughout, the home features a spacious living room with a cathedral ceiling, fireplace, and custom built-ins, plus a light-filled Carolina room. Step outside to a private backyard oasis with a newer, expansive, maintenance-free deck featuring cable railing. Backing up to the Whooping Crane Conservancy, the property enjoys a lush natural buffer and exceptional privacy. A 2-car garage and peaceful cul-de-sac location complete this park-like setting. The attic is spray foam insulated for energy efficiency. Hilton Head Plantation offers an exceptional lifestyle with four golf courses, more than 40 clubs and social groups, and Spring Lake Recreation Area, featuring tennis, pickleball, a newer pool, and an activity center. Residents also enjoy Skull Creek Marina, the Country Club of Hilton Head, and the newly enhanced Dolphin Head Recreation Area and beach. With low POA fees, outstanding amenities, natural beauty, and an ideal Hilton Head Island location, Hilton Head Plantation remains one of the island's most desirable gated communities.

15 Persimmon Place, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$4,300,000

6 Beds ⋅ 7 Baths ⋅ 4,900 SqFt. ⋅ HILTONHEAD-513052 MLS

Located in the private enclave of Atlantic Pointe, this reimagined coastal sanctuary is the second home from the ocean! Designed with a seamless blend of organic modernism and coastal chic elegance, this 6-bedroom, 6.5-bathroom residence delivers an unmatched standard of luxury and proximity to the ocean. Every detail has been meticulously curated for effortless living and high-end entertaining. Offered completely turn-key, the property comes fully furnished down to the finest accessories, cookware, and tableware. Whether as an iconic private retreat or a top-tier investment, homes offering this tier of design and position so close to the beach are exceptionally rare on Hilton Head Island. Atlantic Pointe has its own private pool with tennis and pickleball courts. If you want it all, this has it all!

18 Atlantic Point, Hilton Head Island

Listing courtesy of Hilton Head Area Properties, LLC.

$1,100,000

4 Beds ⋅ 3 Baths ⋅ 2,324 SqFt. ⋅ HILTONHEAD-512901 MLS

Set in the desirable Oyster Reef Crossing section of Hilton Head Plantation, this beautifully appointed 4-bedroom-or 3-bedroom plus office-home offers tranquil lagoon views, excellent bedroom separation, and inviting indoor and outdoor living spaces. Wood floors flow throughout, with tray ceilings highlighting both the great room and primary bedroom. The light-filled kitchen features an island with sink, abundant cabinet and counter space, and skylights, while a separate dining area provides additional space for entertaining. The primary suite is complemented by a beautifully updated bath with a large tiled walk-in shower and freestanding soaking tub. The true highlight is the impressive 20' x 20' screened porch/Carolina room with soaring 16-foot ceilings-an exceptional space for entertaining, dining, or simply relaxing and enjoying the peaceful setting. Outside, the beautifully landscaped and private backyard features a circular stone patio with lagoon and wooded views.Additional features include two built-in Murphy beds, 2.5 baths, and a two-car garage. Enjoy all of this within Hilton Head Plantation, one of Hilton Head Island's most amenity-rich communities, offering golf, tennis, miles of leisure trails, boating and marina access, waterfront recreation, and so much more.

28 Pearl Reef Lane, Hilton Head Island

Listing courtesy of Charter One Realty.

$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.

$225,000

HILTONHEAD-512993 MLS

Clubhouse Lot 259 is often admired by many and now offered for sale. This large lot offers an incomparable blend of privacy, outdoor living, and rental appeal. Designed to accommodate a 45-foot motorcoach plus two vehicles, this expansive clubhouse lot is surrounded by mature trees and lush landscaping that creates a peaceful Lowcountry setting. This desired lot features an outdoor kitchen designed for resort-style living. The kitchen includes a built-in grill, prep and cleanup sink, refrigerator, multiple storage drawers and beautiful granite top. The built-in kitchen lighting creates an inviting atmosphere for evening gatherings and outdoor dining. An added plus is the custom cover protecting the kitchen while you're traveling. The long seating area has a sectional sofa and fire table providing the perfect place to relax and enjoy Hilton Head Island evenings. The lot is enhanced with a full irrigation system and large storage shed. Hilton Head Island Motorcoach Resort is an amenity-rich community designed exclusively for Class A, Class C and Super C motorcoaches, offering a heated pool and hot tub, pickleball and tennis courts, fitness center, clubhouse, and dog park, along with cable, Wi-Fi, water, sewer, and trash pickup. Located just minutes from Coligny Beach, Atlantic Ocean access, miles of bike paths, over 250 restaurants, golf courses, and island shopping, this property offers the ideal blend of resort-style living and the Lowcountry lifestyle. Hilton Head Island is recognized by Condé Nast Traveler magazine as the Best U.S. Island and the Hilton Head Island Motorcoach Resort has taken top honors from Motor-Home Magazine, RV Magazine, RV.com, and USA Today reader's choice awards has put the resort as # 1 Luxury Resort in America.

133 Arrow Road Unit 259, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$279,000

2 Beds ⋅ 2 Baths ⋅ 757 SqFt. ⋅ HILTONHEAD-512879 MLS

Priced as the most affordable villa currently available in Fiddler's Cove, 14E offers an excellent opportunity to own a Hilton Head Island getaway, investment property, or full-time residence close to the beach. This villa is being sold unfurnished and is ready for a new owner's updates and personal touches-an ideal option for buyers who want to renovate to their own taste while building value. Enjoy the convenience of Fiddler's Cove amenities and easy access to Hilton Head's beaches, shopping, dining, golf, and miles of leisure trails. A compelling value in a popular island community!

45 Folly Field Road Unit 14E, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$2,875,000

5 Beds ⋅ 5 Baths ⋅ 3,376 SqFt. ⋅ HILTONHEAD-512720 MLS

Welcome to 11 Gunnery Lane, a beautifully updated and exceptionally spacious 5-bedroom, 4.5-bath Sea Pines residence offering style, comfort, and versatility in a peaceful lagoon setting. Ideal for use as a primary or second home, or as a top tier vacation rental with with established history. Filled with natural light, the home features multiple living and gathering spaces and an easy floor plan equally suited to a primary residence, second home, or vacation property. The main level centers around a bright, open kitchen and living area, complemented by a fabulous bar with wine refrigerator and ice maker-perfect for entertaining. A generous primary suite (with steam shower) plus an additional ensuite guest bedroom provide desirable first-floor accommodations. Upstairs, a second primary suite and flexible family and guest spaces offer exceptional privacy and room for family and friends. Outside, enjoy a private pool and spacious deck overlooking the tranquil lagoon and mature Lowcountry landscape. Direct access to the Sea Pines leisure trail makes exploring the resort by bike or on foot effortless, while the beach is approximately a 10-minute walk away. Additional features include multiple living areas, dedicated office/work space with lagoon views, game and media spaces, full laundry room, two-car garage, abundant storage, and generous parking. Beautifully maintained, thoughtfully updated, and ideally located, 11 Gunnery Lane offers a wonderful combination of space, privacy, proximity to the beach, and effortless Sea Pines living.

11 Gunnery Lane, Hilton Head Island

Listing courtesy of BESTNEST By Beverly Serral.

$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.

$3,495,000

5 Beds ⋅ 5 Baths ⋅ 4,418 SqFt. ⋅ HILTONHEAD-512969 MLS

Experience exceptional waterfront living in prestigious Windmill Harbour, home to the South Carolina Yacht Club and its 15-acre lock-controlled marina. Framed by magnificent live oaks in both the front and rear, this remarkable residence pairs sophisticated architectural details with an effortless Lowcountry lifestyle and includes a coveted deeded 70-foot attached boat slip. A classic Savannah brick entry welcomes you into a grand foyer, where a striking dual-sided electric fireplace creates an impressive introduction to the home. Wide-plank 7-inch European white oak flooring, black windows and sliders, and dramatic cathedral wood-paneled ceilings establish a warm yet refined aesthetic throughout. Designed for seamless indoor-outdoor living, the great room opens through expansive accordion sliding glass doors to a large rear deck overlooking the harbor. Complete with a fireplace and plumbing for a future outdoor kitchen, this exceptional entertaining space takes full advantage of the waterfront setting.The beautifully appointed kitchen features custom inset-panel and panel-ready cabinetry, stainless JennAir appliances, and an impressive 11-foot quartz countertop. A separate scullery provides additional custom cabinetry and valuable prep and storage space. The expansive dining room is surrounded by floor-to-ceiling windows, filling the space with natural light and showcasing the surrounding landscape. Luxurious bathrooms are finished with floor-to-ceiling Italian marble and custom white oak vanities. The primary suite is complemented by a beautifully designed closet with custom wood shelving extending from floor to ceiling. Upstairs, an additional family room features a Juliet balcony overlooking the great room, adding architectural interest and connection between the living spaces. An elevator provides convenient access throughout the home.The ground level offers a spacious two-bay garage with ample additional storage and direct access to an outdoor flex space overlooking the harbor-ideal for extending the home's waterfront lifestyle. From its custom craftsmanship and elevated finishes to its' harbor views and direct boating access, this extraordinary Windmill Harbour residence offers a rare combination of luxury, thoughtful design, and Lowcountry waterfront living.

92 Harbour Passage, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$329,000

1 Beds ⋅ 1 Baths ⋅ 540 SqFt. ⋅ HILTONHEAD-512927 MLS

Completely remodeled and income-producing, this Hilton Head Island Beach & Tennis Resort villa offers a smart opportunity for the savvy investor, second-home buyer, or anyone searching for an easy weekend escape near the beach. With over $30,000 in rental income despite significant owner use, this stylish retreat already demonstrates its vacation-rental appeal. One of its standout features is the setting. Rather than the parking lot views commonly found throughout the resort, this villa overlooks the peaceful marsh, with a view of the Atlantic Ocean from the private balcony. Sip your morning coffee surrounded by Lowcountry scenery, listen to the nearby waves, and catch a glimpse of the ocean sparkling beyond the dunes. Inside, thoughtful updates include wood-slat accent walls, durable LVP flooring, newer stainless appliances, and a beautifully remodeled bath with dual freestanding vanities and marble-look tile. Set on 50+ acres, the resort offers direct beach access via four boardwalks, an oceanfront pool and kiddie pool, tennis, pickleball, volleyball, biking, playground and more. On-site dining at CocoNutz Sports Bar and Jamaica Joe'z Beach Bar adds to the true resort experience. Use it. Rent it. Enjoy it. Whether you're looking for vacation-rental income, your own Hilton Head weekend getaway, or the best of both, this remodeled villa combines an appealing rental history with a marsh-facing location and peek of the Atlantic that helps set it apart.

40 Folly Field Road Unit C325, Hilton Head Island

Listing courtesy of Keller Williams Realty.

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