Hilton Head Island Homes with Playground Amenities

Hilton Head Island Homes with Playground Amenities

Welcome to Hilton Head Island, South Carolina – a coastal paradise known for its stunning beaches, lush landscapes, and vibrant community. Nestled in Beaufort County, this enchanting island is not just a vacation destination; it’s a place where families thrive, and lifelong memories are made. With its temperate climate, picturesque scenery, and an array of recreational activities, Hilton Head Island is the perfect backdrop for your new home.

One of the standout features of homes in this beautiful region is the abundance of properties equipped with playground amenities. Imagine stepping outside your door to find a safe and inviting space where your children can play, explore, and enjoy the great outdoors. These playgrounds are designed to foster creativity and physical activity, allowing your little ones to develop friendships while you relax nearby.

In addition to family-friendly amenities, Hilton Head Island boasts world-class golf courses, pristine beaches, and an array of dining and shopping options. Whether you’re biking along the scenic pathways, indulging in fresh seafood, or soaking up the sun on the sandy shores, there’s always something to do.

Choosing a home with playground amenities on Hilton Head Island means investing in a lifestyle that prioritizes family fun and community connection. With a welcoming atmosphere and an abundance of outdoor activities, you’ll find that Hilton Head Island is more than just a place to live – it’s a place to thrive. Come discover your dream home in this idyllic coastal haven!

Newest Hilton Head Island Homes with Playground Amenities

$760,000
3 Beds ⋅ 3 Baths ⋅ 1,650 SqFt. ⋅ HILTONHEAD-512291 MLS
Turnkey single-level 3-bedroom, 3-bath home blending Lowcountry charm and refined design on over 1/3 acre with peaceful views of Hilton Head Plantation's venerable Dolphin Head Golf Course. Reimagined from the studs in 2019, the light-filled layout features exposed wood beams, tray ceilings, tongue-and-groove accents, custom trim and premium fixtures throughout. The bright eat-in kitchen features Fantasy Brown dolomitic marble, Walker Zanger tile, soft-close cabinetry, high-end Bosch and GE Profile appliances including induction cooktop. Both the primary suite and sunken living room open to the tabby shell back patio with hot tub and grilling area. Inside, the woodburning fireplace and vaulted living room ceiling add warmth and character. Major systems replaced in 2019 include: new roof, energy-efficient windows, HVAC, ductwork, water heater, plumbing, wiring, new LVP, tile flooring and a refreshed garage with epoxy floors, craftsman-inspired lighting and carriage-style door. A short walk or ride to the clubhouse, Dolphin Cafe and Hilton Head Plantation's resort amenities. A beautifully upgraded retreat ready to welcome you home.

27 Pineland Road, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$199,000
HILTONHEAD-512270 MLS
Solitude on this remote street, yet a short path to amenities makes this the perfect blend of privacy and convenience on this meticulously maintained, oversized lot. Featuring immaculate stamped concrete pad and extensive landscaping, this site easily accommodates a 45-foot motorcoach. Priced unfurnished. Just steps from the pool, racquet sports, clubhouse, playground and laundry facilities. Beyond the front gates, enjoy convenient access to shopping, dining, the beach, bike paths and the town trolley. Experience the #1 Motorcoach Resort on the #1 island destination in America - an exceptional blend of lifestyle and investment.

133 Arrow Road Unit 81, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$5,500,000
5 Beds ⋅ 7 Baths ⋅ 7,051 SqFt. ⋅ HILTONHEAD-511760 MLS
BREATHTAKING Mediterranean Estate Home overlooking the 16th Fairway of the Robert Trent Jones Ocean Golf Course in Palmetto Dunes just a Short Walk to the Beach. 7,051 Square Feet with Outstanding Craftsmanship showcases Chef's Kitchen with Spacious Island & Butler's Pantry and Small Laundry Room, 5 Bedroom Suites, Custom Wood Paneled Parlor with Full Bar and Travertine Floored Foyer to a Two-Story Entry with a Grand Marble Staircase. Spacious Second Floor Laundry Room. BEAUTIFUL Raised Invisible Edge Pool and Spa. 5 Covered Porches, Fireplace and Built-In Grill. 6-Car Drive Through Garage, Elevator, Terra Cotta Tile Roof, Paver Driveway and Mature Landscaping. Perfect Home for Relaxing and Entertaining Family, Friends, or Business Outings. Truly EXCEPTIONAL in every way. Being Sold Furnished so just pack your suitcase and Come Enjoy the Best of Life at 11 Sea Lane on Hilton Head Island!

11 Sea Lane, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$649,900
3 Beds ⋅ 2 Baths ⋅ 1,822 SqFt. ⋅ HILTONHEAD-511287 MLS
Moss Creek Lifestyle. Move-In Ready. Easy to Love. A rare opportunity to enjoy the Moss Creek lifestyle in a beautifully updated, move-in-ready home that is comfortable, manageable, and easy to love. Located in desirable Royal Pointe, this charming 3-bedroom, 2-bath home offers 1,822 sq. ft. with an open, inviting floor plan and numerous thoughtful improvements throughout. The remodeled kitchen features updated cabinetry, countertops, appliances and finishes and flows effortlessly into the dining and living areas-perfect for everyday living or entertaining. Updated flooring and fresh interior paint give the home a clean, current feel, while the spacious great room, vaulted ceiling and fireplace add warmth and character.The generous primary suite offers excellent closet space and an updated bath, while two additional bedrooms provide flexibility for guests, a home office or hobbies. Outside, enjoy a beautifully refreshed backyard, mature Lowcountry landscaping and private outdoor living space ideal for relaxing or entertaining. A spacious two-car garage provides additional storage and everyday convenience.For buyers looking to downsize, establish a Lowcountry second home or simply enjoy one of the area's most established private communities without taking on an oversized property, this one is especially compelling. Moss Creek offers two golf courses, clubhouse dining, marina and boating amenities, tennis and pickleball, fitness and swimming facilities, nature preserves and miles of leisure trails-all in an incredibly convenient location just before the Hilton Head Island bridge. Updated, well maintained and ready to enjoy from day one, 3 Royal Pointe Drive offers an exceptional combination of lifestyle, location and value.

3 Royal Pointe Drive, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$225,000
1 Beds ⋅ 2 Baths ⋅ 813 SqFt. ⋅ HILTONHEAD-512049 MLS
Welcome to cozy coastal living in the desirable Marshside community on the north end of Hilton Head Island! This well cared for, updated, and fully furnished 1 bedroom, 1.5 bathroom loft villa is move in ready and priced to sell. The main level offers an inviting living space featuring a cozy fireplace, a convenient half bath, and an updated kitchen equipped with stainless steel appliances. Upstairs, the spacious loft bedroom suite boasts a private full bathroom, a walk-in closet and beautiful sunrise views to start your morning right. Step out onto the back porch to relax and take in the tranquil marsh and landscaped views, perfect for watching local island wildlife. Additional features include an extra exterior storage closet for your beach gear. Residents of Marshside enjoy fantastic community amenities, including a pool, tennis courts, playground, and fitness center. Property is being sold AS-IS with seller to make no repairs (microwave and refrigerator water dispenser as-is; dispenser non-functional). Inspections are welcome.

5 Gumtree Road Unit L-18, Hilton Head Island

Listing courtesy of The Cox Team Brokered by EXP.

$32,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512232 MLS
Welcome to your coastal getaway! Own a deeded 2BR, 2BA quartershare at Brigantine Quarters in Shipyard. Enjoy 13 rotating weeks a year in this beautifully designed residence with vaulted ceilings and a large balcony with golf views. Prime weeks for 2027 include 4th of July and December 18th through New Year's Day 2028. This mini-resort includes tennis, pickleball, pools, a playground, and a private beach gate for BQ owners and guests. Maintenance fee covers appliances, furniture, maintenance upkeep, taxes, Shipyard fees, and more, ensuring a stress-free experience, ideal for personal use or rentals.

55 Barcelona Road Unit 242C, Hilton Head Island

Listing courtesy of The Homesfinder Realty Group.

$3,995,000
5 Beds ⋅ 7 Baths ⋅ 4,566 SqFt. ⋅ HILTONHEAD-512060 MLS
Waterfront living in Wexford doesn't get much better than this and 20 Castlebridge Court offers the ONLY harborfront setting currently available in the community. Set directly on the harbor at the end of a private cul-de-sac, this five-bedroom residence combines exceptional outdoor living with one of the neighborhood's most desirable settings. A heated pool and spa, outdoor fire pit, built-in grilling station, and private dock make the most of life on the water. The spacious floor plan features a grand living room upon entry, adjacent dining room, a generous kitchen enhanced by Sub zero and Viking appliances, two stately gas fireplaces, bonus room, bunk room, three-car garage, and dedicated golf cart bay. The quality of construction does not go unnoticed with solid wood doors, plantation shutters, wide-planked hardwood floors, elevated lighting, and built-in features throughout. Then there is Wexford itself. Boasting a newly redesigned clubhouse with indoor/outdoor dining, community pool, exceptional Arnold Palmer Signature golf, active tennis community, pickle ball, a private marina, and the signature lock-controlled 37 acre inland harbour. The community truly is unlike anything else on Hilton Head Island and for someone looking for harborfront living within Wexford, there is only ONE.

20 Castlebridge Court, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$295,000
2 Beds ⋅ 2 Baths ⋅ 757 SqFt. ⋅ HILTONHEAD-512222 MLS
Fully furnished, updated and welcoming 2nd-floor beach villa. It has updated flooring, king size bed, a new pullout couch, bar unit, new water heater, new dishwasher, private balcony, TVs in every room, stainless steel appliances, updated bathrooms, and in-unit laundry. Gated beach community w/2 seasonally heated pools, hot tub, play & picnic areas, 7 clay Har-Tru tennis courts, 6 packed Har-Tru pickleball courts, 2 indoor racquetball courts, grilling stations, fitness center, game room, and clubhouse. Great location close to shopping, restaurants and most importantly, just down the street from the beautiful beaches of Hilton Head Island. New hot water heater (~2.5 years old).

45 Folly Field Road Unit 13E, Hilton Head Island

Listing courtesy of I Save Realty.

$1,475,000
3 Beds ⋅ 4 Baths ⋅ 2,871 SqFt. ⋅ HILTONHEAD-512115 MLS
Rarely does a like-new home in Hilton Head Plantation pair this level of renovation with a premier address, a private saltwater swimming pool, and screened lanai. Beautifully reimagined in 2026, this private (single-story) residence features, tall ceilings, gorgeous plank flooring, current color selections, and an intelligently designed floor plan. The fully remodeled kitchen is an absolute showcase... Complete with quartz countertops, a downdraft vent range, updated stainless steel appliances, and a generous pantry behind craftsman-style barn doors. The three (en-suite) bathrooms have all been completely transformed and offer a modern and luxurious feel. The private pool was resurfaced in 2025 and includes new pool equipment! The house-wide plumbing was replaced with PEX for additional peace-of-mind! Add to the list spacious bedroom suites, a gas fireplace, a private office nook, epoxy floors in the garage, abundant closets/cabinetry, and professional landscaping outside. This is a high-elevation lot with a pleasant golf backdrop on a quiet, (limited traffic) street near Hilton Head Plantation's main gate. Virtually staged photos are meant to provide spatial information and decor inspiration. No structural modifications have been made.

43 Knollwood Drive, Hilton Head Island

Listing courtesy of Collins Group Realty.

$295,000
2 Beds ⋅ 1 Baths ⋅ 1,080 SqFt. ⋅ HILTONHEAD-512198 MLS
One of the nicest Marshsides to hit the market! Welcome to this light & bright, 2br. and 2bath end-unit villa in popular Marshside Villas. Offered fully furnished and featuring peaceful, double lagoon views, this inviting one-story home has been thoughtfully updated and is ready to enjoy! Completely turnkey, the refreshed kitchen features newer, stainless appliances (all just a few years old), new sink, breakfast bar with additional storage and seating, new lighting and ample cabinet space. The great room with cathedral ceiling and wood-burning fireplace features: smooth ceilings, built-ins, new ceiling fan and added cabinets and shelves. Wood-like laminate flooring throughout, the home features two remodeled baths with custom showers. The end-unit location offers additional privacy and natural light, while the lagoon setting creates a relaxing low country backdrop. Owner occupied with love and care since 2021, a great deal lot of thought has been put into storage and outdoor living space. Furniture, fixtures, TV's, etc all convey as a convenience to the purchaser and seller. Marshside has an excellent reputation for a well-run regime and great location near schools and hospitals.

5 Gumtree Road Unit F-5, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$359,000
2 Beds ⋅ 2 Baths ⋅ 888 SqFt. ⋅ HILTONHEAD-512183 MLS
Incredible opportunity to own a perfect 2 BR villa at the beach! This second floor updated villa has not been rented. This end unit has extra windows for more light. There are tile floors that look like wood in main living areas, Fresh coastal decor & comfortable furnishings make this an easy place to relax. The kitchen is updated with newer cabinets, under counter lighting, pretty quartz countertops and glass back splash & Stainless appliances too. Bath vanities and lighting are newer & bedrooms are nicely furnished. TV's in all rooms. The ocean front resort has the largest ocean front pool on HHI, a second pool, pickleball, tennis, bike rentals, restaurants, volleyball, 24 hour security, convention center and so much more. You are going to love it here!

40 Folly Field Road Unit D9, Hilton Head Island

Listing courtesy of C 21 A Low Country Realty.

$2,300
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512178 MLS
Enjoy the relaxed sophistication of Hilton Head Island during deeded Week 20, ideally positioned in the late May when the island is at its springtime best. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most sought-after settings. This desirable villa overlooks a lush lagoon, providing peaceful views and a tranquil backdrop throughout your stay. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and a vibrant coastal arts and culture scene. Imagine beginning your mornings with refreshing ocean breezes and serene golf course vistas, then setting out to bike beneath towering live oaks along miles of shaded pathways. Spend your afternoons on award-winning fairways, relaxing on the beach, or exploring the island's natural beauty before unwinding with spectacular waterfront sunsets. May's comfortable temperatures and blooming landscapes create the perfect setting for beach walks, outdoor dining, dolphin cruises, and all that Sea Pines has to offer-without the crowds of peak summer. Whether you prefer championship golf, coastal adventures, or simply relaxing on your private balcony overlooking the greens, everything you need is right at your doorstep.

70 Lighthouse Road Unit 2885, Hilton Head Island

Listing courtesy of Lighthouse Realty.

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