Hilton Head Island Homes with Pickleball Association Amenities

Welcome to Hilton Head Island, South Carolina, a captivating coastal paradise nestled in Beaufort County. Renowned for its stunning beaches, lush landscapes, and vibrant community, Hilton Head Island is the perfect blend of relaxation and recreation. With its temperate climate, the island offers year-round outdoor activities, making it an ideal destination for nature lovers and adventure seekers alike.

One of the standout features of Hilton Head Island is its commitment to fostering a lively, engaged community. For those who enjoy active living, homes with Pickleball Association amenities are a fantastic option. Pickleball, a dynamic sport that combines elements of tennis, badminton, and ping-pong, has become increasingly popular among residents and visitors. These homes provide not just a place to live, but a vibrant lifestyle where you can socialize, stay fit, and enjoy friendly competition with neighbors.

Imagine waking up in your beautiful Hilton Head home, stepping outside to a well-maintained pickleball court just a few steps away. Whether you're a seasoned player or a newcomer eager to learn, the community atmosphere is welcoming and inclusive. From organized tournaments to casual games, the Pickleball Association fosters camaraderie and encourages residents to stay active and engaged.

Beyond the courts, Hilton Head Island offers an array of attractions—from world-class golf courses and scenic bike trails to exquisite dining and shopping options. Experience the charm of this coastal gem, where every day feels like a vacation. Embrace the Hilton Head lifestyle and discover your dream home today!

Newest Hilton Head Island Homes with Pickleball Association Amenities

$295,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512265 MLS

Brand new HVAC and HW Heater! Welcome to this amazing unit in building 4, sold fully furnished and fully equipped with everything you need to start vacationing or renting. 2BD/2BA condo, ideally located just steps away from the beaches of Hilton Head. Top-floor unit complete with LVP floors and a spacious open-concept, making it an ideal residence or rental opportunity. Great rental history with a perfect set up for family vacations. Enjoy an array of incredible amenities, including indoor and outdoor pools, convenient beach access, tennis/pickleball courts, and a tropical beach bar. Additionally, numerous restaurants and shops are conveniently located nearby, ensuring the convenience and entertainment of island life. Don't miss the chance to see this exceptional condo today.

663 William Hilton Parkway Unit 4427, Hilton Head Island

Listing courtesy of Lowcountry Live Oak Realty.

$1,150,000

4 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511846 MLS

Rare Dolphin Head opportunity in Hilton Head Plantation. This 4BR/3BTH, 3357 SF home on a 0.42-acre homesite w/stunning lagoon views stretching to the 18th fairway of the Dolphin Head Golf Club-wide unobstructed views, gorgeous sunsets over the water, 50 year roof installed in 2014 and bright light/windows galore. This home was loved and lived in for 25 years. $10,000 seller credit toward updating. Buyers can move in with confidence. Clean stucco report and home inspection completed 7/7/2026. This is a true lagoon-fairway retreat minutes from groceries, Hospital Medical Pavilion, Schools, Spring Lake pool and tennis/pickle-ball and island beaches. HHP is voted over & over as "best community to live in" on the north end of Hilton Head Island.

11 China Cockle Way, Hilton Head Island

Listing courtesy of Charter One Realty.

$3,295,000

4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-511945 MLS

Oceanfront living takes center stage at this inviting residence in Ocean Point, a private section of the prestigious Port Royal community on Hilton Head Island. Set along the Atlantic, the home enjoys an exceptional coastal setting, with the oceanfront property between the residence and beach maintained by Ocean Point-providing owners the beauty of this remarkable landscape without the responsibility of maintaining it themselves.Inside, the home offers a comfortable blend of classic character and refreshed coastal style, with spacious living areas designed to complement the spectacular setting. Warm heart-of-pine floors, a natural connection between the kitchen and Carolina Room, and multiple bedrooms with ocean views create an inviting island retreat. The first-floor primary suite offers a private escape, while generous gathering spaces are ideal for family and entertaining.Ocean Point owners enjoy a private pool immediately adjacent to the property, as well as exclusive beach access. Port Royal's exceptional amenities add even more to the lifestyle, including an oceanfront Olympic-size pool, Beach House, playground, fire pits, pickleball and tennis courts, leisure trails, and private security.Thoughtfully refreshed and beautifully appointed, this special oceanfront residence offers a rare opportunity to enjoy the best of Hilton Head Island-where the ocean, exceptional amenities, and relaxed coastal living are right outside your door.

13 Ocean N Point, Hilton Head Island

Listing courtesy of Charter One Realty.

$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 ⋅ 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 ⋅ 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 ⋅ 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.

$359,000

2 Beds ⋅ 2 Baths ⋅ 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.

$310,000

1 Beds ⋅ 1 Baths ⋅ HILTONHEAD-512176 MLS

Beautifully updated and ideally located just steps from the beach, oceanfront pool, and all the resort amenities, this fully furnished villa is truly move-in ready. Enjoy stylishly renovated bathrooms, a bright and welcoming interior, and the convenience of being located near the front of the community for easy access. Wake up to beautiful Lowcountry sunrises and spend your days enjoying the exceptional amenities, including a beachfront pool, lighted tennis and pickleball courts, on-site restaurant, fitness center, bike rentals, and 24-hour gated security. Whether you're looking for a personal beach retreat, vacation home, or investment property, this villa checks every box. Currently participating in a successful rental program, this turnkey property offers immediate enjoyment and excellent income potential. Just bring your suitcase and start living the coastal lifestyle you've been dreaming of.

40 Folly Field Road Unit A232, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,290,000

4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-512173 MLS

Beautifully updated home in Moss Creek, one of the Hilton Head Island area's premier private golf and marina communities. Offering 3,480 square feet, this spacious mid-century modern Lowcountry home features 4 large bedrooms, including 2 primary suites, and 3.5 beautifully updated baths. The flexible layout includes a private guest suite with 2 bedrooms and a full bath, plus an additional primary suite with ensuite bath - ideal for family and guests. The completely updated kitchen features quartz countertops, new appliances, soft-close cabinetry, and elegant gold hardware. French oak wide-plank flooring flows throughout the main living areas, complemented by smooth ceilings, high-end lighting, and fresh interior and exterior paint. Enjoy the sought-after Moss Creek Lowcountry lifestyle with two 18-hole golf courses, private marina, tennis and pickleball, fitness and clubhouse amenities, all in a gated community conveniently located between Hilton Head Island and Bluffton, SC. A beautifully updated home offering space, flexibility, and the golf-and-marina lifestyle that makes Moss Creek such a special place to call home.

55 Saw Timber Drive, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$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.

$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.

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