Hilton Head Island Homes with Pickleball Amenities

Hilton Head Island Homes with Pickleball Amenities

Welcome to Hilton Head Island, a gem nestled in Beaufort County, South Carolina. Renowned for its stunning beaches, lush landscapes, and vibrant community, Hilton Head offers an unparalleled lifestyle that attracts residents and visitors alike. With a rich history and a commitment to preserving its natural beauty, this island paradise is the perfect backdrop for those seeking both relaxation and recreation.

One of the standout features of Hilton Head Island is its thriving pickleball scene. As one of the fastest-growing sports in the country, pickleball has found a welcoming home here. Many homes in the area are designed with pickleball amenities, allowing residents to enjoy this exciting sport right in their own backyards or within their communities. Imagine stepping out of your beautifully appointed home to a private court, where you can engage in friendly matches with neighbors or hone your skills with family and friends.

In addition to pickleball, Hilton Head Island boasts a myriad of outdoor activities, including world-class golf courses, scenic biking trails, and pristine parks. The island’s commitment to a healthy, active lifestyle is evident in its community-focused amenities, making it an ideal place for families, retirees, and everyone in between.

Whether you’re looking for a cozy cottage or a luxurious estate, homes with pickleball amenities in Hilton Head Island offer the perfect blend of comfort and recreation. Embrace the island lifestyle and discover your dream home on this enchanting coastal retreat, where sunshine, sports, and community await you.

Newest Hilton Head Island Homes with Pickleball Amenities

$395,000
3 Beds ⋅ 2 Baths ⋅ 1,186 SqFt. ⋅ HILTONHEAD-512148 MLS
Desirable and spacious 3-bedroom, 2-bath top-floor corner villa in the highly sought-after, beach-oriented Hilton Head Resort! With no neighbors above, this light-filled villa offers added privacy and beautiful lagoon, marsh, golf course, and tennis court views from the private balcony. The updated kitchen features white cabinetry, stainless steel appliances, granite countertops, and a convenient bar area with sink. Smooth ceilings and LVP flooring throughout create a clean, modern feel. Additional updates include a brand-new in-unit washer and dryer and new HVAC system. Hilton Head Resort offers an exceptional array of amenities, including two outdoor pools, an indoor pool, spa, sauna, jacuzzi, fitness room, and multiple tennis and pickleball courts. Enjoy seasonal dining at the main pool, plus convenient beach access via the private boardwalk with seasonal shuttle service, beach bar, and grill. Strong rental history makes this an excellent opportunity as a vacation getaway, investment property, or both!

663 William Hilton Parkway Unit 4420, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$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 with 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.

$295,000
2 Beds ⋅ 2 Baths ⋅ 831 SqFt. ⋅ 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 ⋅ 3,357 SqFt. ⋅ 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 ⋅ 3,300 SqFt. ⋅ 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 ⋅ 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.

$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.

$310,000
1 Beds ⋅ 1 Baths ⋅ 540 SqFt. ⋅ 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.

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