Hilton Head Island Homes with Pickleball Amenities

Welcome to Hilton Head Island, South Carolina—an enchanting coastal paradise that perfectly blends natural beauty with vibrant community life. Nestled in Beaufort County, this idyllic island is renowned for its stunning beaches, lush landscapes, and a plethora of outdoor activities. With a mild climate year-round, Hilton Head is not just a vacation destination; it’s a lifestyle choice that many are proud to call home.

One of the standout features of Hilton Head Island is its commitment to active living, and what better way to stay fit and have fun than with pickleball? Homes equipped with pickleball amenities are becoming increasingly popular in this charming locale. These residences offer not just a home, but a lifestyle that encourages social interaction and healthy living. Picture yourself stepping out into your backyard to enjoy a friendly match with neighbors or friends, all while basking in the island's warm sunshine.

The real estate market in Hilton Head Island is as diverse as its residents, featuring everything from luxurious oceanfront estates to cozy villas tucked away in tranquil settings. Many communities here are designed with active lifestyles in mind, boasting state-of-the-art pickleball courts, fitness centers, and walking trails that weave through the island's natural beauty.

Whether you're looking to retire, raise a family, or simply escape the hustle and bustle of city life, Hilton Head Island offers a welcoming community where you can thrive. Explore homes with pickleball amenities today, and discover how you can embrace an active, fulfilling lifestyle in this picturesque island haven.

Newest Hilton Head Island Homes with Pickleball Amenities

$779,000

4 Beds ⋅ 3 Baths ⋅ 2,000 SqFt. ⋅ HILTONHEAD-511026 MLS

Updated 4 BR, 3 BA home overlooking scenic Henri's Pond in the gated community of Moss Creek. July 2026 - freshly painted throughout with popcorn ceiling removed and LVP installed in first floor halls, dining room, kitchen, living room and primary bedroom. A highlight of the home is the new large screened-in back porch overlooking Henri's Pond, creating the perfect setting for morning coffee, outdoor dining, or relaxing while enjoying the ever-changing views of the water and surrounding wildlife. The current owner further enhanced the property with a spacious 1-car garage and attached carport, providing exceptional convenience and additional storage. Owner had paver driveway and walkway installed from the street to the front door as well as outdoor decking area facing Henri's Pond. Conveniently located near Bostwick Park, featuring 2 pools, fitness center, and deep-water marina. Moss Creek amenities include 2 private 18-hole golf courses, tennis and pickleball courts, dog park, and nature trails. Move-in ready and ideally suited for enjoying the Lowcountry lifestyle. All major home items - roof, new HVAC and ductwork, PEX piping - recently updated.

283 Moss Creek Drive, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$250,000

2 Beds ⋅ 2 Baths ⋅ 950 SqFt. ⋅ HILTONHEAD-511784 MLS

Step inside this bright and welcoming coastal condo, where one of Hilton Head Resort's LARGER FLOOR PLANS creates a noticeable sense of openness, comfort, and flexibility... The spacious living room, dining area, and kitchen flow together naturally, making the condo feel inviting from the moment you enter and providing plenty of room to unwind after a day at the beach, gather for meals, or entertain family and friends... Warm wood-look flooring, crown molding, soft neutral finishes, and comfortable furnishings give the main living space a relaxed coastal feel, while the kitchen features crisp white cabinetry, GRANITE counters, a double-basin sink, generous prep space, and a convenient pass-through that keeps the kitchen connected to the living area... Both bedrooms are comfortably sized, including a versatile guest room thoughtfully arranged with space for a full-size bed and bunk beds, allowing the condo to accommodate additional guests without sacrificing comfort... The bathrooms have been nicely updated with modern vanities, contemporary fixtures, marble-look tile flooring, and a beautifully tiled walk-in shower with sliding glass doors... One of the most valuable features of this larger layout is the WASHER AND DRYER INSIDE THE CONDO, offering a level of convenience that is especially appealing for full-time living, extended vacations, and short-term rental guests... Additional storage makes it easy to keep beach chairs, luggage, and everyday essentials neatly organized... Offered FULLY FURNISHED and ready to enjoy, this well-maintained villa is located in the preferred Tennis Building #4 with convenient ELEVATOR ACCESS... Hilton Head Resort offers the kind of amenities that make every visit feel like a true coastal escape, including direct beach access by private boardwalk or seasonal shuttle, indoor and outdoor pools, a heated indoor pool, kiddie pool, hot tub, sauna, fitness center, indoor jogging track, lighted tennis and pickleball courts, volleyball, bike rentals and storage, grilling stations, sun decks, garden areas, a deli, and the iconic Coco's on the Beach... Centrally located mid-island near Palmetto Dunes, Shelter Cove Marina and Towne Centre, golf, bike paths, shopping, dining, and entertainment, this condo is an excellent choice as a primary residence, beach getaway, or RENTAL-READY investment property.

663 William Hilton Parkway Unit 4135, Hilton Head Island

Listing courtesy of Real Broker, LLC.

$1,995,000

2 Beds ⋅ 2 Baths ⋅ 1,883 SqFt. ⋅ HILTONHEAD-511684 MLS

Selling a dream located 4th row on Whistling Swan to build your new custom home! Steps away from SP Beach Club restaurants, beach bar and the sandy white beach and Plantation Golf Club. Lot dimensions are 107 X 133 X 103 X 150 = .34/acre. Selling "As- Is"; "Where-Is" with seller making no repairs. No inspections. Possible lease back needed.

1 Whistling Swan Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - The Cottage Group, LLC.

$1,849,500

3 Beds ⋅ 3 Baths ⋅ 2,440 SqFt. ⋅ HILTONHEAD-511596 MLS

Classic Hilton Head Island architecture, perfectly preserved and completely reimagined. Set on a rare corner estate lot of more than three-quarters of an acre in Shipyard Plantation, 37 Kingston Road offers a level of finish and scale rarely found at this price point among the Island's premier gated communities. A complete renovation from top to bottom includes brand new HVAC systems with all new ductwork, a stunning new pool with a Pennsylvania flagstone deck, and designer finishes throughout. Vaulted ceilings, skylights, and thoughtful millwork bring warmth, character, and natural light to every room. The kitchen has been completely updated with white shaker cabinetry, stone countertops, stainless steel appliances, and a center island. The split floor plan offers ideal separation between the primary suite and guest bedrooms, while the generous lot provides the opportunity to add a guest house or casita. The primary suite is spacious and serene, with direct access to the pool and a beautifully renovated bath featuring a marble walk-in shower and double vanity. Every bathroom reflects the same level of craftsmanship and attention to detail found throughout the home. Outside, the new pool and Pennsylvania flagstone deck create a private outdoor retreat surrounded by mature live oaks and classic Lowcountry landscaping. The bonus Carolina room extends the living space, creating a seamless connection between the home's interior and outdoor living areas. Offered furnished and available for immediate enjoyment, the home is just a five-minute bike ride to the Shipyard Beach Club and the Sonesta Resort, and only minutes from some of the Island's best dining, shopping, golf, and recreation. Short-term rental projections are available upon request. Whether the goal is a primary residence, a multigenerational retreat, a second home, or an income-producing investment property, 37 Kingston Road is uniquely positioned to deliver. A rare corner estate, completely renovated, furnished, and ready, at a price that rewards the discerning buyer who knows this market. *Owner is SCREA.

37 Kingston Road, Hilton Head Island

Listing courtesy of ELEVE PROPERTIES Brokered by EXP Realty.

$555,000

2 Beds ⋅ 2 Baths ⋅ 996 SqFt. ⋅ HILTONHEAD-511793 MLS

Experience coastal luxury in this stunning, fully furnished 2-bedroom, 2-bath villa inspired by the sophisticated design and spa-like ambiance of Miami's iconic 1 Hotel. Located in the highly sought-after Admiral's Row section of Hilton Head Beach & Tennis Resort, this turnkey ocean-view retreat is being offered fully furnished and is just steps from one of the East Coast's most breathtaking beaches. The villa has an excellent established rental history. .From the moment you enter, you'll be captivated by panoramic ocean views and an abundance of natural light. The open-concept living space blends modern elegance with comfort, featuring a spacious living area ideal for relaxing or entertaining. The dining area comfortably seats six, while the beautifully updated kitchen is designed for both style and functionality.Step outside to your private ocean-view balcony, complete with a hanging swing, daybed, and bar-height seating-the perfect place to enjoy your morning coffee or unwind while listening to the waves.The primary suite features a king bed and a beautifully renovated ensuite bath. The guest bedroom is ideal for families and guests, offering a queen storage bed, twin bed, and ample storage. Convenient elevator and stair access are located just steps from the villa.Owners and guests enjoy access to Hilton Head Beach & Tennis Resort's exceptional amenities, including the island's largest oceanfront pool and kiddie pool, a second pool located just outside the building, 10 tennis courts, fitness center, playground, grilling and picnic areas, conference facilities, and two on-site restaurants.Whether you're seeking a primary residence, vacation retreat, or investment property, this turnkey, fully furnished villa offers the ultimate Hilton Head lifestyle in one of the island's most desirable beachfront communities. With its premier ocean-oriented location, luxury renovation, resort-style amenities, and strong appeal to vacation renters, this property presents an exceptional opportunity to generate rental income while enjoying your own private coastal getaway.

40 Folly Field Road Unit 215, Hilton Head Island

Listing courtesy of Beach House Boutique.

$234,000

HILTONHEAD-511772 MLS

Enjoy a beautifully landscaped RV lot that has plenty of space to relax and/or entertain. Easily accommodating up to a 42' coach and a tow vehicle this stamped concrete pad will provide you with ample room to spread out and relax at either of the two comfortable sitting areas. This lot includes the sofa with cushions, 2 end tables, coffee table, high-top table with 4 bar hight chairs, two cantilever umbrellas, irrigation, landscape lighting, and the large storage shed. This RV lot is just steps away from all the amazing amenities the resort has to offer, yet gives you the privacy you're looking for on your island getaway! Hilton 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 andSuper C Motorcoaches only. The resort consists of 50 acres of woodland and lush landscape setting accented with live oaks dripping withSpanish Moss, palms trees, ferns and flowering shrubs. The resorts amenities 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 134, Hilton Head Island

Listing courtesy of View Properties.

$699,000

2 Beds ⋅ 2 Baths ⋅ 1,400 SqFt. ⋅ HILTONHEAD-511765 MLS

Discover this diamond in the rough! A 2-bedroom, 2-bath townhouse in the heart of Sea Pines Resort. This light filled villa offers approximately 1,400 square feet of single-level living with vaulted ceilings, an open floor plan, and peaceful lagoon views from the living room, primary suite, and spacious rear deck. Enjoy added privacy along with a welcoming front porch and excellent bedroom separation.Perfect as a primary residence, vacation home, or investment property with short-term rental potential, this villa also offers access to a community pool and tennis courts.Ideally located near the Sea Pines Forest Preserve, Harbour Town and pristine beaches, championship golf, bike trails, marinas, shopping, and dining, this is an outstanding opportunity to enjoy the very best of Hilton Head Island living. Brand new front and rear decks!

35 Lake Forest Drive Unit APT 3304, Hilton Head Island

Listing courtesy of ERA Wilder Realty, Inc.

$259,990

2 Beds ⋅ 2 Baths ⋅ 831 SqFt. ⋅ HILTONHEAD-511405 MLS

Recently refreshed with fresh paint and stylish new furnishings, this ocean-oriented 2-bedroom villa is truly turnkey and ready to enjoy. Whether you're searching for a personal vacation getaway, an income-producing investment, or the perfect combination of both, 4104 Hilton Head Resort presents an exceptional opportunity. With existing reservations already in place, this villa offers immediate rental income potential while giving future owners the flexibility to enjoy everything Hilton Head Island has to offer. Located within the gated Hilton Head Resort community, owners and guests enjoy an impressive collection of resort-style amenities, including indoor and outdoor pools, tennis courts, a fitness center, game room, private beach access, and Coco's on the Beach. Conveniently situated near championship golf courses, shopping, dining, and miles of pristine beaches, this low-maintenance villa makes island living effortless. Whether you're expanding your investment portfolio, purchasing your own coastal retreat, or seeking a property that offers the best of both worlds, this beautifully updated villa delivers outstanding value in one of Hilton Head Island's most amenity-rich beach communities.

663 William Hilton Parkway Unit 4104, Hilton Head Island

Listing courtesy of Real Broker, LLC.

$1,275,000

4 Beds ⋅ 4 Baths ⋅ 3,132 SqFt. ⋅ HILTONHEAD-511593 MLS

This beautiful 4 bedroom, 3.5 bath home offers the perfect blend of comfort, style, and convenience. Located on one of the most desirable streets in HHP with golf and lagoon views within easy walking distance to the Country Club of Hilton Head. Impressive 12ft ceilings, 8ft doors, arched hallway passages, crown molding, travertine stone and hardwood floors create an ideal balance of modern living and timeless appeal. The home has been extensively updated, featuring a recently remodeled kitchen and renovated bathrooms, along with fresh paint throughout. Two new heat pumps including air ducts provide added comfort and efficiency. The versatile bonus room can be used as a home office, media room, exercise area, guest space, or whatever best suits your lifestyle. The impressive three-car garage adds exceptional convenience and storage, complete with new garage doors and durable urethane floor.

52 Old Fort Drive, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$229,900

HILTONHEAD-511742 MLS

Rare perimeter lot opportunity with kitchen, priced for a quick sale. Backing up to the Wexford golf course is the most private area of the park, with a walking path to many of your neighbors behind the lot. This beautifully maintained property features a stamped concrete pad with new Industrial Polyaspartic Epoxy surface accommodating a 45' coach plus two vehicles. The outdoor living area is designed for entertaining, complete with an outdoor kitchen including a Saber grill and extra favorizing grids. The stainless sink has instant hot water as well as a garage. The lot also features an irrigation system and landscape lighting. The newer furnishings are a bonus and are also included. Located within Hilton Head Island Motorcoach Resort, a premier luxury motorcoach-only resort for Class A, Class C, and Super C coaches, owners enjoy 50 acres of beautifully landscaped grounds surrounded by majestic live oaks draped in Spanish moss, palms, flowering shrubs, and lush Lowcountry scenery. Resort amenities include a clubhouse, heated and cooled swimming pool, hot tub, fitness center, tennis and pickleball courts, shuffleboard, basketball court, playground, dog park, laundry facilities, dedicated Wi-Fi with personal modem, cable TV, daily trash pickup, lawn maintenance, water & sewer. Conveniently located just a short bike ride from Coligny Beach Park and within near distance to shopping, dining, and entertainment, this exceptional property offers the perfect combination of luxury, convenience, and investment potential.

133 Arrow Road Unit # 102, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$299,999

2 Beds ⋅ 3 Baths ⋅ 1,025 SqFt. ⋅ HILTONHEAD-511726 MLS

Welcome to this beautifully renovated 2-bedroom, 2.5-bath villa in Woodlake on Hilton Head Island. Peacefully tucked away with a serene lagoon view, this move-in-ready condo has been completely updated with a fresh, modern feel and thoughtful finishes throughout. The renovated kitchen and bathrooms complement the bright and inviting living spaces, creating a comfortable setting to relax or entertain. Both bedrooms offer comfortable private retreats, making this villa a great fit for a full-time residence, second home, or investment property. Enjoy the peaceful setting while still being just minutes from Hilton Head's beaches, restaurants, shopping, and everything the island has to offer. With its peaceful setting, extensive renovations, and convenient island location, this Woodlake villa is one you won't want to miss.

96 Mathews Drive Unit 142, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$825,000

3 Beds ⋅ 2 Baths ⋅ 1,590 SqFt. ⋅ HILTONHEAD-511445 MLS

Located just across the street from Sea Pines Country Club, on a quiet street, this 3-bedroom, 2-bath home offers something increasingly rare in Sea Pines: real opportunity under $1MM. The floorplan flows effortlessly with high ceilings in the family and primary bedroom. Outside, a fenced yard, private patio, and screened porch create the kind of everyday outdoor living buyers dream about. A two-car garage adds convenience rarely found at this price point in Sea Pines. Well loved and full of potential, this home is ready for your vision - bring your style and make it your own, in a location that speaks for itself. Minutes to Harbour Town, the beach, and miles of biking trails, all within the privacy and security Sea Pines is known for.

5 Wood Duck Court, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

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