Hilton Head Island Homes with Pickleball Association amenities

Welcome to Hilton Head Island, South Carolina—a breathtaking coastal paradise nestled in Beaufort County, renowned for its stunning beaches, lush landscapes, and vibrant community spirit. With its rich history and commitment to preserving natural beauty, Hilton Head Island is not just a destination; it’s a lifestyle.

Here, you’ll find an array of charming neighborhoods, each offering unique architectural styles and amenities that cater to a variety of tastes. If you’re a fan of an active lifestyle, you’ll love the homes in communities with Pickleball Association amenities. These residences provide residents with access to top-notch pickleball courts, where you can engage in friendly matches and meet fellow enthusiasts.

Imagine waking up to the sound of waves crashing on the shore, enjoying a morning round of pickleball, and then unwinding on the beach with a book in hand. Hilton Head Island is designed for those who appreciate the finer things in life—whether it’s world-class golf courses, exquisite dining options, or the simple pleasure of sunset strolls along the beach.

The community here is welcoming, with a strong focus on health and wellness, making it an ideal place for families, retirees, and everyone in between. With year-round events, social clubs, and recreational activities, you'll always find something to do.

Discover your dream home on Hilton Head Island, where the sun shines bright, and the spirit of community thrives. Embrace the island life and make every day a vacation!

Newest Hilton Head Island Homes with Pickleball Association amenities

$134,900

HILTONHEAD-513129 MLS

Hilton Head Harbor RV Resort & Marina is a premier waterfront community located directly on the Intracoastal Waterway on Hilton Head Island, South Carolina. All lots feature fee-simple ownership and come fully equipped with concrete pads, water, sewer, 30- and 50-amp electric service, cable TV, and WiFi. The homeowners association handles basic grounds maintenance (mowing, blowing, and trimming) as well as daily on-site trash pickup.Resort amenities include two saltwater pools (one with scenic Intracoastal views), an in-ground hot tub, a tennis court also lined for pickleball, an exercise room, and a laundry facility. On-site boating and recreation options feature a deep-water boat launch, full-service marina with fuel and dockage, watersports rentals, and a highly regarded 5-star restaurant. - This Outer-Loop Lot, # 14, at Hilton Head Harbor RV Resort & Marina is a spacious, tree-shaded lot with a long concrete pad, mature landscaping and attractive stone edging. The deep site offers plenty of room for a large RV and outdoor living, with an updated power pedestal and a peaceful setting along the outer loop.

43 Jenkins Island Road Unit 14, Hilton Head Island

Listing courtesy of Hilton Head Holidays Inc.

$195,000

2 Beds ⋅ 2 Baths ⋅ 831 SqFt. ⋅ HILTONHEAD-513120 MLS

Your island escape awaits at 4125 Hilton Head Resort! This furnished 2-bedroom, 2-bath villa offers approximately 831 square feet of inviting coastal living in a gated community with full-time security and an impressive collection of amenities. Whether you're seeking a second home, vacation retreat, or potential short-term rental, this property offers an appealing combination of comfort, convenience, and value. Inside, coastal colors and an open living and dining area create a welcoming place to gather after a day at the beach. The kitchen features white cabinetry, stainless steel appliances, and a striking blue tile backsplash. Vinyl tile flooring, ceiling fans, keyless entry, and TVs in both bedrooms add everyday convenience, while the front porch offers views of the tennis courts. Take a short stroll along the resort's private boardwalk across the scenic salt marsh to Hilton Head's beautiful sandy beach, or spend the day enjoying the community's two outdoor pools, heated indoor pool, hot tub, sauna, and fitness center. Tennis and pickleball courts, outdoor grilling areas, on-site laundry, and elevator access round out the resort experience. Centrally located on Hilton Head Island, this villa puts shopping, dining, golf, and island attractions within easy reach. Enjoy a coastal getaway of your own with the added appeal of vacation rental potential!

663 William Hilton Parkway Unit 4215, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$2,849,000

4 Beds ⋅ 5 Baths ⋅ 3,925 SqFt. ⋅ HILTONHEAD-512812 MLS

Fully remodeled and beautifully appointed, this exceptional harbourfront home in Wexford offers a relaxed Lowcountry lifestyle with harbour views, a private dock, private pool, and 3,925 square feet of living space. The home features 4 bedrooms, 4 full and 1 half baths, and 2-car plus golf cart garage. Wexford's private marina and harbour provide direct access to the Broad Creek and the Intracoastal Waterway through its 24/7 lock system, one of only three on the East Coast.Upon entering, the formal living room makes an immediate impression with soaring ceilings, exposed beams, a propane fireplace, and expansive windows that fill the space with natural light. Doors open directly to the pool deck, creating an effortless connection between indoor and outdoor living. The inviting family room features high ceilings, floor-to-ceiling windows, an electric fireplace, and direct access to the pool deck.At the heart of the home is a stunning, fully remodeled kitchen with a bright, open design, double islands, top-of-the-line appliances, quartz countertops, and a walk-in pantry. The spacious first-floor primary suite features a beautifully remodeled bath with a zero-entry shower, a soaking tub, and a generous walk-in closet. A first-floor laundry room adds everyday convenience.The outdoor living spaces have been thoughtfully enhanced with a brand-new covered area overlooking the pool and harbour, creating an inviting space for relaxing and entertaining. The newly plastered pool and resurfaced pool deck provide a refreshed outdoor retreat. The generous lot offers plenty of room and privacy, while the 2-car plus golf cart garage provides storage and convenience.Wexford members enjoy a premier private club lifestyle, including an Arnold Palmer Signature golf course, tennis, pickleball, croquet, pool complex, private harbour, fire pit, and newly opened Clubhouse and Harbour Center. Combined with a vibrant social calendar and Wexford's unique marina lifestyle, this is an exceptional opportunity to enjoy the best of private club living on Hilton Head Island.

44 Wexford Club Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$4,400,000

6 Beds ⋅ 6 Baths ⋅ 4,796 SqFt. ⋅ HILTONHEAD-513002 MLS

Like NEW, this state of the art Lowcountry 6BR/5.5BA Beach Home approx 8000+ sq ft under roof offering 2 living rooms, 2 screened porches, huge garage, workshop and large private pool was designed for the way you actually want to live on Hilton Head Island. Open, comfortable, private, premium finishes, with perfectly designed outdoor spaces all just moments from the residents only private beach . Hardwood floors, custom millwork, built-ins and walls of windows carry throughout the home. The kitchen is a showstopper with an oversized island, custom cabinetry, high-end appliances and a true walk-in pantry. The primary suite is equally impressive with a his & her bathrooms w/freestanding soaking tub, oversized tiled shower and a custom his and hers walk-in closets. Outside is where this home really separates itself. Two screened porches create an incredible amount of year-round living space, including an upper porch with fireplace, built-in grill and dining area. Downstairs, another oversized screened living area opens to the private pool, hot tub and beautifully landscaped backyard. Add an elevator, dedicated office, game area, workshop and more storage than you expect to find in an island home, and there's very little this house leaves you wanting. One of the finest homes ever offered for sale in Port Royal situated on a premium oversized extremely private lot in close proximity to the Beach & Port Royal Beach Club.

51 Scarborough Head Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$309,000

1 Beds ⋅ 1 Baths ⋅ 540 SqFt. ⋅ HILTONHEAD-513107 MLS

Turnkey and renovated in 2024, C217 offers Lowcountry marsh and wooded views with convenient beach access. Used exclusively as the owners' private retreat, the villa has been carefully maintained and is located in a building with an elevator. The open kitchen and living area feature quartz countertops, new cabinetry and stainless steel appliances, LVP flooring and a built-in sound system. A new HVAC system was installed in 2026. The villa is offered fully furnished and includes fresh paint in a coastal color and a custom designed bedroom closet. The redesigned bathroom features a white quartz-topped vanity and a tiled walk-in shower with a glass enclosure. Expansive living room windows bring natural light into the living area and frame the private marsh and wooded surroundings. The balcony offers sunrise views overlooking the marsh and trees where birds are frequently seen and heard. Shaded from direct afternoon sun, it creates a great place to relax after a day at the beach. Hilton Head Beach and Tennis Resort amenities include tennis and pickleball courts, swimming pools, on-site dining, a fitness center, playground, laundry facilities and 24-hour security. This villa can easily be used as a primary residence, vacation home or investment property.

40 Folly Field Road Unit C217, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$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.

$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.

$1,475,000

3 Beds ⋅ 4 Baths ⋅ 2,584 SqFt. ⋅ HILTONHEAD-513048 MLS

Walk to the Beach in Palmetto Dunes! Located in the highly desirable, gated Palmetto Dunes oceanfront community, this single-level coastal home is priced for you to add your cosmetic touches. With 3 bedrooms and 3.5 baths, the home features separate living areas, a large kitchen, a fireplace, and vaulted ceilings that create an open feel throughout. Enjoy outdoor living in the beautiful backyard with serene water views and a private pool, perfect for relaxing after a day at the beach. Outdoor shower and 1/2 bath outside. The home is fully furnished and offers you a rare chance to customize a home in one of Hilton Head Island's most sought-after beachfront communities. Just a short walk to the Atlantic Ocean, golf, tennis, and all Palmetto Dunes amenities.

10 Off Shore, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$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.

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