Communities in Maryland with pickleball facilities and homes for sale

Maryland Pickleball Communities

Discover the Best Maryland Pickleball Communities

With its scenic coastal landscapes, vibrant active adult communities, and strong pickleball culture, Maryland pickleball communities are the perfect destination for players of all levels. Whether you're searching for pickleball in Maryland near Washington, D.C., a waterfront retreat on the Chesapeake Bay, or an active adult neighborhood on Maryland’s Eastern Shore, there are communities designed to match your lifestyle.

PCR connects you with the best pickleball communities in Maryland, where you’ll find top-tier courts, competitive leagues, and an engaging social atmosphere. Explore pickleball retirement communities, master-planned developments, and resort-style neighborhoods featuring world-class amenities. Browse community details, view homes for sale in Maryland pickleball communities, and request more information directly from community representatives.

Why Are Pickleball Communities in Maryland Popular?

Maryland is home to a growing number of pickleball communities, thanks to its year-round recreational opportunities, social engagement, and resort-style amenities. Residents of these pickleball communities enjoy many benefits, including:

  • Professionally designed pickleball courts, including indoor and outdoor facilities
  • Organized pickleball leagues and social events, perfect for players of all skill levels
  • Luxury amenities, such as clubhouses, pools, golf courses, and waterfront access
  • A vibrant and welcoming atmosphere, where active adults and retirees can stay fit, engaged, and connected

Whether you're looking for pickleball in Maryland’s coastal regions, the Chesapeake Bay area, or pickleball Maryland communities near Washington, D.C., you'll find an ideal place to live and play.

Living in a Maryland Pickleball Community

From 55+ pickleball retirement communities to all-ages master-planned neighborhoods, Maryland offers a variety of options for pickleball enthusiasts. Some of the most popular areas include:

  • Maryland’s Eastern Shore – Coastal and waterfront communities featuring scenic landscapes and active lifestyle amenities.
  • Southern Maryland – Affordable, peaceful communities with easy access to outdoor recreation and pickleball facilities.
  • Chesapeake Bay Area – Resort-style living with private pickleball courts, marinas, and social clubs.
  • Near Washington, D.C. – Convenient suburban communities offering pickleball leagues and luxury amenities.

No matter your preference or stage in life, pickleball communities in Maryland provide the perfect combination of recreation, social engagement, and modern living. Explore Maryland pickleball communities today and find your ideal home!


Filtered Results (3)

K. Hovnanian's ® Four Seasons at Kent Island

Chester, Maryland Pickleball Community
Chester, Maryland

This 55+ community offers a waterfront resort lifestyle on Chesapeake Bay's largest island. Resort-style amenities for active adults include a 24,000-square-foot waterfront clubhouse, fully-equipped fitness center, tennis & pickleball courts, indoor & outdoor swimming pools, a fishing pier, and walking & biking trails. Low-maintenance single-family homes and condominiums are priced from the $400,000s. Read More...

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Lakeside at Trappe

Trappe, Maryland Pickleball Community
Trappe, Maryland

Situated on the Eastern Shore of Maryland in Talbot County, Lakeside at Trappe is a private master-planned community for all ages. Residents have immediate access to Route 50 with proximity to Annapolis, Easton, and local beaches. Resort-style amenities include an on-site lake, clubhouse, sports courts, swimming pool, fitness center, dog park, and more. Home designs include single-family floorplans up to 3,700+ square feet, 6 bedrooms and 4 bathrooms with options for main-level living. Priced from the $400,000s and up. Home leases are available starting in the $2,000s/month. Read More...

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Swan Point

Swan Point, Maryland Pickleball Community
Swan Point, Maryland

Swan Point is a resort golf and waterfront community in Swan Point, MD. Located about 50 miles south of Washington, D.C., in Chester County, the Southern Maryland community is situated on the Potomac River and Cuckold Creek epitomizing premier Maryland waterfront living. Amenities include a marina, clubhouse with dining options, championship golf course, tennis, pickleball, swimming pool, and walking trails. Developed by Brookfield Residential, the innovative home designs offer several floorplans with buying and leasing options. Lots from $38,500; the unique Maryland real estate ranges from 2,469 – 3,527 square feet with homes priced from the $500,000s. Read More...

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