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 (9)

Bloomfields

Frederick, Maryland Pickleball Community
Frederick, Maryland
Bloomfields is a Maryland 55+ community in Frederick offering new-construction cottages, villas, and single-family Maryland homes for sale. This active adult community in Maryland features a clubhouse, fitness center, pool, pickleball and tennis courts, golf simulator, and walking trails — all just minutes from downtown Frederick and major Central Maryland highways.

Pricing: From the high $300,000s to low $800,000s

Community Type: 55+ Active Adult

Community Amenity: Biking Trails Biking Trails
Community Amenity: Clubhouse Clubhouse
Community Amenity: Community Gardens Community Gardens
Community Amenity: Dog Park Dog Park
Community Amenity: Fitness Fitness
Community Amenity: Golf Nearby Golf Nearby
Community Amenity: Nature Trails Nature Trails
Community Amenity: Pickleball Pickleball
Community Amenity: Playground Playground
Community Amenity: Swimming Swimming
Community Amenity: Tennis Tennis
Community Amenity: Walking Trails Walking Trails

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Carroll Vista

Taneytown, Maryland Pickleball Community
Taneytown, Maryland
Carroll Vista is a Maryland 55+ community in Taneytown offering low-maintenance single-family and attached Maryland homes for sale. This active adult community in Maryland features a 15,000-square-foot clubhouse, indoor and outdoor pools, pickleball, tennis, golf practice facilities, and a vibrant social calendar — all within easy reach of Gettysburg, Baltimore, and Washington, D.C.

Pricing: Homes from the low $300,000s to high $400,000s

Community Type: 55+ Active Adult

Community Amenity: Biking Trails Biking Trails
Community Amenity: Clubhouse Clubhouse
Community Amenity: Community Gardens Community Gardens
Community Amenity: Fitness Fitness
Community Amenity: Golf Golf
Community Amenity: Golf Nearby Golf Nearby
Community Amenity: Nature Trails Nature Trails
Community Amenity: Pickleball Pickleball
Community Amenity: Swimming Swimming
Community Amenity: Tennis Tennis
Community Amenity: Walking Trails Walking Trails

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Crestwood Village

Frederick, Maryland Pickleball Community
Frederick, Maryland
Crestwood Village is a Maryland 55+ community in Frederick offering low-maintenance single-family homes, duplexes, and condos. This active adult community in Maryland features a clubhouse, pools, tennis courts, mini golf, and community transit—all just minutes from downtown Frederick and major Central Maryland highways.

Pricing: Condos, Single-Family Homes from the low $200,000s to low $500,000s

Community Type: 55+ Active Adult

Community Amenity: Clubhouse Clubhouse
Community Amenity: Fitness Fitness
Community Amenity: Golf Nearby Golf Nearby
Community Amenity: Pickleball Pickleball
Community Amenity: Swimming Swimming
Community Amenity: Tennis Tennis

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Cromwell

Frederick, Maryland Pickleball Community
Frederick, Maryland
Cromwell is a Maryland 55+ community in Frederick offering new villas, condos, and single-family Maryland homes for sale. This active adult community in Maryland features a clubhouse, pool, pickleball courts, golf simulator, and walkable access to Linganore Town Center — all minutes from downtown Frederick and I-70.

Pricing: From the low $300,000s to high $800,000s

Community Type: 55+ Active Adult

Community Amenity: Biking Trails Biking Trails
Community Amenity: Clubhouse Clubhouse
Community Amenity: Dog Park Dog Park
Community Amenity: Fitness Fitness
Community Amenity: Golf Nearby Golf Nearby
Community Amenity: Pickleball Pickleball
Community Amenity: Swimming Swimming
Community Amenity: Walking Trails Walking Trails

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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.

Pricing: Low-maintenance single-family homes from the $600,000s and condominiums from the $400,000s.

Community Type: 55+ Active Adult

Community Amenity: Biking Trails Biking Trails
Community Amenity: Boating Boating
Community Amenity: Clubhouse Clubhouse
Community Amenity: Dining Dining
Community Amenity: Dog Park Dog Park
Community Amenity: Fitness Fitness
Community Amenity: Golf Nearby Golf Nearby
Community Amenity: Pickleball Pickleball
Community Amenity: River River
Community Amenity: Swimming Swimming
Community Amenity: Tennis Tennis
Community Amenity: Walking Trails Walking Trails

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K. Hovnanian's Four Seasons at Easton

Easton, Maryland Pickleball Community
Easton, Maryland
K. Hovnanian’s Four Seasons at Easton is a resort-style 55-plus community in Maryland’s Eastern Shore offering low-maintenance homes, curated finishes, and vibrant amenities. This Maryland active adult community features a 6,000-square-foot clubhouse, fitness center, pickleball courts, walking trails, and a pool. Close to downtown Easton and Chesapeake Bay recreation, residents enjoy small-town charm with easy access to Annapolis, D.C., and Delaware beaches—ideal for those seeking homes for sale in Maryland designed for the 55+ lifestyle.

Pricing: Homes priced from the $400,000s.

Community Type: 55+ Active Adult

Community Amenity: Biking Trails Biking Trails
Community Amenity: Clubhouse Clubhouse
Community Amenity: Community Gardens Community Gardens
Community Amenity: Dog Park Dog Park
Community Amenity: Fitness Fitness
Community Amenity: Golf Nearby Golf Nearby
Community Amenity: Nature Trails Nature Trails
Community Amenity: Pickleball Pickleball
Community Amenity: Playground Playground
Community Amenity: Swimming Swimming
Community Amenity: Walking Trails Walking Trails

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Leisure World of Maryland

Silver Spring, Maryland Pickleball Community
Silver Spring, Maryland
Leisure World of Maryland is a gated 55+ community in Silver Spring offering resort-style amenities, an 18-hole golf course, and low-maintenance Maryland homes for sale. Located in Montgomery County near Washington, D.C., this active adult community in Maryland features two clubhouses, on-site services, and a wide variety of condos and single-family homes designed for easy living.

Pricing: Condos and single-family homes from under $100,000 to $800,000+

Community Type: 55+ Active Adult

Community Amenity: Biking Trails Biking Trails
Community Amenity: Clubhouse Clubhouse
Community Amenity: Community Gardens Community Gardens
Community Amenity: Dining Dining
Community Amenity: Fitness Fitness
Community Amenity: Gatehouse Gatehouse
Community Amenity: Golf Golf
Community Amenity: Lake Lake
Community Amenity: Pickleball Pickleball
Community Amenity: Swimming Swimming
Community Amenity: Tennis Tennis
Community Amenity: Walking Trails Walking Trails

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Signature Club at Greenview

New Market, Maryland Pickleball Community
New Market, Maryland
Signature Club at Greenview is a Maryland 55+ community in New Market offering low-maintenance villas and single-family Maryland homes for sale. This active adult community in Maryland features a clubhouse, fitness center, outdoor pool, pickleball courts, and a vibrant social calendar — all minutes from historic Frederick and within easy reach of Washington, D.C. and Baltimore.

Pricing: Homes from the mid $400,000s to high $500,000s

Community Type: 55+ Active Adult

Community Amenity: Biking Trails Biking Trails
Community Amenity: Clubhouse Clubhouse
Community Amenity: Fitness Fitness
Community Amenity: Golf Nearby Golf Nearby
Community Amenity: Lake Lake
Community Amenity: Nature Trails Nature Trails
Community Amenity: Pickleball Pickleball
Community Amenity: Spa Spa
Community Amenity: Swimming Swimming
Community Amenity: Tennis Tennis
Community Amenity: Walking Trails Walking Trails

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The Woodlands of Urbana

Urbana, Maryland Pickleball Community
Urbana, Maryland
The Woodlands of Urbana is a Maryland 55+ community offering luxury single-family homes, villas, and condos in Central Maryland. Located near Frederick and within an hour of D.C. and Baltimore, this active adult community in Maryland features resort-style amenities, pickleball courts, a putting green, clubhouse, and low-maintenance Maryland homes for sale designed for modern living.

Pricing: Condos, villas, and single-family homes from the mid $500,000s to high $700,000s

Community Type: 55+ Active Adult

Community Amenity: Biking Trails Biking Trails
Community Amenity: Clubhouse Clubhouse
Community Amenity: Community Gardens Community Gardens
Community Amenity: Dog Park Dog Park
Community Amenity: Fitness Fitness
Community Amenity: Golf Nearby Golf Nearby
Community Amenity: Land Conservation Land Conservation
Community Amenity: Nature Trails Nature Trails
Community Amenity: Pickleball Pickleball
Community Amenity: Playground Playground
Community Amenity: Swimming Swimming
Community Amenity: Walking Trails Walking Trails

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