Plymouth is one of the most sought-after towns for 55+ living in Massachusetts, offering a rare combination of coastal beauty, historic charm, and housing variety. From walkable harbor views and downtown dining to golf communities and wooded neighborhoods, Plymouth provides one of the largest and most diverse selections of active adult housing in Plymouth County.

With convenient access to beaches, medical facilities, shopping, and Route 3, Plymouth supports an active yet practical year-round lifestyle.

Plymouth has one of the largest concentrations of 55+ communities on the South Shore. Housing styles range from luxury golf communities and detached condominiums to land-lease neighborhoods and resident-owned communities.

Because ownership structures vary significantly from one neighborhood to another, understanding the differences before touring homes is especially important in Plymouth.

Plymouth offers more than twenty established 55+ communities. To make comparison easier, they are grouped by ownership type and lifestyle.

Luxury & Amenity-Focused Communities

These communities often feature clubhouses, pools, fitness centers, golf access, or higher-end finishes:

• Blissful Meadows
• Davis Manor (Downtown / Harbor Views)
• Great Island at The Pinehills (Golf Community)
• Owls Nest / Regency at Pinehills
• Saltash at Chiltonville (Green Initiatives / New Construction)
• Sawyers Reach
• Seton Highlands – Pinehills
• Tinker’s Bluff – Pinehills

Condominium & Townhome Communities

Ownership-based communities where residents typically pay their own real estate taxes:

• Cornerstone Grove
• Ocean Walk
• Rolling Mill Condos
• Summer Reach
• Tara Woods
• Tupper Hill
• Village at Clear Pond (Beach Rights)
• Village Crossing

Land-Lease & Resident-Owned Communities

These communities include leased land or cooperative-style ownership structures, where HOA fees cover land use:

• Casa Bella
• Long Pond Village
• Pinehurst Village
• Plimouth Commons (Resident-Owned Co-op)
• Plymouth Mobile Home Estates (Resident-Owned)
• Westwood Village (Resident-Owned Modular)

Rental & Senior Living Option

• Laurelwood at The Pinehills (Monthly Lease / Assisted Living)

Plymouth’s 55+ communities vary widely in structure and lifestyle.

Depending on the neighborhood, buyers may find:

• Detached or attached condominium homes

• Townhomes

• Golf course communities

• Manufactured or modular homes

• Land-lease ownership models

• Resident-owned cooperative communities

• Luxury amenity centers with pools and fitness facilities

This variety makes Plymouth appealing to buyers across a broad range of price points and lifestyle goals.

Plymouth may appeal to homeowners who:

• Want the largest selection of 55+ communities in the region

• Prefer coastal access and historic charm

• Value golf, clubhouse amenities, or social activity

• Enjoy walkable downtown areas and waterfront dining

As a historic coastal destination, Plymouth is also a popular tourist town, particularly during the summer and fall seasons. For some homeowners, that vibrancy adds energy, dining options, and cultural activity. For others, seasonal traffic and visitor volume are important considerations when choosing a neighborhood.

Because Plymouth offers such a wide range of housing styles and locations — from quieter wooded communities to areas closer to the waterfront — buyers can often find a setting that matches their preferred pace of life.

Understanding how lifestyle, location, and seasonality align with your goals can help determine whether Plymouth is the right fit.

Homeowners often compare Plymouth to:

• Wareham

• Carver

• Kingston

• Duxbury

While Plymouth offers the largest variety of 55+ housing, neighboring towns may differ in price range, density, and coastal proximity.

Not every homeowner chooses age-restricted living.

Additional downsizing options in Plymouth may include:

• Ranch-style single-family homes

• Coastal cottages near the waterfront

• Non-age-restricted condominiums

• Smaller homes within established neighborhoods

Plymouth’s size allows for significant flexibility in both HOA-based and traditional homeownership options.

How many 55+ communities are in Plymouth MA?
Plymouth has more than twenty established 55+ communities, making it one of the largest active adult markets in Plymouth County.

Are there land-lease communities in Plymouth?
Yes. Plymouth includes both land-lease and resident-owned communities, as well as traditional condominium ownership.

Is Plymouth a good town for retirement?
Plymouth may appeal to homeowners seeking coastal lifestyle, golf communities, downtown access, and the largest selection of 55+ housing options in the region.

Plymouth offers strong local support for 55 and older adults through the Plymouth Council on Aging and the Town of Plymouth, which provide programs, services, and information that many residents find helpful when exploring active adult living.