55+ Communities in Massachusetts
31 researched communities across 23 cities, 30 with a legal 55+ or 62+ age restriction. Most are in Plymouth, Topsfield and Holden.
Massachusetts has a real, established 55+/'over-55' condominium market anchored by Greater Boston, a genuine Cape Cod/South Shore retirement corridor, and Massachusetts's own state-specific over-55 condominium exemption framework (MGL c.151B, section 4, paragraph 7).
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Massachusetts community directory
31 communities
Amberwood Farm
Topsfield, MA · Essex County
Condo
Price: Historical range roughly $389,900-$625,000; buyers should confirm current pricing
On-site clubhouse · Cathedral ceilings · Gas fireplaces in many units
Bigelow Farm
Northborough, MA · Worcester County
Attached / townhome
Private community center
Brookside Village
Walpole, MA · Norfolk County
Attached / townhome
Del Webb Chauncy Lake
Westborough, MA · Worcester County
Attached / townhome · Condo
Outdoor swimming pool · Bocce ball courts · Tennis courts
English Commons at Topsfield
Topsfield, MA · Essex County
Attached / townhome · Condo
HOA: Reported at roughly $916-$939 per month
In-ground, heated swimming pool · Professional-grade putting green · Gated community
Great Island by Del Webb at The Pinehills
Plymouth, MA · Plymouth County
Attached / townhome · Single-family
Ballroom and billiards room · Outdoor tennis and bocce courts
Highcrest at Meadow Walk
Sudbury, MA · Middlesex County
Condo · Attached / townhome
Price: Sold units have ranged from the $700Ks to over $1.25 million; the townhome collection is confirmed sold out
Innovative, open floorplans
Holliston Woods
Holliston, MA · Middlesex County
Attached / townhome · Single-family
Price: Reported at roughly $500,000s to $700,000s; current resale pricing should be confirmed with a local agent
Arts room · Game room · Library
Lake Point Village
Lakeville, MA · Plymouth County
Condo
Two fitness centers · Gathering rooms and libraries · Community garden
Martins Landing
North Reading, MA · Middlesex County
Condo
HOA: Individual listings show condo fees ranging roughly from $363 to $535+ per month depending on unit size
Clubhouse with fitness center · Walking and biking trails · Parks and natural space
Meetinghouse Commons
North Andover, MA · Essex County
Attached / townhome · Single-family
Clubhouse with clubroom · Fitness center
Oak Point
Middleborough, MA · Plymouth County
Manufactured
Pickleball and tennis courts · Ballroom
Owls Nest at The Pinehills (Toll Brothers Regency Collection)
Plymouth, MA · Plymouth County
Single-family
Price: Starting from approximately $890,000, per Toll Brothers' own site
Bocce court
Regency at Glen Ellen
Millis, MA · Norfolk County
Single-family · Attached / townhome
7,500-square-foot clubhouse · Outdoor heated pool · Bocce courts
Riverbend Crossing
North Andover, MA · Essex County
Condo
Library area
Riverside Woods
Andover, MA · Essex County
Condo
Clubhouse with fitness center · Deeded garage parking · In-unit washer/dryer
Rockwood Meadows
Upton, MA · Worcester County
Single-family · Attached / townhome
HOA: Historical listing data from 2018 showed roughly $303/month; current figure not publicly confirmed
Community center · Setting abutting Peppercorn Hill
Rolling Green at Topsfield
Topsfield, MA · Essex County
Attached / townhome · Condo
Outdoor pavilion for socializing · Fireplaced living rooms · Attached one- or two-car garages
Sawyer's Reach
Plymouth, MA · Plymouth County
Attached / townhome · Condo · Single-family
Price: Roughly $400,000-$900,000 across product types; buyers should confirm current pricing
Community garden · Parks and natural open space
Seashore Point
Provincetown, MA · Barnstable County
Condo
Elevator access · Gym/fitness area · Library
Southport on Cape Cod
Mashpee, MA · Barnstable County
Condo · Attached / townhome · Single-family
32,000 sq ft Village Center · Indoor and outdoor pools · 400-seat Grand Ballroom
Spyglass Landing
Marshfield, MA · Plymouth County
Attached / townhome
Walking trails and a bike path · Tennis courts · Park and conservation area
Summer Reach
Plymouth, MA · Plymouth County
Attached / townhome · Single-family
Central clubhouse · Outdoor pool · Arts room
The Cottages at Lebaron Hills
Lakeville, MA · Plymouth County
Attached / townhome
Community pond · Wide sidewalks · Attached two-car garages
The Gardens of Wilbraham
Wilbraham, MA · Hampden County
Attached / townhome · Condo
Resort-style clubhouse · Great room for socializing · Game room (billiards, cribbage)
The Seasons at Salisbury
Holden, MA · Worcester County
Attached / townhome · Condo
Price: Started from the low $400,000s; current resale pricing not publicly confirmed
Village at Westminster Place
Holden, MA · Worcester County
Single-family · Attached / townhome
Price: Marketed from the high $300,000s when new sections opened; current resale pricing not publicly confirmed
Full basements · Walking and biking trails · Setting on Chaffin Pond
Villages at Weathervane
Weymouth, MA · Norfolk County
Single-family
Price: Started from the low $500,000s; current resale pricing not publicly confirmed
Villas at Eagles Nest
Franklin, MA · Norfolk County
Condo
Price: Recent unit listings found ranged from roughly $635,000 to over $1 million for penthouse units
Fitness center · Clubroom
Willis Brook at Lynnfield
Lynnfield, MA · Essex County
Single-family
Heated outdoor resort-style pool · Fire pit and event lawn · Barbecue area
Wolcott Woods
Milton, MA · Norfolk County
Attached / townhome · Single-family
Price: Priced starting above $1 million
New construction vs. resale in Massachusetts
Massachusetts's tracked inventory skews toward smaller, denser condominium and townhome developments (20-150 units) rather than the large master-planned communities common in Sun Belt states, with several notable exceptions. Del Webb Chauncy Lake (Westborough, ~700 homes) and Southport on Cape Cod (Mashpee, 749 units) are among the state's largest conventional communities, both now well into their resale era; Oak Point (Middleborough), a land-lease community operated by Hometown America, is larger still at roughly 850-1,150 homes and is self-described as 'New England's largest 55+ retirement community.' Great Island by Del Webb (Plymouth, ~600 homes, built 2002-2015) is fully resale-only, sold out of new construction years ago. At the newer end, Willis Brook at Lynnfield (Toll Brothers, 66 homesites, starting ~$1.5M) and Sawyer's Reach and Summer Reach (both Thorndike Development, Plymouth) represent active or recently active new-construction product. Several communities are explicitly noted in their own marketing as sold out or nearly so (Highcrest at Meadow Walk's townhome collection in Sudbury), a pattern characteristic of the Boston-area market -- thin inventory, frequently sold-out flagship communities, and a shorter list of active options than Sun Belt buyers typically expect. Land-lease manufactured/modular housing has a real but narrow footprint here (1 of 31 communities, Oak Point), consistent with this housing type being less common in dense New England markets.
Taxes and ownership in Massachusetts
Massachusetts has its own state-specific statutory mechanism for permitting 55+/62+ age-restricted housing, distinct in form from the federal Housing for Older Persons Act (HOPA). Massachusetts General Laws Chapter 151B, Section 4, paragraph 7 provides that the word "age," as used in that subsection's general age-discrimination prohibition, "shall not apply to residency in communities consisting of either a structure or structures constructed expressly for use as housing for persons 55 years of age or over or 62 years of age or older," conditioned on the housing owner or manager registering biennially with the Massachusetts Department of Housing and Community Development (now the Executive Office of Housing and Livable Communities). A qualifying unit must be individually owned and occupied by at least one resident 55 or older, with one additional under-55 occupant generally permitted (more if handicapped), and narrow board-approved family-emergency exceptions of up to six months. This state-law registration mechanism operates alongside, rather than in place of, the federal HOPA 80%-occupancy framework -- Massachusetts communities are not required to choose one over the other, and no indication was found that Massachusetts's standard is either stricter or looser than the federal 80% threshold in the way California's Unruh Act (100% occupancy) is stricter. This citation (MGL c.151B, section 4(7)) should be verified against the Massachusetts Legislature's own published text (malegislature.gov) before being relied upon. Massachusetts's "over 55" marketing terminology was found to map reliably to a genuine legal age restriction in the large majority of communities investigated, but not universally: New Seabury (Mashpee) is a golf-resort master plan whose own materials confirm no age restriction despite sitting in the same town as, and being frequently confused with, the genuinely restricted Southport on Cape Cod, and The Villages of Cedar Ridge (Wilbraham) had its original 2007 age restriction formally rescinded by the local planning board. Massachusetts's CCRC/Life Plan Community sector is real and substantial, anchored by Erickson Senior Living's two Massachusetts entrance-fee campuses (Brooksby Village in Peabody, Linden Ponds in Hingham) alongside several standalone nonprofit operators (NewBridge on the Charles, Orchard Cove, North Hill, The Overlook) -- confirmed CCRCs are not included among the for-sale communities profiled here. Massachusetts also has two cooperative-ownership senior communities (The Village at Duxbury, Fox Hill Village) that offer a true share-purchase, resident-governed ownership model directly comparable in structure to Minnesota's statewide Realife Cooperative network, but both are bundled into full continuum-of-care CCRC campuses rather than offered as standalone for-sale ownership product -- both are excluded as CCRCs despite the cooperative wrapper, and no freestanding, non-CCRC cooperative-ownership 55+ community comparable to Minnesota's Realife network was found operating in Massachusetts.
Ready to talk with a local agent?
Connect with a local agent who understands the community, current homes, and buying process.