55+ Communities › Plymouth
55+ community · Plymouth, MA
Tupper Hill
A small 55+ community of 12 condos built in 2022.
What's nearby
Long Pond Road and Route 3.
Selling to make the move
If you're moving here, you're probably selling a home at the same time. I price and market your current home, help you line up the new one, and coordinate both closings so the dates work together. Ask me about homes for sale in Tupper Hill and what your current home would sell for today.
Downsizing into a home in Tupper Hill?
I'm Michael Peppino. For 29 years I've helped South Shore homeowners sell the family home and time the move into a 55+ community, so you only move once.
More 55+ communities in Plymouth
Great Island (Del Webb at The Pinehills)
The largest 55+ community on the South Shore, with 600 homes, a 7,000 sq ft clubhouse and full access to The Pinehills.
Seton Highlands at The Pinehills
A 55+ neighborhood inside The Pinehills, with its own clubhouse and pool.
Regency at Owls Nest (Toll Brothers, The Pinehills)
Toll Brothers' 55+ collection of new single-family homes at The Pinehills. (The separate Preserve section at Owls Nest is not 55+.)
Sawyer's Reach
A gated 55+ community by Thorndike Development, within walking distance of Colony Place shopping.
Summer Reach
A 55+ community by Thorndike Development across from Billington Sea, about a mile from downtown Plymouth.
Rolling Mill
A 55+ townhome community about a mile from downtown Plymouth and close to the hospital.
Tara Woods
A 55+ community of attached homes with a clubhouse and heated pool, near Colony Place.
Chilton Park Village
A small 55+ community about two miles from Plymouth Long Beach.
Davis Manor
A new downtown 55+ condominium building with an elevator, heated garage parking and water views.
Blissful Meadow
A 55+ community of one-level townhomes with a pool, pickleball and putting green.
Ocean Walk
A newer 55+ condominium community with smaller, easy-care homes.
Village Crossing
A 55+ condominium community in South Plymouth, near White Horse Beach.
Community details are compiled from public sources and MLS data as of October 2026 and are not guaranteed. Prices are recent sales or listings, not appraisals. Age rules, fees, unit counts and amenities change; confirm them with the association or listing agent before you buy. Michael Peppino, Massachusetts licensed real estate broker, Real Broker MA, LLC. Equal Housing Opportunity. Sources: MassNeighborhoods.