South Shore, Massachusetts
55+ Communities on the South Shore
A guide to 44 owner-occupied 55+ communities from Milton to Plymouth: townhomes, condos and detached homes with the yard work and snow removal handled for you. Pick a town to start.
How I help you make the move
- Price your current home. A free, detailed market analysis so you know what you can afford next.
- Find the right community. We compare fees, layouts, one-floor living and what's included.
- Sell for top dollar. Prep, staging, marketing and negotiation for the home you're leaving.
- Time both closings. I coordinate the dates so you move once, not twice.
Downsizing into a 55+ community?
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.
Braintree · 1 community
Bridgewater · 2 communities
Stone Meadow
One of the area's larger 55+ neighborhoods, made up of detached one-level ranch homes.
High Pond Estates
An affordable 55+ option of manufactured homes set around a pond.
Duxbury · 1 community
East Bridgewater · 1 community
Halifax · 1 community
Hanover · 3 communities
The Elms of Hanover
A 55+ townhome community on 50 acres with a large clubhouse and function hall.
Spring Meadow
A 55+ community of spacious attached homes with an active clubhouse and about two miles of trails.
Village at Walnut Creek
A 55+ townhome community with a 6,000 sq ft clubhouse and pool, close to Routes 3, 53 and 123.
Hanson · 3 communities
Stonebridge Commons
One of the South Shore's most active 55+ communities, with a full-time activities director and 60 acres of grounds.
Liberty Woods
A newer 55+ townhome community by Ridder, with lawn care, trash and snow removal handled by the association.
Dunham Farm
A smaller, more affordable 55+ community of garden-style condos and townhomes.
Kingston · 1 community
Marshfield · 7 communities
The Seasons
A 55+ community of townhome and garden-style condos near Webster Square, where I recently sold 16 Hayloft Lane for $745,000.
Pudding Hill
A 55+ townhome community next to the 37-acre Pudding Hill Reservation, less than a mile from Marshfield Center.
Spyglass Landing
A coastal 55+ townhome community a short drive from Humarock Beach and the marinas.
Peregrine Woods
A quiet 55+ community of attached homes with a clubhouse, under two miles from Rexhame Beach.
The Maples
A small 55+ condominium community with larger floor plans.
Eames Brook Farm
A boutique 55+ community of just 14 homes.
Highland Green
One of Marshfield's newest 55+ communities, built in 2020.
Milton · 1 community
Norwell · 1 community
Pembroke · 1 community
Plymouth · 13 communities
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.
Tupper Hill
A small 55+ community of 12 condos built in 2022.
Village Crossing
A 55+ condominium community in South Plymouth, near White Horse Beach.
Randolph · 1 community
Rockland · 2 communities
Rockland Glen
A 55+ community of townhomes and a few single-family homes, close to Derby Street and Wompatuck State Park.
Beechwood Village
A 55+ community of detached homes on more than 40 acres.
Scituate · 2 communities
Seaside at Scituate (Carriage Collection)
Toll Brothers' coastal community with 55+ Carriage townhomes, ocean views and resort-style amenities, under a mile from Egypt Beach.
Doctors Hill
A 55+ community of Cape-style townhomes on 40 acres.
Weymouth · 1 community
Villages at Weathervane
Weymouth's 55+ golf community: 149 homes on 170 acres beside a 9-hole course.
Whitman · 2 communities
The Village at Auburnville
A 55+ townhome community with a 5,000 sq ft clubhouse and putting green.
Northville Village
A new community of detached Capes and duplexes by Egan Realty Group, with a second phase of garden-style homes and a clubhouse planned.
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.