This has been a big week at Trailside Estates. Six homes came on the market, three existing listings have new prices, and there are now nine 55+ homes for sale in Rochester, MA, starting at $949,000.
To give everyone a chance to see them, we're holding open houses on both days this weekend: Saturday, October 31 and Sunday, November 1, from 10:30am to 1:00pm. No appointment, no sign-up.
What's New at Trailside
- Six new listings. 39, 40, 43, 44, 45, and 46 Crestwood Circle are now on the market.
- New pricing. 36 and 37 Crestwood Circle are now $999,000, and 38 Crestwood Circle is $1,049,000.
- A new starting price. 40 Crestwood Circle is listed at $949,000, the lowest price in the community.
All Nine Homes for Sale at Trailside Estates
Every home is a 2-bedroom, 2.5-bath duplex-style condominium with a first-floor primary suite, first-floor laundry, and an attached 2-car garage. All are listed exclusively by Realty Quarters on MLS PIN:
- 36 Crestwood Circle — $999,000 · MLS# 73507380 · open this weekend
- 37 Crestwood Circle — $999,000 · MLS# 73507390 · open this weekend
- 38 Crestwood Circle — $1,049,000 · MLS# 73507397 · open this weekend
- 39 Crestwood Circle — $999,000 · MLS# 73595765 · new listing · open this weekend
- 40 Crestwood Circle — $949,000 · MLS# 73595766 · new listing · open this weekend
- 43 Crestwood Circle — $999,000 · MLS# 73595768 · new listing
- 44 Crestwood Circle — $999,000 · MLS# 73595769 · new listing
- 45 Crestwood Circle — $999,000 · MLS# 73595770 · new listing · second-floor bonus room
- 46 Crestwood Circle — $999,000 · MLS# 73595771 · new listing · second-floor bonus room
See photos, specs, and a request form for each home in the available homes section.
The Five Homes Open This Weekend
36, 37, 38, 39, and 40 Crestwood Circle are open both Saturday and Sunday. Realty Quarters agents will be on site both days to walk you through and answer questions.
36, 37, and 38 are finished and staged, so they're the easiest way to picture day-to-day life in a Trailside home: in from the garage, through the kitchen, to the first-floor primary suite and laundry. If you'd like a preview, there's an interactive walkthrough in the 3D tours section.
39 and 40 are a duplex pair from the community's original phase. 40 is the lowest-priced home at Trailside, so it's worth seeing if you've been waiting for a way in under a million dollars.
The New Listings: 43, 44, 45 & 46 Crestwood Circle
Two new duplex buildings bring four more homes to market at $999,000 each. They aren't part of this weekend's open house, but you can call (401) 646-4896 to arrange a showing.
- 43 & 44 Crestwood Circle have a full-width front porch, an open living room, an angled kitchen island, and a deck off the dining area.
- 45 & 46 Crestwood Circle have a covered entry into a foyer, a straight kitchen island, a larger garage, and a second-floor bonus room that works as an office, den, or media room.
First-floor plans for both buildings are in the floor plans section of the main site. New photos are on the way.
Life at Trailside Estates
Trailside Estates is a 55+ active adult community on 38 wooded acres in Rochester, in Plymouth County on the Massachusetts SouthCoast. Amenities are finished and in use today: a clubhouse and pool with a pool deck and cabanas, walking trails, and professionally maintained grounds.
The HOA fee is approximately $500 per month and covers landscaping and lawn care, snow removal, road maintenance, refuse removal, common-area upkeep, the clubhouse and pool, and common-element insurance. Property taxes are paid separately by each owner.
Wondering what ownership really costs? Our guide to the cost of buying a 55+ home in Rochester, MA walks through taxes, closing costs, and HOA fees. For the age rules, see who can live in a 55+ community in Massachusetts. And if you're comparing options in the region, our overview of 55+ communities in southeastern Massachusetts is a good place to start.
Plan Your Visit
Trailside Estates is on Crestwood Circle in Rochester, MA 02770, about 15 minutes from New Bedford, 30 minutes from the Cape Cod Canal, 45 minutes from Providence, and an hour from Boston.
Directions: I-495 South to Exit 3, Route 28 South. Right on Spruce Street (which becomes North Avenue). Left on Snipatuit Road to Crestwood Circle. Follow the signs to the open homes and park nearby.
Frequently Asked Questions
When is the open house?
Saturday, October 31 and Sunday, November 1, 2026, from 10:30am to 1:00pm both days. Drop in any time; no appointment is needed.
Which homes will be open?
36, 37, 38, 39, and 40 Crestwood Circle. For 43, 44, 45, and 46 Crestwood Circle, call (401) 646-4896 to arrange a showing.
How much are homes at Trailside Estates?
Nine homes are for sale, priced from $949,000. 40 Crestwood Circle is $949,000; 36, 37, 39, 43, 44, 45, and 46 are $999,000; and 38 is $1,049,000.
What does the $500 monthly HOA fee include?
Landscaping and lawn care, snow removal, road maintenance, refuse removal, common-area upkeep, the clubhouse and pool, and common-element insurance. Property taxes are paid separately.
Who can live at Trailside Estates?
It's a 55+ community under the federal Housing for Older Persons Act (HOPA): at least one resident of each home must be 55 or older. Visitors of any age are welcome at the open house.
Come see Trailside this weekend.
Saturday, October 31 and Sunday, November 1, 10:30am to 1:00pm. 36, 37, 38, 39, and 40 Crestwood Circle, Rochester, MA 02770. Nine homes for sale from $949,000.