You sell the Weston house you've lived in for decades and want to stay in Weston. Where do you move?
For most long-time owners, the hard part of that question is the number of places available, not the price. Weston's Council on Aging staff say the same thing. Social worker Clarabelle Valcin told the Weston Observer that "a lot of people are interested in downsizing, but they don't see a lot of options in town, so they look to neighboring communities." Executive Director Stephanie Keane put it more plainly in the same piece: "The majority of the people we see leaving are going to continuing care retirement communities."
That piece ran on October 2. Three weeks later, the largest planned addition of downsizer housing in town was off the table for this fall, and the in-town choices left are fewer than most sellers expect.
Nine Condo Sales in One Quarter Was a Busy Quarter
Start with what actually trades. The Weston Observer's Q3 2026 snapshot, built on Warren Group data, counted 38 home and condominium sales in Weston from July through September 2026. The median sale price was about $2.25 million and the average was $2.54 million.
Nine of those 38 sales were condominiums, and that quarter was unusually active. The Observer noted that nine is more than Weston's condo sales in the first two quarters of 2026 combined. So in the busiest condo stretch of the year, a downsizer had nine closed sales to compare against. In the six months before that, fewer than nine changed hands in total.
The prices matter as much as the count. Most Weston condos sold at or below $1 million in 2026, but five of the nine Q3 sales topped $1 million, including one on Pine Summit Circle that closed at nearly $3.48 million. For a seller hoping to free up a large share of their equity, Weston's condo pool works like a small high-end market. When a downsizer can't find the right unit in town, it's usually because no such unit is for sale, not because they can't afford one.
Weston's Senior Housing Is Built Around Income or Care Needs
Beyond the condos, Weston's housing for older adults falls into a few categories. Each one has its own entry rules, and none of them is a market-rate, for-sale home sized for downsizing.
| Option | How it works | What the reporting says |
|---|---|---|
| Brook School Apartments | Independent living near the town center, at market and subsidized rates | 127 people on the subsidized waitlist, with an estimated wait of about five years; subsidized rent is 30% of income for residents earning $91,200 or less |
| Merriam Village | Independent living for low- to moderate-income residents, priced to cover operating costs | About $850 a month for a one-bedroom |
| Maplewood Senior Living | Market-rate housing with care levels | Independent living, assisted living and memory care |
| Manor on North, 135 North Ave. | Age-restricted rental apartments in the former Drabbington Lodge | 17 units planned; status covered below |
Brook School is getting a little bigger. Residents at the 2026 Annual Town Meeting approved $1 million to build two new apartments there. Two units against a 127-person subsidized waitlist shows how far the supply is from the demand.
None of this is new. The Council on Aging's 2019 Aging in Weston needs assessment found that older adults were already concerned about the lack of downsizing and senior housing choices. Keane told the Observer that those concerns remain "prevalent" seven years later.
The Regis Plan Was the Only Large Source of New For-Sale Units
That gap is why the HYM Investment Group proposal at 300 Wellesley St., across from Regis College, mattered to downsizers in particular. According to the Select Board's September 8 minutes, the 215-unit plan included 112 independent living units, 41 assisted living units and 32 memory care units in two connected buildings, plus 30 age-restricted townhomes. HYM described the townhomes as 55-plus homes for sale at market rates. Those 30 townhomes were the only part of the plan that a downsizer could have bought. They would have outnumbered every condo sale Weston recorded in the first three quarters of 2026.
The plan also included affordable housing. HYM offered the town a choice between reserving about 18 units on site or paying $300,000 per unit, roughly $8.1 million, toward off-site affordable housing, according to the Observer's fall project roundup.
Then the timing ran out. The Weston Observer reported that the Select Board voted not to send the zoning change to the November 23 Special Town Meeting. Chair John McDonald noted that the board's meeting was the last day to add items to the warrant, and member Rebecca Mercuri said residents still had outstanding questions. The Planning Board formally closed its public hearing on October 21. Planning Board member Leslie Glynn said her board was "still in the middle of that entire process" when it was halted.
Residents disagreed about the plan. Engage Weston supported it as a way to let more residents stay in town as they age. Neighbors raised concerns about density, traffic and scale, and said a roughly 399,000-square-foot development deserved fuller review before a vote.
The calendar is what matters for downsizers. Regis CFO Thomas Pistorino said the college's contract with HYM depended on the town passing the zoning bylaw and will end at the end of December without it. He wrote earlier that the land would most likely be sold "for an institutional purpose that would maximize the value to Regis." Tom Timko, who chairs both the Elderly Housing Committee and the Affordable Housing Trust, told the Observer that Regis has received "numerous offers from 40B developers." HYM said it is working with Regis to evaluate its options. The Planning Board voted to discuss a senior-living bylaw at its next meeting.
Whatever happens to those 30 acres, 55-plus townhomes for sale are no longer the default outcome.
North Avenue Will Add Rental Units, Not For-Sale Homes
The other new project for older adults is real, but it serves a different need. At 135 North Ave., Weston resident Robert Parsekian is turning the 1899 Drabbington Lodge, most recently Sunrise Assisted Living, into the Manor on North, with 12 one-bedroom and five two-bedroom age-restricted apartments. As of the Observer's September 25 report, demolition was finished and the project was waiting for approval of its fire-suppression system. Parsekian estimated construction would take 12 to 18 months once a building permit is issued.
The units are planned as rentals. The town and Parsekian were working out a master lease modeled on the Brook School arrangement, and Parsekian has nicknamed the project "Brook School North." The lease needs Town Meeting approval. For a downsizer, that makes Manor on North a possible place to rent, but not a place to buy.
Why the Order of a Sale Matters More in Weston
For anyone selling a large Weston home while hoping to stay, selling the house is the easier half, since Weston recorded 38 sales in Q3 2026 alone. The harder half is finding the next home. That pool is a few condos a quarter, plus waitlists and care-based communities.
In practice, that shifts which question to answer first:
- Identify the destination before setting a listing date. In a town where nine condo sales made for a strong quarter, the right unit may come up only a few times a year.
- Price the condo market separately. With five of nine Q3 condo sales above $1 million, downsizing within Weston may free up less equity than the town's overall median suggests.
- Plan a temporary place to live. If the sale closes before the right unit appears, a rental bridge keeps the move from being rushed.
- Get on waitlists early if they apply to you. Keane's advice to the Observer was direct: "Apply early. People don't realize what the waitlists can be."
The calendar for the rest of the year:
- November 23: Weston's Special Town Meeting. The Regis zoning change is not on the warrant.
- The Planning Board's next meeting after October 21: a scheduled discussion of a proposed senior-living bylaw.
- End of December: the HYM–Regis contract terminates without the zoning change, according to Regis's CFO.
A Few Questions That Come Up
Is the Regis senior housing project dead? The proposal is off the November warrant, and Regis said the contract ends at the end of December without a zoning change. HYM said it is weighing options with the college, and the Planning Board has put a senior-living bylaw on a future agenda.
Are there market-rate senior options in Weston now? Maplewood Senior Living offers market-rate independent living, assisted living and memory care in town. Brook School Apartments has both market-rate and subsidized units.
What about the new apartments on Boston Post Road? Modera Weston, at 751 Boston Post Road, is preleasing one-, two- and three-bedroom apartments and townhomes, with completion expected in September 2027.
If you're thinking about selling a Weston home and want to stay in town, the most useful first step is a plan built around where you'll live next, not just the listing. I can help you track which condos come up, figure out what your current home would net, and decide whether a rental bridge makes sense while the Regis land and the North Avenue project play out. Peridot Properties can lay out the timing with you before anything goes on the market. Let's connect.
