"What happens is that the developers, knowing the bylaw, will come in with 34, 24, 14, just to stay under that threshold," Planning Board Chair LeMenager told Winchester News in September.
That quote explains why so few new condos are coming to Winchester Center. Winchester's inclusionary bylaw shapes for-sale buildings so they stop just under each affordable-unit trigger. The state's affordable-housing math favors rentals. And the gap between approval and a shovel in the ground is measured in years. This fall's market really is easing, but the extra choice comes from resale listings, not new buildings.
The bylaw's step function, and the buildings it produces
The inclusionary rule works in steps. As LeMenager described it to Winchester News, a five-unit building owes no affordable units, a six-unit building owes one, 15 units still owes one, and 16 owes two. Each step makes the next unit much more expensive for the developer, so the cheapest building is the one that stops just below the line.
The recent Main Street projects match that pattern. 972 Main St., on the site of a former muffler shop at Main Street and Glenwood Avenue, was approved in fall 2025 as 13 units with one affordable. A development at 910 Main St. has the same count. 972 Main was the first project permitted in the town's Main Street Mixed-Use District. The bylaw describes that district as a walkable corridor on northern Main Street that transitions toward the Center Business District.
The biggest for-sale-style project in the pipeline, at 10 Converse Place and 33 Mt. Vernon St., is 34 units. When the Planning Board held the building to five stories, the developer, Urban Spaces, said the project could not support the affordable units the bylaw required. A board subcommittee reviewed the financials in private and agreed.
Here is what is on the books as of the most recent reporting:
| Project | Developer | Units | Tenure reported | Units that count toward the state's affordable inventory | Latest reported status |
|---|---|---|---|---|---|
| 972 Main St. | Treetop Group | 13 in the approved plan | Not confirmed for revised design | 1 in the approved plan | Withdrawn from special permit Sept. 8, 2026; now by right |
| 10 Converse Pl. / 33 Mt. Vernon St. | Urban Spaces | 34 | Three deed-restricted ownership units | 3 | Revised plans accepted early June 2026; no groundbreaking as of Sept. 2026 |
| Waterfield Commons | Winchester Waterfield MM LLC with Causeway Development | 56 | Rental | All units if eligible; one report puts the SHI addition at 60 | Ground-lease deadline Dec. 31, 2026 |
| 292 Washington St. / Swanton St. | Melanson Development Group | 64 | Rental, 40B | All 64 if eligible | Comprehensive permit granted May 2026 |
The two projects with the most units are both rentals, and the reason is in the state's accounting.
Why the large affordable projects are rentals
Massachusetts expects each town to keep 10% of its housing on the state's Subsidized Housing Inventory. Below that level, developers can use Chapter 40B to override local zoning. Winchester sits at 4.89%, or 395 qualifying units out of 8,073. Reaching 10% would take roughly 807.
The counting rules decide which projects help. Under state guidelines, a rental development counts every one of its units once at least 25% are affordable at or below 80% of area median income. An ownership development counts only its deed-restricted units. A 64-unit rental with 16 affordable units can add 64 to the inventory. The 34-unit Converse Place building adds three.
The target also moves. Every new market-rate unit raises the denominator, and Winchester News reported that most new construction in town means teardowns and subdivided lots producing houses that sell for $1.5 million or more. Suppose all four projects in the table were finished and their qualifying units added to today's 395, using Winchester News' 56-unit count for Waterfield. The total would be about 518, or roughly 6.4%, still close to 290 units short of the line, and that is before counting the market-rate units those same buildings add to the denominator.
The affordable-housing effort therefore goes where each unit counts most, which means rentals. The same Daily Times Chronicle report on Waterfield said the town is trying to grow its affordable stock to avoid unwanted 40B projects. For someone hoping to buy a new condo near the Winchester Center station, the result is that the largest new buildings near downtown are not for sale.
Approved is a long way from built
The second thing limiting supply is time. Every project in the table has been approved. None has been reported under construction.
Waterfield Commons sits on the town parking lot next to the Winchester Center Commuter Rail station. Winchester News describes the plan as 56 apartments, 40 of them affordable. The Daily Times Chronicle reported that the project will add 60 units to the town's Subsidized Housing Inventory. The town and developer signed the original Land Development Agreement on June 26, 2022, and the Daily Times Chronicle reported the 14th amendment to it, which moves the ground-lease deadline to Dec. 31, 2026. In September 2025, Winchester News estimated 8 to 12 months from lease signing to the start of construction, then 18 to 24 months to build.
Converse Place took 10 public hearings between September and February. It was approved with no affordable units on site, in exchange for a $2 million payment to the Affordable Housing Trust plus profit sharing worth up to another $1 million. In April, the Trust and three members of the Housing Partnership Board sued to annul the permit. The case settled in late May after the plaintiffs spent $1.685 million of the $2 million to buy three one-bedroom units in the building and deed-restrict them at 80% of area median income. The Planning Board accepted revised plans in early June, and as of Winchester News' September report, nothing had broken ground.
972 Main St. went the other way. On Sept. 8, the Planning Board accepted Treetop Group's withdrawal of its special-permit plans after design changes, so the project now proceeds by right. It still needs standard building permits and inspections. A fire on the site in mid-April triggered environmental remediation requirements from the state Department of Environmental Protection, and board discussion noted that demolition could uncover other issues.
The town is working on the process side. Planning Board articles for fall Town Meeting would combine site-plan and special-permit review into a single hearing and decision when a project needs both. That is a proposal, not adopted policy, and it would affect future applications more than the four already in the table.
What this fall's numbers are measuring
With no new buildings delivering, every change in the fall market comes from existing homes. The Massachusetts Association of Realtors September 2026 report for Winchester shows the change clearly.
For single-family homes in September 2026:
- Inventory rose to 40 from 31 a year earlier, and months of supply went from 2.1 to 2.7.
- New listings rose to 29 from 21.
- Cumulative days on market rose to 60 from 29.
- Sellers received 97.2% of original list price, down from 99.2%.
- The median sale price was $1.9 million, but on only 11 closings. The year-to-date median through September was $1,765,000, down 2.9%.
The condo side is even thinner. In September 2026, condo inventory doubled to 20 from 10, months of supply climbed to 4.4 from 1.8, and only two sales were pending against eight a year earlier. No condos closed in the month. Year to date through September, 43 condos sold at a $770,000 median, up 1.3%, at 100.5% of original list price. MAR itself cautions that one month can look extreme on samples this small.
Condos that sold earlier in the year went at or above asking, and the 20 now listed are resale units competing with each other. The downtown pipeline adds no for-sale competition this season, and the projects most likely to add units at scale are rentals.
Questions to bring to a Winchester Center condo search
- Is the listing near a pending project site? Converse Place, 972 Main, Waterfield and Washington/Swanton each sit near downtown, and their construction schedules are still open.
- How long has the unit been listed? With months of supply at 4.4 in September, time on market tells you more about a unit than it did a year ago.
- What did comparable units sell for earlier in 2026? The $770,000 year-to-date median and 100.5% of list describe a different market from the one shown by September's two pending sales.
For a fuller look at how Winchester compares with its neighbors, see our post comparing Woburn, Winchester and Lexington on value, along with current Winchester condo listings.
FAQ
Will Converse Place units be sold as condos? The settlement made three one-bedroom units deed-restricted ownership homes. Reporting reviewed for this post does not confirm the tenure of the other 31 units.
What does Washington/Swanton include besides apartments? Melanson Development Group's permitted plan is a three-story building with 64 residential units, 16 of them affordable, about 38,000 square feet of commercial space and 96 parking spaces.
Does "by right" mean 972 Main can start right away? It skips special-permit review, but it still needs building permits and inspections. The site also carries remediation requirements from the April fire.
If you are weighing a Winchester Center condo against a single-family home, or deciding when to list one, Kim Covino & Co will walk you through how these four projects and this fall's resale inventory affect your timing. Request a complimentary home strategy, or begin with a home valuation.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
