Buyers comparing Northern Westchester towns this fall have likely seen the same headline twice: Pleasantville's home prices are up sharply, and Pleasantville has new housing in the pipeline. Put those two facts side by side and the natural conclusion is that relief is coming. More units means more competition among sellers, which means prices soften.
That conclusion doesn't hold up once you look at what's actually being proposed, where, and under what zoning. Two real projects are moving through the village's approval process right now. Neither one adds a single detached home to the market you're actually shopping in.
The Number That Started the Assumption
Over the three months ending in July 2026, the median sale price for a home in Pleasantville reached $1.1 million, up 27.5 percent from the same period a year earlier. Homes are also taking longer to find a buyer, about 28 days on market compared with 18 days a year ago. And yet the volume of homes changing hands barely moved: 23 sold in July, the same number as the July before.
That last figure is the one worth sitting with. If the village's housing stock were adjusting to demand, you'd expect to see more sales alongside the price growth, not the same handful of closings at a much higher number. What you're looking at instead is a fixed set of single-family lots in a village that covers just 1.9 square miles, with buyers competing harder for the same inventory rather than a larger pool of houses coming to market.
That's the backdrop against which the two development proposals need to be read.
What Lennar Is Actually Proposing
The larger of the two projects comes from Lennar, operating locally as US Home, LLC. The proposal covers 20.5 acres behind the Foxwood condominium complex, consolidating three parcels at 1 and 3 Campus Drive and 8 Carey Court. As currently designed, it calls for 102 townhomes: fee-simple homes on their own lots, not condominiums, spread across 22 new buildings.
The unit mix has shifted since Lennar first brought the idea to the Village Board in the fall of 2025. The current plan includes:
- 11 units designated as affordable under village code
- 12 additional smaller units intended as a lower-cost option, described by Lennar's representatives as "naturally affordable"
- 53 first-floor units designed for residents who want to age in place
None of that changes the fundamental zoning problem. The Campus Drive parcels are zoned Campus Office, built for the vacant 144,000-square-foot former Bank of New York building and the smaller office space still partly occupied by Savin Engineering. For Lennar's project to happen, the village would need to approve a zoning map amendment reclassifying the land to a Planned Unit Development, the same designation used for the Toll Brothers townhomes on Washington Avenue and for Foxwood itself. As of the village's most recent public update this summer, that amendment had not been approved. The application is still working through traffic, school, water and sewer, and stormwater review, with no construction date attached to it.
Why the Planning Commission Isn't Sold Yet
The proposal has drawn pointed pushback from the people reviewing it, not just from neighbors. At a Planning Commission session this spring, Chair Russ Klein and member Henry Leyva raised concerns about how the design fits the village.
"I don't think the houses are in the character of Pleasantville with lots of garage doors and cars parked in front," Klein said. Leyva put it more bluntly: "This plan, as designed, just seems like stacked housing spread out over a 20-acre parcel."
Traffic came up too. One commission member flagged the intersection where Manville Road meets Bedford Road, a spot with no traffic light where southbound afternoon traffic from Chappaqua already backs up. Lennar's traffic consultant said the firm's studies accounted for that pattern, but the concern hasn't been resolved to the commission's satisfaction. None of this means the project won't eventually happen. It means there is no approved zoning, no site plan sign-off, and no groundbreaking date, only an application still being negotiated.
The Smaller Project That's Already Approved, and Still Hasn't Broken Ground
The second project is smaller and further along on paper, which makes it the more useful example of how long "approved" can sit before it becomes "built."
Known as The Landmark at 444, the proposal would convert the upper floors of the former Chase Bank building at 444 Bedford Road into 36 apartments, 20 one-bedroom and 16 two-bedroom units, with new construction added over the existing parking lot. Ground-floor retail space is part of the plan as well. The Planning Commission approved the project in July 2025. Every village update since then, through the most recent one this summer, has repeated the same line: a construction start date has not yet been set.
The developer has since gone back to the village to request an extension of the original site plan approval, a procedural step that only comes up when a project hasn't broken ground within its approved window. A conversion of an existing five-story building, on a parcel that didn't require a zoning map change, has still taken more than a year to move from approval to an unset start date. That's the realistic pace for new residential supply in Pleasantville even when the zoning fight is already over.
Why Neither Project Moves the Number You Care About
Here is the piece that gets lost in the "new housing is coming" framing: both projects deliver attached units, townhomes in Lennar's case, apartments in the Landmark at 444 case. Neither adds a detached single-family home to the market.
When an appraiser or a buyer's agent builds a comparison for a Colonial or a Cape in Pleasantville, the pool they draw from is other detached single-family sales. A completed townhouse development behind Foxwood doesn't enter that pool any more than the existing Foxwood units do today. It's a different product, on different zoning, competing for a different buyer. The same is true of 36 apartments carved out of a former bank building. That supply matters if you're looking to rent or to buy an attached unit, but it does nothing to the count of detached houses available in a village that has almost no vacant land left to build them on.
What This Means If You're Comparing Pleasantville to Other Towns
If you're weighing Pleasantville against Chappaqua, Armonk, or another Northern Westchester town and factoring in an assumption that new construction will eventually cool the single-family market here, that assumption isn't supported by what's actually in the pipeline. The math that produced a 27.5 percent price increase over the past year is structural: a fixed lot count in a 1.9-square-mile village, not a temporary supply shortage that new construction is positioned to fix.
If what you actually want is a lower-maintenance, attached home and you're comfortable with a longer timeline, the Lennar project and the Landmark at 444 are worth tracking. Just track them with the right expectations. One still needs a zoning amendment it doesn't currently have. The other has been sitting on an approval for more than a year without a shovel in the ground.
Either way, if you're shopping for a detached single-family house in Pleasantville, the number that matters to you today is the same number that mattered before either project existed.
If you'd like help thinking through what a specific Pleasantville property is actually worth to compete for, or how nearby villages stack up for your particular search, Harriet Libov can walk you through it. Let's Connect.
