Correction: This article was updated on Aug. 14 at 3:45 p.m. to reflect the number of trees that are proposed to be replanted as part of The Osborn’s development plans.
The Osborn is planning a major campus overhaul, but not without concerns from Westchester County officials and some neighbors of the affluent retirement community.
The 56-acre private property on Theall Road, home to The Osborn for more than a century, is set to undergo a sweeping transformation that was unveiled before the city Planning Commission last month. The not-for-profit has proposed a large expansion that includes several new independent- and assisted-living buildings, including 108 new residential units, a wellness amenity center, interior cottages, and basement-level parking garages.
Additionally, the proposal includes the removal of 177 trees of the approximately 1,021 trees on the property to allow for the expansion. But to try and offset some of that loss, The Osborn proposed replanting 230 of those trees in order to maintain several unique species on the property.
Osborn leaders say the project is essential to its long-term viability and its ability to continue delivering high-quality care to current and future residents. But a recent memo from the Westchester County Planning Board, which reviewed the plans, urges the city take a closer look before moving the project forward.
County planning officials — although they have no jurisdiction over the project — made note of several items including environmental impact, infrastructure strain, and, most importantly, the absence of affordable housing in the plans.
While the development plans would add residential units to Rye, a city that rarely sees large-scale multi-family proposals, none are designated as affordable.
Matthew Anderson, CEO and president of The Osborn, said the organization is prepared to address the county’s concerns, noting that similar correspondence was also sent when the changes were first envisioned.
“We haven’t done anything on this campus in well over 25 plus years, and to meet those needs of future seniors, we’re going to need to do something to make that happen,” Anderson told The Record.
Ideas to redevelop the property started back in 2018 but only gained traction after the City Council’s 2022 rezoning, at The Osborn’s request, that created a special use for senior living facilities on large properties — 50 acres or more — in areas that had been designated for single-family homes.
The amendment allowed The Osborn to upgrade its campus in a way that would not have been permissible under the prior zoning — paving the way for this latest proposal.
Pointing to the region’s severe housing shortage, the county requested that the current plans ensure that 10 percent of the new units comply with affordable housing standards, which, in Westchester, generally means they must be affordable to households earning up to 80 percent of the area median income, or about $101,600 for a family of four, according to the county’s housing assessment.

The average monthly rent, based on 2019 housing assessment guidelines for an affordable two-bedroom apartment in Rye is around $1,600, while the average rental market rate for a two-bedroom unit in Westchester is roughly $2,500, county housing data shows.
By comparison, monthly fees for units at The Osborn begin at $5,500, and have a one-time entrance cost of at least $638,000.
“The acute shortage of affordable housing in Westchester County has been documented in the County’s Housing Needs Assessment and it is critical for all of Westchester’s municipalities to play a role in meeting this need, particularly since the economic and social impacts of the affordable housing shortage are spread throughout the County,” the Westchester County Planning Board memo read.
Parking was another sticking point for the board. The Osborn is proposing 685 parking spaces to accompany its new plans, far above the 375 required by city code. While most new spaces would be underground, the county questioned whether that volume is necessary for a senior living community.
Westchester officials suggested exploring transportation alternatives to cut down on car dependency and construction costs.
The application describes efforts to limit environmental impact, including keeping 69 percent of the site green, preserving tree canopy, and expanding detention basins to control stormwater runoff. Still, the county called for more above-ground solutions like rain gardens, and a maintenance plan to keep systems from failing over time.
The Osborn, which is the city’s second highest taxpayer and currently pays about $2.5 million annually in property taxes, emphasized that the project would increase tax revenue without adding students to the public school district.
A recent traffic study also found minimal impact to surrounding roads, with only three additional cars projected at the nearby Osborn Elementary School during peak hours.
But some Rye residents are also voicing concerns about the proposed expansion.
In a letter to the commission in June, Tracy Dalick Irace, who lives on Old Post Road, criticized the plan for removing 177 trees and potentially overwhelming Rye’s stormwater and sewage systems.
She called The Osborn project an example of overdevelopment that could alter neighborhood character and urged the Planning Commission to delay approving it until more environmental reviews and public input are conducted.
“This is a critical moment for Rye,” she wrote in her letter. “Please protect our natural resources, infrastructure, and the long-term character of our community by insisting on a more responsible, community-centered plans.”
After facing pushback, The Osborn has submitted revised plans which include architectural changes to reduce one of its building’s visual impact from Post Road, including adding greenery, and provided updated stormwater data.
Anderson said the project has no set timeline.
The Planning Commission is scheduled to hold a public hearing on the proposal on Sept. 9.


