On the edge of Andersonville and Uptown, on Chicago’s northside, we provide independent housing for older adults in two buildings. Winwood Apartments and Glenwood Apartments are located in a beautiful and convenient neighborhood, close to stores, Lake Michigan, and public transportation. Winwood and Glenwood provide seniors with below-market-rate apartments. Two full-time CMSS coordinators offer support and assistance to tenants upon request.
1406 W Winona St
Chicago, IL 60640
Winwood Apartments is a thirty-one (31) unit apartment building for adults age 62 and older. It is subsidized by the Department of Housing and Urban Development (HUD). The building offers secure residences with modern amenities. To apply, residents must qualify as “very low income” in accordance with HUD guidelines. Rent rates are calculated to be approximately 30% of the resident’s monthly income.
5021 – 5027 N Glenwood Ave
Chicago, IL 60640
Glenwood Apartments is a vintage brick building with thirteen (13) units at the corner of Glenwood and Winnemac Avenues. Residents qualify as “very low income” in accordance with the Department of Housing and Urban Development’s (HUD) guidelines. Rent rates are calculated to be approximately 40% of the resident’s monthly income, subject to minimums and maximums.
The Long-Term Care Equality Index (LEI) is the nation’s foremost benchmarking survey of residential long-term care and senior housing, which promotes equitable treatment and inclusion for LGBT+ residents, visitors, and employees. The LEI recognized both Winwood Apartments and Glenwood Apartments as High Performers.
As a 501(c)(3) non-profit organization, CMSS relies on the generosity of friends and supporters to make our work possible.
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© Chicago Methodist Senior Services 2025