Stunning classic Greystone offering incredible character, spacious floor plans, and strong income potential in the heart of Edgewater. This legal 3-unit building also features a 1-bedroom, 1-bath in-law suite on the lower level, providing additional flexibility and income. The first and second floors each offer expansive 3-bedroom, 1-bath layouts with soaring ceilings, beautiful vintage details, generous room sizes, great natural light, and outdoor space. Much of the original woodwork and architectural character has been preserved while the building has been updated for modern living with forced-air heat, central air conditioning, dishwashers, and other improvements. The top-floor unit is an impressive 2-bedroom, 2-bath residence featuring vaulted ceilings, an updated kitchen and baths, in-unit laundry, a gas fireplace, and a bright, open feel. Current rent roll includes the lower-level 1-bedroom in-law suite at $900/month with a long-term month-to-month tenant; the first-floor 3-bedroom is currently vacant; the second-floor 3-bedroom rents for $1,900/month with a long-term month-to-month tenant; and the top-floor 2-bedroom, 2-bath rents for $2,600/month and is leased through August 2027. The property offers an excellent opportunity for a new owner to make improvements over time and further enhance an already beautiful vintage building. Several of the current rents reflect long-term tenancies and are below current market levels, offering additional income potential as units are updated and rents are brought closer to market. The vacant first-floor unit provides an immediate opportunity to make it your own, establish market rent, or owner-occupy while collecting income from the other units. A rare opportunity to own a beautiful Chicago Greystone combining vintage character, modern conveniences, existing rental income, and future upside. Out of respect for tenant privacy, only floor plans of the occupied units are included in the listing, but a full virtual tour is available. The vacant first-floor unit is available for showings at any time. All other units are available to be shown with a minimum of 48 hours’ notice.
Property Details
Price:
$1,100,000
MLS #:
MRD12769232
Status:
Active Under Contract
Beds:
9
Baths:
5
Type:
Multi Family
Neighborhood:
chiedgewater
Listed Date:
Sep 24, 2026
Year Built:
1903
See this Listing
Schools
School District:
299
Interior
Heating
Natural Gas
Exterior
Architectural Style
Greystone
Community Features
Gated
Construction Materials
Brick, Stone
Fencing
Fenced
Garage Spaces
2
Parking Features
No Garage, Yes, Garage Owned, Detached, Off Alley, Owned, Garage
Parking Spots
3
Parking Total
3
Financial
Tax Year
2025
Taxes
$15,336
Map
Community
- Address5835 N WINTHROP Avenue Chicago IL
- CityChicago
- CountyCook
- Zip Code60660
Market Summary
Current real estate data for Multi Family in Chicago as of Oct 05, 2026
1,367
Multi Family Listed
77
Avg DOM
$530,402
Avg List Price
Property Summary
- 5835 N WINTHROP Avenue Chicago IL is a Multi Family for sale in Chicago, IL, 60660. It is listed for $1,100,000
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Copyright 2026. All rights reserved.
5835 N WINTHROP Avenue
Chicago, IL


