- Overview
- Description
- Property Details
- Location
- Facts & Features
- Getting Around
- Nearby Homes





Street View
$1,100,000
Monthly Est:$5,475
9 Beds
- 5 Baths
--sqft
5835 N Winthrop Ave, Chicago, IL 60660
$1,100,000
$5,475/moEst:
Get Pre-Approved
Multi Family
Built in 1903
$-- HOA
-- sqft lot
--/sqft
Description
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.
- Houzeo last checked: 1 minute ago
- Listing updated: October 2, 2026 at 2:02 pm
- Listing Provided by: Tedi Smola | @properties Christie's International Real Estate (847) 763-0200
- Source: MRED MLS-IL | MLS#: 12769232

Part of
Property Details
Status
Active Under Contract
Type
Multi Family
No. of Stories
-
County
City
Neighborhood
Year Built
1903
HOA Fees
-
Finished Area
- sqft
Lot Size
-- sqft lot
Basement Area
- sqft
MLS Name
MRED MLS
MLS Number
12769232
MLS Status
Contingent
Days on Market
14

Continue Your Journey in App
Find your dream home, receive real-time updates, and many more!
Download App
Continue Your Journey in App
Find your dream home, receive real-time updates, and many more!
Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 9
Bathrooms: 5
Interior
Sewer
Public Sewer
Heating
Natural Gas
Construction
Year Built
Year Built: 1903
Home type
Multi Family
Construction Materials
Brick, Stone
Architectural Style
Greystone
Utilities & Energy
Parking Features
No Garage, Yes, Garage Owned, Detached, Off Alley, Owned, Garage
Basement
Finished, Full
Water Source
Public
Other Features
Community Features
Gated
Price History
| Date | Event | Price |
|---|---|---|
10/02/2026 Source: | Contingent (Active Under Contract) | $1,100,000 $0/sqft |
09/25/2026 Source: | Listed for Sale | $1,100,000 -15.32% $0/sqft |
11/03/2021 Source: | Listing Removed | $1,299,000 $0/sqft |
Edgewater Ranks #139 in Chicago, IL
Homes
Rental Prices
Median Home Price
Nearby Homes
Find Homes by Property Features in Chicago, IL
This representation is based in whole or in part on data supplied by Midwest Real Estate Data, LLC through Oct 09, 2026, 11:15AM. Midwest Real Estate Data, LLC does not guarantee nor is it in any way responsible for its accuracy. Data maintained by Midwest Real Estate Data LLC may not reflect all real estate activity in the market. Based on information submitted to the MLS GRID as of Oct 09, 2026, 11:15AM. All data is obtained from various sources and has not been, and will not be, verified by broker or MLS GRID. Supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. This website may not include listings or property addresses of sellers who have directed their listing brokers to withhold their listing or their property address from display on the Internet. Some IDX listings have been excluded from this website. Information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID, MRED or Houzeo. The use of the MLS GRID Data may be subject to an end user license agreement. Properties displayed may be listed or sold by various participants in the MLS, Listings courtesy of MRED as distributed by MLS GRID. ©2026 Midwest Real Estate Data LLC. All Rights Reserved
Advertising Broker: Jorge Romero | Realty One Group Inc.





