Active Under Contract
Multi family home for sale at 5835 N Winthrop Ave, Chicago, IL 60660 | MLS# 12769232 | Listing updated on 2026-10-02
Photo 1 of Multi family home for sale at 5835 N Winthrop Ave, Chicago, IL 60660 | MLS# 12769232 | Listing updated on 2026-10-02
Photo 2 of Multi family home for sale at 5835 N Winthrop Ave, Chicago, IL 60660 | MLS# 12769232 | Listing updated on 2026-10-02
Photo 3 of Multi family home for sale at 5835 N Winthrop Ave, Chicago, IL 60660 | MLS# 12769232 | Listing updated on 2026-10-02
Photo 4 of Multi family home for sale at 5835 N Winthrop Ave, Chicago, IL 60660 | MLS# 12769232 | Listing updated on 2026-10-02
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Street View

$1,100,000

Monthly Est:$5,475

  • Beds Icon9 Beds
  • Beds Icon
    5 Baths
  • Beds Icon--sqft

5835 N Winthrop Ave, Chicago, IL 60660

$5,475/moEst:

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  • 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 MRED MLS-IL

Part of

Building
5835 N Winthrop Ave
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Property Details

  • Status

    Active Under Contract

  • Type

    Multi Family

  • No. of Stories

    -

  • County

    Cook County

  • City

    Chicago

  • Neighborhood

    Edgewater

  • 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

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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

DateEventPrice

10/02/2026

Source: mls_logoMRED MLS-IL #MRD12769232

Contingent (Active Under Contract)

$1,100,000

$0/sqft

09/25/2026

Source: mls_logoMRED MLS-IL #MRD12769232

Listed for Sale

$1,100,000 -15.32%

$0/sqft

11/03/2021

Source: mls_logoMRED MLS-IL #MRD11164753

Listing Removed

$1,299,000

$0/sqft

Edgewater Ranks #139 in Chicago, IL

Homes for sale
125

Homes

Rental prices
$1,735

Rental Prices

Median Home Price
$270.5K

Median Home Price

Edgewater, Chicago, IL neighborhood guide

Nearby Homes

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

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