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5835 N Winthrop Ave , Chicago, IL 60660
$1,100,000
Est. Payment: $5,902.02/mo
9 Bed
5 Bath
Status: contingent | Days on site: 27
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4420 - 44649,163856
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House 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.

Highlights

Listed by Tedi Smola , 773-552-1122 @properties Christie's International Real Estate , 847-763-0200. Midwest Real Estate Data mls logo

Property Type

Multi-Family

Year Built

1903

County

Cook

Area

CHI - Edgewater

School District

299

Listing ID

12769232

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Interior Features

Bedrooms and Bathrooms
  • ▪ Bedrooms:9
  • ▪ Bathrooms:5
Basement:Finished,Full
Water:Public

Exterior Features

Lot Dimensions:37 X 151
Garage Capacity:3
Zoning:MULTI
Sewer:Public Sewer
Parking Features:No Garage,Yes,Garage Owned,Detached,Off Alley,Owned,Garage
Principal Interest
$5,902
Taxes
$1,278

Home Price

$1,100,000

Loan Details

30 yrs
7.08%

Down Payment

20%
$220,000
All calculations are estimates and provided by Blueroof360. Today’s Rates provided by Blueroof360. Information and interactive calculators are made available to you only as self-help tools for your independent use and are not intended to provide investment or tax advice. We cannot and do not guarantee their applicability or accuracy in regards to your individual circumstances. All examples are hypothetical and are for illustrative purposes. We encourage you to seek personalized advice from qualified professionals regarding all personal finance issues.
Monthly Price:
$5,902.02

Principal

Taxes

Principal Taxes HOA Total
Monthly $5,902.02 $1,278.00 $0.00 $7,180.02
Yearly $70,824.22 $15,336.00 $0.00 $86,160.22
Total $2,124,726.64 $460,080.00 $0.00 $2,584,806.64
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Market insight data is pulled from the same city as the listing being viewed (Chicago, IL).

The schools listed are within a 2-mile radius of the property; however, attendance is not guaranteed. Please contact the local school district to confirm zoning and enrollment options.

Based on information submitted to the MRED as of the date listed below. All data is obtained from various sources and has not been, and will not be, verified by broker or MRED. MRED 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. IDX information is provided exclusively for consumers' personal non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed by MTP or MRED. The use of the MRED Data may be subject to an end user license agreement prescribed by the Member Participant's applicable MLS if any and as amended from time to time.

Based on information submitted to the MLS GRID as of the date listed below. All data is obtained from various sources and may not have been 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. IDX information is provided exclusively for consumers' personal non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant's applicable MLS if any and as amended from time to time. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability. Some listings have been excluded from this website.

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Data last updated: 2026-10-27T04:57:04.000Z

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