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5835 North Winthrop AvenueChicago, IL 60660Price: $1,100,000

  • Price: $1,100,000
  • Est. Mortgage of $/month
  • 1 Day on Market
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$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Sep 24, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $1,100,000List Price
  • 9Bedrooms
  • 5Bathrooms
  • 1903Year Built

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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.

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Listed by Tedi Smola of @properties

Based on information submitted to MRED  as of September 25, 2026 . All data is obtained from various sources and has not been, and will not be, verified by broker or MRED.   All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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