Active Under Contract

$1,100,000

5835 WINTHROP Avenue, Chicago, IL 60660
9 Beds5 Baths9 days
5835 WINTHROP Avenue·Chicago, IL 60660
9Bedrooms
5Bathrooms
1903Year Built
About This Home

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.

MLS# 12769232Listed September 24, 2026Residential IncomeGreystone
Property Details

Beds & Baths

Total Bedrooms9
Total Bathrooms5
Total Rooms22

Size & Structure

Garage Spaces2
Year Built1903
Lot Size37 X 151

Location

CountyCook
TownshipLake View
Zip Code60660

Financial

List Price$1,100,000
Annual Taxes (2025)$15,336
Monthly Tax Est.$1,278
Parcel #14054010150000
Interior Features

Heating

Natural Gas

Basement

FinishedFull
Exterior & Lot

Construction

BrickStone
Utilities & Parking

Sewer

Public Sewer

Water Source

Public

Parking

No GarageYesGarage OwnedDetachedOff AlleyOwnedGarage
HOA & Community

Community Features

Gated
Tax & Financial
Annual Taxes
$15,336
Tax Year 2025
Monthly Tax Est.
$1,278
per month
Property Location

5835 WINTHROP Avenue, Chicago, IL 60660 — Cook County

$1,100,000
5835 WINTHROP Avenue
9 bd5 ba
VL
Vittoria Logli
Top Glenview Agent

IL License 475.178467 · (847) 810-8438

Quick Facts
9 days on market
2-car garage
37 X 151
$15,336/yr taxes
$7,059
estimated monthly payment
Principal & Interest
$5,781/mo
Property Tax
$1,278/mo
$1,100,000
20% — $220,000
3%50%
6.875%
3%12%
Loan Amount
$880,000
Down Payment
$220,000

* Estimated payment only. Actual rates, taxes, and insurance may vary. Contact a lender for a personalized quote.

Listed by
@properties Christie's International Real Estate
Agent: Tedi Smola
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Listing Courtesy: MRED as distributed by MLS GRID | @properties Christie's International Real Estate

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