Lovingly maintained owner-occupied 2-flat in the heart of Andersonville offering incredible flexibility for investors, live-in owners, or multi-generational living. This spacious property features 5 bedrooms and 3 full bathrooms across two well-kept units and a basement filled with vintage charm, timeless character, and true pride of ownership. Generous room sizes, abundant natural light, and thoughtful upkeep help highlight the beautiful original details and classic vintage accents that are found throughout, including stunning built-in cabinetry, rich woodwork, and warm, inviting living spaces. Recent upgrades to the kitchen and bath provide a modern touch in the owner’s unit..this is that rare move-in ready opportunity that blends charm and functionality. The property also includes private balconies, a 2-car garage and outdoor space. There is also a tall basement with laundry room, utility room and endless storage. All situated on a quiet tree-lined street just moments from Lake Michigan and Andersonville’s renowned restaurants, cafes, shopping, nightlife, parks, and public transportation. Whether you’re looking to generate rental income, owner-occupy with supplemental income, or invest in one of Chicago’s most sought-after neighborhoods, this exceptional 2-flat offers endless potential and enduring Chicago character.
Property Details
Price:
$1,100,000
MLS #:
MRD12657840
Status:
Active Under Contract
Beds:
5
Baths:
3
Type:
Multi Family
Neighborhood:
chiedgewater
Listed Date:
May 26, 2026
Year Built:
1909
Schools
School District:
299
Interior
Heating
Natural Gas, Forced Air, Steam, Radiator(s)
Exterior
Construction Materials
Brick
Exterior Features
Balcony
Garage Spaces
2
Other Structures
Garage(s)
Parking Features
Garage Door Opener, Yes, Garage Owned, Detached, Garage
Parking Spots
2
Parking Total
2
Financial
Tax Year
2023
Taxes
$12,269
Listing Agent & Office
Michael Donnelly
Jameson Sotheby’s Intl Realty
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Copyright 2026. All rights reserved.
5227 N Glenwood Avenue
Chicago, IL


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