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$1,311,000

5227 N Glenwood Avenue
Chicago, IL 60640

Multi Family|Sold 07/09/2026
5
Beds
3
Total Baths
1909
Built
County:
Cook
Listing Courtesy of MRED as distributed by MLS Grid of Jameson Sotheby's Intl Realty
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(773) 998-2401
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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.

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Listing Snapshot
Bedrooms 
5
Total Baths 
3
Full Baths 
N/A
Partial Baths 
N/A
Inside Area (SqFt) 
N/A
Lot Size 
N/A
Year Built 
1909
MLS® Number 
12657840
Status 
Sold
Property Tax 
$12,269.11
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
3 days agoListing updated with changes from the MLS®
General Features
Foundation 
Concrete Perimeter
Garage 
Yes
Garage Spaces 
2
Parking 
Garage Door OpenerDetachedGarage
Parking Spaces 
2
Property Sub Type 
Multi Family
Sewer 
Public Sewer
Water Source 
Public
Interior Features
Basement 
UnfinishedFull
Cooling 
Ceiling Fan(s)
Heating 
Hot WaterNatural GasForced AirSteam
Interior 
Entrance Foyer
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Exterior Features
Construction Details 
Brick
Exterior 
Balcony
Other Structures 
Garage(s)
Community Features
MLS Area 
CHI - Edgewater
School District 
299
Township 
Lake View
Schools
School District
299
Elementary School
Unknown
Middle School
Unknown
High School
Unknown
Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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