Under Contract

5227 N Glenwood Avenue

Chicago, IL 60640
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Bed 5

Bed

Bath 3

Bath

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 priva te 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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Detail Ic Property Details

Property Type : Residential Income

Price : $1,100,000

AD Id : 79425928

MLS Id : MRD12657840

Beds : 5

Year Built : 1909

Garage : 2

County : Cook

  • Map Map

Map

Feature Features

  • Bedroom Information

    Total Bedroom: 5 Room Types: Foyer

    Bathroom Information

    Total Baths: 3

    Room Information

    Rooms Total: 24
  • Flooring Information

    Construction Materials: Brick
  • Heating & Cooling

    Heating: Natural Gas, Forced Air, Steam, Radiator(s) WaterSource: Public

  • Building Information

    Year Built: 1909
  • Exterior Features

    Balcony Construction Materials: Brick Foundation Details: Concrete Perimeter

  • Lot Information

    Lot Dimensions: 30x121 Lot Size: Less Than .25 Acre

    Property Information

    Property Type: Residential Income Sub Type: Two to Four Units

  • Listing Price Information

    Original List Price:$1100000

  • Tax Information

    Annual Tax: $12269.11 Tax Year: 2023 Parcel Number: 14081250100000

  • Parking Information

    Total Parking: 2 Garage Door Opener, Yes, Garage Owned, Detached, Garage Is Parking Included in Price: Yes

    Garage Information

    Garage Space: 2

  • Utility Information

    Sewer: Public Sewer Water Source: Public
  • Location Information

    City: Chicago Direction: Foster to Glenwood. North to Property
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ByOwner last updated this listing 06/23/2026 @ 18:20

MLS: MRED #12657840 LISTED BY: Michael Donnelly, Jameson Sotheby's Intl Realty 312-751-0300 SOURCE: Midwest Real Estate Data LLC (MRED) (Listings courtesy of Midwest Real Estate Data LLC (MRED) as distributed by MLS GRID)

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