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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.

Property Details of 5227 North Glenwood Avenue

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Listed by Michael Donnelly of Jameson Sotheby's Intl Realty ((773) 370-2399)

Based on information submitted to MRED  as of May 29, 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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