Listing provided courtesy of Jameson Sotheby's Intl RealtyMREDMLS# 12657840MLS Provider
  • 33 days on site
  • 6 views

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.

Source: MRED, MLS#: 12657840

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  • Property Type
    Residential Income

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Owning this Home

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

Life at 5227 N Glenwood Avenue


Schools


School data courtesy of LiveBy, Inc.
Ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating. The schools displayed on this website are for informational purposes only and may not represent a complete or up-to-date list. School assignments are subject to change and should be verified directly with the local school district. Please contact the appropriate school district to confirm school zoning and enrollment eligibility for this property.

History

Date Event Value Agent
6/4/2026Source: MRED Status Change
Contingent
6/2/2026Source: MRED Status Change
Active
5/28/2026Source: MRED Added to Database
May 28, 2026