5227 N Glenwood Avenue, Chicago, IL 60640

• 5 beds |
• 3 baths

Property Description

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.

Listing Status:

Active

Data Last Updated:

May 31, 2026 at 4:20PM

Listing Office:

Jameson Sotheby's Intl Realty : 773-370-2399

Listing Agent:

Michael Donnelly : 773-370-2399

MLS ID:

12657840

Interior

• Rooms: Foyer
• Basement: UnfinishedFull
• Heating: Natural GasForced AirSteamRadiator(s)

Exterior

• General: Balcony
• Other Structures: Garage(s)
• Parking: Garage Door OpenerYesGarage OwnedDetachedGarageParking spaces: 2

Construction

• General: Concrete Perimeter

Location

• Originating MLS: mred
• School District: 299
• County: Cook

Lot

• Zoning: 14081250100000

Utilities

• Water: Public
• Sewer: Public Sewer

Financial

• Source: mred
• Ownership: Fee Simple