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$1,100,000 Just Listed

  • For Sale
  • Active
  • Multi-Family
  • 5 Total Beds
  • 2 Car Garage
  • Updated 20 hours ago

Next open house:

Open House: 10:30 AM - 1:30 PM

Saturday 5/30 10:30 AM - 1:30 PM

5227 N Glenwood Avenue,Chicago, IL 60640

5227 N Glenwood AvenueChicagoIL60640

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Join us at 5227 N Glenwood Avenue on:

  • Open House: 10:30 AM - 1:30 PM

    Sunday 5/31 10:30 AM - 1:30 PM

    5227 N Glenwood Avenue,Chicago, IL 60640
    5227 N Glenwood AvenueChicagoIL60640

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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.

Full Property Details for 5227 N Glenwood Ave

General

  • Price: $1,100,000
  • Taxes: $12,269 (2023)
  • Status: Active
  • Type: Multi-Family
  • Source: MRED
  • MLS ID: 12657840

Interior

  • Basement: Unfinished

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Upper - Full Baths: 3

Bedrooms

  • Total Bedrooms: 5

Additional Information

  • Equipment: Carbon Monoxide Detectors, Ceiling Fan(s), Water Heater-Gas
  • Other Features: Commuter Bus, Commuter Train

Exterior

  • Exterior Features: Balcony

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Features: Garage Door Opener, Yes, Garage Owned, Detached, Garage

Location

  • Area: CHI - Edgewater
  • County: Cook
  • Township: Lake View
  • Driving Directions: Foster to Glenwood. North to Property

School Information

  • School District: 299
  • Elem School District: 299
  • Midd School District: 299
  • High School District: 299

Heating & Cooling

  • Heating Type: Natural Gas, Forced Air, Steam, Radiator(s)

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Construction: Brick
  • Exterior Const.: Brick
  • Basement: Yes
  • Basement Desc.: Unfinished, Full
  • Foundation: Concrete Perimeter
  • Year Built: 1909
  • Built Before 1978: Yes

Unit Information

  • Units in Building: 2

Additional Structures

  • Other Structures: Garage(s)

Lot Features

  • Lot Size Range: Less than .25 Acre
  • Lot Dimensions: 30 x 121

Financial Considerations

  • Parking Included: Yes
  • Assessment Year: 1909
  • Tax Amount: $12,269.11
  • Tax Year: 2023
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: List Broker Must Accompany
  • Property ID: 14081250100000

Listed by Jameson Sotheby's Intl Realty

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Listing agent

— 5227 N Glenwood Ave —

  • Jameson Sotheby's Intl Realty

(773) 370-2399

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NMLS#: 1598647

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Save up to an additional 20% by bundling your home and auto together!

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Find the right home insurance for your new home!

with our affiliated in-house agency

Request a Quote

Save up to an additional 20% by bundling your home and auto together!

Schools serving 5227 N Glenwood Ave

School District:Chicago Public School District 299
NameGradesDistance
Peirce Elementary Intl Studies School
1423 West Bryn Mawr Avenue, Chicago, IL 60660
K-80.4 mi
Senn High School
5900 North Glenwood Avenue, Chicago, IL 60660
9-120.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Tax History for 5227 N Glenwood Ave

Year
Property Taxes
Change
Tax Assessment
Change
2023
$12,608
—
$77,906
24%
2023
$12,608
3%
$63,071
—
2022
$12,269
2%
$63,071
—
2021
$12,013
16%
$63,071
27%
2020
$10,379
-3%
$49,693
-12%
2019
$10,657
-7%
$56,470
-8%
2018
$11,441
34%
$61,355
42%
2017
$8,555
5%
$43,114
—
2016
$8,135
-10%
$43,114
-17%
2015
$9,018
23%
$51,836
23%
2014
$7,325
2%
$42,050
—
2013
$7,170
1%
$42,050
—
2012
$7,098
—
$42,050
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Jameson Sotheby's Intl Realty

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5227 N Glenwood Avenue, Chicago, IL 60640 (MLS# 12657840) is a Multi-Family property with 2 units containing 5 bedrooms and 0 full bathrooms. 5227 N Glenwood Avenue is currently listed for $1,100,000 and was received on May 26, 2026. Want to learn more about 5227 N Glenwood Avenue? Do you have questions about finding other Multi-Family real estate for sale in Edgewater? You can browse all Edgewater real estate or contact a Coldwell Banker agent to request more information.

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