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$499,900

5253 Wrightwood Ave

Chicago, IL
Contingent
4
Bedrooms
3
Bathrooms
1926
Year Built
53
Days On Market

BIG lovingly maintained updated and preserved brick bungalow with tons of intact vintage charm AND new kitchen & baths on tree lined street. 4 bedrooms (2 up, 2 main level), 3 full baths (1 on each floor), finished basement, 2.5 car garage. Beautiful bright front living room with original stained glass (restored) windows and decorative fireplace flanked by wood book cases with matching glass, vintage tile foyer entryway with coat closet, and large separate dining room with arched top glass door separating the entertaining space from the living quarters and kitchen. New kitchen (2022) features quartz countertops, imported tile backsplash, stainless steel appliances, and carefully designed cabinetry for smart efficient storage (including toe kick drawers) and adjacent breakfast nook and family room hang-out space. Rounding out the main level are two sizable bedrooms and a new full bathroom with shower and vanity. On the 2nd floor, this home has two large bedrooms and a spacious new bathroom with tub/shower combo and vanity. The full basement is finished with tile and drywall and has a laundry room with laundry sink, mini kitchen (cabinets, sink), one full bathroom, abundant storage space, and good ceiling height. Excellent natural light, original oak and maple hardwood flooring, original wood trim, new replacement windows, combination central AC/heat (upstairs) and radiant/boiler heat (throughout house), drain tile+sump, and newer (2023) tear-off roof (on house and garage). Sitting on a 30x125 (extra wide) lot, this home has a cute front yard with a mature magnolia tree, a large back yard space with tons of potential for gardening and entertaining, and an insulated heated 2.5-car garage with epoxy floors & party door, ready to host vehicles and parties & projects. Picturesquely located across from 3+ acre Cragin Park with brand new field house, walking paths, softball fields, soccer/football field, tennis courts, a basketball court, a volleyball court, a playground with a wading/spray pad, and lots of programs for kids, idyllic 5253 W Wrightwood Ave balances historical charm and modern conveniences.

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Listing Information

Listing Updated
20 days ago
Listed By
Michelle Liffick · Jameson Sotheby's Intl Realty, 3127510300
MLS#
12755220
Source
Midwest Real Estate Data (MRED)
Status
Contingent

Facts & Features

Location

Community Information

Address
5253 W Wrightwood Ave, Chicago, IL 60639
City
Chicago
County
Cook
Zip Code
60639

Architecture

Bedrooms
4
Bathrooms
3
Year Built
1926
Style
Bungalow
Construction Materials
Brick
Roof
Asphalt
Garage
Yes
Garage Spaces
2
Parking Features
Garage Door Opener, Garage, Detached, Heated Garage

Features & Amenities

Interior Features
Walk-In Closet(s), Built-in Features
Appliances
Dryer, Dishwasher, Microwave, Refrigerator, Washer, Range, Stainless Steel Appliance(s)
Flooring
Hardwood
Community Features
Clubhouse, Sidewalks, Curbs, Tennis Court(s), Street Lights, Park
Cooling
Ceiling Fan(s), Central Air, Window Unit(s)
Heating
Forced Air, Natural Gas, Steam

Property Features

Sewer
Public Sewer

Tax & Financial Information

List Price
$499,900
Annual Taxes
$8,246

Schools

100/100
Christopher House Chrt Elementary School
Elementary · Grades PK–08 · 0.4 mi
City
Chicago
Students
277
Student body
95% Hispanic / Latino · 3% Black · 1% White
Free/reduced lunch
94%
Phone
(773) 922-7542
100/100
Foreman High School
High · Grades 09–12 · 0.9 mi
City
Chicago
Students
1,025
Student body
78% Hispanic / Latino · 17% Black · 3% White
Free/reduced lunch
95%
Phone
(773) 534-3400
97/100
Belmont-Cragin Elementary School
Elementary · Grades PK–08 · 1.1 mi
City
Chicago
Students
585
Student body
92% Hispanic / Latino · 4% Black · 3% White
Free/reduced lunch
92%
Phone
(773) 534-2900
73/100
Prosser Career Academy High School
High · Grades 09–12 · 0.6 mi
City
Chicago
Students
1,327
Parent reviews
5.0★ avg · 2 reviews
Student body
78% Hispanic / Latino · 19% Black · 2% White
Free/reduced lunch
89%
Phone
(773) 534-3200
65/100
Hanson Park Elementary School
Elementary · Grades PK–08 · 0.4 mi
City
Chicago
Students
1,483
Parent reviews
4.5★ avg · 4 reviews
Student body
96% Hispanic / Latino · 2% White · 1% Black
Free/reduced lunch
96%
Phone
(773) 534-3100
55/100
Lyon Elementary School
Elementary · Grades PK–08 · 1 mi
City
Chicago
Students
1,498
Student body
89% Hispanic / Latino · 6% White · 2% Black
Free/reduced lunch
95%
Phone
(773) 534-3120
54/100
Camras Elementary School
Elementary · Grades PK–08 · 0.8 mi
City
Chicago
Students
896
Student body
91% Hispanic / Latino · 6% White · 2% Asian
Free/reduced lunch
86%
Phone
(773) 534-2960
53/100
Falconer Elementary School
Elementary · Grades PK–06 · 0.7 mi
City
Chicago
Students
896
Student body
94% Hispanic / Latino · 3% White · 2% Black
Free/reduced lunch
93%
Phone
(773) 534-3560

School ratings are provided for informational purposes only and are subject to change. Attendance boundaries are for reference only — contact the school or district directly to verify enrollment eligibility.

Historical Data

Price History

DateEventPrice
10/06/2026Price change$499,900
09/10/2026Listed for sale$549,900

Listed by Michelle Liffick · Jameson Sotheby's Intl Realty · 3127510300

Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, Midwest Real Estate Data (MRED). All rights reserved.

Last Updated: October 13, 2026 at 5:42 PM | Source: Midwest Real Estate Data (MRED) | MLS#: 12755220

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