5253 W Wrightwood Avenue, Chicago, IL

$499,900

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4

Beds

3

Baths

About 5253 W Wrightwood Avenue

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.

Open House

Sun, Oct 11th, 2026 @ 2pm - 3:30pm

Features of 5253 W Wrightwood Avenue

MLS® # 12755220
Price $499,900
Bedrooms 4
Bathrooms 3.00
Full Baths 3
Year Built 1926
Type Residential
Sub-Type Detached Single
Style Bungalow
Status Price Change

Community Information

Address 5253 W Wrightwood Avenue
Area CHI - Belmont Cragin
City Chicago
County Cook
State IL
Zip Code 60639

Amenities

Parking Spaces 3
Parking Garage Door Opener, Heated Garage, Yes, Garage Owned, Detached, Garage
# of Garages 3
Is Waterfront No
Has Pool No

Interior

Interior Features 1st Floor Bedroom, 1st Floor Full Bath, Built-in Features, Walk-In Closet(s), Historic/Period Mlwk, Separate Dining Room, Replacement Windows, Quartz Counters
Appliances Range, Microwave, Dishwasher, Refrigerator, Washer, Dryer, Stainless Steel Appliance(s)
Heating Natural Gas, Forced Air, Steam, Sep Heating Systems - 2+
Cooling Central Air, Partial, Window Unit(s)
Fireplace Yes
# of Fireplaces 1
Fireplaces Decorative
Stories 2 Stories
Has Basement Yes
Basement Finished, Exterior Entry, Full

Exterior

Exterior Brick
Roof Asphalt

School Information

District 299

Additional Information

Days on Market 30
Foreclosure No
Short Sale No
RE / Bank Owned No
HOA Fees Freq. Not Applicable

Listing Details

OfficeJameson Sotheby's Intl Realty

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Listing information last updated on October 9th, 2026 at 2:26pm CDT.