O'Neil Property Group

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$1,595,000
7 Days On Site

1244 W Oakdale Avenue
Chicago, IL 60657

For Sale|Multi Family|Active
7
Beds
4
Total Baths
1886
Built
County:
Cook
Listing Courtesy of MRED as distributed by MLS Grid of Option Premier LLC
1244 W Oakdale Avenue1244 W Oakdale Avenue1244 W Oakdale Avenue1244 W Oakdale Avenue
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Prime Lakeview 2-Flat with additional non-conforming garden unit in the Heart of Southport Corridor. Rare opportunity to own a beautifully maintained and updated multi-family building offering approximately 2,502 square feet of living space with a total of 8 bedrooms and 4 bathrooms, two car detached garage and rooftop deck. Second floor unit can be converted into a duplex-up (plumbing in place), offering room for equity gain. Central Heat & AC in units, 1 & 2. Garden unit has central heat. Whether you're an investor seeking strong rental potential or an owner-occupant looking to supplement expenses with rental income, this property offers exceptional flexibility in one of Chicago's most desirable neighborhoods. The units blend classic Chicago charm with modern updates, featuring hardwood floors throughout, generous room sizes, high ceilings, and abundant natural light in all units. Kitchens in units 1 & 2 showcase rich custom cabinetry, granite countertops , backsplashes, and ample storage. Spacious living and dining areas provide comfortable everyday living and entertaining. Ground floor common area has a full bath, private sauna, as well as laundry. On a picturesque tree-lined street, this prime Lakeview location places you just steps from the Southport Corridor's renowned restaurants, boutiques, coffee shops, grocery stores, and entertainment. Enjoy easy access to Wrigley Field, parks, Lake Michigan, and CTA Brown, Purple, and Red Line trains, providing a convenient commute throughout the city. Combining timeless character, updated interiors, and an unbeatable location, this property presents a rare opportunity to own a classic Chicago multi-unit with strong income potential and long-term value in the heart of Lakeview.

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Listing Snapshot
PriceΒ 
$1,595,000
Days On SiteΒ 
7 Days
BedroomsΒ 
7
Inside Area (SqFt)Β 
N/A
Total BathsΒ 
4
Full BathsΒ 
N/A
Partial BathsΒ 
N/A
Lot SizeΒ 
N/A
Year BuiltΒ 
1886
MLS NumberΒ 
12790591
StatusΒ 
Active
Property TaxΒ 
$17,077
HOA/Condo/Coop FeesΒ 
N/A
Sq Ft SourceΒ 
N/A
Friends & Family
Recent Activity
11 hours agoListing updated with changes from the MLS
2 days agoStatus changed to Active
a week agoListing first seen on site
General Features
GarageΒ 
Yes
Garage SpacesΒ 
2
ParkingΒ 
DetachedGarage
Parking SpacesΒ 
2
Property Sub TypeΒ 
Multi Family
SewerΒ 
Public Sewer
Water SourceΒ 
Public
Interior Features
BasementΒ 
FinishedExterior EntryFull
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Exterior Features
Construction DetailsΒ 
Brick
Patio And PorchΒ 
Porch
Community Features
Accessibility FeaturesΒ 
Therapeutic Whirlpool
MLS AreaΒ 
CHI - Lake View
School DistrictΒ 
Oak Lawn Comm High School
TownshipΒ 
Lake View
Schools
School District
Oak Lawn Comm High School
Elementary School
Unknown
Middle School
Unknown
High School
Oak Lawn Comm High School
Listing Courtesy of MRED as distributed by MLS Grid of Option Premier LLC



Based on information submitted to the MLS GRID as of 2026-11-09 06:24 AM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Last checked: 2026-11-09 06:24 AM UTC
MRED DMCA Copyright Information Copyright Β© 2026 Midwest Real Estate Data LLC. All rights reserved.

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