1244 W Oakdale Avenue Chicago, IL $ 1,595,000
1244 W Oakdale Avenue
$ 1,595,000
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1244 W Oakdale Avenue

Chicago, IL, 60657
$ 1,595,000
Bedrooms7 Baths4.0 Sq 1,688

Monthly Estimate*

$ 11,016

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Multi-Family Home for sale in Chicago, IL

for $1,595,000 with 7 bedrooms and 4 full baths. This 1,688 square foot home was built in 1886.

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 7 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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Multi-Family Active

Price

$ 1,595,000

Bedrooms

7

Full Bath

4

Property Type

Multi-Family

Taxes

$ 17,077

Style

Year Built

1886

Town/City

Chicago

County/Region

Cook

MLS | Web ID

12790591

Features
General
Sewer Public Sewer
Heating Gas
Possession Closing
Garage Spaces 2
Construction Materials Brick
Year Built 1886
Township Lake View
Tax Year 2024
Ownership Fee Simple
County Cook
New Construction N
Property Type Residential Income Two to Four Units
Total Rooms 12
Status Active
Directions From Lake Shore Drive exit at Belmont Ave and head west. Turn south on Racine Ave then west on Oakdale Ave to 1244 W Oakdale Ave. Property is located on the south side of the street in the Lake View
High School Oak Lawn Comm High School
City Chicago
High School District 229
MLS Area CHI - Lake View
Tax Annual Amount 17077
Standard Status Active
Middle/Junior School District 299
Elementary School District 299
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Interior
Basement Finished Exterior Entry Full
Total Bedrooms 7
Room Type Enclosed Porch Utility Room-1st Floor
Total Baths 4
Bedrooms Possible 7
Bathroom Whirlpool
Full Baths Building 4
Half Baths Building 0
Total Number of Units 3
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Exterior
Parking Features Yes Detached Garage
Water Source Public
Total Parking 2
Lot Dimensions 25x125
Waterfront Y/N N
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* Excluded Features
List By
Option Premier Llc

Broker

cory@optionpremier.com

Email

Affordability Calculator

$12,439
Per Month
89%
11%
0%
Monthly Principal & Interest
$11,016
Monthly Property Taxes
$1,423
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
565363 Elementary School
565252 Middle School
Oak Lawn Comm High School High School
Pricing History
DatePricePrice ChangeDescription
11/2/2026$1,595,000 Listed Price

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1244 W Oakdale Avenue, Chicago, IL, 60657 is a Multi-Family Home for sale at $1,595,000 with 1,688 sqft. 1244 W Oakdale Avenue has 7 bedrooms, 4.0 baths, and was built in 1886. The property's zip code is 60657 which is in Chicago, IL