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House for sale at 1244 W Oakdale Ave, Chicago, IL 60657 | MLS# 12790591 | Listing updated on 2026-11-02
Photo 1 of House for sale at 1244 W Oakdale Ave, Chicago, IL 60657 | MLS# 12790591 | Listing updated on 2026-11-02
Photo 2 of House for sale at 1244 W Oakdale Ave, Chicago, IL 60657 | MLS# 12790591 | Listing updated on 2026-11-02
Photo 3 of House for sale at 1244 W Oakdale Ave, Chicago, IL 60657 | MLS# 12790591 | Listing updated on 2026-11-02
Photo 4 of House for sale at 1244 W Oakdale Ave, Chicago, IL 60657 | MLS# 12790591 | Listing updated on 2026-11-02
71+
Beds Icon

Street View

$1,595,000

Monthly Est:$7,939

  • Beds Icon8 Beds
  • Beds Icon
    4 Baths
  • Beds Icon--sqft

1244 W Oakdale Ave, Chicago, IL 60657

$7,939/moEst:

Get Pre-Approved

  • Duplex

  • Built in 1886

  • $-- HOA

  • -- sqft lot

  • --/sqft

Description

Showings will begin November 8th - 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.

  • Houzeo last checked: 3 hours ago
  • Listing updated: November 2, 2026 at 2:47 am
  • Listing Provided by: Cory Tanzer , Serena Phillips DRE #475173716 | Option Premier LLC (312) 500-5808
  • Source: MRED MLS-IL as distributed by MLS GRID | MLS#: 12790591 MRED MLS-IL as distributed by MLS GRID

Property Details

  • Status

    Active

  • Type

    Multi Family

  • No. of Stories

    -

  • County

    Cook County

  • City

    Chicago

  • Neighborhood

    Lake View

  • Year Built

    1886

  • HOA Fees

    -

  • Finished Area

    - sqft

  • Lot Size

    -- sqft lot

  • Basement Area

    - sqft

  • MLS Name

    MRED MLS

  • MLS Number

    12790591

  • MLS Status

    New

  • Days on Market

    1

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 8

    Bathrooms: 4

Interior

  • Sewer

    Public Sewer

  • Heating

    Gas

Construction

  • Year Built

    Year Built: 1886

  • Home type

    Duplex

  • Construction Materials

    Brick

Utilities & Energy

  • Basement

    Finished, Exterior Entry, Full

  • Parking Features

    Yes, Detached, Garage

  • Water Source

    Public

Price History

DateEventPrice

11/02/2026

Source: mls_logoMRED MLS-IL as distributed by MLS GRID #MRD12790591

Listed for Sale

$1,595,000

$0/sqft

Lake View Ranks #5 in Chicago, IL

Homes for sale
210

Homes

Rental prices
$2,369

Rental Prices

Median Home Price
$562K

Median Home Price

Lake View, Chicago, IL neighborhood guide

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This representation is based in whole or in part on data supplied by Midwest Real Estate Data, LLC through Nov 02, 2026, 02:15PM. Midwest Real Estate Data, LLC does not guarantee nor is it in any way responsible for its accuracy. Data maintained by Midwest Real Estate Data LLC may not reflect all real estate activity in the market.

Based on information submitted to the MLS GRID as of Nov 02, 2026, 02:15PM. All data is obtained from various sources and has not been, and will not be, 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. This website may not include listings or property addresses of sellers who have directed their listing brokers to withhold their listing or their property address from display on the Internet. Some IDX listings have been excluded from this website. Information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID, MRED or Houzeo. The use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. Properties displayed may be listed or sold by various participants in the MLS,

Listings courtesy of MRED as distributed by MLS GRID. ©2026 Midwest Real Estate Data LLC. All Rights Reserved

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