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    Illinois Short Term Rental Properties for Sale

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    Chicago, IL Springfield, IL Rockford, IL
    35 results
    Contemporary Chicago Multifamily Property
    $799,000
    3,150 SF

    Contemporary Chicago Multifamily Property

    2832 W WILCOX Street, Chicago, IL 60612

    Move-in ready, flexible two-flat in West Loop.

    • Flexible 2‑flat design allows for single‑family living, generational living, Airbnb, guest suite, or traditional rental income.
    • Upper 2‑level unit features 3 bedrooms, 2.5 baths, open‑concept living space, professional‑grade kitchen, and primary suite with dual walk‑in closets and luxurious bath.
    • English garden‑level unit offers 2 bedrooms, 2 baths, full kitchen, and private side entry.
    • Contemporary design with brick and limestone facade, black windows, and high‑end finishes throughout (quartz countertops, stainless steel appliances, hardwood floors).
    • Includes a large rear deck, backyard, and two‑car garage.
    Updated: May 27
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    Stockton Multi-Use Commercial Property
    $125,000
    2,228 SF

    Stockton Multi-Use Commercial Property

    126 S Main Street, Stockton, IL 61085

    Versatile commercial property with income potential in Stockton, Illinois.

    • Multiple Revenue Streams: Configured as a law office, escape room, and turnkey Airbnb.
    • Turnkey Airbnb: Upper‑level unit is fully furnished with 2 bedrooms, full kitchen, enclosed porch, and dedicated rear parking.
    • Flexible Commercial Space: Main level with front and rear access, four rooms, and a half bath.
    • Ample Parking: Provides convenient access for tenants and customers.
    • Newer Roof: Approximately 10 years old.
    Updated: Apr 17
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    Oak Park Multifamily Investment Opportunity
    $1,200,000
    0.14 Acres

    Oak Park Multifamily Investment Opportunity

    Three income-producing structures in the heart of Oak Park.

    214 Chicago Avenue, Oak Park, IL 60302
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    Versatile Commercial Property in Quincy, IL
    $145,000
    2,500 SF

    Versatile Commercial Property in Quincy, IL

    Commercial property with laundromat, apartment, and flexible business options.

    1123 N 4TH Street, Quincy, IL 62301
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    Vandalia Investment Opportunity
    $125,000
    0.40 Acres

    Vandalia Investment Opportunity

    Income-producing commercial property with high visibility near schools and park.

    1210 N 8th Street, Vandalia, IL 62471
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    Six-Unit Multifamily Investment Opportunity
    $595,000
    0.07 Acres

    Six-Unit Multifamily Investment Opportunity

    Well-maintained Chicago multifamily property with income potential.

    8624 S Maryland Avenue, Chicago, IL 60619
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    Modern-Industrial Chicago Two-Unit Property
    $650,000

    Modern-Industrial Chicago Two-Unit Property

    Unique two-unit property with modern-industrial design and income potential.

    1011 N MOZART Street, Chicago, IL 60622
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    Multi-Unit Property with Income Potential
    $250,000
    0.06 Acres

    Multi-Unit Property with Income Potential

    Versatile multi-unit property with income potential in Chicago, IL.

    5756 S Princeton Avenue, Chicago, IL 60621
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    Lakefront Rental Property in Fox Lake
    $550,000
    0.38 Acres

    Lakefront Rental Property in Fox Lake

    Fully furnished 5-unit property on Nippersink Lake.

    117 Nippersink Road, Fox Lake, IL 60020
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    DeKalb Multifamily Investment Opportunity
    $649,900
    0.12 Acres

    DeKalb Multifamily Investment Opportunity

    Multifamily property for sale in DeKalb, Illinois.

    116 N 9th Street, Dekalb, IL 60115
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    Renovated Multifamily Property in Berwyn
    $508,000

    Renovated Multifamily Property in Berwyn

    Fully renovated duplex with income potential in Berwyn, Illinois.

    2108 Highland Avenue, Berwyn, IL 60402
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    Rockford Multifamily Investment Opportunity
    $215,000
    2,883 SF

    Rockford Multifamily Investment Opportunity

    Four-unit building with long-term tenants and Airbnb potential.

    422 S HENRIETTA Avenue, Rockford, IL 61102
    View details
    Turnkey Furnished Rental Portfolio
    $320,000
    2,450 SF

    Turnkey Furnished Rental Portfolio

    Fully occupied 6-unit rental property with proven income.

    712 Seminary Street, Rockford, IL 61104
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    Turnkey Furnished Rental Portfolio
    $320,000
    2,380 SF

    Turnkey Furnished Rental Portfolio

    Fully occupied 6-unit rental property with proven income.

    722 Seminary Street, Rockford, IL 61104
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    Turnkey Furnished Rental Portfolio
    $320,000
    2,450 SF

    Turnkey Furnished Rental Portfolio

    Fully occupied 6-unit rental property with proven income.

    718 Seminary Street, Rockford, IL 61104
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    Chicago Multifamily Investment Opportunity
    $945,000

    Chicago Multifamily Investment Opportunity

    Updated multifamily property in booming East Humboldt Park.

    843 N Francisco Avenue, Chicago, IL 60622
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    Ottawa Multifamily Investment Opportunity
    $360,000
    0.32 Acres

    Ottawa Multifamily Investment Opportunity

    Four-unit multifamily property with potential for a fifth unit.

    621 Chapel Street, Ottawa, IL 61350
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    Two-Unit Brick Building in Chicago
    $299,999
    0.09 Acres

    Two-Unit Brick Building in Chicago

    Well-maintained two-unit building with income potential and recent upgrades.

    5632 S Wabash Avenue, Chicago, IL 60637
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    Tangled Roots Investment Opportunity
    $4,900,000
    0.11 Acres

    Tangled Roots Investment Opportunity

    Multifaceted hub with restaurant, brew pub, and Airbnb units.

    140 Washington Square, Washington, IL 61571
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    Two Homes, One Property
    $404,900
    0.67 Acres

    Two Homes, One Property

    Two separate homes on a .67 acre lot.

    11471 W Leland Avenue, Beach Park, IL 60099
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    New Ranch-Style Home Near Lake
    $274,900

    New Ranch-Style Home Near Lake

    New ranch home near Lake Shelbyville with Airbnb potential.

    104 E North 2nd Street, Findlay, IL 62534
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    Two-Story Commercial Building in Washington
    $209,900
    0.12 Acres

    Two-Story Commercial Building in Washington

    Two-story commercial building with renovation potential in Washington, Illinois.

    120 Walnut Street, Washington, IL 61571
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    DeKalb Multifamily Investment Opportunity
    $649,900

    DeKalb Multifamily Investment Opportunity

    High-yield 6-unit property in DeKalb's thriving rental market.

    116 North 9th Street, Dekalb, IL 60115
    View details
    Multi-Unit Building Near Logan Square
    $785,000

    Multi-Unit Building Near Logan Square

    Meticulously maintained multi-unit building near public transportation and local dining.

    3036 N Kedzie Avenue, Chicago, IL 60618
    View details

    Illinois Short Term Rental Properties Investment Opportunities Market Analysis

    Explore 35 short term rental properties for sale in Illinois, showcased through 35 active listings on our real estate platform. These investment opportunities span a total of 21,495 square feet of properties for sale, with an estimated market value of $6,438,000.

    Sale prices for short term rental properties in Illinois start at $215,000, averaging $1,073,000, and reaching up to $2,785,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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