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    Illinois Short Term Rental Properties for Sale

    31 results
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    Renovated Multi-Family in Chicago
    $925,000
    0.08 Acres

    Renovated Multi-Family in Chicago

    5426 N Western Ave, Chicago, IL 60625

    Impeccably maintained, fully renovated multi-family property with income potential.

    • Fully renovated in 2023 with new plumbing, electrical, tankless water heaters, central heating/cooling, kitchens, baths, windows, doors, and lighting
    • Two upgraded units: a 4BR/2BA duplex (potential owner's unit) and a 3BR/1BA unit, both with modern amenities
    • Projected 6.8% Cap Rate and strong rental income potential, with Unit #1 recently rented for $4,500 and Unit #2 currently rented at $2,750/month
    • Prime location near shopping, dining, parks, and transit in Lincoln Square, Ravenswood, and Andersonville
    • Unit #1 features a stylish kitchen with SS appliances, quartz counters, and custom closets; Unit #2 has an enclosed porch and refinished floors
    Updated: Mar 3
    View details
    Six-Unit Multifamily Investment Opportunity
    $595,000
    0.07 Acres

    Six-Unit Multifamily Investment Opportunity

    8624 S Maryland Ave, Chicago, IL 60619

    Well-maintained Chicago multifamily property with income potential.

    • Immediate income from two long‑term leases and three active Airbnb units.
    • High rental potential with 6 independent units, each with a kitchen, living room, and dining area.
    • Opportunity to increase value by renovating the unfinished unit.
    • Equipped with a 24‑hour security surveillance system.
    • Six dedicated parking spaces for residents and guests.
    Updated: Feb 27
    View details
    Renovated Two-Flat in Austin
    $475,000

    Renovated Two-Flat in Austin

    Fully renovated 7 bed/3 bath two-flat in Chicago's Austin neighborhood.

    5038 W Fulton St, Chicago, IL 60644
    View details
    Multi-Unit Building with Rental Potential
    $900,000

    Multi-Unit Building with Rental Potential

    Well-maintained Chicago building with multiple units and revenue streams.

    3036 N Kedzie Ave, Chicago, IL 60618
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    Furnished Historic Apartment Building Investment
    $680,000

    Furnished Historic Apartment Building Investment

    Well-maintained, fully furnished 12-unit building in Springfield, Illinois.

    520 S Grand Ave, Springfield, IL 62703
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    Furnished Historic Apartment Building
    $680,000

    Furnished Historic Apartment Building

    Turnkey investment opportunity with 12 furnished units in Springfield.

    520 S Grand Ave, Springfield, IL 62703
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    Two-Unit Brick Building in Chicago
    $339,000
    0.09 Acres

    Two-Unit Brick Building in Chicago

    Well-maintained two-unit building with short-term rental potential.

    5632 S Wabash Ave, Chicago, IL 60637
    View details
    Ottawa Multifamily Investment Opportunity
    $395,000
    0.32 Acres

    Ottawa Multifamily Investment Opportunity

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

    621 Chapel St, Ottawa, IL 61350
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    Classic Chicago Brown Brick Building
    $994,900
    0.08 Acres

    Classic Chicago Brown Brick Building

    Completely transformed 2-unit with finished basement in Irving Park.

    3847 N Spaulding Ave, Chicago, IL 60618
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    Victorian Three-Flat in Oak Park
    $723,000

    Victorian Three-Flat in Oak Park

    Charming Victorian three-flat in Oak Park's historic district.

    227 N Marion St, Oak Park, IL 60302
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    Chicago Two-Unit Flat Opportunity
    $344,900

    Chicago Two-Unit Flat Opportunity

    Solid brick 2-unit flat in Grand Crossing, Chicago.

    7140 S Eberhart Ave, Chicago, IL 60619
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    Historic Limestone Multi-Unit in Chicago
    $499,222
    0.06 Acres

    Historic Limestone Multi-Unit in Chicago

    Rehabbed multi-unit near Downtown Chicago with income potential.

    209 S Albany Ave, Chicago, IL 60612
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    Wicker Park Income Property
    $950,000
    0.05 Acres

    Wicker Park Income Property

    Turnkey income-producing property in Wicker Park with Airbnb potential.

    1730 W Beach Ave, Chicago, IL 60622
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    Logan Square Multi-Unit Investment
    $1,200,000

    Logan Square Multi-Unit Investment

    Three-unit building in Logan Square with income potential.

    2516 W Lyndale St, Chicago, IL 60647
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    Two Homes, One Property
    $414,900
    0.67 Acres

    Two Homes, One Property

    Two separate homes on a .67 acre lot.

    11471 W Leland Ave, Beach Park, IL 60099
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    Turnkey Duplex Investment Opportunity
    Pending
    $139,751

    Turnkey Duplex Investment Opportunity

    Fully furnished duplex operating as a high-performing short-term rental.

    615 S English Ave, Springfield, IL 62704
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    Waterfront Cottages on Loon Lake
    $299,000
    0.19 Acres

    Waterfront Cottages on Loon Lake

    Three waterfront cottages on Loon Lake, ideal for family or investment.

    40286 West Shore Dr, Antioch, IL 60002
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    Tangled Roots Investment Opportunity
    $5,099,999
    0.11 Acres

    Tangled Roots Investment Opportunity

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

    140 Washington Sq, Washington, IL 61571
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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 St, Washington, IL 61571
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    Remodeled Triplex: Turnkey Investment
    $299,000

    Remodeled Triplex: Turnkey Investment

    Remodeled triplex in prime location, ideal for investors or owner-occupants.

    98 W 154 St, Harvey, IL 60426
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    Historic Chicago Multi-Unit Investment Opportunity
    $499,222
    0.06 Acres

    Historic Chicago Multi-Unit Investment Opportunity

    Classic limestone 2-unit near downtown Chicago, fully rehabbed in 2020.

    209 S Albany Ave, Chicago, IL 60612
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    Bellevue Sanctuary Estate
    $1,560,000
    4,306 SF

    Bellevue Sanctuary Estate

    Tropical estate near Playa Organos, ideal for retreats or rentals.

    Bellevue Sanctuary Est, Bensenville, IL 60105
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    Well-Maintained Duplex in Murphysboro, IL
    $199,000
    0.65 Acres

    Well-Maintained Duplex in Murphysboro, IL

    Duplex near Route 13, ideal for investors or landlords.

    5559 Country Club Rd, Murphysboro, IL 62966
    View details
    Carbondale Multifamily Property For Sale
    $56,800

    Carbondale Multifamily Property For Sale

    Large unit with six bedrooms, ideal for various uses.

    701 W Cherry St, Carbondale, IL 62901
    View details

    Illinois Short Term Rental Properties Investment Opportunities Market Analysis

    Explore 31 short term rental properties for sale in Illinois, showcased through 31 active listings on our real estate platform. These investment opportunities span a total of 144,968 square feet of properties for sale, with an estimated market value of $12,299,143.

    Sale prices for short term rental properties in Illinois start at $199,000, averaging $878,510, and reaching up to $5,099,999 — 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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