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    Cook County, IL Short Term Rental Properties for Sale

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    23 properties
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    Brick Triplex with Coach House
    Updated: May 29
    Brick Triplex with Coach House

    214 Chicago Avenue, Oak Park, IL 60302

    $1,150,000
    0.14 AC lot
    Three 3‑bedroom, 1‑bath apartments in the main multifamily building
    Updated 3‑bedroom, 2‑bath coach house with private laundry
    Detached 3‑car brick garage plus open parking
    2020 renovations included new windows and separate HVAC systems
    Finished basement with shared washers, dryers, and private tenant storage
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    Furnished Mixed-Use Property
    Updated: Jul 13
    Furnished Mixed-Use Property

    815 N MILWAUKEE Avenue, Chicago, IL 60622

    $1,450,000
    0.06 AC lot
    3,208 interior/liveable square feet across the main level and loft
    2,522 SF full unfinished basement
    Fully furnished standalone mixed‑use property
    Private unfinished rooftop with brand‑new roof
    Brand‑new dual zoned HVAC system
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    Renovated Brick Triplex
    Renovated Brick Triplex

    6835 S Clyde Avenue, Chicago, IL 60649

    $749,900
    0.08 AC lot

    Fully renovated multifamily property with three spacious residences, a basement, detached garage, and outdoor space.

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    Furnished Short-Term Rental Property
    Furnished Short-Term Rental Property

    815 North Milwaukee Avenue, Chicago, IL 60642

    $1,450,000
    2,500 sqft

    Standalone commercial property with loft space, full basement, private rooftop, and access to nearby Blue Line transit.

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    Updated Georgian Triplex
    Updated Georgian Triplex

    4836 S Dorchester Avenue, Chicago, IL 60615

    $925,000

    Brick three-unit property with a front porch, fenced grounds, public utilities, and a mix of original and updated interior finishes.

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    Brick Duplex with In-Unit Laundry
    Brick Duplex with In-Unit Laundry

    5632 S Wabash Avenue, Chicago, IL 60637

    $299,999
    0.09 AC lot

    Two residences feature three bedrooms and one full bathroom each.

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    Three-Unit Building with Rear Decks
    Three-Unit Building with Rear Decks

    2516 W Lyndale Street, Chicago, IL 60647

    $1,045,000

    Legal triplex with updated interiors, separate HVAC systems, laundry, storage, and gated off-street parking.

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    Fully Renovated Two-Unit Duplex
    Fully Renovated Two-Unit Duplex

    5310 South Wood Street, Chicago, IL 60609

    $442,500
    2,964 sqft

    Fully renovated two-unit property offering duplex-style layouts, including a finished basement with wet bar in Unit 1.

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    Legal 3-Unit Multifamily Building
    Legal 3-Unit Multifamily Building

    2901 N SACRAMENTO Avenue, Chicago, IL 60618

    $1,300,000

    Fully renovated income property with separate utility accounts, updated kitchens, in-unit laundry, and a shared garage.

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    Brick 2-Flat with Rear Parking
    Brick 2-Flat with Rear Parking

    3556 W Dickens Ave, Chicago, IL 60647

    $575,000

    Two residences offer updated kitchens, a private deck, and rear parking within walking distance of The 606 Trail.

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    Renovated Two-Unit Multifamily
    Renovated Two-Unit Multifamily

    1520 N Campbell Avenue, Chicago, IL 60622

    $875,000

    Renovated two-unit building with separate HVAC and utilities, plus a new oversized two-car garage and deck.

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    All-Brick 3-Unit Triplex
    All-Brick 3-Unit Triplex

    6112 S Vernon Avenue, Chicago, IL 60637

    $740,000

    Rehabilitated multifamily property with hardwood flooring, fireplaces, updated systems, and a two-car garage.

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    Greystone Two-Unit Building
    Greystone Two-Unit Building

    7144 S INGLESIDE Avenue, Chicago, IL 60621

    $411,000

    Remodeled interiors and a two-car garage support current short-term rental use.

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    Renovated 3-Flat with Garage
    Renovated 3-Flat with Garage

    6835 S Clyde Ave, Chicago, IL 60649

    $749,900

    Fully renovated all-brick triplex with three 3-bed/2-bath units, a full basement, and a 2-car garage.

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    Boutique Three-Unit Smart Apartments
    Boutique Three-Unit Smart Apartments

    1817 North Lawndale Avenue, Chicago, IL 60647

    $875,000

    Three renovated apartments in an all-electric, smart-controlled building, offered furnished and ready for short- or long-term use.

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    Licensed Bed & Breakfast with Rooftop Terrace
    Licensed Bed & Breakfast with Rooftop Terrace

    1428 N Cleveland Ave, Chicago, IL 60610

    Contact for pricing

    Furnished 2016 brick-and-limestone residence with eight en-suite rooms and substantial outdoor entertaining areas.

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    Renovated Quadplex with Parking
    Renovated Quadplex with Parking

    2638 W Lyndale Street, Chicago, IL 60647

    Contact for pricing

    Four-unit residential property with updated kitchens, mechanical systems, separate utility metering, and rear parking.

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    Mixed-Use Retail and Apartment
    Mixed-Use Retail and Apartment

    7040 S Stony Is Ave, Chicago, IL 60649

    Contact for pricing

    Rehabbed mixed-use building with ground-floor retail/office space and a second-floor 2BR/1BA apartment.

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    Boutique Mixed-Use Building
    Boutique Mixed-Use Building

    1012 W Randolph Street, Chicago, IL 60607

    Contact for pricing

    Mixed-use building with short-term leases near CTA and major employment centers, including Google’s Midwest headquarters.

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    30-Unit Apartment Building with Rooftop Terrace
    30-Unit Apartment Building with Rooftop Terrace

    417 S Dearborn St, Chicago, IL 60605

    Contact for pricing

    Turn-of-the-century property with a ground-level lobby and rooftop club room.

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    Brick Duplex with In-Law Apartment
    Brick Duplex with In-Law Apartment

    873 N Richmond St, Chicago, IL 60622

    Contact for pricing

    Legal two-flat configuration includes a ground-floor in-law unit, shared laundry, storage, and rear parking.

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    Liquor-Licensed Event Kitchen Building
    Liquor-Licensed Event Kitchen Building

    2036 W Roscoe St, Chicago, IL 60618

    Contact for pricing

    Newer construction three-unit building with built-out industrial kitchen, liquor license event space, and furnished residential units.

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    Renovated Legal Two-Flat with Garden Unit
    Renovated Legal Two-Flat with Garden Unit

    1940 N Monticello Avenue, Chicago, IL 60647

    Contact for pricing

    Legal two-flat with a finished garden unit, multiple updated systems, and three kitchens, plus a 2-car garage and carport.

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    Based on your search, we've compiled Potential Opportunities for your consideration. Besides 23 Active Listings in Cook County, IL

    Cook County, IL Short Term Rental Properties Market Trends and Statistics

    Explore 23 short term rental properties for sale in Cook County, IL, showcased through 23 active listings on our real estate platform. These investment opportunities span a total of 5,464 square feet of properties for sale, with an estimated market value of $13,038,299.

    Sale prices for short term rental properties in Cook County, IL start at $299,999, averaging $869,219, and reaching up to $1,450,000 — 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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    Featured Cook County Real Estate Agencies

    Realmo connects you with licensed Cook County CRE brokers providing property specifications, local market pricing, and commercial transaction underwriting support.

    Chicago Real Estate Resources
    932 W. Grace Street Chicago, IL 60613
    Phone: 17733279300
    www.crer.com
    Dream Town Realty
    1950 North Sedgwick Chicago, IL 60614
    Phone: 13122658000
    www.dreamtown.com
    American International Realty Corp.
    6138 N.Lincoln Ave. Chicago, IL 60659
    Phone: 17735099493
    www.airealtyco.com

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