Chicago, IL Short term rental properties for sale

Meticulously Maintained Greystone in Chicago

$975,000

0.14 Acres

Meticulously Maintained Greystone in Chicago

5319 S Maryland Ave, Chicago, IL 60615

Three-unit Greystone near University of Chicago, perfect for owner-occupant.

Meticulously maintained 3‑unit Greystone on an oversized lot, offering strong investment potential and turnkey income.
Prime location near CTA Express, DuSable Lake Shore Drive, Kenwood High School, Lab Schools, Whole Foods, University of Chicago, and Hyde Park amenities.
Recent major upgrades include roof resurfacing, window replacements, and sewer line epoxy‑coating (with 50‑year warranty).
Features a 4‑car detached brick garage, lush gardens, and refurbished rear decks.
Units 2 & 3: 4 bedrooms, 2 baths, double parlors. Unit 1 (owner's unit): 3 bedrooms, 2 baths, connects to a studio garden unit with private entrance and soaker tub.

Updated: Jan 18

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Chicago Multifamily Property with Finished Basement

$994,900

0.08 Acres

Chicago Multifamily Property with Finished Basement

3847 N Spaulding Ave, Chicago, IL 60618

Classic Chicago brown brick 2-unit with finished basement in Irving Park.

Completely renovated 2‑unit building with a 3rd unit in the finished basement, featuring all‑new electrical, plumbing, kitchens, and bathrooms.
Prime location in the highly coveted Irving Park neighborhood, directly across from Chicago International Charter School - Irving Park, and close to transportation (90/94 expressway and Blue Line).
First‑floor duplex offers a rare 4‑bedroom, 2‑bath layout with a spacious primary suite and walk‑in closet.
Fully finished, heated, and air‑conditioned 2.5‑car garage for versatile use (storage, workshop, etc.).
Second‑floor unit features an open‑concept design with quartz finishes, rich hardwood floors, and in‑unit laundry (also in the duplex unit).

Updated: Jan 17

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$499,000

Renovated Two-Flat in Austin Neighborhood

Fully renovated two-flat duplex-down with vintage charm in Chicago's Austin neighborhood.

5038 W Fulton St, Chicago, IL 60644

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$250,000

Rehabilitated Chicago Multifamily Property

Rehabilitated two-unit building with furnishings and parking in Chicago.

5805 S La Salle St, Chicago, IL 60621

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$774,900

Versatile Avondale Triplex Opportunity

Three-unit building in vibrant Avondale, near transportation and amenities.

3107 N Kedzie Ave, Chicago, IL 60618

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Wicker Park Income-Producing Multifamily Property

$950,000

0.05 Acres

Wicker Park Income-Producing Multifamily Property

Turnkey Wicker Park multifamily property generating six figures annually.

1730 W Beach Ave, Chicago, IL 60622

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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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$750,000

Marshall Boulevard Four-Flat Investment

Four-flat building with coach house near transportation, shopping, and dining.

2249 S Marshall Blvd, Chicago, IL 60623

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$180,000

525 SF

Designer Home Near Lakeview

Custom-designed apartment with modern upgrades, near the lake and amenities.

539 W Stratford Pl, Chicago, IL 60657

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$395,000

Stylish Condo with City Views

Southeast corner condo with sweeping city views in River North.

30 E Huron St, Chicago, IL 60611

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$2,785,000

1,560 SF

Gold Coast Investment Portfolio

Commercial and residential condos in a prime location.

1140 N La Salle Dr, Chicago, IL 60610

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Based on your search, we've compiled 15 Potential Opportunities for your consideration. Besides 11 Active listings in Chicago, IL, we suggest exploring several alternatives: 4 properties in Nearby Cities

Explore Opportunities in Nearby Cities

Here are 4 Similar properties we found in Nearby Locations for your consideration.

$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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New Buffalo Office/Residential Opportunity

$495,000

833 SF

New Buffalo Office/Residential Opportunity

Office or home/office opportunity near Lake Michigan resort community.

19409 W Us Highway 12, New Buffalo, MI 49117

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Lake Marie Lakefront Investment Property

$1,099,000

0.39 Acres

Lake Marie Lakefront Investment Property

Lakefront property with two rental units, pier, and pole barn.

26048 W Forest Ave, Antioch, IL 60002

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$1,325,000

5,100 SF

Turnkey Short-Term Rental Business

Established hospitality business in Harbor Country with immediate income potential.

231 E Buffalo St, New Buffalo, MI 49117

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Chicago, IL Short Term Rental Properties Investment Opportunities Market Analysis

Explore 11 short term rental properties for sale in Chicago, IL, showcased through 11 active listings on our real estate platform. These investment opportunities span a total of 14,375 square feet of properties for sale, with an estimated market value of $3,419,122.

Prices for short term rental properties in Chicago, IL start at $499,222, averaging $854,780, and reaching up to $994,900 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

Chicago, IL Short Term Rental Properties for Sale

Meticulously Maintained Greystone in Chicago

Three-unit Greystone near University of Chicago, perfect for owner-occupant.

Chicago Multifamily Property with Finished Basement

Classic Chicago brown brick 2-unit with finished basement in Irving Park.

Renovated Two-Flat in Austin Neighborhood