Real Estate Investment Properties for Sale in Crestwood, IL

Looking for investment property in Crestwood, IL with high ROI ?

Explore a variety of short-term homes & houses in Crestwood, IL. Invest wisely with VRBO & Crestwood, IL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Crestwood, IL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
14244 Kostner Avenue Crestwood, IL Welcome home to this nicely updated 3-bed, 1-bath home in the heart of Crestwood! This hom...	3 beds \| 1 baths \| 900 sq.ft.	$252,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 5.17% Airbnb Rental Income: $1743 Traditional Rental Income: $1869 Airbnb ROI: 2.63% Traditional ROI: 5.17%
5404 135th Street Crestwood, IL Welcome to The Coves of Crestwood, a brand-new luxury townhome community offering modern d...	3 beds \| 3 baths \| 1,514 sq.ft.	$335,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 4.62% Airbnb Rental Income: $1743 Traditional Rental Income: $2735 Airbnb ROI: -0.05% Traditional ROI: 4.62%
5418 135th Street Crestwood, IL NEW CONSTRUCTION!! TO BE BUILT Welcome to The Coves of Crestwood, a brand-new luxury tow...	4 beds \| 4 baths \| 1,963 sq.ft.	$359,900	Airbnb cash on cash: -0.96% Traditional cash on cash: 2.82% Airbnb Rental Income: $1463 Traditional Rental Income: $2309 Airbnb ROI: -0.96% Traditional ROI: 2.82%
5410 135th Street Crestwood, IL NEW CONSTRUCTION!! TO BE BUILT Welcome to The Coves of Crestwood, a brand-new luxury tow...	4 beds \| 4 baths \| 1,963 sq.ft.	$359,900	Airbnb cash on cash: -0.96% Traditional cash on cash: 2.82% Airbnb Rental Income: $1463 Traditional Rental Income: $2309 Airbnb ROI: -0.96% Traditional ROI: 2.82%
5416 135th Street Crestwood, IL NEW CONSTRUCTION!! TO BE BUILT Welcome to The Coves of Crestwood, a brand-new luxury tow...	3 beds \| 3 baths \| 1,514 sq.ft.	$335,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 2.28% Airbnb Rental Income: $1743 Traditional Rental Income: $2000 Airbnb ROI: -0.05% Traditional ROI: 2.28%
5414 135th Street Crestwood, IL NEW CONSTRUCTION!! TO BE BUILT Welcome to The Coves of Crestwood, a brand-new luxury tow...	3 beds \| 3 baths \| 1,514 sq.ft.	$335,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 2.28% Airbnb Rental Income: $1743 Traditional Rental Income: $2000 Airbnb ROI: -0.05% Traditional ROI: 2.28%
5412 135th Street Crestwood, IL NEW CONSTRUCTION!! TO BE BUILT Welcome to The Coves of Crestwood, a brand-new luxury tow...	3 beds \| 3 baths \| 1,514 sq.ft.	$335,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 4.49% Airbnb Rental Income: $1743 Traditional Rental Income: $2695 Airbnb ROI: -0.05% Traditional ROI: 4.49%
13537 Latrobe Avenue Crestwood, IL DON'T SETTLE FOR LESS - GET MORE of the everyday living space you'll love in this well-des...	2 beds \| 3 baths \| 2,200 sq.ft.	$324,873	Airbnb cash on cash: -1.78% Traditional cash on cash: 5.04% Airbnb Rental Income: $1045 Traditional Rental Income: $2766 Airbnb ROI: -1.78% Traditional ROI: 5.04%
5321 Waterbury Drive unit: 502 Crestwood, IL Welcome to this charming condominium at 5321 Waterbury Dr #502 in Crestwood, IL. This firs...	1 beds \| 1 baths \| 800 sq.ft.	$132,500	Airbnb cash on cash: 1.24% Traditional cash on cash: 4.69% Airbnb Rental Income: $1334 Traditional Rental Income: $1363 Airbnb ROI: 1.24% Traditional ROI: 4.69%
4940 134th Court unit: 408 Crestwood, IL	2 beds \| 2 baths \| 1,100 sq.ft.	$205,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 5.56% Airbnb Rental Income: $1045 Traditional Rental Income: $1667 Airbnb ROI: 0.49% Traditional ROI: 5.56%
4432 143rd Street Crestwood, IL FANTASTIC 3 BEDROOM 2 FULL BATH SPLIT LEVEL HOME WITH A FULL SUB-BASEMENT AND AN ATTACHED ...	3 beds \| 2 baths \| 1,900 sq.ft.	$369,900	Airbnb cash on cash: 0.61% Traditional cash on cash: 2.73% Airbnb Rental Income: $1743 Traditional Rental Income: $2000 Airbnb ROI: 0.61% Traditional ROI: 2.73%
4950 134th Court unit: 508 Crestwood, IL Beautiful first-floor Flexicore condo in a well-maintained 55+ community! This spacious 2-...	2 beds \| 2 baths \| 1,234 sq.ft.	$209,950	Airbnb cash on cash: 0.91% Traditional cash on cash: 5.86% Airbnb Rental Income: $1045 Traditional Rental Income: $1667 Airbnb ROI: 0.91% Traditional ROI: 5.86%
13601 Loomis Lane Crestwood, IL Completely refreshed and move in ready. This 3-bedroom, split level home has been freshly ...	3 beds \| 1 baths \| 1,076 sq.ft.	$294,900	Airbnb cash on cash: 0.91% Traditional cash on cash: 3.29% Airbnb Rental Income: $1743 Traditional Rental Income: $1925 Airbnb ROI: 0.91% Traditional ROI: 3.29%
5539 Parkview Court Crestwood, IL This split level style single family home built in 1960 offers 4 bedrooms and 2 bathrooms ...	2 beds \| 2 baths \| 1,695 sq.ft.	$184,800	Airbnb cash on cash: -1.39% Traditional cash on cash: 4.21% Airbnb Rental Income: $1045 Traditional Rental Income: $1667 Airbnb ROI: -1.39% Traditional ROI: 4.21%

Real Estate investment in Crestwood, IL

There are 22 properties for sale in the city of Crestwood . The median list price in Crestwood is $189,900 and the average price per square foot is $152. In March 2026, the average monthly cash on cash return in Crestwood is 5.00%. The average monthly rental income in Crestwood is $1,667.

Crestwood, IL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 22 investment properties available for sale in Crestwood.

In 2026, the best neighborhood to buy investment property is Crestwood.

The ROI for Short-Term is higher than the Long-Term in Crestwood with average rental income of $1,045.

Your search for investment property begins and ends here

Investment Property for Sale in Crestwood, IL

14244 Kostner Avenue

Crestwood, IL

3 beds | 1 baths | 900 sq.ft.

$252,000

Airbnb cash on cash: 2.63%

Traditional cash on cash: 5.17%

Airbnb Rental Income: $1743

Traditional Rental Income: $1869

Airbnb ROI: 2.63%

Traditional ROI: 5.17%

5404 135th Street

Crestwood, IL

3 beds | 3 baths | 1,514 sq.ft.

$335,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: 4.62%

Airbnb Rental Income: $1743

Traditional Rental Income: $2735

Airbnb ROI: -0.05%

Traditional ROI: 4.62%

5418 135th Street

Crestwood, IL

4 beds | 4 baths | 1,963 sq.ft.

$359,900

Airbnb cash on cash: -0.96%

Traditional cash on cash: 2.82%

Airbnb Rental Income: $1463

Traditional Rental Income: $2309

Airbnb ROI: -0.96%

Traditional ROI: 2.82%

5410 135th Street

Crestwood, IL

4 beds | 4 baths | 1,963 sq.ft.

$359,900

Airbnb cash on cash: -0.96%

Traditional cash on cash: 2.82%

Airbnb Rental Income: $1463

Traditional Rental Income: $2309

Airbnb ROI: -0.96%

Traditional ROI: 2.82%

5416 135th Street

Crestwood, IL

3 beds | 3 baths | 1,514 sq.ft.

$335,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: 2.28%

Airbnb Rental Income: $1743

Traditional Rental Income: $2000

Airbnb ROI: -0.05%

Traditional ROI: 2.28%

5414 135th Street

Crestwood, IL

3 beds | 3 baths | 1,514 sq.ft.

$335,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: 2.28%

Airbnb Rental Income: $1743

Traditional Rental Income: $2000

Airbnb ROI: -0.05%

Traditional ROI: 2.28%

5412 135th Street

Crestwood, IL

3 beds | 3 baths | 1,514 sq.ft.

$335,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: 4.49%

Airbnb Rental Income: $1743

Traditional Rental Income: $2695

Airbnb ROI: -0.05%

Traditional ROI: 4.49%

13537 Latrobe Avenue

Crestwood, IL

2 beds | 3 baths | 2,200 sq.ft.

$324,873

Airbnb cash on cash: -1.78%

Traditional cash on cash: 5.04%

Airbnb Rental Income: $1045

Traditional Rental Income: $2766

Airbnb ROI: -1.78%