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
5428 138th Street Crestwood, IL MODERNIZED UPDATED HOME IN THE SOUTH SUBURBS! LOCATED IN CRESTWOOD,IL IS THIS SPACIOUS CAL...	4 beds \| 2 baths \| 1,471 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.3% Airbnb Rental Income: $null Traditional Rental Income: $2451 Airbnb ROI: N/A Traditional ROI: 4.3%
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: -2.03% Traditional cash on cash: 4.62% Airbnb Rental Income: $997 Traditional Rental Income: $2735 Airbnb ROI: -2.03% 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: N/A Traditional cash on cash: 6.03% Airbnb Rental Income: $null Traditional Rental Income: $3394 Airbnb ROI: N/A Traditional ROI: 6.03%
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: N/A Traditional cash on cash: 6.03% Airbnb Rental Income: $null Traditional Rental Income: $3394 Airbnb ROI: N/A Traditional ROI: 6.03%
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: -2.03% Traditional cash on cash: 4.5% Airbnb Rental Income: $997 Traditional Rental Income: $2699 Airbnb ROI: -2.03% Traditional ROI: 4.5%
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: -2.03% Traditional cash on cash: 4.5% Airbnb Rental Income: $997 Traditional Rental Income: $2699 Airbnb ROI: -2.03% Traditional ROI: 4.5%
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: -2.03% Traditional cash on cash: 4.49% Airbnb Rental Income: $997 Traditional Rental Income: $2695 Airbnb ROI: -2.03% Traditional ROI: 4.49%
5321 Waterbury Drive #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.	$131,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 5.67% Airbnb Rental Income: $1312 Traditional Rental Income: $1478 Airbnb ROI: 1.12% Traditional ROI: 5.67%
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: -1.18% Traditional cash on cash: 4.75% Airbnb Rental Income: $997 Traditional Rental Income: $2701 Airbnb ROI: -1.18% Traditional ROI: 4.75%
5739 129th Street #1B Crestwood, IL	2 beds \| 1 baths \| N/A	$167,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 6.29% Airbnb Rental Income: $942 Traditional Rental Income: $1604 Airbnb ROI: -0.03% Traditional ROI: 6.29%
5025 139th Place #512 Crestwood, IL Beautifully maintained third-floor condo in an elevator building and 55+ community, offeri...	2 beds \| 2 baths \| 1,154 sq.ft.	$200,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 10.31% Airbnb Rental Income: $942 Traditional Rental Income: $2326 Airbnb ROI: 1.19% Traditional ROI: 10.31%
14016 Waterbury Drive #1404 Crestwood, IL Cheaper than rent & MOVE-IN READY!!! Welcome to this beautifully updated 2nd floor condo i...	2 beds \| 1 baths \| 1,000 sq.ft.	$170,000	Airbnb cash on cash: -1.44% Traditional cash on cash: 5.27% Airbnb Rental Income: $942 Traditional Rental Income: $1683 Airbnb ROI: -1.44% Traditional ROI: 5.27%
5701 129th Street #2D Crestwood, IL Second floor 2 bedroom, 1 bath condo with private balcony and rare in-unit washer and drye...	2 beds \| 1 baths \| 1,052 sq.ft.	$149,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 8.09% Airbnb Rental Income: $942 Traditional Rental Income: $1739 Airbnb ROI: 0.13% Traditional ROI: 8.09%
12809 Carriage Lane #12 Crestwood, IL Welcome home to this lovingly maintained condo nestled in the peaceful community of Crestw...	2 beds \| 1 baths \| 950 sq.ft.	$149,900	Airbnb cash on cash: -0.47% Traditional cash on cash: 7.09% Airbnb Rental Income: $942 Traditional Rental Income: $1681 Airbnb ROI: -0.47% Traditional ROI: 7.09%
13950 Lavergne Avenue #907 Crestwood, IL Highlands of Crestwood Condominium Welcome to Highlands of Crestwood, a soughtafter 55ando...	2 beds \| 2 baths \| N/A	$207,500	Airbnb cash on cash: -1.21% Traditional cash on cash: 7.95% Airbnb Rental Income: $942 Traditional Rental Income: $2398 Airbnb ROI: -1.21% Traditional ROI: 7.95%
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: -1.88% Traditional cash on cash: 8.82% Airbnb Rental Income: $942 Traditional Rental Income: $2477 Airbnb ROI: -1.88% Traditional ROI: 8.82%

Real Estate investment in Crestwood, IL

There are 31 properties for sale in the city of Crestwood . The median list price in Crestwood is $241,500 and the average price per square foot is $166. In May 2026, the average monthly cash on cash return in Crestwood is 6.00%. The average monthly rental income in Crestwood is $2,390.

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

There are 31 investment properties available for sale in Crestwood.

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

The ROI for Long-Term is higher than the Short-Term in Crestwood with average rental income of $2,390.

Your search for investment property begins and ends here

Investment Property for Sale in Crestwood, IL

5428 138th Street

Crestwood, IL

4 beds | 2 baths | 1,471 sq.ft.

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.3%

Airbnb Rental Income: $null

Traditional Rental Income: $2451

Airbnb ROI: N/A

Traditional ROI: 4.3%

5404 135th Street

Crestwood, IL

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

$335,000

Airbnb cash on cash: -2.03%

Traditional cash on cash: 4.62%

Airbnb Rental Income: $997

Traditional Rental Income: $2735

Airbnb ROI: -2.03%

Traditional ROI: 4.62%

5418 135th Street

Crestwood, IL

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

$359,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.03%

Airbnb Rental Income: $null

Traditional Rental Income: $3394

Airbnb ROI: N/A

Traditional ROI: 6.03%

5410 135th Street

Crestwood, IL

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

$359,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.03%

Airbnb Rental Income: $null

Traditional Rental Income: $3394

Airbnb ROI: N/A

Traditional ROI: 6.03%

5416 135th Street

Crestwood, IL

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

$335,000

Airbnb cash on cash: -2.03%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $997

Traditional Rental Income: $2699

Airbnb ROI: -2.03%

Traditional ROI: 4.5%

5414 135th Street

Crestwood, IL

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

$335,000

Airbnb cash on cash: -2.03%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $997

Traditional Rental Income: $2699

Airbnb ROI: -2.03%

Traditional ROI: 4.5%

5412 135th Street

Crestwood, IL

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

$335,000

Airbnb cash on cash: -2.03%

Traditional cash on cash: 4.49%

Airbnb Rental Income: $997

Traditional Rental Income: $2695

Airbnb ROI: -2.03%

Traditional ROI: 4.49%

5321 Waterbury Drive #502

Crestwood, IL

1 beds | 1 baths | 800 sq.ft.

$131,000

Airbnb cash on cash: 1.12%

Traditional cash on cash: 5.67%

Airbnb Rental Income: $1312

Traditional Rental Income: $1478

Airbnb ROI: 1.12%