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
5215 138th Pl Crestwood, IL GORGEOUS HOME!!! NEW Roof, Furnace, A/C, Windows, Siding, Soffits, Gutters, TANKLESS hot w...	3 beds \| 2 baths \| 1,500 sq.ft.	$314,900	Airbnb cash on cash: 0.69% Traditional cash on cash: 3.47% Airbnb Rental Income: $1562 Traditional Rental Income: $1936 Airbnb ROI: 0.69% Traditional ROI: 3.47%
5547 Fairway Drive Crestwood, IL Welcome home to this exceptional Cape Cod that perfectly blends timeless character and eve...	4 beds \| 2 baths \| 1,535 sq.ft.	$299,000	Airbnb cash on cash: -3.2% Traditional cash on cash: 6.17% Airbnb Rental Income: $86 Traditional Rental Income: $2519 Airbnb ROI: -3.2% Traditional ROI: 6.17%
5700 128th St #9 Crestwood, IL	2 beds \| 1 baths \| 800 sq.ft.	$90,000	Airbnb cash on cash: 5.69% Traditional cash on cash: 9.86% Airbnb Rental Income: $1419 Traditional Rental Income: $1360 Airbnb ROI: 5.69% Traditional ROI: 9.86%
13540 Lawler Avenue #77 Crestwood, IL Welcome home to this spacious and well-maintained 2nd floor condo offering 2 bedrooms and ...	2 beds \| 2 baths \| 1,000 sq.ft.	$163,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 4.02% Airbnb Rental Income: $1419 Traditional Rental Income: $1484 Airbnb ROI: 0.87% Traditional ROI: 4.02%
5554 Linder Ct Crestwood, IL BRICK HOME ON A CUL-DE-SAC SUBURBAN LOT. THIS 3-BEDROOM 2-BATH HOME IS ON A FULLY FENCED B...	3 beds \| 2 baths \| 1,700 sq.ft.	$359,999	Airbnb cash on cash: 0.29% Traditional cash on cash: 4.77% Airbnb Rental Income: $1562 Traditional Rental Income: $2627 Airbnb ROI: 0.29% Traditional ROI: 4.77%
12850 Crestbrook Court #10 Crestwood, IL Welcome home to this beautifully updated 2-bedroom, 1-bath Flexicore condo in the heart of...	2 beds \| 1 baths \| 900 sq.ft.	$151,900	Airbnb cash on cash: 1.68% Traditional cash on cash: 6.23% Airbnb Rental Income: $1419 Traditional Rental Income: $1655 Airbnb ROI: 1.68% Traditional ROI: 6.23%
5418 135th Street Crestwood, IL NEW CONSTRUCTION!! TO BE BUILT Welcome to The Coves of Crestwood, a brand-new luxury tow...	3 beds \| 3 baths \| 1,963 sq.ft.	$359,900	Airbnb cash on cash: -0.72% Traditional cash on cash: 6.03% Airbnb Rental Income: $1562 Traditional Rental Income: $3394 Airbnb ROI: -0.72% 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...	3 beds \| 3 baths \| 1,963 sq.ft.	$359,900	Airbnb cash on cash: -0.72% Traditional cash on cash: 6.03% Airbnb Rental Income: $1562 Traditional Rental Income: $3394 Airbnb ROI: -0.72% 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: -0.53% Traditional cash on cash: 4.5% Airbnb Rental Income: $1562 Traditional Rental Income: $2699 Airbnb ROI: -0.53% 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: -0.53% Traditional cash on cash: 4.5% Airbnb Rental Income: $1562 Traditional Rental Income: $2699 Airbnb ROI: -0.53% 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: -0.53% Traditional cash on cash: 4.49% Airbnb Rental Income: $1562 Traditional Rental Income: $2695 Airbnb ROI: -0.53% Traditional ROI: 4.49%
5739 129th Street #1B Crestwood, IL GREAT INVESTMENT FOR PROSPECTIVE BUYER, UNIT IS RENTABLE! Stop searching and start living!...	2 beds \| 1 baths \| N/A	$159,900	Airbnb cash on cash: 2.61% Traditional cash on cash: 6.61% Airbnb Rental Income: $1419 Traditional Rental Income: $1604 Airbnb ROI: 2.61% Traditional ROI: 6.61%
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.	$199,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 8.74% Airbnb Rental Income: $1419 Traditional Rental Income: $2326 Airbnb ROI: 1.69% Traditional ROI: 8.74%
4223 137th St Crestwood, IL 4223 137th St, Crestwood, IL 60418 \| Other	N/A beds \| N/A baths \| N/A	$165,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.09% Airbnb Rental Income: $null Traditional Rental Income: $771 Airbnb ROI: N/A Traditional ROI: 1.09%
12841 Terrace Lane Crestwood, IL Well-maintained ranch on a quiet street, yet near shopping and with easy highway access. K...	3 beds \| 2 baths \| 1,631 sq.ft.	$325,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 6.27% Airbnb Rental Income: $1562 Traditional Rental Income: $2433 Airbnb ROI: 1.95% Traditional ROI: 6.27%
14109 Kenneth Ct Crestwood, IL 14109 Kenneth Ct, Crestwood, IL 60418 \| Single Family Residential	5 beds \| 3 baths \| 2,900 sq.ft.	$530,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.6% Airbnb Rental Income: $null Traditional Rental Income: $2991 Airbnb ROI: N/A Traditional ROI: 2.6%
5337 Waterbury Court #2505 Crestwood, IL Excellent opportunity for investors or first-time homebuyers! This well-maintained 2-bedro...	2 beds \| 1 baths \| 1,000 sq.ft.	$157,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 5.06% Airbnb Rental Income: $1419 Traditional Rental Income: $1663 Airbnb ROI: 0.62% Traditional ROI: 5.06%
4932 Circle Ct #502 Crestwood, IL 4932 Circle Ct #502, Crestwood, IL 60418 \| Condo/Coop	2 beds \| 2 baths \| 1,100 sq.ft.	$199,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 3.84% Airbnb Rental Income: $1419 Traditional Rental Income: $1681 Airbnb ROI: 0.2% Traditional ROI: 3.84%
13950 Lavergne Avenue #908 Crestwood, IL Highlands of Crestwood Condominium Welcome to Highlands of Crestwood, a sought after 55 an...	2 beds \| 2 baths \| 1,150 sq.ft.	$199,900	Airbnb cash on cash: 1.72% Traditional cash on cash: 8.72% Airbnb Rental Income: $1419 Traditional Rental Income: $2321 Airbnb ROI: 1.72% Traditional ROI: 8.72%
13935 Laramie Avenue #220 Crestwood, IL Welcome home to this inviting 3rd-floor condo offering the perfect blend of comfort, conve...	2 beds \| 2 baths \| 1,160 sq.ft.	$165,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 9.59% Airbnb Rental Income: $1419 Traditional Rental Income: $2110 Airbnb ROI: 2.5% Traditional ROI: 9.59%
5545 W 127th St Crestwood, IL 5545 W 127th St, Crestwood, IL 60418 \| Other	N/A beds \| N/A baths \| N/A	$2,100,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.91% Airbnb Rental Income: $null Traditional Rental Income: $774 Airbnb ROI: N/A Traditional ROI: -2.91%
12850 Crestbrook Ct #10 Crestwood, IL 12850 Crestbrook Ct #10, Crestwood, IL 60418 \| Condo/Coop	2 beds \| 1 baths \| 900 sq.ft.	$151,900	Airbnb cash on cash: 0.31% Traditional cash on cash: 1.88% Airbnb Rental Income: $1419 Traditional Rental Income: $1222 Airbnb ROI: 0.31% Traditional ROI: 1.88%
13124 Forestview Lane Crestwood, IL Welcome to 13124 Forestview Lane in Crestwood's desirable Playfield subdivision! This well...	4 beds \| 2 baths \| 1,455 sq.ft.	$289,900	Airbnb cash on cash: -4.01% Traditional cash on cash: 3.6% Airbnb Rental Income: $86 Traditional Rental Income: $1959 Airbnb ROI: -4.01% Traditional ROI: 3.6%
13514 Short Drive Crestwood, IL Cozy one level living close to everything affordable Crestwood has to offer. Walk to schoo...	3 beds \| 2 baths \| 1,200 sq.ft.	$289,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 5.9% Airbnb Rental Income: $1562 Traditional Rental Income: $2399 Airbnb ROI: 1.18% Traditional ROI: 5.9%
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: 1.96% Traditional cash on cash: 5.67% Airbnb Rental Income: $1439 Traditional Rental Income: $1478 Airbnb ROI: 1.96% Traditional ROI: 5.67%
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: 0.81% Traditional cash on cash: 7.95% Airbnb Rental Income: $1419 Traditional Rental Income: $2398 Airbnb ROI: 0.81% Traditional ROI: 7.95%
5712 128th Street #1D Crestwood, IL Welcome to this bright and comfortable ground level 2 bedroom, 1 bathroom condo. Beautiful...	2 beds \| 1 baths \| 929 sq.ft.	$146,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 4.86% Airbnb Rental Income: $1419 Traditional Rental Income: $1340 Airbnb ROI: 2.38% Traditional ROI: 4.86%

Real Estate investment in Crestwood, IL

There are 37 properties for sale in the city of Crestwood . The median list price in Crestwood is $189,902 and the average price per square foot is $136. In June 2026, the average monthly cash on cash return in Crestwood is 6.00%. The average monthly rental income in Crestwood is $2,309.

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

There are 37 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 $2,309.

Your search for investment property begins and ends here

Investment Property for Sale in Crestwood, IL

5215 138th Pl

Crestwood, IL

3 beds | 2 baths | 1,500 sq.ft.

$314,900

Airbnb cash on cash: 0.69%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $1562

Traditional Rental Income: $1936

Airbnb ROI: 0.69%

Traditional ROI: 3.47%

5547 Fairway Drive

Crestwood, IL

4 beds | 2 baths | 1,535 sq.ft.

$299,000

Airbnb cash on cash: -3.2%

Traditional cash on cash: 6.17%

Airbnb Rental Income: $86

Traditional Rental Income: $2519

Airbnb ROI: -3.2%

Traditional ROI: 6.17%

5700 128th St #9

Crestwood, IL

2 beds | 1 baths | 800 sq.ft.

$90,000

Airbnb cash on cash: 5.69%

Traditional cash on cash: 9.86%

Airbnb Rental Income: $1419

Traditional Rental Income: $1360

Airbnb ROI: 5.69%

Traditional ROI: 9.86%

13540 Lawler Avenue #77

Crestwood, IL

2 beds | 2 baths | 1,000 sq.ft.

$163,000

Airbnb cash on cash: 0.87%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $1419

Traditional Rental Income: $1484

Airbnb ROI: 0.87%

Traditional ROI: 4.02%

5554 Linder Ct

Crestwood, IL

3 beds | 2 baths | 1,700 sq.ft.

$359,999

Airbnb cash on cash: 0.29%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $1562

Traditional Rental Income: $2627

Airbnb ROI: 0.29%

Traditional ROI: 4.77%

12850 Crestbrook Court #10

Crestwood, IL

2 beds | 1 baths | 900 sq.ft.

$151,900

Airbnb cash on cash: 1.68%

Traditional cash on cash: 6.23%

Airbnb Rental Income: $1419

Traditional Rental Income: $1655

Airbnb ROI: 1.68%

Traditional ROI: 6.23%

5418 135th Street

Crestwood, IL

3 beds | 3 baths | 1,963 sq.ft.

$359,900

Airbnb cash on cash: -0.72%

Traditional cash on cash: 6.03%

Airbnb Rental Income: $1562

Traditional Rental Income: $3394

Airbnb ROI: -0.72%

Traditional ROI: 6.03%

5410 135th Street

Crestwood, IL

3 beds | 3 baths | 1,963 sq.ft.

$359,900

Airbnb cash on cash: -0.72%

Traditional cash on cash: 6.03%

Airbnb Rental Income: $1562

Traditional Rental Income: $3394

Airbnb ROI: -0.72%