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
5041 139th Place #406 Crestwood, IL Welcome to this well maintained 2 Bedroom, 2 Bath Condo located on the second floor of an ...	2 beds \| 2 baths \| 1,200 sq.ft.	$200,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 7.77% Airbnb Rental Income: $1186 Traditional Rental Income: $2282 Airbnb ROI: -0.04% Traditional ROI: 7.77%
5704 W 128th Street #1C Crestwood, IL Come see this gorgeous comfy condo! Recently renovated and in prestine condition 2 Bedroom...	2 beds \| 2 baths \| 1,000 sq.ft.	$234,500	Airbnb cash on cash: 0.55% Traditional cash on cash: 6.03% Airbnb Rental Income: $1186 Traditional Rental Income: $2016 Airbnb ROI: 0.55% Traditional ROI: 6.03%
14244 Kostner Avenue Crestwood, IL Welcome home to this nicely updated 3-bed, 1-bath home in the heart of Crestwood! This ho...	3 beds \| 1 baths \| 900 sq.ft.	$268,000	Airbnb cash on cash: 4.05% Traditional cash on cash: 4.81% Airbnb Rental Income: $2238 Traditional Rental Income: $1869 Airbnb ROI: 4.05% Traditional ROI: 4.81%
4920 134th Court #205 Crestwood, IL Beautiful two bedroom, two full bath condo located in the Circle Crest Manor Complex for a...	2 beds \| 2 baths \| 1,200 sq.ft.	$199,900	Airbnb cash on cash: 0.98% Traditional cash on cash: 8.17% Airbnb Rental Income: $1186 Traditional Rental Income: $2163 Airbnb ROI: 0.98% Traditional ROI: 8.17%
13706 Crestview Court Crestwood, IL Welcome home to this beautifully updated 3-bedroom, 2-bath split-level with a sub-basement...	3 beds \| 2 baths \| 1,700 sq.ft.	$389,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.53% Airbnb Rental Income: $2238 Traditional Rental Income: $2276 Airbnb ROI: 1.89% Traditional ROI: 3.53%
5400 135th Street #5404 Crestwood, IL WELCOME TO THE COVES OF CRESTWOOD, ALL BRAND NEW CONSTRUCTION TOWNHOMES , WITH OPEN CONCEP...	3 beds \| 3 baths \| 1,514 sq.ft.	$334,900	Airbnb cash on cash: -0.64% Traditional cash on cash: 2.79% Airbnb Rental Income: $2238 Traditional Rental Income: $2753 Airbnb ROI: -0.64% Traditional ROI: 2.79%
5400 135th Street #5406 Crestwood, IL WELCOME TO THE COVES OF CRESTWOOD, ALL BRAND NEW CONSTRUCTION TOWNHOMES , WITH OPEN CONCEP...	3 beds \| 3 baths \| 1,514 sq.ft.	$334,900	Airbnb cash on cash: -0.64% Traditional cash on cash: 2.79% Airbnb Rental Income: $2238 Traditional Rental Income: $2753 Airbnb ROI: -0.64% Traditional ROI: 2.79%
5204 Midlothian Turnpike #222 Crestwood, IL Nestled in the heart of Crestwood, this Beautifully Updated 2 bedroom 1.5 Bathroom third f...	2 beds \| 2 baths \| 1,000 sq.ft.	$182,900	Airbnb cash on cash: -0.12% Traditional cash on cash: 6.83% Airbnb Rental Income: $1186 Traditional Rental Income: $2009 Airbnb ROI: -0.12% Traditional ROI: 6.83%
13919 W Leamington Drive #806 Crestwood, IL Amazing second floor condo in Crestwood's premier 55+ community this very large two bedroo...	2 beds \| 2 baths \| 1,200 sq.ft.	$192,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 8.22% Airbnb Rental Income: $1186 Traditional Rental Income: $2326 Airbnb ROI: -0.14% Traditional ROI: 8.22%
13537 Latrobe Avenue #7 Crestwood, IL AWESOME SPACIOUS 2 STORY TOWNHOME LOCATED IN THE WELL KEPT CRYSTAL CREST COMPLEX* APPROXIM...	2 beds \| 3 baths \| 2,200 sq.ft.	$324,900	Airbnb cash on cash: -1.44% Traditional cash on cash: 5.38% Airbnb Rental Income: $1186 Traditional Rental Income: $2882 Airbnb ROI: -1.44% Traditional ROI: 5.38%
13933 James Drive #820 Crestwood, IL Beautiful Spacious Condo with large balcony with view of the pond and fountain. Two Spacio...	2 beds \| 2 baths \| 1,100 sq.ft.	$165,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 8.85% Airbnb Rental Income: $1186 Traditional Rental Income: $2292 Airbnb ROI: -0.63% Traditional ROI: 8.85%
13645 Lamon Avenue #A06 Crestwood, IL Step into and experience the perfect blend of modern comfort and classic charm.This spacio...	2 beds \| 2 baths \| 1,000 sq.ft.	$168,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 7.08% Airbnb Rental Income: $1186 Traditional Rental Income: $2013 Airbnb ROI: -0.5% Traditional ROI: 7.08%
13919 James Drive #903 Crestwood, IL Welcome to Sandpiper South Condominiums. This 1st Floor unit is ready for you to call it y...	2 beds \| 2 baths \| 1,000 sq.ft.	$175,000	Airbnb cash on cash: 0% Traditional cash on cash: 7.28% Airbnb Rental Income: $1186 Traditional Rental Income: $2013 Airbnb ROI: 0% Traditional ROI: 7.28%
13422 W Circle Drive #401 Crestwood, IL THIS IS THE ONE! Lovely and bright, this 1st floor condo has it all...just move in and ma...	2 beds \| 2 baths \| 1,000 sq.ft.	$180,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 7.78% Airbnb Rental Income: $1186 Traditional Rental Income: $2063 Airbnb ROI: 0.4% Traditional ROI: 7.78%
14224 Springfield Avenue Crestwood, IL Move right in and start making memories in this beautifully updated raised ranch home nest...	2 beds \| 3 baths \| 1,232 sq.ft.	$325,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 5.08% Airbnb Rental Income: $1186 Traditional Rental Income: $2389 Airbnb ROI: -0.12% Traditional ROI: 5.08%
13426 W Circle Drive #302 Crestwood, IL Move-in ready and beautifully maintained, this spacious 2 bed, 2 bath ground-floor condo i...	2 beds \| 2 baths \| N/A	$179,900	Airbnb cash on cash: 1.43% Traditional cash on cash: 9.72% Airbnb Rental Income: $1186 Traditional Rental Income: $2219 Airbnb ROI: 1.43% Traditional ROI: 9.72%
4210 Midlothian Crestwood, IL Welcome home to this nicely updated 3-bed, 1-bath home in the heart of Crestwood! This hom...	3 beds \| 1 baths \| 1,386 sq.ft.	$289,900	Airbnb cash on cash: 4.32% Traditional cash on cash: 5.14% Airbnb Rental Income: $2238 Traditional Rental Income: $1900 Airbnb ROI: 4.32% Traditional ROI: 5.14%

Real Estate investment in Crestwood, IL

There are 32 properties for sale in the city of Crestwood . The median list price in Crestwood is $199,950 and the average price per square foot is $161. In October 2025, the average monthly cash on cash return in Crestwood is 7.00%. The average monthly rental income in Crestwood is $2,209.

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

There are 32 investment properties available for sale in Crestwood.

In 2025, 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 $1,186.

Your search for investment property begins and ends here

Investment Property for Sale in Crestwood, IL

5041 139th Place #406

Crestwood, IL

2 beds | 2 baths | 1,200 sq.ft.

$200,000

Airbnb cash on cash: -0.04%

Traditional cash on cash: 7.77%

Airbnb Rental Income: $1186

Traditional Rental Income: $2282

Airbnb ROI: -0.04%

Traditional ROI: 7.77%

5704 W 128th Street #1C

Crestwood, IL

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

$234,500

Airbnb cash on cash: 0.55%

Traditional cash on cash: 6.03%

Airbnb Rental Income: $1186

Traditional Rental Income: $2016

Airbnb ROI: 0.55%

Traditional ROI: 6.03%

14244 Kostner Avenue

Crestwood, IL

3 beds | 1 baths | 900 sq.ft.

$268,000

Airbnb cash on cash: 4.05%

Traditional cash on cash: 4.81%

Airbnb Rental Income: $2238

Traditional Rental Income: $1869

Airbnb ROI: 4.05%

Traditional ROI: 4.81%

4920 134th Court #205

Crestwood, IL

2 beds | 2 baths | 1,200 sq.ft.

$199,900

Airbnb cash on cash: 0.98%

Traditional cash on cash: 8.17%

Airbnb Rental Income: $1186

Traditional Rental Income: $2163

Airbnb ROI: 0.98%

Traditional ROI: 8.17%

13706 Crestview Court

Crestwood, IL

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

$389,000

Airbnb cash on cash: 1.89%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $2238

Traditional Rental Income: $2276

Airbnb ROI: 1.89%

Traditional ROI: 3.53%

5400 135th Street #5404

Crestwood, IL

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

$334,900

Airbnb cash on cash: -0.64%

Traditional cash on cash: 2.79%

Airbnb Rental Income: $2238

Traditional Rental Income: $2753

Airbnb ROI: -0.64%

Traditional ROI: 2.79%

5400 135th Street #5406

Crestwood, IL

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

$334,900

Airbnb cash on cash: -0.64%

Traditional cash on cash: 2.79%

Airbnb Rental Income: $2238

Traditional Rental Income: $2753

Airbnb ROI: -0.64%

Traditional ROI: 2.79%

5204 Midlothian Turnpike #222

Crestwood, IL

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

$182,900

Airbnb cash on cash: -0.12%

Traditional cash on cash: 6.83%

Airbnb Rental Income: $1186

Traditional Rental Income: $2009

Airbnb ROI: -0.12%