Real Estate Investment Properties for Sale in Sleepy Hollow, IL

Looking for investment property in Sleepy Hollow, IL with high ROI ?

Explore a variety of short-term homes & houses in Sleepy Hollow, IL. Invest wisely with VRBO & Sleepy Hollow, 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 Sleepy Hollow, IL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
936 Glen Oak Drive SLEEPY HOLLOW, IL Escape to tranquility in this beautifully updated home. Enjoy the best of both worlds with...	4 beds \| 3 baths \| 2,237 sq.ft.	$575,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 2.96% Airbnb Rental Income: $1422 Traditional Rental Income: $3071 Airbnb ROI: -0.91% Traditional ROI: 2.96%
616 Joy Lane SLEEPY HOLLOW, IL Welcome to Joy Ln! This wonderful home has been beautifully maintained, you'll drive up to...	4 beds \| 3 baths \| 2,400 sq.ft.	$515,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 3.83% Airbnb Rental Income: $1422 Traditional Rental Income: $3149 Airbnb ROI: -0.64% Traditional ROI: 3.83%
Investment Properties for Sale in Other Cities of Illinois
2610 W 80th St Chicago , IL 2610 W 80th St, Chicago, IL 60652 \| Single Family Residential	2 beds \| 1 baths \| 855 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.99% Airbnb Rental Income: $null Traditional Rental Income: $1328 Airbnb ROI: N/A Traditional ROI: 1.99%
7801 S Ada Street Chicago , IL Welcome to this stunning, fully remodeled solid-brick single-family home in Auburn Gresham...	3 beds \| 3 baths \| 1,200 sq.ft.	$399,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.56% Airbnb Rental Income: $null Traditional Rental Income: $2306 Airbnb ROI: N/A Traditional ROI: 4.56%
3219 N Richmond St Chicago , IL 3219 N Richmond St, Chicago, IL 60618 \| Single Family Residential	4 beds \| 3 baths \| 1,920 sq.ft.	$885,000	Airbnb cash on cash: N/A Traditional cash on cash: 0% Airbnb Rental Income: $null Traditional Rental Income: $2776 Airbnb ROI: N/A Traditional ROI: 0%
1722 N Keeler Avenue Chicago , IL Hot Hermosa location! Updated single family home on a great block. House went through ext...	3 beds \| 1 baths \| 842 sq.ft.	$299,950	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $1632 Airbnb ROI: N/A Traditional ROI: 3.56%
60 E Monroe St #2001 Chicago , IL 60 E Monroe St #2001, Chicago, IL 60603 \| Condo/Coop	3 beds \| 2 baths \| 1,750 sq.ft.	$1,000,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.56% Airbnb Rental Income: $null Traditional Rental Income: $2745 Airbnb ROI: N/A Traditional ROI: -2.56%
1160 S Michigan Ave #2502 Chicago , IL 1160 S Michigan Ave #2502, Chicago, IL 60605 \| Condo/Coop	2 beds \| 2 baths \| 1,231 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.59% Airbnb Rental Income: $null Traditional Rental Income: $2449 Airbnb ROI: N/A Traditional ROI: 0.59%
7228 N Rogers Avenue Chicago , IL This is a 3 Bedroom, 1.5 Bath, 2 story, frame farm house with 1 Deeded Parking Space. It i...	2 beds \| 3 baths \| 1,600 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.28% Airbnb Rental Income: $null Traditional Rental Income: $2651 Airbnb ROI: N/A Traditional ROI: 4.28%
4343 N Clarendon Avenue #707 Chicago , IL Investors! Welcome to Buena Park. This incredible unit is a large one bedroom one bath wit...	1 beds \| 1 baths \| 790 sq.ft.	$139,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.01% Airbnb Rental Income: $null Traditional Rental Income: $1894 Airbnb ROI: N/A Traditional ROI: 4.01%
4004 N Clarendon Avenue #1 Chicago , IL Welcome to this stunning home featuring beautiful vintage details and millwork with modern...	4 beds \| 2 baths \| 2,750 sq.ft.	$639,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.09% Airbnb Rental Income: $null Traditional Rental Income: $3310 Airbnb ROI: N/A Traditional ROI: 3.09%
9100 S Wallace Street Chicago , IL Welcome to 9100 S Wallace - a beautifully renovated 3-bedroom, 3-bathroom home offering mo...	2 beds \| 3 baths \| 1,312 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.86% Airbnb Rental Income: $null Traditional Rental Income: $1900 Airbnb ROI: N/A Traditional ROI: 4.86%
7216 S CENTRAL PARK Avenue Chicago , IL Well-maintained brick ranch in move-in condition! Features gleaming hardwood floors, origi...	3 beds \| 2 baths \| 1,080 sq.ft.	$290,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.33% Airbnb Rental Income: $null Traditional Rental Income: $2371 Airbnb ROI: N/A Traditional ROI: 6.33%
7205 S HAMLIN Avenue Chicago , IL Maintenance free 4 bedroom ranch with finished basement. 3 bedrooms on the main and one in...	3 beds \| 2 baths \| 1,080 sq.ft.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.15% Airbnb Rental Income: $null Traditional Rental Income: $1877 Airbnb ROI: N/A Traditional ROI: 4.15%

Real Estate investment in Sleepy-hollow, IL

There are 3 properties for sale in the city of Sleepy Hollow . The median list price in Sleepy Hollow is $502,450 and the average price per square foot is $199. In December 2025, the average monthly cash on cash return in Sleepy Hollow is 4.00%. The average monthly rental income in Sleepy Hollow is $3,069.

Sleepy-hollow, IL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 3 investment properties available for sale in Sleepy-hollow.

In 2025, the best neighborhood to buy investment property is SLEEPY HOLLOW.

The ROI for Long-Term is higher than the Short-Term in Sleepy-hollow with average rental income of $3,069.

Your search for investment property begins and ends here

Investment Property for Sale in Sleepy Hollow, IL

936 Glen Oak Drive

SLEEPY HOLLOW, IL

4 beds | 3 baths | 2,237 sq.ft.

$575,000

Airbnb cash on cash: -0.91%

Traditional cash on cash: 2.96%

Airbnb Rental Income: $1422

Traditional Rental Income: $3071

Airbnb ROI: -0.91%

Traditional ROI: 2.96%

616 Joy Lane

SLEEPY HOLLOW, IL

4 beds | 3 baths | 2,400 sq.ft.

$515,000

Airbnb cash on cash: -0.64%

Traditional cash on cash: 3.83%

Airbnb Rental Income: $1422

Traditional Rental Income: $3149

Airbnb ROI: -0.64%

Traditional ROI: 3.83%

Investment Properties for Sale in Other Cities of Illinois

Chicago , IL

2 beds | 1 baths | 855 sq.ft.

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.99%

Airbnb Rental Income: $null

Traditional Rental Income: $1328

Airbnb ROI: N/A

Traditional ROI: 1.99%

Chicago , IL

3 beds | 3 baths | 1,200 sq.ft.

$399,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.56%

Airbnb Rental Income: $null

Traditional Rental Income: $2306

Airbnb ROI: N/A

Traditional ROI: 4.56%

Chicago , IL

4 beds | 3 baths | 1,920 sq.ft.

$885,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0%

Airbnb Rental Income: $null

Traditional Rental Income: $2776

Airbnb ROI: N/A

Traditional ROI: 0%

Chicago , IL

3 beds | 1 baths | 842 sq.ft.

$299,950

Airbnb cash on cash: N/A

Traditional cash on cash: 3.56%

Airbnb Rental Income: $null

Traditional Rental Income: $1632

Airbnb ROI: N/A

Traditional ROI: 3.56%

Chicago , IL

3 beds | 2 baths | 1,750 sq.ft.

$1,000,000

Airbnb cash on cash: N/A

Traditional cash on cash: -2.56%

Airbnb Rental Income: $null

Traditional Rental Income: $2745

Airbnb ROI: N/A

Traditional ROI: -2.56%

Chicago , IL

2 beds | 2 baths | 1,231 sq.ft.

$415,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.59%

Airbnb Rental Income: $null

Traditional Rental Income: $2449

Airbnb ROI: N/A

Traditional ROI: 0.59%

Chicago , IL

2 beds | 3 baths | 1,600 sq.ft.

$415,000

Airbnb cash on cash: N/A