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
847 Hemlock Dr SLEEPY HOLLOW, IL Welcome to this inviting and well maintained 3-bedroom, 2-bathroom home situated on a gene...	3 beds \| 2 baths \| 2,070 sq.ft.	$440,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 3.63% Airbnb Rental Income: $2086 Traditional Rental Income: $2609 Airbnb ROI: 1.06% Traditional ROI: 3.63%
616 Joy Ln SLEEPY HOLLOW, IL Welcome to Joy Ln! This wonderful home has been beautifully maintained, you'll drive up to...	3 beds \| 2 baths \| 2,164 sq.ft.	$479,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 4.19% Airbnb Rental Income: $2086 Traditional Rental Income: $3149 Airbnb ROI: 0.62% Traditional ROI: 4.19%
1009 Shagbark Ln SLEEPY HOLLOW, IL AVAILABLE MAY DELIVERY! * SPECIAL INCENTIVES AVAILABLE! HOMESITE # 1805 Introducing the Ma...	3 beds \| 2 baths \| 1,767 sq.ft.	$409,490	Airbnb cash on cash: -0.17% Traditional cash on cash: 2.8% Airbnb Rental Income: $2086 Traditional Rental Income: $2691 Airbnb ROI: -0.17% Traditional ROI: 2.8%
5+ Frontenac Dr SLEEPY HOLLOW, IL 5+ Frontenac Dr, SLEEPY HOLLOW, IL 60118 \| Other	N/A beds \| N/A baths \| N/A	$262,000	Airbnb cash on cash: 0.76% Traditional cash on cash: -0.31% Airbnb Rental Income: $1523 Traditional Rental Income: $816 Airbnb ROI: 0.76% Traditional ROI: -0.31%
22 Plum Ct SLEEPY HOLLOW, IL Welcome home to this beautifully updated 4 bedroom, 2 bathroom home nestled on a spacious ...	4 beds \| 2 baths \| 2,249 sq.ft.	$409,900	Airbnb cash on cash: 3.87% Traditional cash on cash: 4.09% Airbnb Rental Income: $3416 Traditional Rental Income: $2743 Airbnb ROI: 3.87% Traditional ROI: 4.09%
727 Jamestowne Rd SLEEPY HOLLOW, IL 727 Jamestowne Rd, SLEEPY HOLLOW, IL 60118 \| Single Family Residential	4 beds \| 2 baths \| 2,736 sq.ft.	$549,900	Airbnb cash on cash: 1.74% Traditional cash on cash: 1.33% Airbnb Rental Income: $3416 Traditional Rental Income: $2447 Airbnb ROI: 1.74% Traditional ROI: 1.33%
725 Pimlico Pkwy SLEEPY HOLLOW, IL 725 Pimlico Pkwy, SLEEPY HOLLOW, IL 60118 \| Single Family Residential	4 beds \| 2 baths \| 2,645 sq.ft.	$575,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 1.13% Airbnb Rental Income: $3416 Traditional Rental Income: $2445 Airbnb ROI: 1.52% Traditional ROI: 1.13%
919 Shagbark Ln SLEEPY HOLLOW, IL 919 Shagbark Ln, SLEEPY HOLLOW, IL 60118 \| Townhouse	3 beds \| 2 baths \| 1,767 sq.ft.	$402,990	Airbnb cash on cash: -0.12% Traditional cash on cash: 2.33% Airbnb Rental Income: $2086 Traditional Rental Income: $2475 Airbnb ROI: -0.12% Traditional ROI: 2.33%
915 Shagbark Ln SLEEPY HOLLOW, IL 915 Shagbark Ln, SLEEPY HOLLOW, IL 60118 \| Townhouse	3 beds \| 2 baths \| 1,767 sq.ft.	$405,990	Airbnb cash on cash: -0.15% Traditional cash on cash: 2.29% Airbnb Rental Income: $2086 Traditional Rental Income: $2475 Airbnb ROI: -0.15% Traditional ROI: 2.29%
1008 Shagbark Ln SLEEPY HOLLOW, IL 1008 Shagbark Ln, SLEEPY HOLLOW, IL 60118 \| Townhouse	3 beds \| 2 baths \| 1,840 sq.ft.	$399,490	Airbnb cash on cash: -0.1% Traditional cash on cash: 2.53% Airbnb Rental Income: $2086 Traditional Rental Income: $2533 Airbnb ROI: -0.1% Traditional ROI: 2.53%
1124 Crane Dr SLEEPY HOLLOW, IL 1124 Crane Dr, SLEEPY HOLLOW, IL 60118 \| Single Family Residential	4 beds \| 2 baths \| 2,300 sq.ft.	$494,900	Airbnb cash on cash: 2.29% Traditional cash on cash: 1.51% Airbnb Rental Income: $3416 Traditional Rental Income: $2298 Airbnb ROI: 2.29% Traditional ROI: 1.51%
205 Sharon Dr SLEEPY HOLLOW, IL 205 Sharon Dr, SLEEPY HOLLOW, IL 60118 \| Single Family Residential	4 beds \| 2 baths \| 2,013 sq.ft.	$425,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 2.23% Airbnb Rental Income: $3416 Traditional Rental Income: $2273 Airbnb ROI: 3.19% Traditional ROI: 2.23%
1004 Shagbark Ln SLEEPY HOLLOW, IL 1004 Shagbark Ln, SLEEPY HOLLOW, IL 60118 \| Townhouse	3 beds \| 2 baths \| 1,840 sq.ft.	$424,490	Airbnb cash on cash: -0.28% Traditional cash on cash: 2.15% Airbnb Rental Income: $2086 Traditional Rental Income: $2518 Airbnb ROI: -0.28% Traditional ROI: 2.15%
1010 Shagbark Ln SLEEPY HOLLOW, IL 1010 Shagbark Ln, SLEEPY HOLLOW, IL 60118 \| Townhouse	3 beds \| 2 baths \| 1,767 sq.ft.	$399,490	Airbnb cash on cash: -0.1% Traditional cash on cash: 2.28% Airbnb Rental Income: $2086 Traditional Rental Income: $2438 Airbnb ROI: -0.1% Traditional ROI: 2.28%
1006 Shagbark Ln SLEEPY HOLLOW, IL 1006 Shagbark Ln, SLEEPY HOLLOW, IL 60118 \| Townhouse	3 beds \| 2 baths \| 1,767 sq.ft.	$379,490	Airbnb cash on cash: 0.07% Traditional cash on cash: 2.63% Airbnb Rental Income: $2086 Traditional Rental Income: $2461 Airbnb ROI: 0.07% Traditional ROI: 2.63%
1113 Crane Dr SLEEPY HOLLOW, IL 1113 Crane Dr, SLEEPY HOLLOW, IL 60118 \| Single Family Residential	5 beds \| 2 baths \| 3,930 sq.ft.	$600,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.86% Airbnb Rental Income: $null Traditional Rental Income: $2398 Airbnb ROI: N/A Traditional ROI: 0.86%
617 Arlington Pkwy SLEEPY HOLLOW, IL 617 Arlington Pkwy, SLEEPY HOLLOW, IL 60118 \| Single Family Residential	4 beds \| 2 baths \| 3,150 sq.ft.	$499,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 1.92% Airbnb Rental Income: $3416 Traditional Rental Income: $2504 Airbnb ROI: 2.25% Traditional ROI: 1.92%
1803 Paula Ct SLEEPY HOLLOW, IL 1803 Paula Ct, SLEEPY HOLLOW, IL 60118 \| Single Family Residential	5 beds \| 3 baths \| 3,494 sq.ft.	$589,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.08% Airbnb Rental Income: $null Traditional Rental Income: $3033 Airbnb ROI: N/A Traditional ROI: 2.08%
1000 Shagbark Ln SLEEPY HOLLOW, IL 1000 Shagbark Ln, SLEEPY HOLLOW, IL 60118 \| Townhouse	3 beds \| 2 baths \| 1,840 sq.ft.	$428,490	Airbnb cash on cash: -0.31% Traditional cash on cash: 2.05% Airbnb Rental Income: $2086 Traditional Rental Income: $2496 Airbnb ROI: -0.31% Traditional ROI: 2.05%
172 Hilltop Ct SLEEPY HOLLOW, IL 172 Hilltop Ct, SLEEPY HOLLOW, IL 60118 \| Single Family Residential	4 beds \| 3 baths \| 4,260 sq.ft.	$476,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 2.51% Airbnb Rental Income: $3416 Traditional Rental Income: $2657 Airbnb ROI: 2.51% Traditional ROI: 2.51%
745 Jamestowne Ct SLEEPY HOLLOW, IL 745 Jamestowne Ct, SLEEPY HOLLOW, IL 60118 \| Single Family Residential	4 beds \| 2 baths \| 3,150 sq.ft.	$524,950	Airbnb cash on cash: 1.98% Traditional cash on cash: 1.64% Airbnb Rental Income: $3416 Traditional Rental Income: $2493 Airbnb ROI: 1.98% Traditional ROI: 1.64%

Real Estate investment in Sleepy-hollow, IL

There are 25 properties for sale in the city of Sleepy Hollow . The median list price in Sleepy Hollow is $464,722 and the average price per square foot is $177. In October 2026, the average monthly cash on cash return in Sleepy Hollow is 2.00%. The average monthly rental income in Sleepy Hollow is $2,475.

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

There are 25 investment properties available for sale in Sleepy-hollow.

In 2026, 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 $2,475.

Your search for investment property begins and ends here

Investment Property for Sale in Sleepy Hollow, IL

847 Hemlock Dr

SLEEPY HOLLOW, IL

3 beds | 2 baths | 2,070 sq.ft.

$440,000

Airbnb cash on cash: 1.06%

Traditional cash on cash: 3.63%

Airbnb Rental Income: $2086

Traditional Rental Income: $2609

Airbnb ROI: 1.06%

Traditional ROI: 3.63%

616 Joy Ln

SLEEPY HOLLOW, IL

3 beds | 2 baths | 2,164 sq.ft.

$479,000

Airbnb cash on cash: 0.62%

Traditional cash on cash: 4.19%

Airbnb Rental Income: $2086

Traditional Rental Income: $3149

Airbnb ROI: 0.62%

Traditional ROI: 4.19%

1009 Shagbark Ln

SLEEPY HOLLOW, IL

3 beds | 2 baths | 1,767 sq.ft.

$409,490

Airbnb cash on cash: -0.17%

Traditional cash on cash: 2.8%

Airbnb Rental Income: $2086

Traditional Rental Income: $2691

Airbnb ROI: -0.17%

Traditional ROI: 2.8%

5+ Frontenac Dr

SLEEPY HOLLOW, IL

N/A beds | N/A baths | N/A

$262,000

Airbnb cash on cash: 0.76%

Traditional cash on cash: -0.31%

Airbnb Rental Income: $1523

Traditional Rental Income: $816

Airbnb ROI: 0.76%

Traditional ROI: -0.31%

22 Plum Ct

SLEEPY HOLLOW, IL

4 beds | 2 baths | 2,249 sq.ft.

$409,900

Airbnb cash on cash: 3.87%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $3416

Traditional Rental Income: $2743

Airbnb ROI: 3.87%

Traditional ROI: 4.09%

727 Jamestowne Rd

SLEEPY HOLLOW, IL

4 beds | 2 baths | 2,736 sq.ft.

$549,900

Airbnb cash on cash: 1.74%

Traditional cash on cash: 1.33%

Airbnb Rental Income: $3416

Traditional Rental Income: $2447

Airbnb ROI: 1.74%

Traditional ROI: 1.33%

725 Pimlico Pkwy

SLEEPY HOLLOW, IL

4 beds | 2 baths | 2,645 sq.ft.

$575,000

Airbnb cash on cash: 1.52%

Traditional cash on cash: 1.13%

Airbnb Rental Income: $3416

Traditional Rental Income: $2445

Airbnb ROI: 1.52%

Traditional ROI: 1.13%

919 Shagbark Ln

SLEEPY HOLLOW, IL

3 beds | 2 baths | 1,767 sq.ft.

$402,990

Airbnb cash on cash: -0.12%

Traditional cash on cash: 2.33%

Airbnb Rental Income: $2086

Traditional Rental Income: $2475

Airbnb ROI: -0.12%