Real Estate Investment Properties for Sale in Chester Town, NY

Looking for investment property in Chester Town, NY with high ROI ?

Explore a variety of short-term homes & houses in Chester Town, NY. Invest wisely with VRBO & Chester Town, NY 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 Chester Town, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
21 Atateka Trail Chester Town, NY BACK ON THE MARKET!! BREATHTAKING WATERFRONT VIEWS! This charming 1300 square foot four-b...	4 beds \| 2 baths \| 1,300 sq.ft.	$399,900	Airbnb cash on cash: 6.8% Traditional cash on cash: 5.32% Airbnb Rental Income: $4481 Traditional Rental Income: $2991 Airbnb ROI: 6.8% Traditional ROI: 5.32%
44 Clarkson Road Chester Town, NY BEACH RIGHTS ON LOON LAKE. Own your own slice of the Adirondacks with this lovely ranch ho...	3 beds \| 2 baths \| 1,736 sq.ft.	$389,900	Airbnb cash on cash: 6.15% Traditional cash on cash: 7.48% Airbnb Rental Income: $3924 Traditional Rental Income: $3566 Airbnb ROI: 6.15% Traditional ROI: 7.48%
Investment Properties for Sale in Other Cities of New-york
50 Bradburn Street Rochester , NY Delayed showings/negotiations. Showings to commence on 11/15/24, negotiations begin on 11/...	3 beds \| 1 baths \| 1,772 sq.ft.	$149,900	Airbnb cash on cash: 6.68% Traditional cash on cash: 7.42% Airbnb Rental Income: $2031 Traditional Rental Income: $1610 Airbnb ROI: 6.68% Traditional ROI: 7.42%
998 Mount Read Boulevard Rochester , NY This updated 3BR 2BA home offers modern upgrades and timeless charm. Inside, youâll find...	3 beds \| 2 baths \| 1,064 sq.ft.	$189,900	Airbnb cash on cash: 3.99% Traditional cash on cash: 7.21% Airbnb Rental Income: $1859 Traditional Rental Income: $1941 Airbnb ROI: 3.99% Traditional ROI: 7.21%
78 Stage Ln New York , NY 78 Stage Ln, New York, NY 10304 \| Townhouse	3 beds \| 2 baths \| 2,300 sq.ft.	$678,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 2.07% Airbnb Rental Income: $5856 Traditional Rental Income: $3117 Airbnb ROI: 4.56% Traditional ROI: 2.07%
109-41 164th Street So.Jamaica , NY Welcome to this fully detached single family home located in Jamaica. It has 3 bedroom on ...	3 beds \| 3 baths \| 1,072 sq.ft.	$664,900	Airbnb cash on cash: 0.8% Traditional cash on cash: 3.23% Airbnb Rental Income: $2086 Traditional Rental Income: $3135 Airbnb ROI: 0.8% Traditional ROI: 3.23%
99-03 207th Street New York , NY , Additional information: Appearance:Excellent	5 beds \| 3 baths \| N/A	$1,450,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.16% Airbnb Rental Income: $null Traditional Rental Income: $4817 Airbnb ROI: N/A Traditional ROI: 2.16%
80 Suffolk Road Island Park , NY Ahoy, water enthusiasts! If you've been dreaming of a waterfront escape that's as refreshi...	5 beds \| 3 baths \| 3,082 sq.ft.	$774,999	Airbnb cash on cash: 5.35% Traditional cash on cash: 3.13% Airbnb Rental Income: $7809 Traditional Rental Income: $4719 Airbnb ROI: 5.35% Traditional ROI: 3.13%
130 Delafield Lane Newburgh , NY Welcome to the Meadow Winds community! This beautiful multi-level townhouse offers 2 bedro...	2 beds \| 3 baths \| 2,206 sq.ft.	$387,000	Airbnb cash on cash: 5.61% Traditional cash on cash: 4.86% Airbnb Rental Income: $4257 Traditional Rental Income: $3086 Airbnb ROI: 5.61% Traditional ROI: 4.86%
34 Black Stallion Court Middletown , NY This home is ready for you to move right in! This home located in the desirable Meadows Co...	3 beds \| 2 baths \| 1,188 sq.ft.	$289,000	Airbnb cash on cash: 9.99% Traditional cash on cash: 5.93% Airbnb Rental Income: $4464 Traditional Rental Income: $2426 Airbnb ROI: 9.99% Traditional ROI: 5.93%
179 Reservoir Road Middletown , NY Welcome to the OPPORTUNITY OF A LIFETIME! This one-of-a-kind home with its one-of-a-kind y...	3 beds \| 2 baths \| 3,080 sq.ft.	$699,999	Airbnb cash on cash: 2.65% Traditional cash on cash: 2.51% Airbnb Rental Income: $4464 Traditional Rental Income: $3438 Airbnb ROI: 2.65% Traditional ROI: 2.51%
9 Chester Drive Yonkers , NY Recently renovated Large single family home in colonial heights ready to occupy. First fl...	3 beds \| 2 baths \| 1,400 sq.ft.	$775,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 2.59% Airbnb Rental Income: $3189 Traditional Rental Income: $3637 Airbnb ROI: 0.97% Traditional ROI: 2.59%
384 Hawthorne Avenue Yonkers , NY Short Sale Subject to third party Approval / Need TLC, SOLD As Is. All info deemed reliabl...	3 beds \| 1 baths \| 1,497 sq.ft.	$530,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 3.56% Airbnb Rental Income: $3189 Traditional Rental Income: $3169 Airbnb ROI: 2.15% Traditional ROI: 3.56%
377 N Broadway #702 Yonkers , NY Welcome to this lovely one bedroom with Breathtaking Direct Views of the Hudson River and ...	1 beds \| 1 baths \| 800 sq.ft.	$162,500	Airbnb cash on cash: 4.02% Traditional cash on cash: 4.29% Airbnb Rental Income: $2765 Traditional Rental Income: $2157 Airbnb ROI: 4.02% Traditional ROI: 4.29%
100-56 223rd Street New York , NY Well kept very spacious single family home located at the heart of Queens Village, featuri...	4 beds \| 3 baths \| 1,632 sq.ft.	$849,000	Airbnb cash on cash: 6.43% Traditional cash on cash: 3.22% Airbnb Rental Income: $8135 Traditional Rental Income: $4052 Airbnb ROI: 6.43% Traditional ROI: 3.22%
976 Van Duzer St New York , NY 976 Van Duzer St, New York, NY 10304 \| Single Family Residential	3 beds \| 2 baths \| 864 sq.ft.	$750,000	Airbnb cash on cash: 3.87% Traditional cash on cash: 0.83% Airbnb Rental Income: $5856 Traditional Rental Income: $2568 Airbnb ROI: 3.87% Traditional ROI: 0.83%
2773 South Shore Road Old Forge , NY This beautifully appointed home has everything you could desire. There are 4 bedrooms, 4 ...	4 beds \| 5 baths \| 2,354 sq.ft.	$999,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 3.56% Airbnb Rental Income: $5092 Traditional Rental Income: $4502 Airbnb ROI: 3.08% Traditional ROI: 3.56%

Real Estate investment in Chester-town, NY

There are 2 properties for sale in the city of Chester Town . The median list price in Chester Town is $394,900 and the average price per square foot is $260. In January 2025, the average monthly cash on cash return in Chester Town is 6.00%. The average monthly rental income in Chester Town is $3,279.

Chester-town, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 2 investment properties available for sale in Chester-town.

In 2025, the best neighborhood to buy investment property is Chester Town.

The ROI for Short-Term is higher than the Long-Term in Chester-town with average rental income of $4,203.

Your search for investment property begins and ends here

Investment Property for Sale in Chester Town, NY

21 Atateka Trail

Chester Town, NY

4 beds | 2 baths | 1,300 sq.ft.

$399,900

Airbnb cash on cash: 6.8%

Traditional cash on cash: 5.32%

Airbnb Rental Income: $4481

Traditional Rental Income: $2991

Airbnb ROI: 6.8%

Traditional ROI: 5.32%

44 Clarkson Road

Chester Town, NY

3 beds | 2 baths | 1,736 sq.ft.

$389,900

Airbnb cash on cash: 6.15%

Traditional cash on cash: 7.48%

Airbnb Rental Income: $3924

Traditional Rental Income: $3566

Airbnb ROI: 6.15%

Traditional ROI: 7.48%

Investment Properties for Sale in Other Cities of New-york

Rochester , NY

3 beds | 1 baths | 1,772 sq.ft.

$149,900

Airbnb cash on cash: 6.68%

Traditional cash on cash: 7.42%

Airbnb Rental Income: $2031

Traditional Rental Income: $1610

Airbnb ROI: 6.68%

Traditional ROI: 7.42%

Rochester , NY

3 beds | 2 baths | 1,064 sq.ft.

$189,900

Airbnb cash on cash: 3.99%

Traditional cash on cash: 7.21%

Airbnb Rental Income: $1859

Traditional Rental Income: $1941

Airbnb ROI: 3.99%

Traditional ROI: 7.21%

New York , NY

3 beds | 2 baths | 2,300 sq.ft.

$678,000

Airbnb cash on cash: 4.56%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $5856

Traditional Rental Income: $3117

Airbnb ROI: 4.56%

Traditional ROI: 2.07%

So.Jamaica , NY

3 beds | 3 baths | 1,072 sq.ft.

$664,900

Airbnb cash on cash: 0.8%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $2086

Traditional Rental Income: $3135

Airbnb ROI: 0.8%

Traditional ROI: 3.23%

New York , NY

5 beds | 3 baths | N/A

$1,450,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.16%

Airbnb Rental Income: $null

Traditional Rental Income: $4817

Airbnb ROI: N/A

Traditional ROI: 2.16%

Island Park , NY

5 beds | 3 baths | 3,082 sq.ft.

$774,999

Airbnb cash on cash: 5.35%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $7809

Traditional Rental Income: $4719

Airbnb ROI: 5.35%

Traditional ROI: 3.13%

Newburgh , NY

2 beds | 3 baths | 2,206 sq.ft.

$387,000

Airbnb cash on cash: 5.61%