Airbnb Properties for Sale in Chester, NY

Looking for a vacation rental investment in Chester, NY with high ROI ?

Explore a range of newly added short-term rental homes in Chester, NY. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Chester, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2607 Whispering Hills Chester, NY WHISPERING HILLS! LOW TAXES! Cul-de-sac Location! 2 Bedrooms! 1 1 /2 Bathrooms! 2 Car Gara...	2 beds \| 2 baths \| 1,086 sq.ft.	$319,900	Airbnb cash on cash: 4.34% Traditional cash on cash: 3.98% Airbnb Rental Income: $3216 Traditional Rental Income: $2384 Airbnb ROI: 4.34% Traditional ROI: 3.98%
2 Grand View Terrace Chester, NY *Welcome Home to this great commuter location in the desirable Valley View subdivision...	4 beds \| 3 baths \| 3,480 sq.ft.	$749,900	Airbnb cash on cash: 3.14% Traditional cash on cash: 2.09% Airbnb Rental Income: $5845 Traditional Rental Income: $3948 Airbnb ROI: 3.14% Traditional ROI: 2.09%
76 Restdale Road Chester, NY Welcome to 76 Restdale Road, an exquisitely updated 4-bedroom, 2.5-bath home nestled on 1....	4 beds \| 3 baths \| 2,838 sq.ft.	$699,999	Airbnb cash on cash: 4.21% Traditional cash on cash: 3.23% Airbnb Rental Income: $5845 Traditional Rental Income: $4038 Airbnb ROI: 4.21% Traditional ROI: 3.23%
152 Gibson Hill Road Chester, NY Set back from the road, nestled behind mature native and ornamental trees sits this statel...	4 beds \| 3 baths \| 3,176 sq.ft.	$799,000	Airbnb cash on cash: 3.02% Traditional cash on cash: 1.71% Airbnb Rental Income: $5845 Traditional Rental Income: $3704 Airbnb ROI: 3.02% Traditional ROI: 1.71%
1002 Whispering Hills Chester, NY This charming three-bedroom, two-bath townhouse is nestled in the Whispering Hills communi...	3 beds \| 2 baths \| 1,316 sq.ft.	$345,000	Airbnb cash on cash: 7.44% Traditional cash on cash: 4.19% Airbnb Rental Income: $4830 Traditional Rental Income: $2781 Airbnb ROI: 7.44% Traditional ROI: 4.19%
278 Gibson Hill Road Chester, NY AMAZING PROPERTY -- offers something for everyone! Gorgeously restored 3,977 square foot c...	4 beds \| 3 baths \| 3,977 sq.ft.	$784,000	Airbnb cash on cash: 3.58% Traditional cash on cash: 2.22% Airbnb Rental Income: $5845 Traditional Rental Income: $3683 Airbnb ROI: 3.58% Traditional ROI: 2.22%
16 Fini Terrace Chester, NY Discover the enchanting tranquility of Rock Ridge Estates, where this magnificent Colonial...	4 beds \| 3 baths \| 2,654 sq.ft.	$635,000	Airbnb cash on cash: 4.24% Traditional cash on cash: 2.97% Airbnb Rental Income: $5845 Traditional Rental Income: $3927 Airbnb ROI: 4.24% Traditional ROI: 2.97%
1301 Kings Highway Chester, NY Located just outside the quaint village of Sugar Loaf sits this 1835 farm house. Situated ...	4 beds \| 3 baths \| 2,676 sq.ft.	$649,900	Airbnb cash on cash: 4.81% Traditional cash on cash: 3.04% Airbnb Rental Income: $5845 Traditional Rental Income: $3610 Airbnb ROI: 4.81% Traditional ROI: 3.04%
11 Saddle Hill Road Chester, NY Welcome to 11 Saddle River Rd, a beautifully updated home situated on a tranquil private r...	4 beds \| 4 baths \| 4,489 sq.ft.	$1,100,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 1.11% Airbnb Rental Income: $5845 Traditional Rental Income: $4011 Airbnb ROI: 1.77% Traditional ROI: 1.11%
2706 Whispering Hills Chester, NY Welcome to this beautiful and cozy 2 bedrooms condo with 1.5 bathrooms and 2 car garages i...	2 beds \| 2 baths \| 1,086 sq.ft.	$315,000	Airbnb cash on cash: 4.29% Traditional cash on cash: 3.84% Airbnb Rental Income: $3216 Traditional Rental Income: $2357 Airbnb ROI: 4.29% Traditional ROI: 3.84%
504 Bull Mill Road Chester, NY A NEW HOME IS A NEW BEGINNING!! Impressive home - redone to perfection is waiting for you!...	4 beds \| 3 baths \| 2,777 sq.ft.	$790,000	Airbnb cash on cash: 3.16% Traditional cash on cash: 2.1% Airbnb Rental Income: $5845 Traditional Rental Income: $3905 Airbnb ROI: 3.16% Traditional ROI: 2.1%
40 Mountainside Drive Chester, NY FANTASTIC NEW CONSTRUCTION to be built!! FULLY CUSTOM BUILD opportunity for your DREAM HO...	4 beds \| 3 baths \| 2,500 sq.ft.	$799,900	Airbnb cash on cash: 3.17% Traditional cash on cash: 2.92% Airbnb Rental Income: $5845 Traditional Rental Income: $4495 Airbnb ROI: 3.17% Traditional ROI: 2.92%
128 Booth Road Chester, NY A/O 11/4 Welcome to your sanctuary in Chester, New York! This impeccable four-bedroom, 2 1...	4 beds \| 3 baths \| 2,102 sq.ft.	$549,920	Airbnb cash on cash: 5.8% Traditional cash on cash: 3.45% Airbnb Rental Income: $5845 Traditional Rental Income: $3474 Airbnb ROI: 5.8% Traditional ROI: 3.45%
1107 Whispering Hills Chester, NY Discover Easy Living at 1107 Whispering Hills! Embrace the simplicity and elegance of this...	2 beds \| 2 baths \| 1,086 sq.ft.	$279,900	Airbnb cash on cash: 4.64% Traditional cash on cash: 4.17% Airbnb Rental Income: $3216 Traditional Rental Income: $2369 Airbnb ROI: 4.64% Traditional ROI: 4.17%
1807 Whispering Hills Chester, NY Welcome to 1807 Whispering Hills, Chester Your Dream Home Awaits! This 2 bedroom 1.5 ba...	2 beds \| 2 baths \| 1,086 sq.ft.	$299,000	Airbnb cash on cash: 4.7% Traditional cash on cash: 4.09% Airbnb Rental Income: $3216 Traditional Rental Income: $2321 Airbnb ROI: 4.7% Traditional ROI: 4.09%
77 Surrey Road Chester, NY Pride of ownership at it's finest! What an honor to represent this original owner's home! ...	5 beds \| 3 baths \| 2,136 sq.ft.	$549,000	Airbnb cash on cash: 6.94% Traditional cash on cash: 4.06% Airbnb Rental Income: $6466 Traditional Rental Income: $3719 Airbnb ROI: 6.94% Traditional ROI: 4.06%
60 Rose Ann Lane Chester, NY Serenity awaits! Come home to your pristine 4 bdrm, 3 ba Colonial nestled on 1.3 acres in ...	4 beds \| 3 baths \| 2,326 sq.ft.	$569,999	Airbnb cash on cash: 5.22% Traditional cash on cash: 3.47% Airbnb Rental Income: $5845 Traditional Rental Income: $3750 Airbnb ROI: 5.22% Traditional ROI: 3.47%
6 Railroad Avenue Chester, NY BEAUTIFUL DUPLEX!! Very Well Maintained! Two Units! First Floor Unit has 2 Bedrooms and ! ...	4 beds \| 3 baths \| 2,922 sq.ft.	$599,900	Airbnb cash on cash: 3.75% Traditional cash on cash: 3.68% Airbnb Rental Income: $4830 Traditional Rental Income: $3797 Airbnb ROI: 3.75% Traditional ROI: 3.68%
4 Greycourt Road Chester, NY Magnificent sprawling ranch situated on a park like setting with 2.80 acres with mature la...	3 beds \| 2 baths \| N/A	$599,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 2.62% Airbnb Rental Income: $4830 Traditional Rental Income: $3141 Airbnb ROI: 3.86% Traditional ROI: 2.62%
2910 Whispering Hills Chester, NY OPEN HOUSE - SUNDAY - NOV. 17th - 12PM-1:30PM. (Due to system issues, open houses are not ...	3 beds \| 3 baths \| 1,331 sq.ft.	$365,000	Airbnb cash on cash: 7.27% Traditional cash on cash: 4.86% Airbnb Rental Income: $4830 Traditional Rental Income: $3009 Airbnb ROI: 7.27% Traditional ROI: 4.86%

Vacation Rentals in Chester

There are 20 vacation rental properties available for sale in the city of Chester . The median list price of Airbnb properties available for sale in Chester is $599,900 and the average price per square foot is $233. The cash on cash return on vacation rentals in Chester is 4.00%. The average monthly short term rental income in Chester is $5,845.

Chester, NY Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 20 Airbnb properties available for sale in Chester.

In 2025, the best neighborhood to buy short term rental property is Chester.

In January 2025, the average Airbnb occupancy rate in Chester is 51%.

Airbnb data on vacation rentals in Chester, NY is available at Mashvisor. You can access data such as listings, real-time pricing trends, Chester, NY market insights, guest information and booking details, seasonality trends and historical Chester, NY Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Chester, NY

2607 Whispering Hills

Chester, NY

2 beds | 2 baths | 1,086 sq.ft.

$319,900

Airbnb cash on cash: 4.34%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $3216

Traditional Rental Income: $2384

Airbnb ROI: 4.34%

Traditional ROI: 3.98%

2 Grand View Terrace

Chester, NY

4 beds | 3 baths | 3,480 sq.ft.

$749,900

Airbnb cash on cash: 3.14%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $5845

Traditional Rental Income: $3948

Airbnb ROI: 3.14%

Traditional ROI: 2.09%

76 Restdale Road

Chester, NY

4 beds | 3 baths | 2,838 sq.ft.

$699,999

Airbnb cash on cash: 4.21%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $5845

Traditional Rental Income: $4038

Airbnb ROI: 4.21%

Traditional ROI: 3.23%

152 Gibson Hill Road

Chester, NY

4 beds | 3 baths | 3,176 sq.ft.

$799,000

Airbnb cash on cash: 3.02%

Traditional cash on cash: 1.71%

Airbnb Rental Income: $5845

Traditional Rental Income: $3704

Airbnb ROI: 3.02%

Traditional ROI: 1.71%

1002 Whispering Hills

Chester, NY

3 beds | 2 baths | 1,316 sq.ft.

$345,000

Airbnb cash on cash: 7.44%

Traditional cash on cash: 4.19%

Airbnb Rental Income: $4830

Traditional Rental Income: $2781

Airbnb ROI: 7.44%

Traditional ROI: 4.19%

278 Gibson Hill Road

Chester, NY

4 beds | 3 baths | 3,977 sq.ft.

$784,000

Airbnb cash on cash: 3.58%

Traditional cash on cash: 2.22%

Airbnb Rental Income: $5845

Traditional Rental Income: $3683

Airbnb ROI: 3.58%

Traditional ROI: 2.22%

16 Fini Terrace

Chester, NY

4 beds | 3 baths | 2,654 sq.ft.

$635,000

Airbnb cash on cash: 4.24%

Traditional cash on cash: 2.97%

Airbnb Rental Income: $5845

Traditional Rental Income: $3927

Airbnb ROI: 4.24%

Traditional ROI: 2.97%

1301 Kings Highway

Chester, NY

4 beds | 3 baths | 2,676 sq.ft.

$649,900

Airbnb cash on cash: 4.81%

Traditional cash on cash: 3.04%

Airbnb Rental Income: $5845

Traditional Rental Income: $3610

Airbnb ROI: 4.81%