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
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%
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%
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%
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: 4.92% Traditional cash on cash: 4.09% Airbnb Rental Income: $3290 Traditional Rental Income: $2321 Airbnb ROI: 4.92% Traditional ROI: 4.09%
7 Garden Street Chester, NY Attention buyers Fully available! Don't let the size of this home fool you. This perfectly...	3 beds \| 2 baths \| 1,435 sq.ft.	$392,900	Airbnb cash on cash: 9.35% Traditional cash on cash: 4.23% Airbnb Rental Income: $5853 Traditional Rental Income: $2805 Airbnb ROI: 9.35% Traditional ROI: 4.23%
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.	$665,000	Airbnb cash on cash: 4.68% Traditional cash on cash: 2.95% Airbnb Rental Income: $5845 Traditional Rental Income: $3610 Airbnb ROI: 4.68% Traditional ROI: 2.95%
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%
60 Evan Road Chester, NY WARWICK SCHOOL DISTRICT & No Hoa Fees! Welcome to Kings Estate; centrally located to Ches...	3 beds \| 3 baths \| 1,452 sq.ft.	$395,000	Airbnb cash on cash: 9.78% Traditional cash on cash: 5.23% Airbnb Rental Income: $5853 Traditional Rental Income: $3004 Airbnb ROI: 9.78% Traditional ROI: 5.23%
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: 9.76% Traditional cash on cash: 4.86% Airbnb Rental Income: $5853 Traditional Rental Income: $3009 Airbnb ROI: 9.76% Traditional ROI: 4.86%
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: 5.03% Traditional cash on cash: 4.33% Airbnb Rental Income: $3290 Traditional Rental Income: $2369 Airbnb ROI: 5.03% Traditional ROI: 4.33%
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: 5.39% Traditional cash on cash: 2.62% Airbnb Rental Income: $5853 Traditional Rental Income: $3141 Airbnb ROI: 5.39% Traditional ROI: 2.62%
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%
1911 Whispering Hills Chester, NY Welcome to your dream oasis nestled in the heart of Chester, NY This meticulously renovate...	3 beds \| 2 baths \| 1,316 sq.ft.	$364,999	Airbnb cash on cash: 9.94% Traditional cash on cash: 3.98% Airbnb Rental Income: $5853 Traditional Rental Income: $2646 Airbnb ROI: 9.94% Traditional ROI: 3.98%
40 Farmingdale Road Chester, NY Beautifully renovated 4-bedroom, 3-bathroom split-level home nestled on 4.3 acres of stunn...	4 beds \| 3 baths \| 2,269 sq.ft.	$499,000	Airbnb cash on cash: 6.69% Traditional cash on cash: 4.56% Airbnb Rental Income: $5845 Traditional Rental Income: $3688 Airbnb ROI: 6.69% Traditional ROI: 4.56%
5 Oxford Springs Road Chester, NY ONE OF A KIND GEM! Nestled in a private setting on 3.3 acres, this unique house welcomes ...	3 beds \| 2 baths \| 2,608 sq.ft.	$625,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 1.91% Airbnb Rental Income: $5853 Traditional Rental Income: $3022 Airbnb ROI: 4.77% Traditional ROI: 1.91%
3406 Whispering Hills Chester, NY Welcome to this beautifully maintained 2 bedroom, 1.5 bath condo nestled in the heart of C...	2 beds \| 2 baths \| 1,086 sq.ft.	$289,000	Airbnb cash on cash: 4.97% Traditional cash on cash: 4.05% Airbnb Rental Income: $3290 Traditional Rental Income: $2302 Airbnb ROI: 4.97% Traditional ROI: 4.05%
31 Grand View Terrace Chester, NY *Welcome Home to this great commuter location in the desirable Valley View subdivision...	4 beds \| 4 baths \| 4,658 sq.ft.	$799,900	Airbnb cash on cash: 2.83% Traditional cash on cash: 2.75% Airbnb Rental Income: $5845 Traditional Rental Income: $4624 Airbnb ROI: 2.83% Traditional ROI: 2.75%
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%
12 Meadow Avenue Chester, NY New Village Colonial with all the options, walk out basement with 10 ft ceiling height, ro...	4 beds \| 3 baths \| 2,050 sq.ft.	$609,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 3.18% Airbnb Rental Income: $5845 Traditional Rental Income: $3766 Airbnb ROI: 4.79% Traditional ROI: 3.18%
38 Rebecca Road Chester, NY Multiple offer situation submit highest/best offers by 10am Sept 9th --- WELCOME HOME!...	4 beds \| 3 baths \| 1,910 sq.ft.	$575,000	Airbnb cash on cash: 5.43% Traditional cash on cash: 3.14% Airbnb Rental Income: $5845 Traditional Rental Income: $3454 Airbnb ROI: 5.43% Traditional ROI: 3.14%
11 Townsend Place Chester, NY Welcome to your dream home! This beautifully maintained split-level house, in a cul-de-sac...	3 beds \| 2 baths \| 1,788 sq.ft.	$499,000	Airbnb cash on cash: 6.92% Traditional cash on cash: 3.7% Airbnb Rental Income: $5853 Traditional Rental Income: $3187 Airbnb ROI: 6.92% Traditional ROI: 3.7%
3606 Whispering Hills Chester, NY FANTASTIC 2 bedroom, 1 1/2 bath condo/townhouse (2 floors) with an attached 2 car garage -...	2 beds \| 2 baths \| 1,086 sq.ft.	$264,000	Airbnb cash on cash: 5.97% Traditional cash on cash: 5.37% Airbnb Rental Income: $3290 Traditional Rental Income: $2404 Airbnb ROI: 5.97% Traditional ROI: 5.37%
412 Laroe Road Chester, NY This extraordinarily charming totally updated high ranch is sitting on 2.4 private landsc...	3 beds \| 2 baths \| 1,848 sq.ft.	$579,000	Airbnb cash on cash: 5.61% Traditional cash on cash: 2.83% Airbnb Rental Income: $5853 Traditional Rental Income: $3181 Airbnb ROI: 5.61% Traditional ROI: 2.83%

Vacation Rentals in Chester

There are 24 vacation rental properties available for sale in the city of Chester . The median list price of Airbnb properties available for sale in Chester is $575,000 and the average price per square foot is $237. The cash on cash return on vacation rentals in Chester is 5.00%. 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 24 Airbnb properties available for sale in Chester.

In 2024, the best neighborhood to buy short term rental property is Chester.

In November 2024, the average Airbnb occupancy rate in Chester is 35%.

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

128 Booth Road

Chester, NY

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%

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%

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%

1807 Whispering Hills

Chester, NY

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

$299,000

Airbnb cash on cash: 4.92%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $3290

Traditional Rental Income: $2321

Airbnb ROI: 4.92%

Traditional ROI: 4.09%

7 Garden Street

Chester, NY

3 beds | 2 baths | 1,435 sq.ft.

$392,900

Airbnb cash on cash: 9.35%

Traditional cash on cash: 4.23%

Airbnb Rental Income: $5853

Traditional Rental Income: $2805

Airbnb ROI: 9.35%

Traditional ROI: 4.23%

1301 Kings Highway

Chester, NY

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

$665,000

Airbnb cash on cash: 4.68%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $5845

Traditional Rental Income: $3610

Airbnb ROI: 4.68%

Traditional ROI: 2.95%

11 Saddle Hill Road

Chester, NY

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%

60 Evan Road

Chester, NY

3 beds | 3 baths | 1,452 sq.ft.

$395,000

Airbnb cash on cash: 9.78%

Traditional cash on cash: 5.23%

Airbnb Rental Income: $5853

Traditional Rental Income: $3004

Airbnb ROI: 9.78%