Airbnb Properties for Sale in Windsor, NY

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

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

Airbnb For Sale in Windsor, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
57 Chestnut St Windsor, NY Nestled in the picturesque hills of Windsor, this beautiful newly renovated home offers bo...	4 beds \| 2 baths \| 1,500 sq.ft.	$290,000	Airbnb cash on cash: 8.72% Traditional cash on cash: 7.2% Airbnb Rental Income: $3887 Traditional Rental Income: $2633 Airbnb ROI: 8.72% Traditional ROI: 7.2%
580 Honey Hollow Rd Windsor, NY 580 Honey Hollow Rd, Windsor, NY 13865 \| Other	3 beds \| N/A baths \| 966 sq.ft.	$83,500	Airbnb cash on cash: 8.68% Traditional cash on cash: 5.06% Airbnb Rental Income: $1454 Traditional Rental Income: $726 Airbnb ROI: 8.68% Traditional ROI: 5.06%
79 Saxby Road Rd Windsor, NY 79 Saxby Rd, Windsor, NY 13865 \| Other	N/A beds \| N/A baths \| N/A	$116,640	Airbnb cash on cash: 5.58% Traditional cash on cash: 2.09% Airbnb Rental Income: $1454 Traditional Rental Income: $630 Airbnb ROI: 5.58% Traditional ROI: 2.09%
250 Saxby Road Rd Windsor, NY 250 Saxby Rd, Windsor, NY 13865 \| Other	N/A beds \| N/A baths \| N/A	$132,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 1.56% Airbnb Rental Income: $1454 Traditional Rental Income: $630 Airbnb ROI: 4.65% Traditional ROI: 1.56%
253 Fenesey Rd Windsor, NY 253 Fenesey Rd, Windsor, NY 13865 \| Other	N/A beds \| N/A baths \| N/A	$332,160	Airbnb cash on cash: 0.28% Traditional cash on cash: -0.98% Airbnb Rental Income: $1454 Traditional Rental Income: $630 Airbnb ROI: 0.28% Traditional ROI: -0.98%
139 Saxby Road Rd Windsor, NY 139 Saxby Rd, Windsor, NY 13865 \| Other	N/A beds \| N/A baths \| N/A	$300,240	Airbnb cash on cash: 0.59% Traditional cash on cash: -0.8% Airbnb Rental Income: $1454 Traditional Rental Income: $630 Airbnb ROI: 0.59% Traditional ROI: -0.8%
190 Saxby Road Rd Windsor, NY 190 Saxby Rd, Windsor, NY 13865 \| Other	N/A beds \| N/A baths \| N/A	$228,480	Airbnb cash on cash: 1.61% Traditional cash on cash: -0.21% Airbnb Rental Income: $1454 Traditional Rental Income: $630 Airbnb ROI: 1.61% Traditional ROI: -0.21%
280 Saxby Road Rd Windsor, NY 280 Saxby Rd, Windsor, NY 13865 \| Other	N/A beds \| N/A baths \| N/A	$360,480	Airbnb cash on cash: 0.04% Traditional cash on cash: -1.12% Airbnb Rental Income: $1454 Traditional Rental Income: $630 Airbnb ROI: 0.04% Traditional ROI: -1.12%
230 Old Route 17 St Windsor, NY 230 Old Route 17 St, Windsor, NY 13865 \| Single Family Residential	4 beds \| 2 baths \| 1,120 sq.ft.	$199,999	Airbnb cash on cash: 9.83% Traditional cash on cash: 5% Airbnb Rental Income: $3887 Traditional Rental Income: $1910 Airbnb ROI: 9.83% Traditional ROI: 5%
51 Bennett Rd Windsor, NY 51 Bennett Rd, Windsor, NY 13865 \| Other	3 beds \| N/A baths \| N/A	$75,000	Airbnb cash on cash: 8.14% Traditional cash on cash: 3.57% Airbnb Rental Income: $1454 Traditional Rental Income: $630 Airbnb ROI: 8.14% Traditional ROI: 3.57%
139 Gaf Lake Rd Windsor, NY 139 Gaf Lake Rd, Windsor, NY 13865 \| Other	N/A beds \| N/A baths \| N/A	$225,000	Airbnb cash on cash: 1.67% Traditional cash on cash: -0.42% Airbnb Rental Income: $1454 Traditional Rental Income: $577 Airbnb ROI: 1.67% Traditional ROI: -0.42%
300 Dodd Rd Windsor, NY 300 Dodd Rd, Windsor, NY 13865 \| Other	N/A beds \| N/A baths \| 5,865,354 sq.ft.	$360,000	Airbnb cash on cash: 0.05% Traditional cash on cash: -1.11% Airbnb Rental Income: $1454 Traditional Rental Income: $630 Airbnb ROI: 0.05% Traditional ROI: -1.11%
62 North Rd Windsor, NY 62 North Rd, Windsor, NY 13865 \| Other	N/A beds \| N/A baths \| N/A	$348,100	Airbnb cash on cash: 0.09% Traditional cash on cash: -1.25% Airbnb Rental Income: $1454 Traditional Rental Income: $577 Airbnb ROI: 0.09% Traditional ROI: -1.25%
130 William Law Rd Windsor, NY 130 William Law Rd, Windsor, NY 13865 \| Other	4 beds \| N/A baths \| N/A	$200,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 0.14% Airbnb Rental Income: $1454 Traditional Rental Income: $630 Airbnb ROI: 2.21% Traditional ROI: 0.14%
140 Bell Rd Windsor, NY 140 Bell Rd, Windsor, NY 13865 \| Other	N/A beds \| N/A baths \| N/A	$85,000	Airbnb cash on cash: 7.91% Traditional cash on cash: 3.44% Airbnb Rental Income: $1454 Traditional Rental Income: $630 Airbnb ROI: 7.91% Traditional ROI: 3.44%
199 Tennent Road Rd Windsor, NY 199 Tennent Road Rd, Windsor, NY 13865 \| Other	N/A beds \| N/A baths \| N/A	$192,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 0.25% Airbnb Rental Income: $1454 Traditional Rental Income: $630 Airbnb ROI: 2.41% Traditional ROI: 0.25%
135 & 137 Caribou Tr Trl Windsor, NY 135 & 137 Caribou Tr Trl, Windsor, NY 13865 \| Single Family Residential	2 beds \| 1 baths \| 640 sq.ft.	$199,900	Airbnb cash on cash: 3.68% Traditional cash on cash: 0.96% Airbnb Rental Income: $2162 Traditional Rental Income: $1060 Airbnb ROI: 3.68% Traditional ROI: 0.96%
869 State Route 79 Windsor, NY Nestled on nearly 2 private acres in the Windsor School District, this well-maintained hom...	4 beds \| 2 baths \| 1,750 sq.ft.	$285,000	Airbnb cash on cash: 8.59% Traditional cash on cash: 6.35% Airbnb Rental Income: $3887 Traditional Rental Income: $2449 Airbnb ROI: 8.59% Traditional ROI: 6.35%

Vacation Rentals in Windsor

There are 18 vacation rental properties available for sale in the city of Windsor . The median list price of Airbnb properties available for sale in Windsor is $247,000 and the average price per square foot is $10. The cash on cash return on vacation rentals in Windsor is 2.00%. The average monthly short term rental income in Windsor is $1,454.

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

There are 18 Airbnb properties available for sale in Windsor.

In 2026, the best neighborhood to buy short term rental property is Windsor.

In September 2026, the average Airbnb occupancy rate in Windsor is 26%.

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

Your search for investment property begins and ends here

Airbnb For Sale in Windsor, NY

57 Chestnut St

Windsor, NY

4 beds | 2 baths | 1,500 sq.ft.

$290,000

Airbnb cash on cash: 8.72%

Traditional cash on cash: 7.2%

Airbnb Rental Income: $3887

Traditional Rental Income: $2633

Airbnb ROI: 8.72%

Traditional ROI: 7.2%

580 Honey Hollow Rd

Windsor, NY

3 beds | N/A baths | 966 sq.ft.

$83,500

Airbnb cash on cash: 8.68%

Traditional cash on cash: 5.06%

Airbnb Rental Income: $1454

Traditional Rental Income: $726

Airbnb ROI: 8.68%

Traditional ROI: 5.06%

79 Saxby Road Rd

Windsor, NY

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

$116,640

Airbnb cash on cash: 5.58%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $1454

Traditional Rental Income: $630

Airbnb ROI: 5.58%

Traditional ROI: 2.09%

250 Saxby Road Rd

Windsor, NY

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

$132,000

Airbnb cash on cash: 4.65%

Traditional cash on cash: 1.56%

Airbnb Rental Income: $1454

Traditional Rental Income: $630

Airbnb ROI: 4.65%

Traditional ROI: 1.56%

253 Fenesey Rd

Windsor, NY

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

$332,160

Airbnb cash on cash: 0.28%

Traditional cash on cash: -0.98%

Airbnb Rental Income: $1454

Traditional Rental Income: $630

Airbnb ROI: 0.28%

Traditional ROI: -0.98%

139 Saxby Road Rd

Windsor, NY

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

$300,240

Airbnb cash on cash: 0.59%

Traditional cash on cash: -0.8%

Airbnb Rental Income: $1454

Traditional Rental Income: $630

Airbnb ROI: 0.59%

Traditional ROI: -0.8%

190 Saxby Road Rd

Windsor, NY

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

$228,480

Airbnb cash on cash: 1.61%

Traditional cash on cash: -0.21%

Airbnb Rental Income: $1454

Traditional Rental Income: $630

Airbnb ROI: 1.61%

Traditional ROI: -0.21%

280 Saxby Road Rd

Windsor, NY

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

$360,480

Airbnb cash on cash: 0.04%

Traditional cash on cash: -1.12%

Airbnb Rental Income: $1454

Traditional Rental Income: $630

Airbnb ROI: 0.04%