Real Estate Investment Properties for Sale in Windsor, NY

Looking for investment property in Windsor, NY with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
134 Main St Windsor, NY Historical Home with 4BRs & 1.5 BAs. Spacious Living Room, Oversized Dining Rm is perfect ...	5 beds \| 2 baths \| 1,696 sq.ft.	$220,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.79% Airbnb Rental Income: $null Traditional Rental Income: $2442 Airbnb ROI: N/A Traditional ROI: 8.79%
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%
0 Grove St Row Windsor, NY 0 Grove St Row, Windsor, NY 13865 \| Other	N/A beds \| N/A baths \| N/A	$450,000	Airbnb cash on cash: -0.5% Traditional cash on cash: -1.51% Airbnb Rental Income: $1454 Traditional Rental Income: $597 Airbnb ROI: -0.5% Traditional ROI: -1.51%
20 Main St Windsor, NY 20 Main St, Windsor, NY 13865 \| Other	N/A beds \| N/A baths \| N/A	$649,000	Airbnb cash on cash: -1.17% Traditional cash on cash: -1.83% Airbnb Rental Income: $1454 Traditional Rental Income: $627 Airbnb ROI: -1.17% Traditional ROI: -1.83%
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%
100 Main St Windsor, NY 100 Main St, Windsor, NY 13865 \| Condo/Coop	3 beds \| 1 baths \| 3,320 sq.ft.	$199,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 2.87% Airbnb Rental Income: $1259 Traditional Rental Income: $1144 Airbnb ROI: 1.37% Traditional ROI: 2.87%
33 Academy St Windsor, NY 33 Academy St, Windsor, NY 13865 \| Single Family Residential	3 beds \| 1 baths \| 900 sq.ft.	$93,500	Airbnb cash on cash: 5.75% Traditional cash on cash: 11.56% Airbnb Rental Income: $1259 Traditional Rental Income: $1390 Airbnb ROI: 5.75% Traditional ROI: 11.56%

Real Estate investment in Windsor, NY

There are 8 properties for sale in the city of Windsor . The median list price in Windsor is $247,000 and the average price per square foot is $79. In July 2026, the average monthly cash on cash return in Windsor is 7.00%. The average monthly rental income in Windsor is $1,390.

Windsor, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 8 investment properties available for sale in Windsor.

In 2026, the best neighborhood to buy investment property is Windsor.

The ROI for Long-Term is higher than the Short-Term in Windsor with average rental income of $1,390.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, NY

134 Main St

Windsor, NY

5 beds | 2 baths | 1,696 sq.ft.

$220,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.79%

Airbnb Rental Income: $null

Traditional Rental Income: $2442

Airbnb ROI: N/A

Traditional ROI: 8.79%

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%

0 Grove St Row

Windsor, NY

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

$450,000

Airbnb cash on cash: -0.5%

Traditional cash on cash: -1.51%

Airbnb Rental Income: $1454

Traditional Rental Income: $597

Airbnb ROI: -0.5%

Traditional ROI: -1.51%

20 Main St

Windsor, NY

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

$649,000

Airbnb cash on cash: -1.17%

Traditional cash on cash: -1.83%

Airbnb Rental Income: $1454

Traditional Rental Income: $627

Airbnb ROI: -1.17%

Traditional ROI: -1.83%

869 State Route 79

Windsor, NY

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%

100 Main St

Windsor, NY

3 beds | 1 baths | 3,320 sq.ft.

$199,000

Airbnb cash on cash: 1.37%

Traditional cash on cash: 2.87%

Airbnb Rental Income: $1259

Traditional Rental Income: $1144

Airbnb ROI: 1.37%

Traditional ROI: 2.87%

33 Academy St

Windsor, NY

3 beds | 1 baths | 900 sq.ft.

$93,500

Airbnb cash on cash: 5.75%

Traditional cash on cash: 11.56%

Airbnb Rental Income: $1259

Traditional Rental Income: $1390

Airbnb ROI: 5.75%

Traditional ROI: 11.56%

Real Estate investment in Windsor, NY

Windsor, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

How many investment properties are available for sale in Windsor?

Which neighborhoods in Windsor to invest in 2026?

Long-Term vs. Short-Term Rentals in Windsor, New York: Which will earn the best returns?

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