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
945 Anne Road Windsor, NY If you like country living surrounded by nature, this home is for you! This interesting ho...	3 beds \| 2 baths \| 2,100 sq.ft.	$164,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 11.43% Airbnb Rental Income: $880 Traditional Rental Income: $2302 Airbnb ROI: 0.2% Traditional ROI: 11.43%
280 Dodd Rd Windsor, NY Let your country-living dreams come true with this park-like estate, in a very private loc...	4 beds \| 5 baths \| 5,374 sq.ft.	$1,299,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 2.08% Airbnb Rental Income: $3887 Traditional Rental Income: $5690 Airbnb ROI: -0.1% Traditional ROI: 2.08%
Investment Properties for Sale in Other Cities of New-york
284 Bayview Avenue Inwood , NY Explore this inviting 4 bedrooms, 3 bathroom home with a main floor bedroom and full bath....	4 beds \| 3 baths \| 1,350 sq.ft.	$599,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.59% Airbnb Rental Income: $1452 Traditional Rental Income: $3124 Airbnb ROI: -0.17% Traditional ROI: 3.59%
28 Upton Place Rochester , NY This Colonial is located on a dead-end street within walking distance to Charlotte Beach. ...	3 beds \| 2 baths \| 1,591 sq.ft.	$144,900	Airbnb cash on cash: 6.12% Traditional cash on cash: 11.35% Airbnb Rental Income: $1942 Traditional Rental Income: $2155 Airbnb ROI: 6.12% Traditional ROI: 11.35%
174 Winton Road S Rochester , NY Well maintained 2,214 sq ft 3 bedroom colonial close to U of R and East Ave! Hardwood floo...	3 beds \| 4 baths \| 2,214 sq.ft.	$375,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 5.74% Airbnb Rental Income: $1931 Traditional Rental Income: $3353 Airbnb ROI: 0.25% Traditional ROI: 5.74%
124 E 28th Street New York , NY Opportunity Awaits in Flatbush! Welcome to this semi-detached single-family home nestled ...	5 beds \| 2 baths \| 1,333 sq.ft.	$649,999	Airbnb cash on cash: 9.69% Traditional cash on cash: 4.14% Airbnb Rental Income: $8645 Traditional Rental Income: $3648 Airbnb ROI: 9.69% Traditional ROI: 4.14%
68-61 Yellowstone Boulevard #303 New York , NY THE UNIT: Enjoy the best of city and serene! Welcome to the beautifully-reno'ed, quiet and...	2 beds \| 2 baths \| 1,200 sq.ft.	$649,000	Airbnb cash on cash: 1.31% Traditional cash on cash: 2.19% Airbnb Rental Income: $3258 Traditional Rental Income: $3059 Airbnb ROI: 1.31% Traditional ROI: 2.19%
30-33 92nd Street New York , NY This beautifully maintained 4-bedroom, 2.5-bathroom home is designed for comfort, flexibil...	4 beds \| 3 baths \| 1,716 sq.ft.	$880,000	Airbnb cash on cash: 7.28% Traditional cash on cash: 2.76% Airbnb Rental Income: $9164 Traditional Rental Income: $3738 Airbnb ROI: 7.28% Traditional ROI: 2.76%
150-21 95th Street #2 New York , NY This spacious corner-unit condominium on the 2nd floor, in Ozone Park offers 3 bedrooms an...	3 beds \| 2 baths \| 1,130 sq.ft.	$558,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 3.1% Airbnb Rental Income: $1510 Traditional Rental Income: $3059 Airbnb ROI: -0.72% Traditional ROI: 3.1%
38-34 209th Street New York , NY This sun-drenched 5-Bedroom, 3-Bath home offers exceptional comfort and versatility. Nestl...	5 beds \| 3 baths \| 2,247 sq.ft.	$1,456,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.53% Airbnb Rental Income: $null Traditional Rental Income: $4519 Airbnb ROI: N/A Traditional ROI: 1.53%
620 Ocean Terrace New York , NY Amazing all brick Contemporary located on beautiful Todt hill! 4 Oversized Bedrooms, 3 bat...	4 beds \| 3 baths \| 4,950 sq.ft.	$2,150,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 0.4% Airbnb Rental Income: $7742 Traditional Rental Income: $4203 Airbnb ROI: 1.43% Traditional ROI: 0.4%
16 Mickardan Court New York , NY Priced Cheaper Than a Condo! Welcome to this charming semi-detached single-family home in ...	3 beds \| 3 baths \| 1,200 sq.ft.	$488,888	Airbnb cash on cash: 8.24% Traditional cash on cash: 4.4% Airbnb Rental Income: $5856 Traditional Rental Income: $2933 Airbnb ROI: 8.24% Traditional ROI: 4.4%
200 Coverly Avenue New York , NY Experience the ultimate in transformative living, surrounded by nature and awakened to bre...	5 beds \| 4 baths \| 3,801 sq.ft.	$1,899,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.09% Airbnb Rental Income: $null Traditional Rental Income: $5073 Airbnb ROI: N/A Traditional ROI: 1.09%
17 Waterstone Road Greenwood Lake , NY 🌊 A Must-See Greenwood Lake Gem - Pictures Can't Capture These Views! 🌊Thi...	3 beds \| 3 baths \| 1,564 sq.ft.	$649,900	Airbnb cash on cash: 2% Traditional cash on cash: 3.15% Airbnb Rental Income: $3470 Traditional Rental Income: $3400 Airbnb ROI: 2% Traditional ROI: 3.15%
183-36 Dunlop Avenue New York , NY Discover this meticulously maintained brick home in the vibrant neighborhood of St. Albans...	5 beds \| 2 baths \| 1,694 sq.ft.	$698,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.92% Airbnb Rental Income: $null Traditional Rental Income: $3768 Airbnb ROI: N/A Traditional ROI: 3.92%
16 Mapleton Avenue New York , NY Lot size 20x100, building size 12x55, Zoning R3-1. It is a great opportunity to use or inv...	2 beds \| 1 baths \| 528 sq.ft.	$350,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 4.96% Airbnb Rental Income: $2049 Traditional Rental Income: $2147 Airbnb ROI: 3.05% Traditional ROI: 4.96%
144 Winchester Avenue New York , NY Location, location, location! This beautifully renovated single-family detached home is ne...	2 beds \| 2 baths \| 1,000 sq.ft.	$769,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 1.53% Airbnb Rental Income: $1482 Traditional Rental Income: $2430 Airbnb ROI: -0.4% Traditional ROI: 1.53%

Real Estate investment in Windsor, NY

There are 4 properties for sale in the city of Windsor . The median list price in Windsor is $239,500 and the average price per square foot is $96. In September 2025, the average monthly cash on cash return in Windsor is 8.00%. The average monthly rental income in Windsor is $2,472.

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

There are 4 investment properties available for sale in Windsor.

In 2025, 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 $2,472.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, NY

945 Anne Road

Windsor, NY

3 beds | 2 baths | 2,100 sq.ft.

$164,000

Airbnb cash on cash: 0.2%

Traditional cash on cash: 11.43%

Airbnb Rental Income: $880

Traditional Rental Income: $2302

Airbnb ROI: 0.2%

Traditional ROI: 11.43%

280 Dodd Rd

Windsor, NY

4 beds | 5 baths | 5,374 sq.ft.

$1,299,000

Airbnb cash on cash: -0.1%

Traditional cash on cash: 2.08%

Airbnb Rental Income: $3887

Traditional Rental Income: $5690

Airbnb ROI: -0.1%

Traditional ROI: 2.08%

Investment Properties for Sale in Other Cities of New-york

Inwood , NY

4 beds | 3 baths | 1,350 sq.ft.

$599,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $1452

Traditional Rental Income: $3124

Airbnb ROI: -0.17%

Traditional ROI: 3.59%

Rochester , NY

3 beds | 2 baths | 1,591 sq.ft.

$144,900

Airbnb cash on cash: 6.12%

Traditional cash on cash: 11.35%

Airbnb Rental Income: $1942

Traditional Rental Income: $2155

Airbnb ROI: 6.12%

Traditional ROI: 11.35%

Rochester , NY

3 beds | 4 baths | 2,214 sq.ft.

$375,000

Airbnb cash on cash: 0.25%

Traditional cash on cash: 5.74%

Airbnb Rental Income: $1931

Traditional Rental Income: $3353

Airbnb ROI: 0.25%

Traditional ROI: 5.74%

New York , NY

5 beds | 2 baths | 1,333 sq.ft.

$649,999

Airbnb cash on cash: 9.69%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $8645

Traditional Rental Income: $3648

Airbnb ROI: 9.69%

Traditional ROI: 4.14%

New York , NY

2 beds | 2 baths | 1,200 sq.ft.

$649,000

Airbnb cash on cash: 1.31%

Traditional cash on cash: 2.19%

Airbnb Rental Income: $3258

Traditional Rental Income: $3059

Airbnb ROI: 1.31%

Traditional ROI: 2.19%

New York , NY

4 beds | 3 baths | 1,716 sq.ft.

$880,000

Airbnb cash on cash: 7.28%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $9164

Traditional Rental Income: $3738

Airbnb ROI: 7.28%

Traditional ROI: 2.76%

New York , NY

3 beds | 2 baths | 1,130 sq.ft.

$558,000

Airbnb cash on cash: -0.72%