Real Estate Investment Properties for Sale in Windsor, VT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
223 Taylor Drive Windsor, VT This lovely home has plenty of sunny light filled space. Home features a large kitchen/eat...	4 beds \| 3 baths \| 2,468 sq.ft.	$615,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.78% Airbnb Rental Income: $null Traditional Rental Income: $3946 Airbnb ROI: N/A Traditional ROI: 3.78%
Investment Properties for Sale in Other Cities of Vermont
303 Winding Way Killington , VT Nestled at the top of a quiet dead-end road, this 4-bedroom single-family home sits on a g...	4 beds \| 3 baths \| 1,750 sq.ft.	$599,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 3.75% Airbnb Rental Income: $1963 Traditional Rental Income: $3417 Airbnb ROI: 0.22% Traditional ROI: 3.75%
133 E Mountain Rd #3A1 Killington , VT 2-Bedroom, 2-Bath Unit in Mountain Green â Building 3 Welcome to this inviting 2-bedroom...	2 beds \| 2 baths \| 913 sq.ft.	$238,000	Airbnb cash on cash: -2.86% Traditional cash on cash: 3.48% Airbnb Rental Income: $1259 Traditional Rental Income: $2286 Airbnb ROI: -2.86% Traditional ROI: 3.48%
41 Two Brook Dr Wilmington , VT Fantastic four-season upscale 4bdrm/5 bath home just minutes from Hermitage Club, Mount Sn...	4 beds \| 3 baths \| 3,420 sq.ft.	$898,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 5.54% Airbnb Rental Income: $1976 Traditional Rental Income: $6604 Airbnb ROI: -0.62% Traditional ROI: 5.54%
225 Spectacle Pond Rd Brighton , VT Discover year-round lakeside living with this inviting 3-bedroom, 2-bath home on the shore...	2 beds \| 2 baths \| 2,358 sq.ft.	$569,900	Airbnb cash on cash: 0.11% Traditional cash on cash: 3.02% Airbnb Rental Income: $1916 Traditional Rental Income: $2959 Airbnb ROI: 0.11% Traditional ROI: 3.02%
24 Antler Loop Dover , VT This charming 3-bedroom, 2-bath dutch colonial home sits atop a knoll, overlooking a pictu...	3 beds \| 2 baths \| 1,943 sq.ft.	$470,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 4.56% Airbnb Rental Income: $1369 Traditional Rental Income: $3189 Airbnb ROI: -0.52% Traditional ROI: 4.56%
1576 RIPLEY ROAD Waterbury , VT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2.5 baths \| 2,305 sq.ft.	$597,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 3.94% Airbnb Rental Income: $4294 Traditional Rental Income: $3543 Airbnb ROI: 3.66% Traditional ROI: 3.94%
1422 Cabot Rd Woodbury , VT Country contemporary home features 4 beds,1-1/2 baths. A main level bedroom,half bath and ...	4 beds \| 1 baths \| 1,530 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.22% Airbnb Rental Income: $null Traditional Rental Income: $3162 Airbnb ROI: N/A Traditional ROI: 6.22%

Real Estate investment in Windsor, VT

There are 1 properties for sale in the city of Windsor . The median list price in Windsor is $640,000 and the average price per square foot is $195. In February 2026, the average monthly cash on cash return in Windsor is 4.00%. The average monthly rental income in Windsor is $3,946.

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

There are 1 investment properties available for sale in Windsor.

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

The ROI for Short-Term is higher than the Long-Term in Windsor with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, VT

223 Taylor Drive

Windsor, VT

4 beds | 3 baths | 2,468 sq.ft.

$615,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.78%

Airbnb Rental Income: $null

Traditional Rental Income: $3946

Airbnb ROI: N/A

Traditional ROI: 3.78%

Investment Properties for Sale in Other Cities of Vermont

303 Winding Way

Killington , VT

4 beds | 3 baths | 1,750 sq.ft.

$599,000

Airbnb cash on cash: 0.22%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $1963

Traditional Rental Income: $3417

Airbnb ROI: 0.22%

Traditional ROI: 3.75%

133 E Mountain Rd #3A1

Killington , VT

2 beds | 2 baths | 913 sq.ft.

$238,000

Airbnb cash on cash: -2.86%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $1259

Traditional Rental Income: $2286

Airbnb ROI: -2.86%

Traditional ROI: 3.48%

41 Two Brook Dr

Wilmington , VT

4 beds | 3 baths | 3,420 sq.ft.

$898,000

Airbnb cash on cash: -0.62%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $1976

Traditional Rental Income: $6604

Airbnb ROI: -0.62%

Traditional ROI: 5.54%

225 Spectacle Pond Rd

Brighton , VT

2 beds | 2 baths | 2,358 sq.ft.

$569,900

Airbnb cash on cash: 0.11%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $1916

Traditional Rental Income: $2959

Airbnb ROI: 0.11%

Traditional ROI: 3.02%

24 Antler Loop

Dover , VT

3 beds | 2 baths | 1,943 sq.ft.

$470,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $1369

Traditional Rental Income: $3189

Airbnb ROI: -0.52%

Traditional ROI: 4.56%

1576 RIPLEY ROAD

Waterbury , VT

3 beds | 2.5 baths | 2,305 sq.ft.

$597,000

Airbnb cash on cash: 3.66%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $4294

Traditional Rental Income: $3543

Airbnb ROI: 3.66%

Traditional ROI: 3.94%

1422 Cabot Rd

Woodbury , VT

4 beds | 1 baths | 1,530 sq.ft.

$399,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.22%

Airbnb Rental Income: $null

Traditional Rental Income: $3162