Real Estate Investment Properties for Sale in West Windsor, VT

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
166 Jewett Road West Windsor, VT Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restora...	5 beds \| 5 baths \| 3,212 sq.ft.	$3,350,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.8% Airbnb Rental Income: $null Traditional Rental Income: $6845 Airbnb ROI: N/A Traditional ROI: 0.8%
325 Cemetery Road West Windsor, VT Farm at Gaelic Crossing is an equestrian property set on 26.72Â± acres, has dramatic views...	4 beds \| 2 baths \| 2,554 sq.ft.	$1,325,000	Airbnb cash on cash: -1.47% Traditional cash on cash: -0.26% Airbnb Rental Income: $2298 Traditional Rental Income: $3218 Airbnb ROI: -1.47% Traditional ROI: -0.26%
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.	$569,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 3.99% Airbnb Rental Income: $1535 Traditional Rental Income: $3417 Airbnb ROI: -0.38% Traditional ROI: 3.99%
1329 Newfane Road Wardsboro , VT Nature lovers rejoice! Escape to the charm of rural Vermont with this rustic cottage retre...	3 beds \| 1 baths \| 1,192 sq.ft.	$319,900	Airbnb cash on cash: 0.88% Traditional cash on cash: 4.32% Airbnb Rental Income: $1374 Traditional Rental Income: $1990 Airbnb ROI: 0.88% Traditional ROI: 4.32%
225 Spectacle Pond Road 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: -1.94% Traditional cash on cash: 3.02% Airbnb Rental Income: $607 Traditional Rental Income: $2959 Airbnb ROI: -1.94% Traditional ROI: 3.02%
15 Bears Den Road Dover , VT A rare opportunity to enjoy the best of both worlds â the privacy of a single-family hom...	3 beds \| 3 baths \| 2,016 sq.ft.	$775,000	Airbnb cash on cash: -1.67% Traditional cash on cash: 1.33% Airbnb Rental Income: $994 Traditional Rental Income: $2804 Airbnb ROI: -1.67% Traditional ROI: 1.33%
12 Hamilton Place Richford , VT Spacious, affordable, move-in ready village home. Detached garage with room for storage. L...	3 beds \| 2 baths \| 1,780 sq.ft.	$225,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.94% Airbnb Rental Income: $null Traditional Rental Income: $3127 Airbnb ROI: N/A Traditional ROI: 11.94%
350 Main St Castleton , VT Beautiful 1890 farm house located in a quant college town. Walking distance to Amtrak sta...	N/A beds \| 3 baths \| 2,769 sq.ft.	$450,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 3.11% Airbnb Rental Income: $549 Traditional Rental Income: $2089 Airbnb ROI: -1.21% Traditional ROI: 3.11%
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: 1.45% Traditional cash on cash: 3.94% Airbnb Rental Income: $2815 Traditional Rental Income: $3543 Airbnb ROI: 1.45% Traditional ROI: 3.94%
1422 Cabot Road Woodbury , VT Country contemporary home features 4 beds,1-1/2 baths. A main level bedroom,half bath and ...	4 beds \| 2 baths \| 1,530 sq.ft.	$389,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 6.4% Airbnb Rental Income: $1062 Traditional Rental Income: $3162 Airbnb ROI: -0.36% Traditional ROI: 6.4%
1511 West Hill Road Lincoln , VT Fall in love with the great outdoors at this spectacular hill side contemporary home with ...	3 beds \| 3 baths \| 3,036 sq.ft.	$715,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 3.1% Airbnb Rental Income: $2597 Traditional Rental Income: $3811 Airbnb ROI: 0.34% Traditional ROI: 3.1%

Real Estate investment in West-windsor, VT

There are 2 properties for sale in the city of West Windsor . The median list price in West Windsor is $1,325,000 and the average price per square foot is $613. In May 2026, the average monthly cash on cash return in West Windsor is 3.00%. The average monthly rental income in West Windsor is $3,585.

West-windsor, VT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 2 investment properties available for sale in West-windsor.

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

The ROI for Short-Term is higher than the Long-Term in West-windsor with average rental income of $1,586.

Your search for investment property begins and ends here

Investment Property for Sale in West Windsor, VT

166 Jewett Road

West Windsor, VT

5 beds | 5 baths | 3,212 sq.ft.

$3,350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.8%

Airbnb Rental Income: $null

Traditional Rental Income: $6845

Airbnb ROI: N/A

Traditional ROI: 0.8%

325 Cemetery Road

West Windsor, VT

4 beds | 2 baths | 2,554 sq.ft.

$1,325,000

Airbnb cash on cash: -1.47%

Traditional cash on cash: -0.26%

Airbnb Rental Income: $2298

Traditional Rental Income: $3218

Airbnb ROI: -1.47%

Traditional ROI: -0.26%

Investment Properties for Sale in Other Cities of Vermont

Killington , VT

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

$569,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 3.99%

Airbnb Rental Income: $1535

Traditional Rental Income: $3417

Airbnb ROI: -0.38%

Traditional ROI: 3.99%

Wardsboro , VT

3 beds | 1 baths | 1,192 sq.ft.

$319,900

Airbnb cash on cash: 0.88%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $1374

Traditional Rental Income: $1990

Airbnb ROI: 0.88%

Traditional ROI: 4.32%

Brighton , VT

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

$569,900

Airbnb cash on cash: -1.94%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $607

Traditional Rental Income: $2959

Airbnb ROI: -1.94%

Traditional ROI: 3.02%

Dover , VT

3 beds | 3 baths | 2,016 sq.ft.

$775,000

Airbnb cash on cash: -1.67%

Traditional cash on cash: 1.33%

Airbnb Rental Income: $994

Traditional Rental Income: $2804

Airbnb ROI: -1.67%

Traditional ROI: 1.33%

Richford , VT

3 beds | 2 baths | 1,780 sq.ft.

$225,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.94%

Airbnb Rental Income: $null

Traditional Rental Income: $3127

Airbnb ROI: N/A

Traditional ROI: 11.94%

Castleton , VT

N/A beds | 3 baths | 2,769 sq.ft.

$450,000

Airbnb cash on cash: -1.21%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $549

Traditional Rental Income: $2089

Airbnb ROI: -1.21%

Traditional ROI: 3.11%

Waterbury , VT

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

$597,000

Airbnb cash on cash: 1.45%