Real Estate Investment Properties for Sale in Winhall, VT

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
14 Old Ridge Road Winhall, VT This mountain home is beautifully furnished with a refined design that perfectly balances ...	4 beds \| 4 baths \| 4,270 sq.ft.	$1,975,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 0.43% Airbnb Rental Income: $2966 Traditional Rental Income: $4323 Airbnb ROI: -0.68% Traditional ROI: 0.43%
17 Signal Hill Road Winhall, VT 17 Signal Hill Road offers Vermont charm in a secluded mountain setting. With over 2,400 s...	5 beds \| 4 baths \| 2,468 sq.ft.	$599,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 5.88% Airbnb Rental Income: $2652 Traditional Rental Income: $4694 Airbnb ROI: 1.1% Traditional ROI: 5.88%
Investment Properties for Sale in Other Cities of Vermont
133 East Mountain Road #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: 1.38% Airbnb Rental Income: $1259 Traditional Rental Income: $1814 Airbnb ROI: -2.86% Traditional ROI: 1.38%
41 Two Brook Drive Wilmington , VT Fantastic four-season upscale 4bdrm/5 bath home just minutes from Hermitage Club, Mount Sn...	4 beds \| 5 baths \| 3,420 sq.ft.	$939,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 5.25% Airbnb Rental Income: $1976 Traditional Rental Income: $6604 Airbnb ROI: -0.63% Traditional ROI: 5.25%
22 Lower Howes Road #A89 Wilmington , VT Section A - end of the road, low on the Hill, this Chalet style home has a lot of desirabl...	3 beds \| 2 baths \| 2,100 sq.ft.	$514,999	Airbnb cash on cash: 0.01% Traditional cash on cash: 4.2% Airbnb Rental Income: $1685 Traditional Rental Income: $3232 Airbnb ROI: 0.01% Traditional ROI: 4.2%
153 Westminster Road Putney , VT Combining the charm of an 1820's fully restored historic home, with a 1,600 sq. ft. additi...	4 beds \| 3 baths \| 3,104 sq.ft.	$695,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 3.6% Airbnb Rental Income: $2644 Traditional Rental Income: $4103 Airbnb ROI: 0.38% Traditional ROI: 3.6%
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: 0.11% Traditional cash on cash: 3.02% Airbnb Rental Income: $1916 Traditional Rental Income: $2959 Airbnb ROI: 0.11% Traditional ROI: 3.02%
16 Nutmeg Lane Dover , VT Step into this warm, inviting home, and you may never want to leave. Tucked away on a priv...	3 beds \| 2 baths \| 2,000 sq.ft.	$519,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 3.87% Airbnb Rental Income: $1369 Traditional Rental Income: $3247 Airbnb ROI: -0.86% Traditional ROI: 3.87%
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.	$480,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 4.45% Airbnb Rental Income: $1369 Traditional Rental Income: $3189 Airbnb ROI: -0.53% Traditional ROI: 4.45%
320 Old Bow Road Weathersfield , VT Spacious Country Retreat with Stunning Views! Experience the perfect blend of space, priva...	4 beds \| 5 baths \| 4,009 sq.ft.	$997,000	Airbnb cash on cash: 0% Traditional cash on cash: 5.05% Airbnb Rental Income: $2584 Traditional Rental Income: $6647 Airbnb ROI: 0% Traditional ROI: 5.05%
3 Church Street Brandon , VT * OPEN HOUSE-September 21st from 2:00-4:00 * Enjoy the charm of small-town living with th...	3 beds \| 2 baths \| 1,195 sq.ft.	$270,000	Airbnb cash on cash: 3.32% Traditional cash on cash: 9.97% Airbnb Rental Income: $2018 Traditional Rental Income: $3186 Airbnb ROI: 3.32% Traditional ROI: 9.97%
8 Hillside Acres Vergennes , VT Discover this beautifully reimagined 3-bedroom, 1.5-bath home in a peaceful country-style ...	3 beds \| 2 baths \| 1,505 sq.ft.	$374,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.17% Airbnb Rental Income: $null Traditional Rental Income: $3062 Airbnb ROI: N/A Traditional ROI: 6.17%
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%
6141 VT Route 15 Wolcott , VT Donât miss this wonderful single-level homeâeasy to maintain and truly move-in ready! ...	3 beds \| 1 baths \| 2,192 sq.ft.	$275,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 5.68% Airbnb Rental Income: $1503 Traditional Rental Income: $2151 Airbnb ROI: 1.48% Traditional ROI: 5.68%

Real Estate investment in Winhall, VT

There are 3 properties for sale in the city of Winhall . The median list price in Winhall is $719,000 and the average price per square foot is $244. In December 2025, the average monthly cash on cash return in Winhall is 1.00%. The average monthly rental income in Winhall is $4,156.

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

There are 3 investment properties available for sale in Winhall.

In 2025, the best neighborhood to buy investment property is Winhall.

The ROI for Long-Term is higher than the Short-Term in Winhall with average rental income of $4,156.

Your search for investment property begins and ends here

Investment Property for Sale in Winhall, VT

14 Old Ridge Road

Winhall, VT

4 beds | 4 baths | 4,270 sq.ft.

$1,975,000

Airbnb cash on cash: -0.68%

Traditional cash on cash: 0.43%

Airbnb Rental Income: $2966

Traditional Rental Income: $4323

Airbnb ROI: -0.68%

Traditional ROI: 0.43%

17 Signal Hill Road

Winhall, VT

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

$599,000

Airbnb cash on cash: 1.1%

Traditional cash on cash: 5.88%

Airbnb Rental Income: $2652

Traditional Rental Income: $4694

Airbnb ROI: 1.1%

Traditional ROI: 5.88%

Investment Properties for Sale in Other Cities of Vermont

Killington , VT

2 beds | 2 baths | 913 sq.ft.

$238,000

Airbnb cash on cash: -2.86%

Traditional cash on cash: 1.38%

Airbnb Rental Income: $1259

Traditional Rental Income: $1814

Airbnb ROI: -2.86%

Traditional ROI: 1.38%

Wilmington , VT

4 beds | 5 baths | 3,420 sq.ft.

$939,000

Airbnb cash on cash: -0.63%

Traditional cash on cash: 5.25%

Airbnb Rental Income: $1976

Traditional Rental Income: $6604

Airbnb ROI: -0.63%

Traditional ROI: 5.25%

Wilmington , VT

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

$514,999

Airbnb cash on cash: 0.01%

Traditional cash on cash: 4.2%

Airbnb Rental Income: $1685

Traditional Rental Income: $3232

Airbnb ROI: 0.01%

Traditional ROI: 4.2%

Putney , VT

4 beds | 3 baths | 3,104 sq.ft.

$695,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $2644

Traditional Rental Income: $4103

Airbnb ROI: 0.38%

Traditional ROI: 3.6%

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%

Dover , VT

3 beds | 2 baths | 2,000 sq.ft.

$519,000

Airbnb cash on cash: -0.86%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $1369

Traditional Rental Income: $3247

Airbnb ROI: -0.86%

Traditional ROI: 3.87%

Dover , VT

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

$480,000

Airbnb cash on cash: -0.53%