Real Estate Investment Properties for Sale in Bennington, VT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
32 Albe Drive Bennington, VT MOVE RIGHT IN AND MAKE YOURSELF AT HOME This beautifully maintained residence is perfect f...	2 beds \| 1 baths \| 2,142 sq.ft.	$277,700	Airbnb cash on cash: 3.61% Traditional cash on cash: 6.37% Airbnb Rental Income: $2045 Traditional Rental Income: $2237 Airbnb ROI: 3.61% Traditional ROI: 6.37%
99 Coolidge Avenue Bennington, VT This cute 3-bedroom, 1-bath cape offers comfortable in-town living with a fully fenced yar...	3 beds \| 1 baths \| 1,047 sq.ft.	$219,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 7.45% Airbnb Rental Income: $1295 Traditional Rental Income: $2157 Airbnb ROI: 1.34% Traditional ROI: 7.45%
205 County Street Bennington, VT This well maintained 2-unit home exceptional flexibility for buyers, allowing for a variet...	5 beds \| 2 baths \| 1,860 sq.ft.	$235,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 11.75% Airbnb Rental Income: $1085 Traditional Rental Income: $3379 Airbnb ROI: -0.24% Traditional ROI: 11.75%
318 North Street Bennington, VT Versatile mixed-use property with strong potential as a duplex or owner-occupied investmen...	N/A beds \| N/A baths \| 1,680 sq.ft.	$275,000	Airbnb cash on cash: -1.73% Traditional cash on cash: 4.15% Airbnb Rental Income: $645 Traditional Rental Income: $1874 Airbnb ROI: -1.73% Traditional ROI: 4.15%
683 Water St Bennington, VT Much larger than it looks and completely redone in 2022, with the only evidence remaining ...	3 beds \| 2 baths \| 1,500 sq.ft.	$339,900	Airbnb cash on cash: -0.01% Traditional cash on cash: 4.34% Airbnb Rental Income: $1295 Traditional Rental Income: $2280 Airbnb ROI: -0.01% Traditional ROI: 4.34%
113 Main Street Bennington, VT Charming downtown family home with modern upgrades and timeless appeal. This beautifully u...	3 beds \| 1 baths \| 1,092 sq.ft.	$230,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 5.71% Airbnb Rental Income: $1295 Traditional Rental Income: $1788 Airbnb ROI: 1.59% Traditional ROI: 5.71%
19 Royal St Bennington, VT Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after N...	4 beds \| 1 baths \| 1,735 sq.ft.	$365,000	Airbnb cash on cash: -1.62% Traditional cash on cash: 4.16% Airbnb Rental Income: $739 Traditional Rental Income: $2407 Airbnb ROI: -1.62% Traditional ROI: 4.16%
100 McCarthy Acres Rd Bennington, VT Nearly Lakefront Living in the Heart of North Bennington! Come for the space-stay for the ...	5 beds \| 3 baths \| 2,938 sq.ft.	$359,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.37% Airbnb Rental Income: $null Traditional Rental Income: $4256 Airbnb ROI: N/A Traditional ROI: 10.37%
126 Washington Avenue Bennington, VT Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Benn...	6 beds \| 3 baths \| 5,208 sq.ft.	$399,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 9.3% Airbnb Rental Income: $1085 Traditional Rental Income: $4529 Airbnb ROI: -0.9% Traditional ROI: 9.3%
38 Oak Ridge Lane Bennington, VT Convenient one-level living meets modern style and design in this beautifully crafted ranc...	3 beds \| 2 baths \| 1,404 sq.ft.	$359,900	Airbnb cash on cash: 0.43% Traditional cash on cash: 6.57% Airbnb Rental Income: $1295 Traditional Rental Income: $2964 Airbnb ROI: 0.43% Traditional ROI: 6.57%
124 Elm Street Bennington, VT An exceptional opportunity to own a prominent historic Victorian property in the heart of ...	N/A beds \| N/A baths \| 8,888 sq.ft.	$950,000	Airbnb cash on cash: -2.55% Traditional cash on cash: -0.78% Airbnb Rental Income: $645 Traditional Rental Income: $1909 Airbnb ROI: -2.55% Traditional ROI: -0.78%
856 Matteson Road Bennington, VT Nestled on 5 private acres, this custom-built log home offers the perfect blend of rustic ...	3 beds \| 2 baths \| 2,501 sq.ft.	$579,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 3.6% Airbnb Rental Income: $1295 Traditional Rental Income: $3325 Airbnb ROI: -0.9% Traditional ROI: 3.6%

Real Estate investment in Bennington, VT

There are 17 properties for sale in the city of Bennington . The median list price in Bennington is $273,609 and the average price per square foot is $114. In June 2026, the average monthly cash on cash return in Bennington is 8.00%. The average monthly rental income in Bennington is $2,347.

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

There are 17 investment properties available for sale in Bennington.

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

The ROI for Long-Term is higher than the Short-Term in Bennington with average rental income of $2,347.

Your search for investment property begins and ends here

Investment Property for Sale in Bennington, VT

32 Albe Drive

Bennington, VT

2 beds | 1 baths | 2,142 sq.ft.

$277,700

Airbnb cash on cash: 3.61%

Traditional cash on cash: 6.37%

Airbnb Rental Income: $2045

Traditional Rental Income: $2237

Airbnb ROI: 3.61%

Traditional ROI: 6.37%

99 Coolidge Avenue

Bennington, VT

3 beds | 1 baths | 1,047 sq.ft.

$219,000

Airbnb cash on cash: 1.34%

Traditional cash on cash: 7.45%

Airbnb Rental Income: $1295

Traditional Rental Income: $2157

Airbnb ROI: 1.34%

Traditional ROI: 7.45%

205 County Street

Bennington, VT

5 beds | 2 baths | 1,860 sq.ft.

$235,000

Airbnb cash on cash: -0.24%

Traditional cash on cash: 11.75%

Airbnb Rental Income: $1085

Traditional Rental Income: $3379

Airbnb ROI: -0.24%

Traditional ROI: 11.75%

318 North Street

Bennington, VT

N/A beds | N/A baths | 1,680 sq.ft.

$275,000

Airbnb cash on cash: -1.73%

Traditional cash on cash: 4.15%

Airbnb Rental Income: $645

Traditional Rental Income: $1874

Airbnb ROI: -1.73%

Traditional ROI: 4.15%

683 Water St

Bennington, VT

3 beds | 2 baths | 1,500 sq.ft.

$339,900

Airbnb cash on cash: -0.01%

Traditional cash on cash: 4.34%

Airbnb Rental Income: $1295

Traditional Rental Income: $2280

Airbnb ROI: -0.01%

Traditional ROI: 4.34%

113 Main Street

Bennington, VT

3 beds | 1 baths | 1,092 sq.ft.

$230,000

Airbnb cash on cash: 1.59%

Traditional cash on cash: 5.71%

Airbnb Rental Income: $1295

Traditional Rental Income: $1788

Airbnb ROI: 1.59%

Traditional ROI: 5.71%

19 Royal St

Bennington, VT

4 beds | 1 baths | 1,735 sq.ft.

$365,000

Airbnb cash on cash: -1.62%

Traditional cash on cash: 4.16%

Airbnb Rental Income: $739

Traditional Rental Income: $2407

Airbnb ROI: -1.62%

Traditional ROI: 4.16%

100 McCarthy Acres Rd

Bennington, VT

5 beds | 3 baths | 2,938 sq.ft.

$359,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.37%

Airbnb Rental Income: $null

Traditional Rental Income: $4256

Airbnb ROI: N/A