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
205 County Street Bennington, VT This well maintained 2-unit home exceptional flexibility for buyers, allowing for a varie...	5 beds \| 2 baths \| 1,860 sq.ft.	$235,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 11.75% Airbnb Rental Income: $1723 Traditional Rental Income: $3379 Airbnb ROI: 2.16% 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: -1.66% Traditional cash on cash: 4.15% Airbnb Rental Income: $668 Traditional Rental Income: $1874 Airbnb ROI: -1.66% 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: -0.06% Traditional cash on cash: 4.53% Airbnb Rental Income: $1204 Traditional Rental Income: $2280 Airbnb ROI: -0.06% Traditional ROI: 4.53%
113 Main Street Bennington, VT Charming downtown family home with modern upgrades. This beautifully updated 3-bedroom hom...	3 beds \| 1 baths \| 1,092 sq.ft.	$230,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 5.71% Airbnb Rental Income: $1204 Traditional Rental Income: $1788 Airbnb ROI: 1.24% Traditional ROI: 5.71%
210 Division Street Bennington, VT Turnkey Two-Unit Investment Opportunity in a Prime Downtown Location! This beautifully ren...	4 beds \| 2 baths \| 1,980 sq.ft.	$199,000	Airbnb cash on cash: -1.1% Traditional cash on cash: 8.6% Airbnb Rental Income: $735 Traditional Rental Income: $2257 Airbnb ROI: -1.1% Traditional ROI: 8.6%
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: -1.63% Traditional cash on cash: 4.16% Airbnb Rental Income: $735 Traditional Rental Income: $2407 Airbnb ROI: -1.63% Traditional ROI: 4.16%
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: 0.21% Traditional cash on cash: 6.57% Airbnb Rental Income: $1204 Traditional Rental Income: $2964 Airbnb ROI: 0.21% 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.	$975,000	Airbnb cash on cash: -2.49% Traditional cash on cash: -0.79% Airbnb Rental Income: $668 Traditional Rental Income: $1909 Airbnb ROI: -2.49% Traditional ROI: -0.79%
106 Park Street #2 Bennington, VT Freshly updated 2-story townhouse in a convenient downtown Bennington location! This 2BR h...	2 beds \| 3 baths \| 1,156 sq.ft.	$199,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 9.39% Airbnb Rental Income: $1784 Traditional Rental Income: $2668 Airbnb ROI: 2.14% Traditional ROI: 9.39%
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: -1.04% Traditional cash on cash: 3.6% Airbnb Rental Income: $1204 Traditional Rental Income: $3325 Airbnb ROI: -1.04% Traditional ROI: 3.6%
20 Sage St Bennington, VT 20 Sage St, Bennington, VT 05257 \| Single Family Residential	4 beds \| 1 baths \| 1,127 sq.ft.	$219,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 8.71% Airbnb Rental Income: $735 Traditional Rental Income: $2494 Airbnb ROI: -1.28% Traditional ROI: 8.71%
8 West St Bennington, VT 8 West St, Bennington, VT 05257 \| Single Family Residential	3 beds \| 1 baths \| 1,408 sq.ft.	$299,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 5.13% Airbnb Rental Income: $1204 Traditional Rental Income: $2345 Airbnb ROI: -0.31% Traditional ROI: 5.13%

Real Estate investment in Bennington, VT

There are 20 properties for sale in the city of Bennington . The median list price in Bennington is $404,990 and the average price per square foot is $168. In May 2026, the average monthly cash on cash return in Bennington is 7.00%. The average monthly rental income in Bennington is $2,551.

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

There are 20 investment properties available for sale in Bennington.

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

The ROI for Short-Term is higher than the Long-Term in Bennington with average rental income of $1,204.

Your search for investment property begins and ends here

Investment Property for Sale in Bennington, VT

205 County Street

Bennington, VT

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

$235,000

Airbnb cash on cash: 2.16%

Traditional cash on cash: 11.75%

Airbnb Rental Income: $1723

Traditional Rental Income: $3379

Airbnb ROI: 2.16%

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: -1.66%

Traditional cash on cash: 4.15%

Airbnb Rental Income: $668

Traditional Rental Income: $1874

Airbnb ROI: -1.66%

Traditional ROI: 4.15%

683 Water St

Bennington, VT

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

$339,900

Airbnb cash on cash: -0.06%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $1204

Traditional Rental Income: $2280

Airbnb ROI: -0.06%

Traditional ROI: 4.53%

113 Main Street

Bennington, VT

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

$230,000

Airbnb cash on cash: 1.24%

Traditional cash on cash: 5.71%

Airbnb Rental Income: $1204

Traditional Rental Income: $1788

Airbnb ROI: 1.24%

Traditional ROI: 5.71%

210 Division Street

Bennington, VT

4 beds | 2 baths | 1,980 sq.ft.

$199,000

Airbnb cash on cash: -1.1%

Traditional cash on cash: 8.6%

Airbnb Rental Income: $735

Traditional Rental Income: $2257

Airbnb ROI: -1.1%

Traditional ROI: 8.6%

19 Royal St

Bennington, VT

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

$365,000

Airbnb cash on cash: -1.63%

Traditional cash on cash: 4.16%

Airbnb Rental Income: $735

Traditional Rental Income: $2407

Airbnb ROI: -1.63%

Traditional ROI: 4.16%

38 Oak Ridge Lane

Bennington, VT

3 beds | 2 baths | 1,404 sq.ft.

$359,900

Airbnb cash on cash: 0.21%

Traditional cash on cash: 6.57%

Airbnb Rental Income: $1204

Traditional Rental Income: $2964

Airbnb ROI: 0.21%

Traditional ROI: 6.57%

124 Elm Street

Bennington, VT

N/A beds | N/A baths | 8,888 sq.ft.

$975,000

Airbnb cash on cash: -2.49%

Traditional cash on cash: -0.79%

Airbnb Rental Income: $668

Traditional Rental Income: $1909

Airbnb ROI: -2.49%