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: 3.47% Traditional cash on cash: 6.37% Airbnb Rental Income: $2002 Traditional Rental Income: $2237 Airbnb ROI: 3.47% Traditional ROI: 6.37%
305 Weeks Street Bennington, VT Experience refined living in this beautifully appointed tri-level townhouse-style condomin...	3 beds \| 2 baths \| 1,632 sq.ft.	$205,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 11.86% Airbnb Rental Income: $1810 Traditional Rental Income: $3002 Airbnb ROI: 3.21% Traditional ROI: 11.86%
107 Jefferson Avenue Bennington, VT Terrific in town location for this 3 bedroom, 2 bathroom home in Bennington. Offering livi...	3 beds \| 2 baths \| 1,608 sq.ft.	$225,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 11.05% Airbnb Rental Income: $1810 Traditional Rental Income: $3029 Airbnb ROI: 3.03% Traditional ROI: 11.05%
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: -0.71% Traditional cash on cash: 4.15% Airbnb Rental Income: $964 Traditional Rental Income: $1874 Airbnb ROI: -0.71% 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.	$319,900	Airbnb cash on cash: 1.48% Traditional cash on cash: 4.67% Airbnb Rental Income: $1810 Traditional Rental Income: $2280 Airbnb ROI: 1.48% Traditional ROI: 4.67%
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: 3.56% Traditional cash on cash: 5.71% Airbnb Rental Income: $1810 Traditional Rental Income: $1788 Airbnb ROI: 3.56% Traditional ROI: 5.71%
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.	$329,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 10.37% Airbnb Rental Income: $2567 Traditional Rental Income: $4256 Airbnb ROI: 3.53% Traditional ROI: 10.37%
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: 1.7% Traditional cash on cash: 6.57% Airbnb Rental Income: $1810 Traditional Rental Income: $2964 Airbnb ROI: 1.7% Traditional ROI: 6.57%
81 Honeysuckle Ln Bennington, VT 81 Honeysuckle Ln, Bennington, VT 05257 \| Single Family Residential	5 beds \| 3 baths \| 5,524 sq.ft.	$650,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 4.29% Airbnb Rental Income: $2473 Traditional Rental Income: $4448 Airbnb ROI: 0.05% Traditional ROI: 4.29%
1278 Harrington Rd Bennington, VT 1278 Harrington Rd, Bennington, VT 05201 \| Single Family Residential	3 beds \| 2 baths \| 2,379 sq.ft.	$595,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 2.38% Airbnb Rental Income: $1810 Traditional Rental Income: $3020 Airbnb ROI: -0.68% Traditional ROI: 2.38%

Real Estate investment in Bennington, VT

There are 18 properties for sale in the city of Bennington . The median list price in Bennington is $267,340 and the average price per square foot is $110. In September 2026, the average monthly cash on cash return in Bennington is 7.00%. The average monthly rental income in Bennington is $2,479.

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

There are 18 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 $2,479.

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: 3.47%

Traditional cash on cash: 6.37%

Airbnb Rental Income: $2002

Traditional Rental Income: $2237

Airbnb ROI: 3.47%

Traditional ROI: 6.37%

305 Weeks Street

Bennington, VT

3 beds | 2 baths | 1,632 sq.ft.

$205,000

Airbnb cash on cash: 3.21%

Traditional cash on cash: 11.86%

Airbnb Rental Income: $1810

Traditional Rental Income: $3002

Airbnb ROI: 3.21%

Traditional ROI: 11.86%

107 Jefferson Avenue

Bennington, VT

3 beds | 2 baths | 1,608 sq.ft.

$225,000

Airbnb cash on cash: 3.03%

Traditional cash on cash: 11.05%

Airbnb Rental Income: $1810

Traditional Rental Income: $3029

Airbnb ROI: 3.03%

Traditional ROI: 11.05%

318 North Street

Bennington, VT

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

$275,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 4.15%

Airbnb Rental Income: $964

Traditional Rental Income: $1874

Airbnb ROI: -0.71%

Traditional ROI: 4.15%

683 Water St

Bennington, VT

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

$319,900

Airbnb cash on cash: 1.48%

Traditional cash on cash: 4.67%

Airbnb Rental Income: $1810

Traditional Rental Income: $2280

Airbnb ROI: 1.48%

Traditional ROI: 4.67%

113 Main Street

Bennington, VT

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

$230,000

Airbnb cash on cash: 3.56%

Traditional cash on cash: 5.71%

Airbnb Rental Income: $1810

Traditional Rental Income: $1788

Airbnb ROI: 3.56%

Traditional ROI: 5.71%

100 McCarthy Acres Rd

Bennington, VT

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

$329,000

Airbnb cash on cash: 3.53%

Traditional cash on cash: 10.37%

Airbnb Rental Income: $2567

Traditional Rental Income: $4256

Airbnb ROI: 3.53%

Traditional ROI: 10.37%

38 Oak Ridge Lane

Bennington, VT

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

$359,900

Airbnb cash on cash: 1.7%

Traditional cash on cash: 6.57%

Airbnb Rental Income: $1810

Traditional Rental Income: $2964

Airbnb ROI: 1.7%