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
318 North St Bennington, VT A former florist shop for 2 decades, this mixed-use property is now a blank slate ready fo...	1 beds \| 1 baths \| 1,680 sq.ft.	$295,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.81% Airbnb Rental Income: $1036 Traditional Rental Income: $1874 Airbnb ROI: -0.51% Traditional ROI: 3.81%
2092 N Bennington Rd Bennington, VT Waterfront Bungalow style house offering 3 bedrooms and 2 bathrooms. This home has 2 bedro...	3 beds \| 1 baths \| 900 sq.ft.	$269,900	Airbnb cash on cash: 2.82% Traditional cash on cash: 6.81% Airbnb Rental Income: $1952 Traditional Rental Income: $2454 Airbnb ROI: 2.82% Traditional ROI: 6.81%
113 Main St 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: 4.1% Traditional cash on cash: 5.71% Airbnb Rental Income: $1952 Traditional Rental Income: $1788 Airbnb ROI: 4.1% Traditional ROI: 5.71%
112 Norton St Bennington, VT Move-in ready 2BR/1.5BA ranch on a sunny 0.27-acre lot offering comfort, updates, and easy...	2 beds \| 1 baths \| 1,564 sq.ft.	$295,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 6.07% Airbnb Rental Income: $1143 Traditional Rental Income: $2410 Airbnb ROI: 0.14% Traditional ROI: 6.07%
704 Fox Hill Rd Bennington, VT House hunting in Vermont and can't find what you want? Or it sold before you had time to ...	3 beds \| 2 baths \| 1,535 sq.ft.	$575,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 4.18% Airbnb Rental Income: $1952 Traditional Rental Income: $3067 Airbnb ROI: 1.14% Traditional ROI: 4.18%
126 Washington Ave Bennington, VT Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Benn...	6 beds \| N/A baths \| 5,208 sq.ft.	$399,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 8.91% Airbnb Rental Income: $2057 Traditional Rental Income: $4529 Airbnb ROI: 1.18% Traditional ROI: 8.91%
848 Coleville Rd Bennington, VT The House that Love Built-Multigenerational Comfort &Thoughtful Design Tucked away in a p...	4 beds \| 3 baths \| 2,030 sq.ft.	$425,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 6.4% Airbnb Rental Income: $1564 Traditional Rental Income: $3606 Airbnb ROI: 0.14% Traditional ROI: 6.4%
38 Oak Ridge Ln Bennington, VT Convenient one-level living meets modern style and design in this beautifully crafted ranc...	3 beds \| 2 baths \| 1,404 sq.ft.	$369,900	Airbnb cash on cash: 1.97% Traditional cash on cash: 6.37% Airbnb Rental Income: $1952 Traditional Rental Income: $2964 Airbnb ROI: 1.97% Traditional ROI: 6.37%
207 Silver St Bennington, VT Tastefully renovated antique home that retained it character 4 bed 2 bath home with gleam...	4 beds \| 2 baths \| 2,000 sq.ft.	$299,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 9.24% Airbnb Rental Income: $1564 Traditional Rental Income: $3384 Airbnb ROI: 1.18% Traditional ROI: 9.24%
726 Rice Ln Bennington, VT Welcome to this charming Cape-style home, nestled in a peaceful country setting just momen...	2 beds \| 2 baths \| 911 sq.ft.	$245,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 7.07% Airbnb Rental Income: $1143 Traditional Rental Income: $2297 Airbnb ROI: 0.44% Traditional ROI: 7.07%
103 Norton St Bennington, VT 103 Norton St, Bennington, VT 05201 \| Single Family Residential	4 beds \| 2 baths \| 1,728 sq.ft.	$339,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 6.79% Airbnb Rental Income: $1564 Traditional Rental Income: $3173 Airbnb ROI: 0.33% Traditional ROI: 6.79%
89 Merson St Bennington, VT 89 Merson St, Bennington, VT 05201 \| Single Family Residential	3 beds \| 1 baths \| 1,829 sq.ft.	$349,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 2.72% Airbnb Rental Income: $1952 Traditional Rental Income: $1876 Airbnb ROI: 1.34% Traditional ROI: 2.72%
14 Robinson Ave Bennington, VT 14 Robinson Ave, Bennington, VT 05201 \| Single Family Residential	3 beds \| 1 baths \| 1,254 sq.ft.	$219,500	Airbnb cash on cash: 3.6% Traditional cash on cash: 7.28% Airbnb Rental Income: $1952 Traditional Rental Income: $2203 Airbnb ROI: 3.6% Traditional ROI: 7.28%
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: -2.37% Traditional cash on cash: -0.79% Airbnb Rental Income: $790 Traditional Rental Income: $1909 Airbnb ROI: -2.37% Traditional ROI: -0.79%
682 Fox Hill Rd Bennington, VT Soak up the mountain view from a brand new custom built home. Desirable neighborhood with...	3 beds \| 2 baths \| 1,416 sq.ft.	$625,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 3.58% Airbnb Rental Income: $1952 Traditional Rental Income: $2975 Airbnb ROI: 0.95% Traditional ROI: 3.58%
16 West Rd Bennington, VT 16 West Rd, Bennington, VT 05201 \| Single Family Residential	7 beds \| 5 baths \| 6,392 sq.ft.	$1,495,000	Airbnb cash on cash: -1.86% Traditional cash on cash: 1.82% Airbnb Rental Income: $2057 Traditional Rental Income: $6639 Airbnb ROI: -1.86% Traditional ROI: 1.82%
328 Chester Knoll Dr Bennington, VT Well-maintained 2005 tri-level home offering comfortable, easy living in a desirable resid...	3 beds \| 3 baths \| 2,148 sq.ft.	$389,900	Airbnb cash on cash: 0.86% Traditional cash on cash: 7.6% Airbnb Rental Income: $1952 Traditional Rental Income: $3903 Airbnb ROI: 0.86% Traditional ROI: 7.6%
1086 West Rd Bennington, VT 1086 West Rd, Bennington, VT 05201 \| Single Family Residential	9 beds \| 5 baths \| 6,956 sq.ft.	$1,950,000	Airbnb cash on cash: -2.1% Traditional cash on cash: 0.42% Airbnb Rental Income: $2057 Traditional Rental Income: $6098 Airbnb ROI: -2.1% Traditional ROI: 0.42%
301 Northside Dr Bennington, VT 301 Northside Dr, Bennington, VT 05201 \| Other	N/A beds \| N/A baths \| N/A	$2,190,000	Airbnb cash on cash: -2.71% Traditional cash on cash: -2.33% Airbnb Rental Income: $790 Traditional Rental Income: $1227 Airbnb ROI: -2.71% Traditional ROI: -2.33%
720 N Branch St Bennington, VT 720 N Branch St, Bennington, VT 05201 \| Other	N/A beds \| N/A baths \| N/A	$1,950,000	Airbnb cash on cash: -2.68% Traditional cash on cash: -2.27% Airbnb Rental Income: $790 Traditional Rental Income: $1227 Airbnb ROI: -2.68% Traditional ROI: -2.27%
22 Morse Rd Bennington, VT 22 Morse Rd, Bennington, VT 05201 \| Other	N/A beds \| N/A baths \| N/A	$475,000	Airbnb cash on cash: -2.04% Traditional cash on cash: -0.33% Airbnb Rental Income: $790 Traditional Rental Income: $1227 Airbnb ROI: -2.04% Traditional ROI: -0.33%
1758 East Rd Bennington, VT 1758 East Rd, Bennington, VT 05201 \| Single Family Residential	2 beds \| 1 baths \| 1,064 sq.ft.	$265,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 4.08% Airbnb Rental Income: $1143 Traditional Rental Income: $1833 Airbnb ROI: -0.19% Traditional ROI: 4.08%

Real Estate investment in Bennington, VT

There are 28 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 $170. In March 2026, the average monthly cash on cash return in Bennington is 7.00%. The average monthly rental income in Bennington is $2,410.

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

There are 28 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 $2,410.

Your search for investment property begins and ends here

Investment Property for Sale in Bennington, VT

318 North St

Bennington, VT

1 beds | 1 baths | 1,680 sq.ft.

$295,000

Airbnb cash on cash: -0.51%

Traditional cash on cash: 3.81%

Airbnb Rental Income: $1036

Traditional Rental Income: $1874

Airbnb ROI: -0.51%

Traditional ROI: 3.81%

2092 N Bennington Rd

Bennington, VT

3 beds | 1 baths | 900 sq.ft.

$269,900

Airbnb cash on cash: 2.82%

Traditional cash on cash: 6.81%

Airbnb Rental Income: $1952

Traditional Rental Income: $2454

Airbnb ROI: 2.82%

Traditional ROI: 6.81%

113 Main St

Bennington, VT

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

$230,000

Airbnb cash on cash: 4.1%

Traditional cash on cash: 5.71%

Airbnb Rental Income: $1952

Traditional Rental Income: $1788

Airbnb ROI: 4.1%

Traditional ROI: 5.71%

112 Norton St

Bennington, VT

2 beds | 1 baths | 1,564 sq.ft.

$295,000

Airbnb cash on cash: 0.14%

Traditional cash on cash: 6.07%

Airbnb Rental Income: $1143

Traditional Rental Income: $2410

Airbnb ROI: 0.14%

Traditional ROI: 6.07%

704 Fox Hill Rd

Bennington, VT

3 beds | 2 baths | 1,535 sq.ft.

$575,000

Airbnb cash on cash: 1.14%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $1952

Traditional Rental Income: $3067

Airbnb ROI: 1.14%

Traditional ROI: 4.18%

126 Washington Ave

Bennington, VT

6 beds | N/A baths | 5,208 sq.ft.

$399,000

Airbnb cash on cash: 1.18%

Traditional cash on cash: 8.91%

Airbnb Rental Income: $2057

Traditional Rental Income: $4529

Airbnb ROI: 1.18%

Traditional ROI: 8.91%

848 Coleville Rd

Bennington, VT

4 beds | 3 baths | 2,030 sq.ft.

$425,000

Airbnb cash on cash: 0.14%

Traditional cash on cash: 6.4%

Airbnb Rental Income: $1564

Traditional Rental Income: $3606

Airbnb ROI: 0.14%

Traditional ROI: 6.4%

38 Oak Ridge Ln

Bennington, VT

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

$369,900

Airbnb cash on cash: 1.97%

Traditional cash on cash: 6.37%

Airbnb Rental Income: $1952

Traditional Rental Income: $2964

Airbnb ROI: 1.97%