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.

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Bennington, VT

Search for Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Bennington, Vermont. Browse all of Mashvisor’s Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 19 Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
318 North Street Bennington, VT A former florist shop for 2 decades, this mixed-use property is now a blank slate ready fo...	1 beds \| 2 baths \| 1,680 sq.ft.	$295,000	Airbnb cash on cash: -1.64% Traditional cash on cash: 3.81% Airbnb Rental Income: $661 Traditional Rental Income: $1874 Airbnb ROI: -1.64% Traditional ROI: 3.81%
2092 N Bennington Road Bennington, VT Waterfront Bungalow style house offering 3 bedrooms and 2 bathrooms. This home has 2 bedro...	3 beds \| 2 baths \| 900 sq.ft.	$269,900	Airbnb cash on cash: 0.67% Traditional cash on cash: 6.81% Airbnb Rental Income: $1294 Traditional Rental Income: $2454 Airbnb ROI: 0.67% Traditional ROI: 6.81%
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: 1.58% Traditional cash on cash: 5.71% Airbnb Rental Income: $1294 Traditional Rental Income: $1788 Airbnb ROI: 1.58% 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: -2.34% Traditional cash on cash: 8.6% Airbnb Rental Income: $456 Traditional Rental Income: $2257 Airbnb ROI: -2.34% Traditional ROI: 8.6%
704 Fox Hill Road 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: 0.12% Traditional cash on cash: 4.18% Airbnb Rental Income: $1294 Traditional Rental Income: $3067 Airbnb ROI: 0.12% Traditional ROI: 4.18%
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: -0.31% Traditional cash on cash: 9.3% Airbnb Rental Income: $1350 Traditional Rental Income: $4529 Airbnb ROI: -0.31% 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: $1294 Traditional Rental Income: $2964 Airbnb ROI: 0.43% Traditional ROI: 6.57%
726 Rice Lane Bennington, VT Welcome to this charming Cape-style home, nestled in a peaceful country setting just momen...	2 beds \| 2 baths \| 911 sq.ft.	$225,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 7.77% Airbnb Rental Income: $1264 Traditional Rental Income: $2297 Airbnb ROI: 1.04% Traditional ROI: 7.77%
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: -2.58% Traditional cash on cash: -0.79% Airbnb Rental Income: $566 Traditional Rental Income: $1909 Airbnb ROI: -2.58% Traditional ROI: -0.79%
682 Fox Hill Road 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: 0.01% Traditional cash on cash: 3.58% Airbnb Rental Income: $1294 Traditional Rental Income: $2975 Airbnb ROI: 0.01% Traditional ROI: 3.58%
55 Eden Way #3B Bennington, VT Move right in to this immaculate 2-bedroom condo in the highly desirable Apple Ridge commu...	2 beds \| 1 baths \| 938 sq.ft.	$215,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 5.5% Airbnb Rental Income: $1264 Traditional Rental Income: $2100 Airbnb ROI: -0.06% Traditional ROI: 5.5%
303 Prospect Street Bennington, VT Nestled on a quiet residential street, this beautifully maintained home effortlessly blend...	3 beds \| 2 baths \| 1,463 sq.ft.	$370,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 6.19% Airbnb Rental Income: $1294 Traditional Rental Income: $3044 Airbnb ROI: -0.01% Traditional ROI: 6.19%
432 South Street #B-2 Bennington, VT Updated and ready to go. This 2 bedroom upstairs condo is perfect for those who don't want...	2 beds \| 2 baths \| 852 sq.ft.	$159,900	Airbnb cash on cash: 0.58% Traditional cash on cash: 9.28% Airbnb Rental Income: $1264 Traditional Rental Income: $2193 Airbnb ROI: 0.58% Traditional ROI: 9.28%
525 Jennings Brook Drive Bennington, VT Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-...	2 beds \| 2 baths \| 1,190 sq.ft.	$350,000	Airbnb cash on cash: -1.8% Traditional cash on cash: 5.9% Airbnb Rental Income: $1264 Traditional Rental Income: $3395 Airbnb ROI: -1.8% Traditional ROI: 5.9%
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: -0.15% Traditional cash on cash: 9.39% Airbnb Rental Income: $1264 Traditional Rental Income: $2668 Airbnb ROI: -0.15% Traditional ROI: 9.39%

Your search for investment property begins and ends here

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Bennington, VT

318 North Street

Bennington, VT

1 beds | 2 baths | 1,680 sq.ft.

$295,000

Airbnb cash on cash: -1.64%

Traditional cash on cash: 3.81%

Airbnb Rental Income: $661

Traditional Rental Income: $1874

Airbnb ROI: -1.64%

Traditional ROI: 3.81%

2092 N Bennington Road

Bennington, VT

3 beds | 2 baths | 900 sq.ft.

$269,900

Airbnb cash on cash: 0.67%

Traditional cash on cash: 6.81%

Airbnb Rental Income: $1294

Traditional Rental Income: $2454

Airbnb ROI: 0.67%

Traditional ROI: 6.81%

113 Main Street

Bennington, VT

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

$230,000

Airbnb cash on cash: 1.58%

Traditional cash on cash: 5.71%

Airbnb Rental Income: $1294

Traditional Rental Income: $1788

Airbnb ROI: 1.58%

Traditional ROI: 5.71%

210 Division Street

Bennington, VT

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

$199,000

Airbnb cash on cash: -2.34%

Traditional cash on cash: 8.6%

Airbnb Rental Income: $456

Traditional Rental Income: $2257

Airbnb ROI: -2.34%

Traditional ROI: 8.6%

704 Fox Hill Road

Bennington, VT

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

$575,000

Airbnb cash on cash: 0.12%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $1294

Traditional Rental Income: $3067

Airbnb ROI: 0.12%

Traditional ROI: 4.18%

126 Washington Avenue

Bennington, VT

6 beds | 3 baths | 5,208 sq.ft.

$399,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 9.3%

Airbnb Rental Income: $1350

Traditional Rental Income: $4529

Airbnb ROI: -0.31%

Traditional ROI: 9.3%

38 Oak Ridge Lane

Bennington, VT

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: $1294

Traditional Rental Income: $2964

Airbnb ROI: 0.43%

Traditional ROI: 6.57%

726 Rice Lane

Bennington, VT

2 beds | 2 baths | 911 sq.ft.

$225,000

Airbnb cash on cash: 1.04%

Traditional cash on cash: 7.77%

Airbnb Rental Income: $1264

Traditional Rental Income: $2297

Airbnb ROI: 1.04%