Real Estate Investment Properties for Sale in Brattleboro, VT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1177 Western Avenue Brattleboro, VT So much to offer! This 4 bedroom 2 bath has plenty of room for all! It features a large ...	4 beds \| 2 baths \| 1,733 sq.ft.	$279,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.69% Airbnb Rental Income: $null Traditional Rental Income: $3355 Airbnb ROI: N/A Traditional ROI: 9.69%
192 Western Avenue Brattleboro, VT Timeless 1855 classic with historic charm just minutes to downtown Brattleboro. Step back ...	3 beds \| 2 baths \| 2,066 sq.ft.	$568,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 3.4% Airbnb Rental Income: $1386 Traditional Rental Income: $3146 Airbnb ROI: -0.71% Traditional ROI: 3.4%
109 Central Street Brattleboro, VT The current owner is occupying as a single family and therefore there are no filings on le...	4 beds \| 2 baths \| 1,808 sq.ft.	$300,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.28% Airbnb Rental Income: $null Traditional Rental Income: $3210 Airbnb ROI: N/A Traditional ROI: 8.28%
164 Chestnut Street Brattleboro, VT Just right for new beginnings! This raised ranch affords the new home buyer a cozy place...	3 beds \| 1 baths \| 1,323 sq.ft.	$319,900	Airbnb cash on cash: 0.31% Traditional cash on cash: 5.26% Airbnb Rental Income: $1386 Traditional Rental Income: $2455 Airbnb ROI: 0.31% Traditional ROI: 5.26%
290 Guilford Street Brattleboro, VT This meticulously maintained 3-bedroom, 2-bath ranch surprises with its spacious layout an...	3 beds \| 2 baths \| 1,728 sq.ft.	$335,000	Airbnb cash on cash: 0% Traditional cash on cash: 6.63% Airbnb Rental Income: $1386 Traditional Rental Income: $3053 Airbnb ROI: 0% Traditional ROI: 6.63%
230 Western Avenue Brattleboro, VT This beautifully renovated in-town home blends character, comfort, and convenience. From t...	4 beds \| 3 baths \| 1,887 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.8% Airbnb Rental Income: $null Traditional Rental Income: $3573 Airbnb ROI: N/A Traditional ROI: 4.8%
58 Oak Street Brattleboro, VT Come experience the elegance and charm of this stunning in-town retreat! Close to the town...	5 beds \| 4 baths \| 3,748 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.9% Airbnb Rental Income: $null Traditional Rental Income: $2536 Airbnb ROI: N/A Traditional ROI: 1.9%
1089 Marlboro Road Brattleboro, VT The one you have been waiting for! This traditional New England cape with a twist checks ...	3 beds \| 2 baths \| 1,703 sq.ft.	$385,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 5.6% Airbnb Rental Income: $1386 Traditional Rental Income: $3123 Airbnb ROI: -0.38% Traditional ROI: 5.6%
131 Stark Road Brattleboro, VT Remember when you were 6 and the Hundred Acre Wood seemed as big as the whole world? Now ...	5 beds \| 5 baths \| 4,908 sq.ft.	$1,400,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.5% Airbnb Rental Income: $null Traditional Rental Income: $6349 Airbnb ROI: N/A Traditional ROI: 2.5%

Real Estate investment in Brattleboro, VT

There are 10 properties for sale in the city of Brattleboro . The median list price in Brattleboro is $442,000 and the average price per square foot is $190. In October 2025, the average monthly cash on cash return in Brattleboro is 5.00%. The average monthly rental income in Brattleboro is $3,178.

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

There are 10 investment properties available for sale in Brattleboro.

In 2025, the best neighborhood to buy investment property is Brattleboro.

The ROI for Short-Term is higher than the Long-Term in Brattleboro with average rental income of $1,386.

Your search for investment property begins and ends here

Investment Property for Sale in Brattleboro, VT

1177 Western Avenue

Brattleboro, VT

4 beds | 2 baths | 1,733 sq.ft.

$279,900

Airbnb cash on cash: N/A

Traditional cash on cash: 9.69%

Airbnb Rental Income: $null

Traditional Rental Income: $3355

Airbnb ROI: N/A

Traditional ROI: 9.69%

192 Western Avenue

Brattleboro, VT

3 beds | 2 baths | 2,066 sq.ft.

$568,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $1386

Traditional Rental Income: $3146

Airbnb ROI: -0.71%

Traditional ROI: 3.4%

109 Central Street

Brattleboro, VT

4 beds | 2 baths | 1,808 sq.ft.

$300,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.28%

Airbnb Rental Income: $null

Traditional Rental Income: $3210

Airbnb ROI: N/A

Traditional ROI: 8.28%

164 Chestnut Street

Brattleboro, VT

3 beds | 1 baths | 1,323 sq.ft.

$319,900

Airbnb cash on cash: 0.31%

Traditional cash on cash: 5.26%

Airbnb Rental Income: $1386

Traditional Rental Income: $2455

Airbnb ROI: 0.31%

Traditional ROI: 5.26%

290 Guilford Street

Brattleboro, VT

3 beds | 2 baths | 1,728 sq.ft.

$335,000

Airbnb cash on cash: 0%

Traditional cash on cash: 6.63%

Airbnb Rental Income: $1386

Traditional Rental Income: $3053

Airbnb ROI: 0%

Traditional ROI: 6.63%

230 Western Avenue

Brattleboro, VT

4 beds | 3 baths | 1,887 sq.ft.

$499,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.8%

Airbnb Rental Income: $null

Traditional Rental Income: $3573

Airbnb ROI: N/A

Traditional ROI: 4.8%

58 Oak Street

Brattleboro, VT

5 beds | 4 baths | 3,748 sq.ft.

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.9%

Airbnb Rental Income: $null

Traditional Rental Income: $2536

Airbnb ROI: N/A

Traditional ROI: 1.9%

1089 Marlboro Road

Brattleboro, VT

3 beds | 2 baths | 1,703 sq.ft.

$385,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 5.6%

Airbnb Rental Income: $1386

Traditional Rental Income: $3123

Airbnb ROI: -0.38%