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
81 Chapin Street Brattleboro, VT Step into an 1880s Victorian re-imagined for the 21st century. Located moments from downt...	3 beds \| 3 baths \| 1,246 sq.ft.	$475,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 4.41% Airbnb Rental Income: $1114 Traditional Rental Income: $2920 Airbnb ROI: -0.5% Traditional ROI: 4.41%
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.	$285,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 6.02% Airbnb Rental Income: $1114 Traditional Rental Income: $2455 Airbnb ROI: -0.37% Traditional ROI: 6.02%
108 Morningside Commons Brattleboro, VT Take a deep breath...enjoy your free time...sit back and wait for the walks to be clear, t...	2 beds \| 2 baths \| 1,139 sq.ft.	$250,000	Airbnb cash on cash: -1.68% Traditional cash on cash: 5.7% Airbnb Rental Income: $1114 Traditional Rental Income: $2482 Airbnb ROI: -1.68% Traditional ROI: 5.7%
5 Reynolds Drive Brattleboro, VT Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily pro...	5 beds \| 3 baths \| 2,360 sq.ft.	$294,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.84% Airbnb Rental Income: $null Traditional Rental Income: $3793 Airbnb ROI: N/A Traditional ROI: 10.84%
39 Brookside Drive #7 Brattleboro, VT Move right in! This condo has had some updates to include new scratch resistant vinyl plan...	1 beds \| 1 baths \| 685 sq.ft.	$159,500	Airbnb cash on cash: -3.13% Traditional cash on cash: 5.34% Airbnb Rental Income: $718 Traditional Rental Income: $1701 Airbnb ROI: -3.13% Traditional ROI: 5.34%
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.	$339,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 6.48% Airbnb Rental Income: $1114 Traditional Rental Income: $3123 Airbnb ROI: -1.01% Traditional ROI: 6.48%
131 Stark Road Brattleboro, VT Remember when you were 6 and the Hundred Acre Wood seemed as big as the whole world? Now ...	4 beds \| 5 baths \| 4,908 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.44% Airbnb Rental Income: $null Traditional Rental Income: $6349 Airbnb ROI: N/A Traditional ROI: 4.44%
925 Hinesburg Road Brattleboro, VT Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minut...	5 beds \| 8 baths \| 7,430 sq.ft.	$899,800	Airbnb cash on cash: N/A Traditional cash on cash: 6.74% Airbnb Rental Income: $null Traditional Rental Income: $7855 Airbnb ROI: N/A Traditional ROI: 6.74%
556 South Main Street Brattleboro, VT What a great way to start your home ownership! A tenant can help with the monthly expenses...	6 beds \| 2 baths \| 2,112 sq.ft.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.36% Airbnb Rental Income: $null Traditional Rental Income: $3378 Airbnb ROI: N/A Traditional ROI: 10.36%
25 Cottage Street Brattleboro, VT Sweet neighborhood. This would be a great location for an owner to live in one unit and re...	6 beds \| 4 baths \| 3,264 sq.ft.	$380,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.58% Airbnb Rental Income: $null Traditional Rental Income: $5157 Airbnb ROI: N/A Traditional ROI: 11.58%
10 Birge Street Brattleboro, VT Invest in your own home town! Full tenant roster with the easy access to laundry across t...	5 beds \| 4 baths \| 3,002 sq.ft.	$370,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.28% Airbnb Rental Income: $null Traditional Rental Income: $4923 Airbnb ROI: N/A Traditional ROI: 11.28%
573 South Main Street Brattleboro, VT Just around the corner! From the middle and high school, Oak grove elementary! Pop aroun...	2 beds \| 1 baths \| 3,312 sq.ft.	$350,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 3.47% Airbnb Rental Income: $1114 Traditional Rental Income: $2141 Airbnb ROI: -0.79% Traditional ROI: 3.47%
39 Atwood Street Brattleboro, VT First time offered, EVER... built and loved by the current family, it is time to pass the ...	3 beds \| 2 baths \| 1,152 sq.ft.	$345,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 5.53% Airbnb Rental Income: $1114 Traditional Rental Income: $2668 Airbnb ROI: -0.42% Traditional ROI: 5.53%
87 Orchard Street #87 Brattleboro, VT If you love light, this is your new home! This condo is special, in that it is one of onl...	4 beds \| 4 baths \| 2,800 sq.ft.	$397,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.32% Airbnb Rental Income: $null Traditional Rental Income: $4698 Airbnb ROI: N/A Traditional ROI: 8.32%
16 Washington Street Brattleboro, VT Fabulous potential with this in-town home on a great neighborhood street just a few short ...	4 beds \| 3 baths \| 2,209 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.13% Airbnb Rental Income: $null Traditional Rental Income: $3691 Airbnb ROI: N/A Traditional ROI: 9.13%
552 - 554 Hinesburg Road Brattleboro, VT Unique opportunity to own a nearly 40 acre tract and 2 homes on Hinesburg Road in a great ...	4 beds \| 1 baths \| 1,248 sq.ft.	$300,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.15% Airbnb Rental Income: $null Traditional Rental Income: $2612 Airbnb ROI: N/A Traditional ROI: 5.15%
40 Brookside Drive #8 Brattleboro, VT Don't wait to come view this newly remodeled, low maintenance, affordable and desirable gr...	1 beds \| 1 baths \| 700 sq.ft.	$179,000	Airbnb cash on cash: -2.95% Traditional cash on cash: 4.6% Airbnb Rental Income: $718 Traditional Rental Income: $1695 Airbnb ROI: -2.95% Traditional ROI: 4.6%

Real Estate investment in Brattleboro, VT

There are 23 properties for sale in the city of Brattleboro . The median list price in Brattleboro is $325,000 and the average price per square foot is $144. In May 2026, the average monthly cash on cash return in Brattleboro is 6.00%. The average monthly rental income in Brattleboro is $3,167.

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

There are 23 investment properties available for sale in Brattleboro.

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

The ROI for Long-Term is higher than the Short-Term in Brattleboro with average rental income of $3,167.

Your search for investment property begins and ends here

Investment Property for Sale in Brattleboro, VT

81 Chapin Street

Brattleboro, VT

3 beds | 3 baths | 1,246 sq.ft.

$475,000

Airbnb cash on cash: -0.5%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $1114

Traditional Rental Income: $2920

Airbnb ROI: -0.5%

Traditional ROI: 4.41%

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.

$285,000

Airbnb cash on cash: -0.37%

Traditional cash on cash: 6.02%

Airbnb Rental Income: $1114

Traditional Rental Income: $2455

Airbnb ROI: -0.37%

Traditional ROI: 6.02%

108 Morningside Commons

Brattleboro, VT

2 beds | 2 baths | 1,139 sq.ft.

$250,000

Airbnb cash on cash: -1.68%

Traditional cash on cash: 5.7%

Airbnb Rental Income: $1114

Traditional Rental Income: $2482

Airbnb ROI: -1.68%

Traditional ROI: 5.7%

5 Reynolds Drive

Brattleboro, VT

5 beds | 3 baths | 2,360 sq.ft.

$294,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.84%

Airbnb Rental Income: $null

Traditional Rental Income: $3793

Airbnb ROI: N/A

Traditional ROI: 10.84%

39 Brookside Drive #7

Brattleboro, VT

1 beds | 1 baths | 685 sq.ft.

$159,500

Airbnb cash on cash: -3.13%

Traditional cash on cash: 5.34%

Airbnb Rental Income: $718

Traditional Rental Income: $1701

Airbnb ROI: -3.13%

Traditional ROI: 5.34%

1089 Marlboro Road

Brattleboro, VT

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

$339,000

Airbnb cash on cash: -1.01%

Traditional cash on cash: 6.48%

Airbnb Rental Income: $1114

Traditional Rental Income: $3123

Airbnb ROI: -1.01%

Traditional ROI: 6.48%

131 Stark Road

Brattleboro, VT

4 beds | 5 baths | 4,908 sq.ft.

$899,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.44%

Airbnb Rental Income: $null

Traditional Rental Income: $6349

Airbnb ROI: N/A