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
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: -0.62% Traditional cash on cash: 6.02% Airbnb Rental Income: $1033 Traditional Rental Income: $2455 Airbnb ROI: -0.62% Traditional ROI: 6.02%
116 Birge Street #3 Brattleboro, VT Welcome to Esteyville! Here, history, location, and distinctivenessÂ excel. This rare, NYC...	1 beds \| 1 baths \| 2,000 sq.ft.	$289,000	Airbnb cash on cash: -2.74% Traditional cash on cash: 2.72% Airbnb Rental Income: $691 Traditional Rental Income: $1872 Airbnb ROI: -2.74% Traditional ROI: 2.72%
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%
135 Country Hill Brattleboro, VT Built in 2004 in this much-loved neighborhood, on a desirable one-way cul-de-sac, beautifu...	3 beds \| 3 baths \| 2,128 sq.ft.	$395,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 5.96% Airbnb Rental Income: $1033 Traditional Rental Income: $3432 Airbnb ROI: -1.5% Traditional ROI: 5.96%
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.	$350,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 6.24% Airbnb Rental Income: $1033 Traditional Rental Income: $3123 Airbnb ROI: -1.21% Traditional ROI: 6.24%
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%
176 High Street Brattleboro, VT Conveniently located in Brattleboro Center, this historic three-family home offers the per...	5 beds \| 4 baths \| 3,064 sq.ft.	$459,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.81% Airbnb Rental Income: $null Traditional Rental Income: $4923 Airbnb ROI: N/A Traditional ROI: 8.81%
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: -1.02% Traditional cash on cash: 3.47% Airbnb Rental Income: $1024 Traditional Rental Income: $2141 Airbnb ROI: -1.02% 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.	$353,900	Airbnb cash on cash: -0.64% Traditional cash on cash: 5.37% Airbnb Rental Income: $1033 Traditional Rental Income: $2668 Airbnb ROI: -0.64% Traditional ROI: 5.37%
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%
72 Landmark Hill Drive Brattleboro, VT What will the next life be for this iconic property? From popular and innovative hair sa...	8 beds \| 4 baths \| 6,466 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.94% Airbnb Rental Income: $null Traditional Rental Income: $5427 Airbnb ROI: N/A Traditional ROI: 5.94%
23 Wilsons Woods Road Brattleboro, VT Welcome to 23 Wilsons Woods Road, a meticulously maintained Colonial-style home that offer...	4 beds \| 4 baths \| 2,312 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.21% Airbnb Rental Income: $null Traditional Rental Income: $4372 Airbnb ROI: N/A Traditional ROI: 6.21%
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: -3.08% Traditional cash on cash: 4.6% Airbnb Rental Income: $691 Traditional Rental Income: $1695 Airbnb ROI: -3.08% Traditional ROI: 4.6%

Real Estate investment in Brattleboro, VT

There are 24 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 $140. In March 2026, the average monthly cash on cash return in Brattleboro is 6.00%. The average monthly rental income in Brattleboro is $3,171.

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

There are 24 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 $3,171.

Your search for investment property begins and ends here

Investment Property for Sale in Brattleboro, VT

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: -0.62%

Traditional cash on cash: 6.02%

Airbnb Rental Income: $1033

Traditional Rental Income: $2455

Airbnb ROI: -0.62%

Traditional ROI: 6.02%

116 Birge Street #3

Brattleboro, VT

1 beds | 1 baths | 2,000 sq.ft.

$289,000

Airbnb cash on cash: -2.74%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $691

Traditional Rental Income: $1872

Airbnb ROI: -2.74%

Traditional ROI: 2.72%

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%

135 Country Hill

Brattleboro, VT

3 beds | 3 baths | 2,128 sq.ft.

$395,000

Airbnb cash on cash: -1.5%

Traditional cash on cash: 5.96%

Airbnb Rental Income: $1033

Traditional Rental Income: $3432

Airbnb ROI: -1.5%

Traditional ROI: 5.96%

1089 Marlboro Road

Brattleboro, VT

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

$350,000

Airbnb cash on cash: -1.21%

Traditional cash on cash: 6.24%

Airbnb Rental Income: $1033

Traditional Rental Income: $3123

Airbnb ROI: -1.21%

Traditional ROI: 6.24%

556 South Main Street

Brattleboro, VT

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%

176 High Street

Brattleboro, VT

5 beds | 4 baths | 3,064 sq.ft.

$459,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.81%

Airbnb Rental Income: $null

Traditional Rental Income: $4923

Airbnb ROI: N/A