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
390 Pleasant Valley Road Brattleboro, VT Escape to this beautifully updated home set on 25.9 idyllic acres of forests, meadows and ...	4 beds \| 4 baths \| 4,491 sq.ft.	$1,249,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.46% Airbnb Rental Income: $null Traditional Rental Income: $5293 Airbnb ROI: N/A Traditional ROI: 1.46%
111 Central Street Brattleboro, VT This adorable single-level home offers easy living with a functional layout and comfortabl...	3 beds \| 1 baths \| 1,008 sq.ft.	$270,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 4.52% Airbnb Rental Income: $1796 Traditional Rental Income: $1784 Airbnb ROI: 2.65% Traditional ROI: 4.52%
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 t...	3 beds \| 1 baths \| 1,323 sq.ft.	$285,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 6.02% Airbnb Rental Income: $1796 Traditional Rental Income: $2455 Airbnb ROI: 1.74% Traditional ROI: 6.02%
1644 Upper Dummerston Road Brattleboro, VT Found It! Live all on one level and tuck the guests in upstairs! The kitchen is modern wit...	2 beds \| 2 baths \| 1,499 sq.ft.	$385,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 5.61% Airbnb Rental Income: $1254 Traditional Rental Income: $2839 Airbnb ROI: 0.12% Traditional ROI: 5.61%
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: -1.19% Traditional cash on cash: 5.7% Airbnb Rental Income: $1254 Traditional Rental Income: $2482 Airbnb ROI: -1.19% 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.	$284,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.25% Airbnb Rental Income: $null Traditional Rental Income: $3793 Airbnb ROI: N/A Traditional ROI: 11.25%
39 Locust Street Brattleboro, VT Sweet and charming from an era of wonderful wood work, polished floors and rooms with a pu...	4 beds \| 2 baths \| 1,800 sq.ft.	$369,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.37% Airbnb Rental Income: $null Traditional Rental Income: $3352 Airbnb ROI: N/A Traditional ROI: 6.37%
16 School Street Brattleboro, VT Attention Investors & 1031 Exchange Buyers! A premier, turn-key investment opportunity is ...	12 beds \| 6 baths \| 6,000 sq.ft.	$540,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.6% Airbnb Rental Income: $null Traditional Rental Income: $6782 Airbnb ROI: N/A Traditional ROI: 10.6%
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.	$149,900	Airbnb cash on cash: -2.98% Traditional cash on cash: 5.74% Airbnb Rental Income: $767 Traditional Rental Income: $1701 Airbnb ROI: -2.98% Traditional ROI: 5.74%
94 Brets Road Brattleboro, VT Beautifully cared-for 3 bedroom, 3 bath single family condo in a desirable small associati...	3 beds \| 3 baths \| 2,594 sq.ft.	$499,000	Airbnb cash on cash: -1.15% Traditional cash on cash: 2.25% Airbnb Rental Income: $1796 Traditional Rental Income: $2891 Airbnb ROI: -1.15% Traditional ROI: 2.25%
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%
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 th...	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 S Main Street Brattleboro, VT Just around the corner! From the middle and high school, Oak grove elementary! Pop around ...	2 beds \| 1 baths \| 3,312 sq.ft.	$350,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 3.47% Airbnb Rental Income: $1254 Traditional Rental Income: $2141 Airbnb ROI: -0.44% 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: 1.33% Traditional cash on cash: 5.53% Airbnb Rental Income: $1796 Traditional Rental Income: $2668 Airbnb ROI: 1.33% Traditional ROI: 5.53%
87 Orchard Street #87 Brattleboro, VT Nestled in the sought-after Orchard Street neighborhood, this beautiful townhouse offers b...	4 beds \| 4 baths \| 2,800 sq.ft.	$359,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.29% Airbnb Rental Income: $null Traditional Rental Income: $4698 Airbnb ROI: N/A Traditional ROI: 9.29%
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%

Real Estate investment in Brattleboro, VT

There are 22 properties for sale in the city of Brattleboro . The median list price in Brattleboro is $324,832 and the average price per square foot is $128. In June 2026, the average monthly cash on cash return in Brattleboro is 6.00%. The average monthly rental income in Brattleboro is $2,920.

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

There are 22 investment properties available for sale in Brattleboro.

In 2026, 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 $1,525.

Your search for investment property begins and ends here

Investment Property for Sale in Brattleboro, VT

390 Pleasant Valley Road

Brattleboro, VT

4 beds | 4 baths | 4,491 sq.ft.

$1,249,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.46%

Airbnb Rental Income: $null

Traditional Rental Income: $5293

Airbnb ROI: N/A

Traditional ROI: 1.46%

111 Central Street

Brattleboro, VT

3 beds | 1 baths | 1,008 sq.ft.

$270,000

Airbnb cash on cash: 2.65%

Traditional cash on cash: 4.52%

Airbnb Rental Income: $1796

Traditional Rental Income: $1784

Airbnb ROI: 2.65%

Traditional ROI: 4.52%

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: 1.74%

Traditional cash on cash: 6.02%

Airbnb Rental Income: $1796

Traditional Rental Income: $2455

Airbnb ROI: 1.74%

Traditional ROI: 6.02%

1644 Upper Dummerston Road

Brattleboro, VT

2 beds | 2 baths | 1,499 sq.ft.

$385,000

Airbnb cash on cash: 0.12%

Traditional cash on cash: 5.61%

Airbnb Rental Income: $1254

Traditional Rental Income: $2839

Airbnb ROI: 0.12%

Traditional ROI: 5.61%

108 Morningside Commons

Brattleboro, VT

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

$250,000

Airbnb cash on cash: -1.19%

Traditional cash on cash: 5.7%

Airbnb Rental Income: $1254

Traditional Rental Income: $2482

Airbnb ROI: -1.19%

Traditional ROI: 5.7%

5 Reynolds Drive

Brattleboro, VT

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

$284,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.25%

Airbnb Rental Income: $null

Traditional Rental Income: $3793

Airbnb ROI: N/A

Traditional ROI: 11.25%

39 Locust Street

Brattleboro, VT

4 beds | 2 baths | 1,800 sq.ft.

$369,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.37%

Airbnb Rental Income: $null

Traditional Rental Income: $3352

Airbnb ROI: N/A