Single Family Residence at 211 Pleasant Valley Road, Brattleboro
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$545,000

Under contract
211 Pleasant Valley Road
Brattleboro, VT 05301
Listed by Chris Long · BHG Masiello Brattleboro
Bedrooms
2
Bathrooms
1
Living area
N/A
Year built
1942

About this home

Perched atop this scenic hillside on 6 acres, this distinctive contemporary home and classic gambrel two-story barn once enjoyed sweeping easterly views to Mount Wantastiquet and distant Mount Monadnock. Glimpses of the long-range views exist but will need to be reclaimed. Located on highly desirable Pleasant Valley Road in West Brattleboro, the property offers an exceptional combination of rural Vermont charm, privacy and convenience, with easy access to town. The beautiful Pleasant Valley Reservoir and the recreational opportunities provided by its protected land, trail system and class 4 road network are an underutilized outdoor paradise just down the road. The home's striking flat roof design, redwood siding, and clean mid-century modern influences create a timeless architectural aesthetic. Inside, the open concept living/dining and kitchen area is filled with natural light from the expansive windows that frame the surrounding landscape. An East/SE facing corner deck provides the perfect setting for morning coffee and sunrise views. The main level features two bedrooms and a full bath updated in 2026. The finished walkout lower level offers a spacious additional living space. The impressive gambrel barn once housed horses in its 3-5 stall lower level and has water and power. The top level of the barn is open clear span with a drive-in door ideal for vehicles and equipment storage, a wood shop, workshop, studio space or a variety of other uses including a possible second dwelling unit with applicable permits. The open land in front of the barn was once a dressage arena and provides an excellent level outdoor space for recreation, animals or agriculture. The remainder of the property includes a mix of open field, young growth forest and established yard areas surrounding the home with abundant room for large gardens and outdoor fun. Despite its peaceful country setting skiing, golf, hiking and biking are only minutes away. A rare one-of-a-kind Vermont property.

Property details

MLS
Prime MLS
MLS #
5094642
Property type
Single Family Residence
Subdivision
N/A
Status
Under contract
Days on market
34
On market date
N/A
Stories
N/A
Total bathrooms
1
Garage spaces
2
Parking spaces
N/A
Lot size
5.9 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Chesterfield Central School
6.84 mi away · Grades 0-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
273
Student:teacher ratio
10.9:1
District
Chesterfield School District
Middle
Hinsdale Middle High School
8.5 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
127
Student:teacher ratio
9.8:1
District
Hinsdale School District
High
Hinsdale High School
8.5 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
140
Student:teacher ratio
8.2:1
District
Hinsdale School District

Market position

How this listing compares to current activity in Brattleboro, from live MLS data.

On the market 34 days -- 177 fewer days than Brattleboro's current average of 211 days.
For reference, the median list price across 83 active listings in Brattleboro right now is $299,000.

Mortgage calculator

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Est. monthly payment
$3,432/mo
$109,000 down
$436,000 loan
Principal & interest$2,828
Property tax (est.)$454
Home insurance (est.)$150

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Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 07/18/26.