Single Family Residence at 390 Pleasant Valley Road, Brattleboro
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$1,100,000

Under contract
390 Pleasant Valley Road
Brattleboro, VT 05301
Listed by Kristen Ziter Taylor · Brattleboro Area Realty
Bedrooms
4
Bathrooms
2.5
Living area
N/A
Year built
1974

About this home

Price Improvement! Escape to this beautifully updated home set on 25.9 idyllic acres of forests, meadows and stone walls, while only minutes from amenities including the local creekside farmers market, treasured food co-op and Brattleboro's vibrant downtown. A gorgeous stone floor and blown glass windows in the entry vestibule set the tone as you are drawn to the stunning great room. The home tastefully captures the historic essence of Vermont with its chestnut beams, wide plank flooring and stylish yet unpretentious design. Interior features offer the perfect balance of grandeur and intimacy with oversized windows that bathe the rooms in natural light, 3 fireplaces and authentic lighting. The kitchen is a culinary haven with state-of-the-art appliances and stunning Brazilian countertops, providing ample workspace and an eat-in area. The first floor also offers a formal dining room, a guest/primary suite with a private entrance and laundry, an office, and it's completed by a sitting room where the current owners gather around the piano. Upstairs you'll find a generous primary suite, two bedrooms, and one with a connecting room, an ideal playroom or office. The walk-out basement is partially finished with a workout room, laundry room and abundant storage. The house includes high-speed fiber internet and a whole-house generator. The attached 2-car garage is heated and a second heated detached 2-car garage with a finished loft above is perfect for playing pool and foosball with family & friends. Relaxation comes easily by the inviting in-ground pool overlooking tranquil woodlands, the stone-terraced landscape and native wildlife. This special property is nestled in a friendly community on a country road, adjacent to 367 acres of protected land with trails perfect for hiking, biking and snowshoeing. Just 2 hrs to Boston, 3.5 hrs to NYC with direct Amtrak to NYC. Easy drive to ski mountains.

Property details

MLS
Prime MLS
MLS #
5088064
Property type
Single Family Residence
Subdivision
N/A
Status
Under contract
Days on market
64
On market date
N/A
Stories
N/A
Total bathrooms
2.5
Garage spaces
4
Parking spaces
N/A
Lot size
25.9 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
7.08 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
8.84 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
8.84 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 64 days -- 147 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
$6,774/mo
$220,000 down
$880,000 loan
Principal & interest$5,708
Property tax (est.)$917
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.