390 Pleasant Valley Rd

Brattleboro, VT 05301

$1,249,000
Price
4
Beds
4,491 Sq. Ft.
$278 / Sq. Ft.
4,491
Sq. Ft.
$278
per Sq. Ft.
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Description

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...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.
  1. Listed by Kristen Ziter Taylor • Brattleboro Area Realty

Property Details for 390 Pleasant Valley Road

Zoning
res
LISTING UPDATED: 05/15/2026 08:28 PM

Property Details for 390 Pleasant Valley Road

StatusActive
MLS #5088064
Days on Market19
Taxes$25,293 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1974
Lot Size25.90 AC / 1,128,204 SF
CountyWindham County
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Location

Listing Courtesy of Brattleboro Area Realty
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Building Information for 390 Pleasant Valley Road

Stories2Year Built1974Building Size-Lot Size25.90 AC / 1,128,204 SF

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$8,332 per month

30 year fixed, 6.36% Interest

Principal and Interest

$6,224

Property Taxes

$2,108

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 390 Pleasant Valley Road

Summary
Location and General Information
  • City: Brattleboro
  • County: VT-Windham
  • Directions: From Western Ave/RT9 take Meadowbrook to left on Pleasant Valley.5th home on the left. See sign
  • Latitude: 42.881356106362119
  • Longitude: -72.608567034393332
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05301
Taxes and HOA Information
  • SPAN Number: 081-025-13418
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 4.00
  • Driveway: Paved
Property
Lot Information
  • Lot Features: Country Setting, Field/Pasture, Level, Sloping, Wooded, Near Country Club, Neighborhood
  • Lot Size Acres: 25.9
  • Road Frontage Length: 985.0
  • Total Finished Area: 4491.0
  • Above Grade Finished Area: 4000.0
  • Above Grade Finished Area Source: Measured
  • Above Grade Unfinished Area: 0.0
  • Below Grade Finished Area: 491.0
  • Below Grade Finished Area Source: Measured
  • Below Grade Unfinished Area: 2420.0
  • BelowGradeUnfinishedAreaSource: Public Records
  • Lot Size Square Feet: 1128204.0
  • Total Area: 6911.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Easements: Yes
  • Flood Zone: No
  • PreConstruction: No
  • Suitable Use: Agriculture, Horse/Animal Farm, Field/Pasture, Woodland
  • Surveyed: Yes
  • Year Built: 1974
  • High School: Brattleboro High School
  • Middle/Jr School: Brattleboro Area Middle School
  • Elementary School: Brattleboro Elem Schools
Utilities
  • Electric Company: GMP
  • Fuel Company: Dead River
  • Electric: 200+ Amp Service
  • Sewer: 1000 Gallon, Leach Field
  • Water Source: Drilled Well
  • Utilities: Cable Available, Telephone Available
  • Internet: Fiber Optic Internt Avail
Interior and Exterior Features
Exterior Features
  • Construction Materials: Wood Frame, Wood Siding
  • Roof: Architectural Shingle
Interior Features
  • Appliances: Dishwasher, Dryer, Freezer, Electric Range, Gas Range, Refrigerator, Washer
  • Basement: Yes
  • Basement Access Type: Walkout
  • Basement Description: Concrete, Full, Partially Finished, Interior Stairs
  • Rooms: Level 1: Level 1: Bedroom, Level 1: Full Bathroom, Level 1: 1/2 Bathroom, Level 1: Den, Level 1: Dining Room, Level 1: Great Room, Level 1: Kitchen, Level 1: Living Room, Level 1: Office/Study, Level 1: Other
  • Rooms: Level 2: Level 2: Bedroom, Level 2: Full Bathroom, Level 2: Other
  • Rooms: Level B: Level B: Other, Level B: Rec Room, Level B: Workshop
  • Flooring: Carpet, Ceramic Tile, Hardwood
  • Heating: Oil, Baseboard
  • Cooling: Mini Split
  • Total Stories: 2
  • Rooms Total: 11
  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms One Quarter: 0
  • Bathrooms Three Quarter: 1
  • Bedrooms Total: 4
  • Bathrooms Total: 4
Room Information
Room 1
  • Room Dimensions: 13.5x25.4
  • Room Level: 1
  • Room Type: Living Room
Room 2
  • Room Dimensions: 12.5x20.8
  • Room Level: 1
  • Room Type: Den
Room 3
  • Room Dimensions: 4.1x6.7
  • Room Level: 1
  • Room Type: Bathroom Half
Room 4
  • Room Dimensions: 12.6x13.5
  • Room Level: 1
  • Room Type: Office/Study
Room 5
  • Room Dimensions: 11.8x22
  • Room Level: 1
  • Room Type: Dining Room
Room 6
  • Room Dimensions: 15.4x21.7
  • Room Level: 1
  • Room Type: Kitchen
Room 7
  • Room Dimensions: 4.8x6.5
  • Room Level: 1
  • Room Type: Other
Room 8
  • Room Dimensions: 20.11x23.11
  • Room Level: 1
  • Room Type: Great Room
Room 9
  • Room Dimensions: 13.3x15.5
  • Room Level: 1
  • Room Type: Bedroom
Room 10
  • Room Dimensions: 4.11x7.3
  • Room Level: 1
  • Room Type: Bathroom Full
Room 11
  • Room Dimensions: 7.4x10.1
  • Room Level: 1
  • Room Type: Other
Room 12
  • Room Dimensions: 7.9x8.7
  • Room Level: 2
  • Room Type: Bathroom Full
Room 13
  • Room Dimensions: 11.3x13.6
  • Room Level: 2
  • Room Type: Bedroom
Room 14
  • Room Dimensions: 14.11x21.6
  • Room Level: 2
  • Room Type: Other
Room 15
  • Room Dimensions: 11.4x13.5
  • Room Level: 2
  • Room Type: Bedroom
Room 16
  • Room Dimensions: 13.5x16.5
  • Room Level: 2
  • Room Type: Bedroom
Room 17
  • Room Dimensions: 13.3x15.4
  • Room Level: 2
  • Room Type: Other
Room 18
  • Room Dimensions: 8.6x14.6
  • Room Level: 2
  • Room Type: Bathroom Full
Room 19
  • Room Dimensions: 11.10x19.7
  • Room Level: Basement
  • Room Type: Workshop
Room 20
  • Room Dimensions: 13.3x20.5
  • Room Level: Basement
  • Room Type: Other
Room 21
  • Room Dimensions: 11.10x19.7
  • Room Level: Basement
  • Room Type: Rec Room

Property History for 390 Pleasant Valley Road

DateEvent & SourcePriceAppreciation
May 11, 2026

Listed (Active)

New England Real Estate Network #5088064

$1,249,000—
Sep 21, 2020

Sold (Public Record)

Public Record #680757171

$875,000

+3.5% / yr

Sep 15, 2020

Sold

New England Real Estate Network #4822063

$875,000—
DateEvent & SourcePrice
05/11/2026

Listed (Active)

New England Real Estate Network #5088064

$1,249,000
09/21/2020

Sold (Public Record)

Public Record #680757171

$875,000

+3.5% / yr

09/15/2020

Sold

New England Real Estate Network #4822063

$875,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 390 Pleasant Valley Road

Taxable ValueLand$196,390Additions$561,480Total$757,870
Tax Record2024$24,608 ($2,051 / month)
Home Facts
Beds4Baths3.5Total Finished SqFt4,866 SqFtAbove Grade Finished SqFt4,866 SqFtStories2Lot Size1,128,204 SqFtStyleSingle Family ResidenceYear Built1974CountyWINDHAMAPN(025) 00060126.000

Schools near 390 Pleasant Valley Road

This home is within Windham Southeast Unified Union School District #96.
Rating
School
Type
Grades
Distance
Academy School
Public - PK to 6
Brattleboro Area Middle School
Public - 7 to 8
Brattleboro Senior Uhsd #6
Public - 9 to 12
Green Street School
Public - PK to 6
Rating
School
Distance
Academy School
PublicPK to 6

Brattleboro Area Middle School
Public7 to 8

Brattleboro Senior Uhsd #6
Public9 to 12

Green Street School
PublicPK to 6

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 390 Pleasant Valley Road, Brattleboro, VT 05301

390 Pleasant Valley Road is a single family home for sale in Brattleboro, VT 05301. This property was listed for sale on May 11, 2026 by Brattleboro Area Realty, it's currently listed at $1,249,000. It has been on the market for a total of 19 days and was last sold on September 21, 2020. This listing's school district is Windham Southeast Unified Union School District #96. Nearby schools include Academy School, Brattleboro Area Middle School and Brattleboro Senior Uhsd #6. 390 Pleasant Valley Road is a 4-bed, 4-bath, 4,491 sqft single family home built in 1974.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Brattleboro Area Realty

Copyright 2026 PrimeMLS, Inc. 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 06/03/2026 05:40 AM