Listed by Kristen Ziter Taylor • Brattleboro Area Realty. Bought with Four Seasons Sotheby's Int'l Realty.
Sold on Aug 2026
$1,175,000
4
bd
•
3.5 ba
•
4,491
sq ft
390 Pleasant Valley Rd, Brattleboro, VT 05301
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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.
Single-familyProperty Type
1974Year Built
25.9 acresLot Size
$262Price/Sq.Ft.
4 car garageParking
Listed by Kristen Ziter Taylor• Brattleboro Area Realty
Bought with Cindy Leinonen• Four Seasons Sotheby's Int'l Realty
Est. $4,163 per month, based on comparable rentals
Sale and tax history for 390 Pleasant Valley Rd
Sale History
Tax History
Date
Event
Price
PrimeMLS #5088064
Aug 24, 2026
Sold
$1,175,000
$262/sq ft
Jul 17, 2026
Contingent
—
Jul 8, 2026
Price Changed
$1,100,000
$245/sq ft
May 15, 2026
Listed
$1,249,000
$278/sq ft
May 11, 2026
Coming Soon
$1,249,000
$278/sq ft
PrimeMLS #4822063
Sep 15, 2020
Sold
$875,000
$195/sq ft
Aug 24, 2020
Pending
—
Aug 12, 2020
Listed
$875,000
$195/sq ft
This sophisticated country property is comprised of nearly 26 acres of lush open meadow and mature forest in rural West Brattleboro offering complete peace and tranquility yet only minutes to town. The property is located adjacent to hundreds of acres of town property and the Pleasant Valley Reservoir offering miles of fantastic trails for hiking/biking. The attention to detail both inside and out of this home is stunning. The professionally landscaped grounds are afforded natural shade from towering hardwood trees and feature beautiful formal gardens, stone walls/terraces and walkways, private lawn areas and a long winding crushed stone drive flanked by orchard trees. The 20 X 40 inground pool, pergola and surrounding deck area is extremely private and designed to take full advantage of the mid and late day sun for entertaining or relaxing. Two car direct entry heated garage beneath and a two bay heated detached garage with game room above. The home features custom detail throughout the main living area including exposed beams, wide pine /hardwood /ceramic tile flooring, crown molding, 3 fireplaces and overall superb craftmanship. The kitchen boasts Brazilian granite counter tops and island, hardwood cabinetry, cathedral ceiling and high end appliances. The great room is flooded with natural light and has an impressive fireplace. The home also offers two master suites, one on each level, a formal dining with built-in cupboards, office/study and much more. Simply perfect!!
PrimeMLS #4616047
Jul 27, 2017
Sold
$785,000
$175/sq ft
Mar 3, 2017
Contingent
—
Jan 30, 2017
Listed
$795,000
$177/sq ft
+25
This stately and elegant country home is beautifully sited on almost 26 acres of lush property with formal gardens, stone walls & walkways and mixed woodland, all bordering a huge parcel of beautiful reservoir land. The location is private and serene on desirable Pleasant Valley Road, yet only a short ride to vibrant downtown Brattleboro. The exterior includes a 20X40 in-ground pool with large entertainment deck, pergola, garden shed and a detached heated 2-car garage with finished Game Room above. The interior is stunning with large principal rooms all incorporating precise finish work and custom upgrades throughout. Special features include: Wide board and hardwood flooring, crown molding, 3 fireplaces, wine room, whole house generator, alarm and System 2000 boiler. Of note is the superb Great Room with fireplace, inviting formal Living Room with Ash flooring and fireplace, Family Room with fireplace and chestnut beams, custom Kitchen with Brazilian granite counters, cathedral ceiling, top end appliances & Venetian glass lighting, sophisticated Dining Room with built-in cupboards & formal beam work and two Master Suites in addition to two guest Bedrooms, one with Playroom. Rarely does a home of this quality and location come on the market---a superb choice for the discerning buyer!!!
Year
Property tax
Land + Additions
Assessment*
2025
$13,292 (−2.2%)
$196,390 + $561,480
$757,870
2024
$13,587 (+11.7%)
$196,390 + $561,480
$757,870
2023
$12,166 (−44.9%)
$196,390 + $561,480
$757,870
2022
$22,070 (−0.9%)
$196,390 + $561,480
$757,870
2021
$22,277 (+1.3%)
$196,390 + $561,480
$757,870
2020
$21,991 (+3.8%)
$196,390 + $561,480
$757,870
2019
$21,192 (+0.2%)
$196,390 + $561,480
$757,870
2018
$21,149 (−1.0%)
$196,390 + $561,480
$757,870
2017
$21,364 (+0.2%)
$196,390 + $561,480
$757,870
2016
$21,315 (−0.9%)
$196,390 + $561,480
$757,870
2015
$21,505 (+0.8%)
$196,390 + $561,480
$757,870
2014
$21,338
$196,390 + $561,480
$757,870
2013
$196,390 + $561,480
$757,870
Public record
Public record
Zoning
Beds
4
Baths
3.5
Stories
2
Lot width
—
Lot depth
—
Lot size
25.9 Acres
Year renovated
—
Sq. Ft.
—
Year built
1974
Style
Single Family Residential
County
Windham County
APN
08102513418
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 8, 2026.
RL
Rural District
The Rural District encompasses land primarily in the western, upland portion of Brattleboro, which features large tracts of undeveloped woodlands, working farmland and very-low density residential development. This land is not served by municipal water and sewer or by roads that are capable of accommodating heavy traffic, and extending or upgrading infrastructure in this district is strongly discouraged. The purpose of this district is to protect these remote and relatively inaccessible rural lands from fragmentation, development and undue environmental disturbance by maintaining a very low-density settlement pattern and large tracts of working lands or natural areas in accordance with the policies of the Brattleboro Town Plan.