390 Pleasant Valley Road, Brattleboro, VT, 05301 | $1,249,000

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.

Features

  • Rooms: 11
  • Bedrooms: 4
  • Baths: 2 full / 1 three-quarter / 1 half
  • Style: Colonial
  • Year Built: 1974
  • Garage: 4-car Garage
  • Heating: Oil,Baseboard
  • Cooling: Mini Split
  • Basement: Concrete,Full,Partially Finished,Interior Stairs
  • Approx Sq. Feet: 4,491
  • Acreage: 25.9
  • Est. Taxes: $25,293
  • Lot Desc: Country Setting,Field/Pasture,Level,Sloping,Wooded,Near Country Club,Neighborhood
  • Elem. School: Brattleboro Elem Schools
  • Middle School: Brattleboro Area Middle School
  • High School: Brattleboro High School
  • MLS#: 5088064
  • Website: https://www.raveis.com
    /eprop/5088064/390pleasantvalleyroad_brattleboro_vt?source=qrflyer
©2026 New England Real Estate Network, 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 PrimMLS. 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 5/22/2026
Listing courtesy of Brattleboro Area Realty   Phone: 802-257-1335
Listing Agent: Kristen Ziter Taylor

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Frank KolbSenior Vice President - Coaching & Strategic, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 81725

203.980.8025

Frank.Kolb@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
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Our Insurance Division:

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390 Pleasant Valley Road, Brattleboro, VT, 05301

$1,249,000

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Frank Kolb

Senior Vice President - Coaching & Strategic

William Raveis Mortgage, LLC

Phone: 203.980.8025

Frank.Kolb@raveis.com

NMLS Mortgage Loan Originator ID 81725

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $999,200 $999,200 $999,200
Term 360 months 360 months 180 months
Initial Interest Rate** 5.500% 6.250% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.165% 6.361% 6.183%
Monthly Tax Payment $2,108 $2,108 $2,108
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $5,673 $6,152 $8,432
Total Monthly Payment $7,906 $8,385 $10,665

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.