5 Hillwinds North, Brattleboro, VT, 05301 | $795,000

Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9. 4 acre woodland lot with snowshoe trails in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered porch that opens into a marble floored foyer with skylight, entry closet and stained-glass windows. Adjacent, opens into a warm, spacious family room with cherry wainscoting, a gas stone fireplace, curved architectural accents and mud room access. The formal living room features a brick fireplace and is surrounded by classic post & beam architecture and stained glass windows. The open kitchen & dining area are ideal for entertaining and impress with cherry cabinetry, quartz countertops, stainless appliances, and sliders to an expansive deck with serene views. A den, half bath, and laundry closet complete the main level. Upstairs offers four bedrooms, including a stunning primary suite with cathedral ceiling, triple closets, fireplace, and Palladian windows. There is a tucked-away guest room that enjoys a private ¾ bath. The finished lower level includes a generous game room with wet bar, half bath, propane stove, & TV area—pool table included! A detached 2-car garage with storage, a garden shed, and timeless craftsmanship throughout make this a truly rare offering.

Features

  • Rooms: 11
  • Bedrooms: 4
  • Baths: 1 full / 1 three-quarter / 2 half
  • Style: Contemporary,Post and Beam
  • Year Built: 1986
  • Garage: 2-car Garage
  • Heating: Oil,Electric,Hot Water,Radiant Floor
  • Cooling: None
  • Basement: Concrete,Concrete Floor,Partial,Partially Finished,Storage Space
  • Approx Sq. Feet: 3,600
  • Acreage: 11.4
  • Est. Taxes: $15,576
  • Lot Desc: Corner,Country Setting,Field/Pasture,Landscaped,Major Road Frontage,Mountain View,Near Country Club,Near Golf Course,Near Paths
  • School District: Windham Southeast
  • MLS#: 5081610
  • Website: https://www.raveis.com
    /prop/5081610/5hillwindsnorth_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 4/28/2026
Listing courtesy of Berkley & Veller Greenwood Country   Phone: 802-254-6400
Listing Agent: Robert Doyle

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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

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5 Hillwinds North, Brattleboro, VT, 05301

$795,000

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 Conforming*
30 Year
Fixed-Rate Conforming
15 Year
Fixed-Rate Conforming
Loan Amount $636,000 $636,000 $636,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.750% 6.250% 5.375%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.275% 6.398% 5.595%
Monthly Tax Payment $1,298 $1,298 $1,298
H/O Insurance Payment $92 $92 $92
Initial Principal & Interest Pmt $3,712 $3,916 $5,155
Total Monthly Payment $5,102 $5,306 $6,545

* 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.