Skip to content
Bean Group
Sold for $762,900Sold

Sold Aug 19, 2026

beds
4
baths
4
sq ft
3,600
Built
1986

5 Hillwinds North

Brattleboro, VT 05301

This property is no longer actively marketed. The last publicly available listing details are shown below; contact us for current availability.

About this home

New updates: roof replacement with 30 year architectural shingles completed and six new skylights with remote control shades installed. 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. 12/1/25 new System 2000 boiler, recently paved drive and so many beautiful appointments.

Listing last checked: Listing updated:

Listed by Robert Doyle · Berkley & Veller Greenwood Country · MLS #5081610

Request property information

Select a document to start a request. You can add others in the form. Availability varies.

Details at a glance

Interior5 property facts
Rooms
11
Heating
Hot Water, Radiant, Oil, Electric, Radiant Floor
Cooling
None
Flooring
Carpet, Ceramic Tile, Hardwood, Marble, Other
Basement
Yes · Concrete, Concrete Floor, Partial, Partially Finished, Storage Space
Building5 property facts
Style
Single Family Residence
Year built
1986
Garage
2
Parking
2
Roof
Shingle
Land & utilities5 property facts
Lot size
11.4 acres
Water
Well
Sewer
Septic Tank
Pool
Not reported
Zoning
Residential
Financial2 property facts
Annual taxes
$15,576
Assessment year
2025

Location

Explore the area

Get to know the neighborhood and explore local school information as you picture life here.

Explore more of Brattleboro

Continue your search in Brattleboro.

Need help making sense of this home?

About 5 Hillwinds North

Is this home available for a showing?

This home is no longer actively marketed. Ask our team about its current status or similar homes.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.