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Offered at $769,900Active Under Contract
beds
4
baths
4
sq ft
3,600
Built
1986

5 Hillwinds North

Brattleboro, VT 05301

Residential · Active Under Contract · MLS #5081610
Listing Courtesy of Berkley & Veller Greenwood Country | Robert Doyle

The home

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.

Property information

Details at a glance

Interior4 property facts
Rooms
11
Heating
Hot Water, Radiant, Oil, Electric, Radiant Floor
Cooling
None
Flooring
Carpet, Ceramic Tile, Hardwood, Marble, Other
Building5 property facts
Style
Single Family Residence
Year built
1986
Garage
2
Parking
2
Roof
Shingle
Land & utilities4 property facts
Lot size
11.4 acres
Water
Well
Sewer
Septic Tank
Zoning
Residential
Financial2 property facts
Annual taxes
$15,576
Assessment year
2025

Plan your purchase

Estimated monthly cost

Explore costs at the $769,900 asking price. Adjust the assumptions to your situation.

Known monthly costs$5,191 / monthAdjust
Principal & interest
$3,893
Property tax
$1,298
Insurance
Not entered
HOA
Not entered

Listing annual taxes: $15,576. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.

Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.

The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.

Listing history

Price and status timeline

No additional listing history is available for public display.

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Price & market context

See how this home compares with active listings in Brattleboro.

This home compared with active listings in Brattleboro
MetricThis homeLocal listings
List price$769,900$292,500163% above local
Price / sq ft$214$2102% above local
Days on market13362115% above local

Active city listing statistics from PrimeMLS as of September 11, 2026. Asking prices are not completed-sale values.

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Common questions

About 5 Hillwinds North

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Request a tour of 5 Hillwinds North and a Bean Group agent will help coordinate an available time with the listing side.

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

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