- 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.
Compare with confidence
Price & market context
See how this home compares with active listings in Brattleboro.
| Metric | This home | Local listings |
|---|---|---|
| List price | $769,900 | $292,500163% above local |
| Price / sq ft | $214 | $2102% above local |
| Days on market | 133 | 62115% above local |
Active city listing statistics from PrimeMLS as of September 11, 2026. Asking prices are not completed-sale values.
Keep exploring
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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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