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

Brattleboro, VT, 05301
$ 795,000
Bedrooms4 Baths2.2 Sq 3,600

Monthly Estimate*

$ 4,895

Listed by Robert Doyle, Berkley & Veller Greenwood Country, 802-254-6400, robert.doyle@berkleyveller.com
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Single Family Home for sale in Brattleboro, VT

for $795,000 with 4 bedrooms and 2 full baths, 2 half baths. This 3,600 square foot home was built in 1986 on a lot size of 11.4.

Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on 11 acres of landscaped grounds with lawns, stone walls, gardens, and woodland 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.

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Single Family Active

Price

$ 795,000

Bedrooms

4

Full Bath

2

Half Bath

2

Property Type

Single Family

Taxes

$ 0

Style

Contemporary,Post and Beam

Lot Size

11.4

Year Built

1986

Town/City

Brattleboro

County/Region

Windham

MLS | Web ID

5081610

Features
Interior
Basement Description Concrete Concrete Floor Partial Partially Finished Storage Space
Interior Amenities Cathedral Ceiling Gas Fireplace Wood Fireplace 3+ Fireplaces Kitchen Island Kitchen/Dining LED Lighting Natural Light Skylight Vaulted Ceiling Wet Bar
Basement Yes
Flooring Carpet Ceramic Tile Hardwood Marble Other
Beds 4
Total Rooms 11
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General
Road Frontage Yes
Sewer Septic
Heating Oil Electric Hot Water Radiant Floor
Cooling None
Utilities Propane
Roof Asphalt Shingle
Appliances Gas Cooktop Dishwasher Dryer Microwave Wall Oven Refrigerator Washer Domestic Water Heater Tank Water Heater
Garage Yes
Flood Zone No
Zoning Residential
3/4 Baths 1
Full Baths 1
Half Baths 2
Bathrooms 4
Year Built 1986
Electric 200+ Amp Service Circuit Breaker(s)
Subdivision Hillwinds
Style Contemporary Post and Beam
Stories Count 2
Construction Status Existing
Type Single Family
Accessibility Features 1st Floor 1/2 Bathroom 1st Floor 3 Ft. Doors
Auction No
Tax Year 2025
Status Detail 0
Covenants Yes
Construction Materials Post and Beam Wood Frame
Directions Upper Dummerston Road to Hillwinds Road. Take to the first right (Hillwinds North) and the house is the first on the right.
City Brattleboro
School District Windham Southeast
Seasonal No
DOM 1
Price Per Sq Ft Total AG 220.83
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Exterior
Lot Features Corner Country Setting Field/Pasture Landscaped Major Road Frontage Mountain View Near Country Club Near Golf Course Near Paths
Exterior Amenities Deck Garden Space Patio Covered Porch Shed Double Pane Window(s) Handicap Modified
Driveway Paved
Lot Size Area 11.4
Water Source Drilled Well
Parking Features Auto Open Storage Above Paved Detached
Garage Capacity 2
Foundation Poured Concrete
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* Excluded Features
List By
Robert Doyle

Listing Agent

Berkley & Veller Greenwood Country

Broker

(802) 254-6400

Phone

robert.doyle@berkleyveller.com

Email

Affordability Calculator

$4,895
Per Month
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Monthly Principal & Interest
$4,895
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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4683570 Elementary School
4891864 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
4/1/2026$795,000 Listed Price

Map


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5 Hillwinds North, Brattleboro, VT, 05301 is a Single Family Home for sale at $795,000 with 3,600 sqft and a lot size of 11.4. 5 Hillwinds North has 4 bedrooms, 2.2 baths, and was built in 1986. The property's zip code is 05301 which is in Brattleboro, VT