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Land with Home for Sale in Brattleboro, Vermont

5 Hillwinds N, Brattleboro, VT 05301

$795,000
11.4 acres
Active sale
ago
Est $5,111/mo

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.

3,600
Sq feet
4
Beds
1
Full bath
1
3/4 bath
2
1/2 baths
1986
Built

Location

Street address
5 Hillwinds N
Community
Hillwinds
School district
Windham Southeast
Elevation
493 feet
Coordinates
42.8921, -72.5985

Directions

Upper Dummerston Road to Hillwinds Road. Take to the first right (Hillwinds North) and the house is the first on the right.

Property details

Acreage
11.4 acres
Zoning
Residential
MLS #
NNEREN 5081610
Posted

Property taxes

2025
$15,576

Details and features

Listing

Type
Residential
Subtype
Single Family Residence

Exterior

Parking Spaces
2
Parking
Garage, Paved or Surfaced

Structure

Basement
Yes
Heating
Electric, Hot Water, Oil, Radiant, Radiant Floor
Roof
Asphalt, Shingle

Interior

Room Count
11
Rooms
Basement, Bathroom x 4, Bedroom x 4, Den, Family Room, Kitchen, Living Room
Flooring
Carpet, Ceramic Tile, Hardwood, Marble, Tile
Appliances
Cooktop, Dishwasher, Dryer, Gas Cooktop, Microwave, Refrigerator, Washer

Listing history

DateEventPriceChangeSource
Apr 1, 2026New listing$795,000NNEREN
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This 11.4-acre property is located at 5 Hillwinds N in Brattleboro, VT 05301. The property is available for sale for $795,000. It has a 3,600 sq ft 4 bedroom, 1 bath house built in 1986.

Checked 1 hour ago — Updated

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