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Land with Home for Sale in Brattleboro, Vermont

5 Hillwinds N, Brattleboro, VT 05301

$749,000
11.4 acres
Active sale
$46k drop
Est $5,125/mo

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 3/4 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
Zip code
05301
Community
Hillwinds
School district
Windham Southeast
Elevation
493 feet
Coordinates
42.8916, -72.5958

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

Lot

Features
Corner, Country Setting, Field/Pasture, Landscaped, Major Road Frontage, Mountain View, Near Country Club, Near Golf Course, Near Paths

Exterior

Parking
Open
Pool
Deck, Patio, Porch
Features
Covered Porch, Double Pane Window(s), Garden Space, Handicap Modified, Shed

Structure

Style
Contemporary
Stories
2
Water
Well
Heating
Electric, Hot Water, Oil, Radiant, Radiant Floor
Materials
Post and Beam, Wood Frame
Roof
Shingle

Interior

Room Count
11
Rooms
Basement, Bathroom x 4, Bedroom x 4, Den, Dining Room, Family Room, Game Room
Flooring
Carpet, Hardwood, Marble, Tile-Ceramic
Fireplaces
Yes
Appliances
Dishwasher, Domestic Water Heater, Dryer, Gas Cooktop, Microwave, Refrigerator, Tank Water Heater, Wall Oven, Washer
Accessibility
Accessible Approach With Ramp
Features
3+ Fireplaces, Cathedral Ceiling, Gas Fireplace, Kitchen Island, Kitchen/Dining, LED Lighting, Natural Light, Skylight, Vaulted Ceiling, Wet Bar, Wood Fireplace

Property utilities

CategoryTypeStatus
GasPropaneConnected

Listing history

DateEventPriceChangeSource
July 3, 2026Back on market$749,000NNEREN
June 26, 2026Under contract$749,000NNEREN
June 9, 2026Price drop$749,000$46,000 -5.8%NNEREN
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, priced at $749,000. It has a 3,600 square foot 4-bedroom, 3-bath house built in 1986.

Listed by Berkley & Veller Greenwood Country, (802) 254-6400

Checked 2 hours agoUpdated Source

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