
Land with Home for Sale in Brattleboro, Vermont
5 Hillwinds N, Brattleboro, VT 05301
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.
Location
- Street address
- 5 Hillwinds N
- County
- Windham County
- Zip code
- 05301
- Community
- Hillwinds
- School district
- Windham Southeast
- Elevation
- 493 feet
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
| Category | Type | Status |
|---|---|---|
| Gas | Propane | Connected |
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| July 3, 2026 | Back on market | $749,000 | — | NNEREN |
| June 26, 2026 | Under contract | $749,000 | — | NNEREN |
| June 9, 2026 | Price drop | $749,000 | $46,000 -5.8% | NNEREN |
| Apr 1, 2026 | New listing | $795,000 | — | NNEREN |





































