This beautiful Colonial blends timeless design with contemporary enhancements. Set on over 2 acres of landscaped grounds, the property offers a country setting just minutes from Brattleboro. Inside, the floor plan has been expanded with large, light-filled rooms & custom features. The gourmet kitchen is a showstopper, w/Quartz counters, custom cabinetry, top-tier appliances, glass tile backsplash and walnut accents-perfect for entertaining. The great room features a Palladian window array, HW floors, ceiling fan, & patio doors to the deck for seamless indoor-outdoor living. The formal living room includes HW floors, FP, and French doors. A formal dining room provides the perfect setting for gatherings & special occasions. Additional highlights include a first-floor library with cathedral ceiling & built-in bookcases, a lower-level family and a generous mudroom with 1/2 bath. The primary bedroom features an ensuite bath & walk-in closet, while 4 additional bedrooms and 4 baths ensure room for all. Step outside to your private oasis with a stunning inground pool and a fully equipped stainless outdoor kitchen featuring granite countertops, built-in grill, refrigerator, sink, burner station, beverage center--perfect for Summer gatherings. Stunning sunrises, TimberTech Deck and saltwater pool all add to the appeal. Craftsmanship and care are evident throughout this fine home offering comfort, style & a location that combines the best of VT living. Delayed showings begin 7/12.
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Listed by:
Robert Doyle,
Berkley & Veller Greenwood Country Off:802-254-6400
Bought with: BHG Masiello Brattleboro
$925,000
65 Hillwinds North Road, Brattleboro, VT 05301
5beds
4,150sqft
Single Family Residence
Built in 1983
2.24 Acres Lot
$933,000 Zestimate®
$223/sqft
$5,549 Estimated rent
Home value
$933,000
$616,000 - $1.42M
$5,549/mo
Zestimate® history
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Zillow last checked: 7 hours ago
Listing updated: October 01, 2025 at 12:16pm
Listed by:
Robert Doyle,
Berkley & Veller Greenwood Country Off:802-254-6400
Bought with:
Steve Schoppmeyer
BHG Masiello Brattleboro
Source: PrimeMLS,MLS#: 5050760
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 2
- 3/4 bathrooms: 2
- 1/2 bathrooms: 1
Heating
- Propane, Baseboard, Electric, Hot Water, Radiant
Cooling
- Mini Split
Appliances
- Included: Dishwasher, Dryer, Microwave, Electric Range, Refrigerator, Washer, Domestic Water Heater, Tank Water Heater, Warming Drawer
- Laundry: 2nd Floor Laundry
Features
- Cathedral Ceiling(s), Ceiling Fan(s), Dining Area, Hearth, Primary BR w/ BA, Walk-In Closet(s)
- Flooring: Carpet, Ceramic Tile, Hardwood
- Windows: Double Pane Windows
- Basement: Bulkhead,Climate Controlled,Full,Partially Finished,Exterior Stairs,Walkout,Interior Access,Basement Stairs,Interior Entry
- Attic: Pull Down Stairs
- Has fireplace: Yes
- Fireplace features: Gas
Interior area
- Total structure area: 4,550
- Total interior livable area: 4,150 sqft
- Finished area above ground: 3,550
- Finished area below ground: 600
Property
Parking
- Total spaces: 2
- Parking features: Paved
- Garage spaces: 2
Features
- Levels: Two
- Stories: 2
- Patio & porch: Patio, Porch
- Exterior features: Deck, Garden, Other - See Remarks, Built in Gas Grill
- Has private pool: Yes
- Pool features: In Ground
- Fencing: Invisible Pet Fence
- Has view: Yes
- View description: Mountain(s)
- Frontage length: Road frontage: 253
Lot
- Size: 2.24 Acres
- Features: Country Setting, Landscaped, Trail/Near Trail, Walking Trails, Neighborhood
Details
- Zoning description: Residential
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Contemporary
- Property subtype: Single Family Residence
Materials
- Wood Frame, Clapboard Exterior
- Foundation: Poured Concrete
- Roof: Architectural Shingle,Standing Seam
Condition
- New construction: No
- Year built: 1983
Utilities & green energy
- Electric: 200+ Amp Service, Circuit Breakers
- Sewer: Septic Tank
- Utilities for property: Propane
Community & neighborhood
Security
- Security features: Security
Location
- Region: Brattleboro
- Subdivision: Hillwinds
Other
Other facts
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 10/1/2025 | Sold | $925,000+9%$223/sqft |
Source:  PrimeMLS #5050760 Report a problem | ||
| 7/15/2025 | Contingent | $849,000$205/sqft |
Source: PrimeMLS #5050760 Report a problem | ||
| 7/9/2025 | Listed for sale | $849,000$205/sqft |
Source: PrimeMLS #5050760 Report a problem | ||
Public tax history
Tax history is unavailable.
Neighborhood: 05301
Nearby schools
GreatSchools rating
- 5/10Academy SchoolGrades: PK-6Distance: 3 mi
- 6/10Dummerston SchoolsGrades: PK-8Distance: 4.1 mi
- NAWindham Regional Career CenterGrades: 9-12Distance: 4.4 mi
Schools provided by the listing agent
- District: Windham Southeast
Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Vermont
- Windham County
- Brattleboro
- 05301
- 65 Hillwinds North Road