Light and thoughtful architect designed home on a lovely 12 acre hilltop. Set in a magical landscape of exposed ledge, old stone walls & established perennial gardens. Stunning views of both Mt Ascutney and Little Ascutney. Spacious and airy, large windows and south-facing skylights provide passive solar warmth throughout the 4 bedroom home. Open layout is clean and efficient with cathedral ceilings & custom touches. Drilled well. The kitchen has smart, functional design. Dining/Family room and sunken living room. Large primary bedroom with ensuite bath, laundry, and deck. A perfect spot for anyone who enjoys the outdoors. Direct access to recreational trails. Close to Ascutney Outdoors, WW Town Forest & the Brownsville Butcher & Pantry. A peaceful homestead in a truly special corner of Vermont. Listing price adjusted to reflect older roof, decks & skylights. All still serviceable.
Closed
Listed by:
Dana S Waters,
Dark Horse Realty 802-484-7388,
Paula Waters,
Dark Horse Realty
Bought with: BHG Masiello Brattleboro
$525,000
77 Winding Road, West Windsor, VT 05037
4beds
2,380sqft
Single Family Residence
Built in 1988
12.2 Acres Lot
$525,300 Zestimate®
$221/sqft
$3,195 Estimated rent
Home value
$525,300
$468,000 - $594,000
$3,195/mo
Zestimate® history
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What's special
Zillow last checked: 8 hours ago
Listing updated: December 16, 2025 at 08:12am
Listed by:
Dana S Waters,
Dark Horse Realty 802-484-7388,
Paula Waters,
Dark Horse Realty
Bought with:
Carol A Cole
BHG Masiello Brattleboro
Source: PrimeMLS,MLS#: 5064038
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 2
- Full bathrooms: 2
Heating
- Propane, Baseboard, Passive Solar, Radiant, Wood Stove
Cooling
- None
Appliances
- Included: Dishwasher, Dryer, Freezer, Microwave, Gas Range, Refrigerator, Washer, Propane Water Heater
- Laundry: 1st Floor Laundry
Features
- Cathedral Ceiling(s), Ceiling Fan(s), Dining Area, Primary BR w/ BA, Natural Light
- Flooring: Carpet, Hardwood, Tile
- Windows: Skylight(s)
- Basement: Concrete,Partial,Unfinished,Interior Access,Exterior Entry,Basement Stairs,Walk-Out Access
- Fireplace features: Wood Stove Hook-up
Interior area
- Total structure area: 2,380
- Total interior livable area: 2,380 sqft
- Finished area above ground: 2,180
- Finished area below ground: 200
Property
Parking
- Total spaces: 2
- Parking features: Gravel, Right-Of-Way (ROW), Detached
- Garage spaces: 2
Features
- Levels: Two
- Stories: 2
- Exterior features: Balcony, Deck, Shed
- Has view: Yes
- View description: Mountain(s)
- Frontage length: Road frontage: 435
Lot
- Size: 12.20 Acres
- Features: Corner Lot, Country Setting, Recreational, Rolling Slope, Secluded, Sloped, Trail/Near Trail, Walking Trails, Wooded
Details
- Parcel number: 73823510591
- Zoning description: Res
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence
Materials
- Wood Frame, Clapboard Exterior
- Foundation: Concrete
- Roof: Asphalt Shingle
Condition
- New construction: No
- Year built: 1988
Utilities & green energy
- Electric: 100 Amp Service, Circuit Breakers, Underground
- Sewer: 1000 Gallon, On-Site Septic Exists, Septic Tank
- Utilities for property: Cable
Community & neighborhood
Location
- Region: Brownsville
Other
Other facts
- Road surface type: Gravel, Paved
Price history
| Date | Event | Price |
|---|---|---|
| 12/15/2025 | Sold | $525,000+1%$221/sqft |
Source:  PrimeMLS #5064038 | ||
| 10/2/2025 | Listed for sale | $520,000+85.7%$218/sqft |
Source: PrimeMLS #5064038 | ||
| 11/28/2016 | Sold | $280,000$118/sqft |
Source: PrimeMLS #4466187 | ||
| 12/22/2003 | Sold | $280,000$118/sqft |
Source: Public Record | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $522,000 +47.5% |
| 2023 | -- | $353,800 |
| 2022 | -- | $353,800 |
Find assessor info on the county website
Neighborhood: 05037
Nearby schools
GreatSchools rating
- 6/10Weathersfield SchoolGrades: PK-8Distance: 5.4 mi
- 4/10Windsor SchoolGrades: PK-12Distance: 5.6 mi
- NAReading Elementary SchoolGrades: PK-4Distance: 1.8 mi
Schools provided by the listing agent
- Elementary: Albert Bridge School
- Middle: Windsor High School
- High: Windsor High School
- District: Windsor 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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