Set on a quiet private road in the heart of Dorset, Vermont, this distinguished four bedroom Colonial blends classic New England architecture with modern comfort. Framed by mountain views and surrounded by natural beauty, the property offers the perfect balance of privacy, charm, and convenience. Inside, you’ll find inviting spaces designed for both everyday living and gracious entertaining. Three fireplaces provide warmth and character throughout the home, creating cozy gathering spots in every season. The finished walkout basement extends the living space, ideal for a family room, home office, or guest suite. Outdoors, the property continues to impress. A dedicated garden space invites you to cultivate your own vegetables, herbs, or flowers, while the mountain backdrop offers year-round beauty. The private setting allows you to enjoy peaceful mornings on the porch or evenings by the fire, all just minutes from Dorset village amenities.
Closed
Listed by: Four Seasons Sotheby's Int'l Realty
Bought with: Four Seasons Sotheby's Int'l Realty
$875,000
81 Windward Hill, Dorset, VT 05251
4beds
4,650sqft
Single Family Residence
Built in 1981
5.8 Acres Lot
$920,600 Zestimate®
$188/sqft
$7,767 Estimated rent
Home value
$920,600
Estimated sales range
Not available
$7,767/mo
Zestimate® history
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List your homeWhat's special
Dedicated garden spaceMountain viewsQuiet private roadNatural beautyFinished walkout basementInviting spaces
Zillow last checked:
Listing updated:
Listed by:
Adrienne Sherwood,
Four Seasons Sotheby's Int'l Realty 802-362-4551
Bought with:
Adrienne Sherwood
Four Seasons Sotheby's Int'l Realty
Source: PrimeMLS,MLS#: 5061525
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 2
- 3/4 bathrooms: 1
- 1/2 bathrooms: 1
Heating
- Wood, Baseboard, Hot Water, Zoned
Cooling
- Wall Unit(s), Whole House Fan
Appliances
- Included: Dishwasher, Dryer, Range Hood, Microwave, Electric Range, Refrigerator, Washer, Owned Water Heater, Exhaust Fan
- Laundry: 1st Floor Laundry
Features
- Dining Area, Primary BR w/ BA, Natural Light
- Flooring: Carpet, Ceramic Tile, Hardwood, Laminate, Manufactured, Tile, Wood, Vinyl Plank
- Basement: Climate Controlled,Concrete,Daylight,Finished,Full,Insulated,Interior Stairs,Storage Space,Walkout,Exterior Entry,Basement Stairs,Interior Entry
- Has fireplace: Yes
- Fireplace features: Wood Burning, 3+ Fireplaces
Interior area
- Total structure area: 4,750
- Total interior livable area: 4,650 sqft
- Finished area above ground: 3,060
- Finished area below ground: 1,590
Property
Parking
- Total spaces: 2
- Parking features: Paved, Auto Open, Direct Entry, Driveway, Garage, Attached
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: 2.5
- Stories: 2
- Patio & porch: Porch, Covered Porch
- Exterior features: Garden, Shed, Storage
- Has view: Yes
- View description: Mountain(s)
- Frontage length: Road frontage: 564
Lot
- Size: 5.80 Acres
- Features: Country Setting, Landscaped, Views
Details
- Parcel number: 18005710929
- Zoning description: Residential
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Wood Frame
- Foundation: Concrete
- Roof: Asphalt Shingle
Condition
- New construction: No
- Year built: 1981
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: Private Sewer, Septic Tank
- Utilities for property: Cable Available, Phone Available, Fiber Optic Internt Avail
Community & neighborhood
Location
- Region: Dorset
Other
Other facts
- Road surface type: Gravel
Price history
| Date | Event | Price |
|---|---|---|
| 12/19/2025 | Sold | $875,000-7.9%$188/sqft |
Source:  PrimeMLS #5061525 Report a problem | ||
| 12/7/2025 | Contingent | $950,000$204/sqft |
Source: PrimeMLS #5061525 Report a problem | ||
| 10/21/2025 | Price change | $950,000-2.6%$204/sqft |
Source: PrimeMLS #5061525 Report a problem | ||
| 9/16/2025 | Listed for sale | $975,000+68.4%$210/sqft |
Source: PrimeMLS #5061525 Report a problem | ||
| 3/19/2025 | Listing removed | $5,000$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 2/23/2025 | Price change | $5,000-9.1%$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 12/19/2024 | Listed for rent | $5,500$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 1/20/2022 | Listing removed | -- |
Source: Zillow Rental Manager Report a problem | ||
| 1/15/2022 | Listed for rent | $5,500$1/sqft |
Source: Zillow Rental Manager Report a problem | ||
| 5/27/2021 | Sold | $579,000$125/sqft |
Source: PrimeMLS #4853063 Report a problem | ||
| 3/31/2016 | Listing removed | $579,000$125/sqft |
Source: Pinnacle Realty #4456595 Report a problem | ||
| 10/18/2015 | Listed for sale | $579,000-3.2%$125/sqft |
Source: Pinnacle Realty #4456595 Report a problem | ||
| 6/7/2015 | Listing removed | $598,000$129/sqft |
Source: Four Seasons Sotheby's International Realty #4397607 Report a problem | ||
| 1/1/2015 | Listed for sale | $598,000$129/sqft |
Source: Lang McLaughry Real Estate #4397607 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $565,800 |
| 2023 | -- | $565,800 |
| 2022 | -- | $565,800 |
| 2021 | -- | $565,800 |
| 2020 | -- | $565,800 |
| 2019 | -- | $565,800 0% |
| 2018 | -- | $565,820 |
| 2017 | -- | $565,820 +0% |
| 2016 | -- | $565,800 +9900% |
| 2015 | -- | $5,658 |
| 2014 | -- | $5,658 |
| 2013 | -- | $5,658 -18.4% |
| 2012 | -- | $6,935 |
| 2011 | -- | $6,935 |
| 2010 | -- | $6,935 |
| 2009 | -- | $6,935 |
| 2008 | -- | $6,935 |
| 2007 | -- | $6,935 |
Find assessor info on the county website
Neighborhood: 05251
Nearby schools
GreatSchools rating
- 6/10Dorset Elementary SchoolGrades: PK-8Distance: 0.8 mi
- NABurr & Burton AcademyGrades: 9-12Distance: 4 mi
Schools provided by the listing agent
- Elementary: Dorset Elementary School
- Middle: Dorset Elementary School
- District: Taconic and Green Regional
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
- Bennington County
- Dorset
- 05251
- 81 Windward Hill
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