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.

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Tax Information

Tax Year2025

Location

Building Number81
StreetWindward Hill
TownDorset
StateVT
Zip05251
CountyBennington
DistrictTaconic and Green Regional
Elementary SchoolDorset Elementary School
Junior HighDorset Elementary School
High SchoolChoice
Flood Zone Y/NNo
Address81 Windward Hill

Interior

Interior FeaturesDining Area, Wood Fireplace,3+ Fireplaces, Primary BR w/ BA, Natural Light,1st Floor Laundry
Room 1 TypeKitchen
Room 1 Level1
FloorsCarpet, Ceramic Tile, Hardwood, Laminate, Manufactured, Tile, Wood, Vinyl Plank
Room 2 TypeDining Room
Room 2 Level1
Room 3 TypeDen
Room 3 Level1
Room 4 TypeLiving Room
Room 4 Level1
Room 5 TypeLaundry Room
Room 5 Level1
Stories2.5
Room 6 TypeMudroom
Room 6 Level1
Room 7 TypeFamily Room
Room 7 LevelBasement
Room 8 TypeRec Room
Room 8 Level1
Room 9 TypePrimary BR Suite
Room 9 Level2
Room 10 TypeBedroom
Room 10 Level2
Room 11 TypeBedroom
Room 11 Level2
Room 12 TypeBedroom
Room 12 Level2

Parking

Parking Spaces2
GarageYes
Parking DescriptionAuto Open, Direct Entry, Driveway, Garage, Paved, Attached

Building

Year Built1981
Building ConstructionWood Frame
ConstructionExisting
Property StyleColonial
Bedrooms4
Bathroom4
Total Baths4
3/4 Baths1
Half Bath1
Total Rooms10
Square Feet4,650
APX Unfin Below Grade100
BasementClimate Controlled, Concrete, Daylight, Finished, Full, Insulated, Interior Stairs, Storage Space, Walkout, Exterior Access, Basement Stairs
FoundationConcrete

Exterior

Exterior FeaturesGarden Space, Porch, Covered Porch, Shed, Storage
Exterior Colorblue
RoofAsphalt Shingle

Amenities

AmenitiesAir Conditioner, Dehumidifier
PricePerSqFt204.3

Other

Delayed ShowingsNo
SeasonalNo
Page763
Date Listed09/16/2025
View Count6

Rooms

Full Bath2

Basic Information

MLS Number5061525
MLS StatusActive Under Contract
Virtual TourView Tour
StatusActive With Contract
Property TypeSingle Family
List Price$950,000
Listing Agent NameAdrienne Sherwood
Broker NameFour Seasons Sotheby's Int'l Realty

Property

Acreage5.8
Lot DescriptionCountry Setting, Landscaped, Mountain View, View
AreaVT-Bennington
DrivewayPaved
RoadsCul-de-Sac, Dead End, Gravel, Private Road, Shared, Easement, Privately Maintained
Road Frontage564

Utilities

Heat SystemWood, Baseboard, Hot Water, Multi Zone
WaterDrilled Well
SewerPrivate, Septic
Electric200+ Amp Service
UtilitiesCable Available, Telephone Available

Legal

Taxes$11,747.6
Tax ReductionNo
ZoningResidential
Surveyed Y/NUnknown

Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated December 6, 2025 9:37 AM EST

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81 Windward HillDorset, VT 05251MLS Number 5061525

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