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Courtesy of Andrea Kaplan of Four Seasons Sotheby's Int'l Realty: .

376 Windward Hill

Dorset, VT 05251
  • $2,375,000
  • STATUS: Active
  • ON SITE: 66 Days
  • MLS #: 5036105
UPDATED: 56 min ago
$2,375,000
  • 4
    BEDS
  • 12.67
    ACRES
  • 4
    BATHS
  • 1
    1/2 BATHS
  • 5,696
    SQFT
  • $417
    $/SQFT
Type:
Single-Family Home
Built:
1965
County:
Area:

School Information

Elementary School:
Middle School:
High School:
School District:

Description

Welcome to 376 Windward Hill, a stunning Southern Vermont estate with breathtaking views of the Taconic and Green Mountain Ranges. Spanning 12 acres, the property features a private trout pond and tranquil waterfall, creating a serene atmosphere. Inside, the home combines timeless elegance with modern comfort. Herringbone brick and hardwood floors lead to the expansive living room, highlighted by a two-story stone fireplace. This grand space flows seamlessly into the formal dining area, which opens to a screened porch and wrap-around deck, perfect for enjoying mountain vistas. The gourmet kitchen boasts a cozy bar, ample cabinetry, a butler's pantry, and top-of-the-line appliances. The primary suite offers sweeping views, deck access, and a spa-like bathroom with a jacuzzi tub and steam shower. The home includes three additional spacious bedrooms and a versatile office, plus a lower level with an exercise room, workshop, and family room for relaxation and productivity. Located minutes from Manchester and Dorset, 376 Windward Hill offers the perfect balance of privacy and convenience, making it an ideal retreat for both relaxation and entertaining.

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© Copyright 2025 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 2025-06-20T14:06:16.33.
www.livingvermont.com/homes/162560409
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376 Windward Hill Dorset, VT 05251

  • Price: $2,375,000
  • Status: Active
  • On Site: 66 Days
  • Updated: 56 min ago
  • MLS #: 5036105
4
Beds
4
Baths
1
½ Baths
12.67
Acres
5,696
SQFT
$417
$/SQFT
1965
Built
County:
Bennington
Area:
Dorset
Elementary School:
Dorset Elementary School
Middle School:
The Dorset School
High School:
Choice
School District:
Taconic And Green Regional
Property Description
Welcome to 376 Windward Hill, a stunning Southern Vermont estate with breathtaking views of the Taconic and Green Mountain Ranges. Spanning 12 acres, the property features a private trout pond and tranquil waterfall, creating a serene atmosphere. Inside, the home combines timeless elegance with modern comfort. Herringbone brick and hardwood floors lead to the expansive living room, highlighted by a two-story stone fireplace. This grand space flows seamlessly into the formal dining area, which opens to a screened porch and wrap-around deck, perfect for enjoying mountain vistas. The gourmet kitchen boasts a cozy bar, ample cabinetry, a butler's pantry, and top-of-the-line appliances. The primary suite offers sweeping views, deck access, and a spa-like bathroom with a jacuzzi tub and steam shower. The home includes three additional spacious bedrooms and a versatile office, plus a lower level with an exercise room, workshop, and family room for relaxation and productivity. Located minutes from Manchester and Dorset, 376 Windward Hill offers the perfect balance of privacy and convenience, making it an ideal retreat for both relaxation and entertaining.
Exterior Features

Architectural Style Contemporary Color White Construction Materials Wood FrameWood Exterior Driveway Gravel Exterior Features DeckGazeboPorch - Screened Has Garage Yes Lot Features Country SettingLandscapedMountain ViewPondRolling Parking Auto OpenHeated GarageDrivewayAttached Road Frontage No Roof Standing Seam

Interior Features

Appliances Cooktop - GasDishwasherDryerMicrowaveOven - DoubleOven - WallRefrigeratorWasherWater Heater - Owned Cooling Other Equipment Generator - Standby Flooring BrickCarpetCeramic TileWood Foundation Concrete Has Basement No Heating PropaneBaseboardElectricHot AirRadiant Ceiling Interior Features BlindsFireplaces - 2Living/DiningPrimary BR w/ BANatural LightVaulted CeilingWalk-in Closet Quarter Baths 0 Rooms Level1 Level 1: Exercise RoomLevel 1: Family RoomLevel 1: Workshop Rooms Level2 Level 2: BedroomLevel 2: Dining RoomLevel 2: Great RoomLevel 2: KitchenLevel 2: Primary Bdm SteLevel 2: Office/Study Rooms Total 12 Sq Ft Approx Fin Above Grade 5696 Sq Ft Approx Fin Below Grade 0

Property Features

Auction No Construction Status Existing Covenants Yes Documents Available CovenantsDeedTax Map Electric 200 AmpCircuit Breaker(s)Generator Electric Company Green Mountain Power Flood Zone No Foreclosed / Bank Owned / REO No Fuel Company Dead River Possession At Closing Pre Construction No Property Type Single Family Road Frontage Type AssociationDead EndPrivate RoadPrivately Maintained Seasonal No Sewer ConcreteSeptic Span Number 180-057-10652 Surveyed Yes Tax Gross Amount 19656.62 Tax Year 2025 Taxes Tbd No Timeshare Fractional Own No Utilities Cable - AvailableGas - LP/BottleTelephone Available Water Source Drilled Well Zoning Residential

Courtesy of Andrea Kaplan of Four Seasons Sotheby's Int'l Realty: .


© Copyright 2025 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 2025-06-20T14:06:16.33.
 
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