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.

Listing Tools

More Info

Tax Information

  • Tax Year2025

Parking

  • Parking Spaces3
  • GarageYes
  • Parking DescriptionAuto Open, Heated Garage, Driveway, Attached

Rooms

  • Full Bath4

Basic Information

  • MLS Number5036105
  • MLS StatusActive
  • StatusACT
  • Property TypeSingle Family
  • List Price$2,375,000
  • Listing Agent NameAndrea Kaplan
  • Broker NameFour Seasons Sotheby's Int'l Realty

Location

  • Building Number376
  • StreetWindward Hill
  • TownDorset
  • StateVT
  • Zip05251
  • CountyBennington
  • DistrictTaconic and Green Regional
  • Elementary SchoolDorset Elementary School
  • Junior HighThe Dorset School
  • High SchoolChoice
  • Flood Zone Y/NNo
  • Address376 Windward Hill

Building

  • Year Built1965
  • Building ConstructionWood Frame, Wood Exterior
  • ConstructionExisting
  • Property StyleContemporary
  • Bedrooms4
  • Bathroom5
  • Total Baths5
  • Half Bath1
  • Total Rooms12
  • Square Feet5,696
  • FoundationConcrete

Property

  • Acreage12.67
  • Lot DescriptionCountry Setting, Landscaped, Mountain View, Pond, Rolling
  • AreaVT-Bennington
  • DrivewayGravel
  • RoadsAssociation, Dead End, Private Road, Privately Maintained

Interior

  • Interior FeaturesBlinds, Fireplaces - 2, Living/Dining, Primary BR w/ BA, Natural Light, Vaulted Ceiling, Walk-in Closet
  • Room 1 TypeGreat Room
  • Room 1 Level2
  • FloorsBrick, Carpet, Ceramic Tile, Wood
  • Room 2 TypeDining Room
  • Room 2 Level2
  • Room 3 TypeKitchen
  • Room 3 Level2
  • Room 4 TypePrimary BR Suite
  • Room 4 Level2
  • Room 5 TypeBedroom
  • Room 5 Level2
  • Stories2
  • Room 6 TypeBedroom
  • Room 6 Level2
  • Room 7 TypeBedroom
  • Room 7 Level2
  • Room 8 TypeOffice/Study
  • Room 8 Level2
  • Room 9 TypeFamily Room
  • Room 9 Level1
  • Room 10 TypeExercise Room
  • Room 10 Level1
  • Room 11 TypeWorkshop
  • Room 11 Level1

Exterior

  • Exterior FeaturesDeck, Gazebo, Porch - Screened
  • Exterior ColorWhite
  • RoofStanding Seam

Utilities

  • Heat SystemPropane, Baseboard, Electric, Hot Air, Radiant Ceiling
  • WaterDrilled Well
  • SewerConcrete, Septic
  • Electric200 Amp, Circuit Breaker(s), Generator
  • UtilitiesCable - Available, Gas - LP/Bottle, Telephone Available

Amenities

  • AmenitiesGenerator - Standby
  • PricePerSqFt416.96

Other

  • Delayed ShowingsNo
  • SeasonalNo
  • Page418
  • Date Listed04/14/2025
  • View Count1

Map Location

Listed by Andrea Kaplan of Four Seasons Sotheby's Int'l Realty
Broker Reciprocity 

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 May 23, 2025 4:22 AM EDT

 

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