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Beautifully maintained contemporary home on 3.62 private acres with elevated westerly views of Mt. Equinox and spectacular sunsets. Designed by renown architect Deborah Berke, Dean of the Yale School of Architecture, this light-filled home offers the ease of main-level living with a first-floor primary suite, laundry, bright office, den with custom built-ins, and spacious living room with vaulted ceiling, wood-burning fireplace, and oak floors. The kitchen features a center island and Aga stove, opening to dining and living areas ideal for everyday comfort and entertaining. Upstairs are two generous guest bedrooms, abundant closets - including a cedar-lined walk-in - and a full bath. Enjoy the seasons from the screened porch or custom fieldstone patio with sitting wall and awnings. Quality features include central air, whole-house generator, security system, water filtration, standing-seam metal roof, Andersen windows, attached two-car garage, and excellent dry basement storage. Minutes to Manchester and Dorset, this private, move-in-ready property offers convenience, comfort, and enduring Vermont charm.

More Info

Tax Information

  • Tax Year2027

Location

  • Building Number88
  • StreetWindward South Road
  • TownDorset
  • StateVT
  • Zip05251
  • CountyBennington
  • SubdivisionWindward South
  • DistrictTaconic and Green Regional
  • Elementary SchoolDorset Elementary School
  • Junior HighManchester Elementary& Middle
  • High SchoolBurr and Burton Academy
  • Map14
  • Flood Zone Y/NNo
  • Address88 Windward South Road

Interior

  • Interior FeaturesBlinds, Cedar Closet, Dining Area, Wood Fireplace,1 Fireplace, Kitchen Island, Primary BR w/ BA, Natural Light, Security, Soaking Tub, Vaulted Ceiling, Walk-in Closet, Programmable Thermostat,1st Floor Laundry
  • Room 1 TypeKitchen
  • Room 1 Level1
  • Room 1 Dimensions15 x 11
  • FloorsCarpet, Hardwood
  • Room 2 TypeDining Room
  • Room 2 Level1
  • Room 2 Dimensions14 x 11
  • Room 3 TypeLiving Room
  • Room 3 Level1
  • Room 3 Dimensions25 x 16
  • Room 4 TypeDen
  • Room 4 Level1
  • Room 4 Dimensions15 x 9
  • Room 5 TypePrimary Bedroom
  • Room 5 Level1
  • Room 5 Dimensions15 x 15
  • Stories2
  • Room 6 TypeBedroom
  • Room 6 Level2
  • Room 6 Dimensions19 x 11
  • Room 7 TypeBedroom
  • Room 7 Level2
  • Room 7 Dimensions15 x 14

Parking

  • Parking Spaces2
  • GarageYes
  • Parking DescriptionAuto Open, Driveway, Garage, Parking Spaces 6+, Unpaved, Attached

Building

  • Year Built1981
  • Building ConstructionWood Siding
  • ConstructionExisting
  • Property StyleContemporary
  • Bedrooms3
  • Bathroom3
  • Total Baths3
  • Half Bath1
  • Total Rooms7
  • Square Feet3,094
  • APX Unfin Below Grade1273
  • BasementConcrete, Concrete Floor, Crawl Space, Full, Insulated, Interior Stairs, Storage Space, Unfinished
  • FoundationPoured Concrete

Exterior

  • Exterior FeaturesPartial Fence, Garden Space, Patio, Screened Porch, Double Pane Window(s)
  • Exterior Colorgrey
  • RoofStanding Seam

Amenities

  • Accessibility Amenities1st Floor 1/2 Bathroom,1st Floor Bedroom,1st Floor Full Bathroom,1st Floor Hrd Surfce Flr, Grab Bars in Bathroom, Hard Surface Flooring,1st Floor Laundry
  • AmenitiesAir Conditioner, CO Detector, Security System, Smoke Detector, Standby Generator
  • PetsYes
  • PricePerSqFt379.77

Other

  • SeasonalNo
  • Page335
  • Date Listed09/07/2026

Rooms

  • Full Bath2

Basic Information

  • MLS Number5108534
  • MLS StatusActive
  • Virtual TourView Tour
  • StatusACT
  • Property TypeSingle Family
  • List Price$1,175,000
  • Listing Agent NameDavid Halligan
  • Broker NameFour Seasons Sotheby's Int'l Realty

Property

  • Acreage3.62
  • Lot DescriptionCountry Setting, Landscaped, Mountain View, Sloping, Subdivision, View, Wooded, Neighborhood, Rural, Private
  • AreaVT-Bennington
  • Lot46
  • DrivewayGravel
  • RoadsDead End, Gravel, Private Road, Privately Maintained
  • Road Frontage386

Utilities

  • Heat SystemOil, Forced Air, Hot Air, In Floor
  • WaterDrilled Well
  • SewerSeptic
  • Electric200+ Amp Service, Circuit Breaker(s), Generator
  • UtilitiesCable

Water Body

  • Water AccessNo
  • Water ViewNo

Map Location

Driving Directions

Broker Reciprocity 

Copyright 2026 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 September 8, 2026 7:08 AM UTC

 

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