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Courtesy of David Halligan of Four Seasons Sotheby's Int'l Realty: .

88 Windward South

Dorset, VT 05251
  • $1,175,000
  • STATUS: Active Under Contract
  • ON SITE: 38 Days
  • MLS #: 5108534
Under Contract
UPDATED: 23 min ago
$1,175,000
  • 3
    BEDS
  • 3.62
    ACRES
  • 2
    BATHS
  • 1
    1/2 BATHS
  • 3,094
    SQFT
  • $380
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1981
County:
Area:

School Information

Elementary School:
School District:

Description

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.

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© Copyright 2026 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 2026-10-16T14:06:32.783.
www.livingvermont.com/homes/180943796
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88 Windward South Dorset, VT 05251

  • Price: $1,175,000
  • Status: Active Under Contract
  • On Site: 38 Days
  • Updated: 23 min ago
  • MLS #: 5108534
3
Beds
2
Baths
1
½ Baths
3.62
Acres
3,094
SQFT
$380
$/SQFT
1981
Built
Neighborhood:
Windward South
County:
Bennington
Area:
Dorset
Elementary School:
Dorset Elementary School
Middle School:
Manchester Elementary& Middle
High School:
Burr And Burton Academy
School District:
Taconic And Green Regional
Property Description
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.
Exterior Features

Architectural Style Contemporary Color grey Construction Materials Wood Siding Driveway Gravel Exterior Features Partial FenceÂGarden SpacePatioScreened PorchDouble Pane Window(s) Has Garage Yes Lot Features Country SettingLandscapedMountain ViewSlopingSubdivisionViewWoodedNeighborhoodRuralPrivate Lot Number 46 Owned Land Yes Parking Auto OpenDrivewayGarageParking Spaces 6+UnpavedAttached Road Frontage Yes Road Frontage Length 386 Roof Standing Seam Water Body Access YN No Water View YN No Waterfront Property No

Interior Features

Appliances DishwasherDryerMicrowaveWall OvenGas RangeRefrigeratorWasherDomestic Water HeaterOwned Water Heater Basement Access Type Interior Basement Description ConcreteConcrete FloorCrawl SpaceFullInsulatedInterior StairsStorage SpaceUnfinished Cooling Central AC Flooring CarpetHardwood Foundation Poured Concrete Has Basement Yes Heating OilForced AirHot AirIn Floor Interior Features BlindsCedar ClosetDining AreaWood Fireplace1 FireplaceKitchen IslandPrimary BR w/ BANatural LightSecuritySoaking TubVaulted CeilingWalk-in ClosetProgrammable Thermostat1st Floor Laundry Quarter Baths 0 Rooms Level1 Level 1: DenLevel 1: Dining RoomLevel 1: KitchenLevel 1: Living RoomLevel 1: Primary Bedroom Rooms Level2 Level 2: Bedroom Rooms Total 7 Sq Ft Approx Fin Above Grade 3094 Sq Ft Approx Fin Below Grade 0

Property Features

Assessment Amount 1034600 Assessment Year 2026 Block 00 Construction Status Existing Covenants Yes Documents Available DeedProperty DisclosureTax Map Easements Unknown Electric 200+ Amp ServiceCircuit Breaker(s)Generator Electric Company Green Mountain power Features Accessibility 1st Floor 1/2 Bathroom1st Floor Bedroom1st Floor Full Bathroom1st Floor Hrd Surfce FlrGrab Bars in BathroomHard Surface Flooring1st Floor Laundry Financing Possible Opt CashConventional Flood Zone No Negotiable Furnishings Planned Urban Developmt No Possession At Closing Possible Use Residential Pre Construction No Property Type Single Family Resort No Restrictions None Road Frontage Type Dead EndGravelPrivate RoadPrivately Maintained Seasonal No Sewer Septic Span Number 180-057-10086 Special Listing Conditions None Surveyed Unknown Tax Gross Amount 14045.72 Tax Year 2027 Taxes Tbd Yes Timeshare Fractional Own No Utilities Cable Water Source Drilled Well Zoning residential

Courtesy of David Halligan of Four Seasons Sotheby's Int'l Realty: .


© Copyright 2026 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 2026-10-16T14:06:32.783.
 
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