Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural surroundings. Just a short drive from Stratton and Mt Snow ski resorts. The moment you arrive; the home’s striking presence is undeniable. A porte-cochre welcomes you, setting the tone for the beauty that lies within. The heart of the home is the gourmet chef’s kitchen, anchored by a La Cornue stove, rich custom cabinetry, and an expansive island.Douglas fir beams and wide oak floors lend warmth and character, while a masonry fireplace in the great room offers the perfect setting to unwind after a day on the slopes. One of the home’s most captivating features is its silo with a winding staircase illuminated by gas lanterns. A bonus playroom above the three-car garage provides additional space for recreation, while a custom wine room and private movie theater elevate the home’s entertainment offerings. The seamless connection between indoor and outdoor living is one of the home’s greatest attributes. Heated pool, hot tub and fireplace sit against a backdrop of vast mountain views. The landscape is adorned with a sea of peony bushes, adding vibrant color to the meticulously designed gardens.

Listing Tools

More Info

Tax Information

  • Tax Year2024

Parking

  • Parking Spaces6
  • GarageYes

Rooms

  • Full Bath5

Basic Information

  • MLS Number5030672
  • MLS StatusActive
  • Virtual TourView Tour
  • StatusACT
  • Property TypeSingle Family
  • List Price$3,995,000
  • Listing Agent NameBetsy Wadsworth
  • Broker NameFour Seasons Sotheby's Int'l Realty

Location

  • Building Number816
  • StreetBlack Bear Road
  • TownJamaica
  • StateVT
  • Zip05343
  • CountyWindham
  • DistrictWindham Central
  • Elementary SchoolJamaica Village School
  • Junior HighLeland Gray Union Middle/High
  • High SchoolLeland Gray
  • Flood Zone Y/NUnknown
  • Address816 Black Bear Road

Building

  • Year Built2010
  • Building ConstructionTimber Frame, Wood Siding
  • ConstructionExisting
  • Property StyleCraftsman, Post and Beam
  • Bedrooms4
  • Bathroom6
  • Total Baths6
  • Half Bath1
  • Total Rooms19
  • Square Feet5,500
  • BasementFinished
  • FoundationConcrete

Property

  • Acreage44.47
  • Lot DescriptionCountry Setting, Landscaped, Mountain View, Orchards, Recreational, Ski Area, Trail/Near Trail, Walking Trails, Wooded, Mountain, Near Skiing, Near Snowmobile Trails
  • AreaVT-Windham
  • DrivewayPaved
  • RoadsPublic Maintained Road

Interior

  • Interior FeaturesBlinds, Cathedral Ceiling, Ceiling Fan, Dining Area, Draperies, Wood Fireplace, Hearth, In-Law Suite, Kitchen Island, Kitchen/Living, Primary BR w/ BA, Natural Light, Natural Woodwork, Vaulted Ceiling, Walk-in Closet, Walk-in Pantry,1st Floor Laundry, Basement Laundry
  • Room 1 TypeMudroom
  • Room 1 Level1
  • FloorsCarpet, Ceramic Tile, Hardwood, Tile, Wood
  • Room 2 TypeLaundry Room
  • Room 2 Level1
  • Room 3 TypeBathroom Half
  • Room 3 Level1
  • Room 4 TypeFoyer
  • Room 4 Level1
  • Room 5 TypeEat-in Kitchen
  • Room 5 Level1
  • Stories2.5
  • Room 6 TypeKitchen/Living
  • Room 6 Level1
  • Room 7 TypeDining Room
  • Room 7 Level1
  • Room 8 TypeGreat Room
  • Room 8 Level1
  • Room 9 TypePrimary BR Suite
  • Room 9 Level1
  • Room 10 TypeBedroom with Bath
  • Room 10 Level2
  • Room 11 TypeBedroom with Bath
  • Room 11 Level2
  • Room 12 TypeBedroom
  • Room 12 Level2
  • Room 13 TypeMedia Room
  • Room 13 LevelBasement
  • Room 14 TypeOffice/Study
  • Room 14 LevelBasement
  • Room 15 TypeBedroom with Bath
  • Room 15 LevelBasement
  • Room 16 TypeBathroom Half
  • Room 16 LevelBasement
  • Room 17 TypeFamily Room
  • Room 17 LevelBasement
  • Room 18 TypeLaundry Room
  • Room 18 LevelBasement
  • Room 19 TypeBonus Room
  • Room 19 Level2
  • Room 19 DimensionsOver Garage

Exterior

  • Exterior FeaturesDeck, Garden Space, Hot Tub, Patio, In-Ground Pool, Covered Porch
  • Exterior ColorBrown
  • RoofMetal, Standing Seam

Utilities

  • Heat SystemPropane, Solar, Heat Pump, Multi Zone, Radiant Floor
  • WaterDrilled Well
  • SewerSeptic
  • ElectricCircuit Breaker(s)
  • UtilitiesPropane

Amenities

  • AmenitiesSecurity System, Hardwired Smoke Detector, Standby Generator
  • PricePerSqFt726.36

Other

  • SeasonalNo
  • Page530
  • Date Listed03/01/2025
  • View Count23

Map Location

Listed by Betsy Wadsworth of Four Seasons Sotheby's Int'l Realty
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 February 18, 2026 7:22 AM EST

 

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