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Courtesy of Betsy Wadsworth of Four Seasons Sotheby's Int'l Realty: .

816 Black Bear Road

Jamaica, VT 05343
  • $3,995,000
  • STATUS: Active
  • MLS #: 5030672
UPDATED: 97 min ago
$3,995,000
  • 4
    BEDS
  • 44.47
    ACRES
  • 5
    BATHS
  • 1
    1/2 BATHS
  • 5,500
    SQFT
  • $726
    $/SQFT
Type:
Single-Family Home
Built:
2010
County:
Area:

School Information

Elementary School:
High School:
School District:

Description

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-cochère 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.

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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 2026-02-17T11:05:52.217.
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816 Black Bear Road Jamaica, VT 05343

  • Price: $3,995,000
  • Status: Active
  • On Site: Days
  • Updated: 97 min ago
  • MLS #: 5030672
4
Beds
5
Baths
1
½ Baths
44.47
Acres
5,500
SQFT
$726
$/SQFT
2010
Built
County:
Windham
Area:
Jamaica
Elementary School:
Jamaica Village School
Middle School:
Leland Gray Union Middle/High
High School:
Leland Gray
School District:
Windham Central
Property Description
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-cochère 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.
Exterior Features

Architectural Style CraftsmanPost and Beam Color Brown Construction Materials Timber FrameWood Siding Driveway Paved Exterior Features DeckGarden SpaceHot TubPatioIn-Ground PoolCovered Porch Has Garage Yes Lot Features Country SettingLandscapedMountain ViewOrchardsRecreationalSki AreaTrail/Near TrailWalking TrailsWoodedMountainNear SkiingNear Snowmobile Trails Road Frontage TBD Roof MetalStanding Seam

Interior Features

Appliances DishwasherDryerMicrowaveRefrigeratorWasherDual Fuel RangeExhaust Fan Basement Access Type Walkout Basement Description Finished Cooling None Flooring CarpetCeramic TileHardwoodTileWood Foundation Concrete Green Energy Efficient HVACWater heater Has Basement Yes Heating PropaneSolarHeat PumpMulti ZoneRadiant Floor Interior Features BlindsCathedral CeilingCeiling FanDining AreaDraperiesWood FireplaceHearthIn-Law SuiteKitchen IslandKitchen/LivingPrimary BR w/ BANatural LightNatural WoodworkVaulted CeilingWalk-in ClosetWalk-in Pantry1st Floor LaundryBasement Laundry Quarter Baths 0 Rooms Level B Level B: 1/2 BathroomLevel B: Family RoomLevel B: Laundry RoomLevel B: Media RoomLevel B: Office/Study Rooms Level1 Level 1: 1/2 BathroomLevel 1: Dining RoomLevel 1: FoyerLevel 1: Great RoomLevel 1: Kitchen/LivingLevel 1: Eat-in KitchenLevel 1: Laundry RoomLevel 1: Primary Bdm SteLevel 1: Mudroom Rooms Level2 Level 2: BedroomLevel 2: Bonus Room Rooms Total 19 Sq Ft Approx Fin Above Grade 5500 Sq Ft Approx Fin Below Grade 0

Property Features

Auction No Construction Status Existing Covenants No Electric Circuit Breaker(s) Electric Company GMP Flood Zone Unknown Foreclosed / Bank Owned / REO No Green Energy Generation Solar Pre Construction No Property Type Single Family Road Frontage Type Public Maintained Road Seasonal No Sewer Septic Span Number 324-101-11593 Surveyed Yes Tax Gross Amount 41949.05 Tax Year 2024 Taxes Tbd No Timeshare Fractional Own No Utilities Propane Water Source Drilled Well Zoning No zoning

Courtesy of Betsy Wadsworth 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 2026-02-17T11:05:52.217.
 
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