$3,995,000
 $21,446 est/mo Sourced by Back At You

816 Black Bear Road,Jamaica, VT 05343

Jamaica, VT 05343

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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.

Details

MLS #5096846
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
Status(10) Active - Active
Year2010
Days On Site103
Listing Provided ByFour Seasons Sotheby's Int'l Realty | Betsy Wadsworth

Features

Bed(s)4
Bath(s) 6 Total
Garage6
BasementY
PoolYes
Story(s)2
ZoningNo zoning
Acreage44.47

Interior

Rooms Total19
CoolingNone
HeatingPropane, Solar, Heat Pump, Zoned, Radiant Floor
Interior FeaturesBlinds, Cathedral Ceiling(s), Ceiling Fan(s), Dining Area, Draperies, Wood Fireplace, Hearth, In-Law Floorplan, Kitchen Island, Kitchen/Living, Primary BR w/ BA, Natural Light, Natural Woodwork, Vaulted Ceiling(s), Walk-In Closet(s), Walk-in Pantry, 1st Floor Laundry, Basement Laundry
AppliancesDishwasher, Dryer, Microwave, Refrigerator, Washer, Dual Fuel Range, Exhaust Fan

Exterior

Exterior FeaturesDeck, Garden, Hot Tub, Patio, In-Ground Pool, Covered Porch
RoofMetal, Standing Seam
Construction MaterialsTimber Frame, Wood Siding
Foundation DetailsConcrete
Lot FeaturesCountry Setting, Landscaped, Mountain View, Orchard(s), Recreational, Ski Area, Trail/Near Trail, Walking Trails, Wooded, Mountain, Near Skiing, Near Snowmobile Trails

Parking

Garage Yes / NoYes

Utilities

UtilitiesPropane
ElectricCircuit Breakers
SewerSeptic Tank

Taxes

Tax Annual Amount51349.9
Tax Year2026

Area Information

StateVT
CountyWindham
CityJamaica
Zip Code05343
AreaVT Windham
School DistrictWindham Central
Elementary SchoolJamaica Village School
High SchoolLelandGray
Listing VS Median (in 05343)
Price:
$3,995,000
low | high
Med:
$2,399,000
89.949937421777% of Average
On site:
103
low | high
Med:
1103
9.338168631006% of Average
Sourced by Back At You

Market Activity 05343

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Learn More About This Property

StateVT
CountyWindham
CityJamaica
Zip Code05343
AreaVT Windham
School DistrictWindham Central
Elementary SchoolJamaica Village School
High SchoolLelandGray
Listing VS Median (in 05343)
Price:
$3,995,000
low | high
Med:
$2,399,000
89.949937421777% of Average
On site:
103
low | high
Med:
1103
9.338168631006% of Average
Sourced by Back At You
Listing Updated: September 29, 2026 at 6:26:20 AM PDT