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Offered at $3,995,000Active
beds
4
baths
6
sq ft
5,500
Built
2010

816 Black Bear Road

Jamaica, VT 05343

Residential · Active · MLS #5096846
Listing Courtesy of Four Seasons Sotheby's Int'l Realty | Betsy Wadsworth

The home

About this home

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.

Property information

Details at a glance

Interior4 property facts
Rooms
19
Heating
Heat Pump, Radiant, Propane, Solar, Radiant Floor
Cooling
None
Flooring
Carpet, Ceramic Tile, Hardwood, Tile, Wood
Building5 property facts
Style
Single Family Residence
Year built
2010
Garage
6
Parking
6
Roof
Metal
Land & utilities4 property facts
Lot size
44.47 acres
Water
Well
Sewer
Septic Tank
Zoning
No zoning
Financial2 property facts
Annual taxes
$51,350
Assessment year
2026

Plan your purchase

Estimated monthly cost

Explore costs at the $3,995,000 asking price. Adjust the assumptions to your situation.

Known monthly costs$24,480 / monthAdjust
Principal & interest
$20,201
Property tax
$4,279
Insurance
Not entered
HOA
Not entered

Listing annual taxes: $51,350. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.

Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.

The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.

Listing history

Price and status timeline

No additional listing history is available for public display.

Compare with confidence

Price & market context

See how this home compares with active listings in Jamaica.

This home compared with active listings in Jamaica
MetricThis homeLocal listings
List price$3,995,000$825,000384% above local
Price / sq ft$726$36897% above local
Days on market4711057% below local

Active city listing statistics from PrimeMLS as of September 11, 2026. Asking prices are not completed-sale values.

Keep exploring

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About 816 Black Bear Road

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Request a tour of 816 Black Bear Road and a Bean Group agent will help coordinate an available time with the listing side.

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Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

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