Property
$4,495,50044.47 Acres4 beds • 5 baths • 1 half bath • 5,500 sq ft
For Sale
For Sale
$4,495,50044.47 Acres
For Sale
4 beds • 5 baths • 1 half bath • 5,500 sq ft

816 Black Bear Road, Jamaica, VT 05343 - Windham County

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Property ID 22767809

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Single Family - Jamaica, VT

Set atop a scenic Vermont hillside, this five-bedroom custom-built home by The Wadsworth Design Build/Vermont Barns is a stunning 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 Mount Snow ski resorts, it is the ultimate retreat. 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. Exposed 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 fire place sit against a backdrop of vast mountain views. The surrounding landscape is adorned with a sea of peony bushes, adding vibrant color to the meticulously designed gardens.

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Four Seasons Sotheby's Int'l Realty

Dover, VT

(888) 526-4050
Listing provided by
Betsy Wadsworth
Four Seasons Sotheby's Int'l Realty(888) 526-4050
Source: ListHub, MLS# 5030672
Listing status: Active
Listing last updated: September 23, 2025 at 6:00 PM
Listing last checked: December 1, 2025 at 10:30 AM
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Betsy Wadsworth

Four Seasons Sotheby's Int'l Realty
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Betsy Wadsworth

Four Seasons Sotheby's Int'l Realty