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816 Black Bear Road, 
Jamaica, VT 05343

$3,995,000


4

Beds


6

Baths


5,500

Sq Ft


Single Family

Active

Listed by

Betsy Wadsworth

Four Seasons Sotheby'S Int'L Realty

802-464-1200

Last updated:

January 1, 2026, 08:41 PM

MLS#

5030672

Source:

PrimeMLS

About This Home

816 Black Bear Road

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.

Home Facts

Single Family

6 Baths

4 Bedrooms

Built in 2010

Price Summary

3,995,000

$726 per Sq. Ft.

MLS #:

5030672

Last Updated:

January 1, 2026, 08:41 PM

Added:

a year ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

6

Full Bathrooms:

5

Interior

Living Area:

5,500 Sq. Ft.


Structure

Structure

Building Area:

5,500 Sq. Ft.

Year Built:

2010


Lot

Lot Size (Sq. Ft):

1,937,113


Finances & Disclosures

Finances

Price:

$3,995,000

Price per Sq. Ft:

$726 per Sq. Ft.

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Copyright 2026 Prime MLS, Inc. 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 Prime MLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated January 15, 2026

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.