For Sale
Single family home for sale at 816 Black Bear Rd, Jamaica, VT 05343 | MLS# 5096846 | Listing updated on 2026-10-25
Photo 1 of Single family home for sale at 816 Black Bear Rd, Jamaica, VT 05343 | MLS# 5096846 | Listing updated on 2026-10-25
Photo 2 of Single family home for sale at 816 Black Bear Rd, Jamaica, VT 05343 | MLS# 5096846 | Listing updated on 2026-10-25
Photo 3 of Single family home for sale at 816 Black Bear Rd, Jamaica, VT 05343 | MLS# 5096846 | Listing updated on 2026-10-25
Photo 4 of Single family home for sale at 816 Black Bear Rd, Jamaica, VT 05343 | MLS# 5096846 | Listing updated on 2026-10-25
55+
Beds Icon

Street View

Listed by: Betsy Wadsworth | Four Seasons Sotheby's Int'l Realty (802) 464-1200

$3,995,000

Monthly Est:$19,885

  • Beds Icon4 Beds
  • Beds Icon
    6 Baths
  • Beds Icon5,500sqft

816 Black Bear Rd, Jamaica, VT 05343

$19,885/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 2010

  • $-- HOA

  • 44.47 acres lot

  • $726/sq.ft

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.

  • Houzeo last checked: 12 hours ago
  • Listing updated: October 25, 2026 at 9:00 pm
  • Source: NEREN/Prime MLS-NH | MLS#: 5096846 NEREN/Prime MLS-NH

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Vt Windham County

  • City

    Jamaica

  • Neighborhood

    --

  • Year Built

    2010

  • HOA Fees

    -

  • Finished Area

    5,500 sqft

  • Lot Size

    44.47 acres lot

  • Basement Area

    - sqft

  • MLS Name

    NEREN/Prime MLS

  • MLS Number

    5096846

  • MLS Status

    (10) Active - Active

  • Days on Market

    130

Continue Your Journey in App

Find your dream home, receive real-time updates, and many more!

Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 6

Interior

  • Exterior Features

    Deck, Garden, Hot Tub, Patio, In Ground Pool, Covered Porch

  • Appliances

    Dishwasher, Dryer, Microwave, Refrigerator, Washer, Dual Fuel Range, Exhaust Fan

  • Flooring

    Ceramic Tile, Carpet, Hardwood, Tile, Wood

  • Cooling

    None

  • Interior Features

    Blinds, 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

  • Sewer

    Septic Tank

  • Heating

    Propane, Solar, Heat Pump, Zoned, Radiant Floor

Construction

  • Year Built

    Year Built: 2010

  • Home type

    Single Family Residence

  • Foundation Details

    Concrete

  • Roof

    Metal, Standing Seam

  • Architectural Style

    Craftsman, Post And Beam

  • Construction Materials

    Timber Frame, Wood Siding

  • Property Condition

    Existing

Utilities & Energy

  • Water Source

    Drilled Well

  • Utilities

    Propane

  • Basement

    Finished

  • Electric

    Circuit Breakers

Other Features

  • Lot Features

    Country Setting, Landscaped, Mountain View, Orchard(s), Recreational, Ski Area, Trail/near Trail, Walking Trails, Wooded, Mountain, Near Skiing, Near Snowmobile Trails

Price History

DateEventPrice

10/25/2026

Source: mls_logoNEREN/Prime MLS-NH #5096846

Listed for Sale

$3,995,000

$726/sqft

04/20/2026

Source: mls_logoNEREN/Prime MLS-NH #5030672

Off Market

$3,995,000

$726/sqft

Nearby Homes

Based on information from PrimeMLS Inc. through Nov 02, 2026, 02:16PM. This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information. The listing broker's offer of compensation is made only to other real estate licensees who are participant members of PrimeMLS. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display 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 Nov 02, 2026, 02:16PM. © 2026 PrimeMLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

Skip to Main Content