816 Black Bear Rd

Jamaica, VT 05343

$3,995,000
Price
4
Beds
5,500 Sq. Ft.
$726 / Sq. Ft.
5,500
Sq. Ft.
$726
per Sq. Ft.
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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...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.
  1. Listed by Betsy Wadsworth • Four Seasons Sotheby's Int'l Realty

Property Details for 816 Black Bear Road

Zoning
No zoning
LISTING UPDATED: 06/26/2026 01:01 PM

Property Details for 816 Black Bear Road

StatusActive
MLS #5096846
Days on Market5
Taxes$44,455 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built2010
Lot Size44.47 AC / 1,937,113 SF
CountyWindham County
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Location

Listing Courtesy of Four Seasons Sotheby's Int'l Realty
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Building Information for 816 Black Bear Road

Stories2Year Built2010Building Size-Lot Size44.47 AC / 1,937,113 SF

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$23,612 per month

30 year fixed, 6.36% Interest

Principal and Interest

$19,908

Property Taxes

$3,705

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 816 Black Bear Road

Summary
Location and General Information
  • City: Jamaica
  • County: VT-Windham
  • Directions: West Jamaica Road to Black Bear, Follow up to the top bear right and follow the road until you come to the gate.
  • Latitude: 43.075497141544837
  • Longitude: -72.831028008598309
  • Road Frontage: TBD
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05343
Taxes and HOA Information
  • SPAN Number: 324-101-11593
  • Tax Rate: 44,445.00%
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 6.00
  • Driveway: Paved
Property
Lot Information
  • Lot Features: Country Setting, Landscaped, Mountain View, Orchards, Recreational, Ski Area, Trail/Near Trail, Walking Trails, Wooded, Mountain, Near Skiing, Near Snowmobile Trails
  • Lot Size Acres: 44.47
  • Total Finished Area: 5500.0
  • Above Grade Finished Area: 5500.0
  • Above Grade Finished Area Source: Public Records
  • Above Grade Unfinished Area: 0.0
  • Below Grade Finished Area: 0.0
  • Below Grade Unfinished Area: 0.0
  • Lot Size Square Feet: 1937113.0
  • Total Area: 5500.0
Property and Assessments
  • Current Use: No
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: Unknown
  • Year Built: 2010
  • School District: Windham Central
  • High School: Leland Gray
  • Middle/Jr School: Leland Gray Union Middle/High
  • Elementary School: Jamaica Village School
Green Features
  • Green Energy Efficient: HVAC, Water heater
  • Green Energy Generation: Solar
  • Green Indoor Air Quality: Ventilation
Utilities
  • Electric Company: GMP
  • Electric: Circuit Breaker(s)
  • Sewer: Septic
  • Water Source: Drilled Well
  • Utilities: Propane
  • Internet: High Speed Intrnt Avail
Interior and Exterior Features
Exterior Features
  • Color: Brown
  • Construction Materials: Timber Frame, Wood Siding
  • Roof: Metal, Standing Seam
Interior Features
  • Appliances: Dishwasher, Dryer, Microwave, Refrigerator, Washer, Dual Fuel Range, Exhaust Fan
  • Basement: Yes
  • Basement Access Type: Walkout
  • Basement Description: Finished
  • Rooms: Level 1: Level 1: 1/2 Bathroom, Level 1: Dining Room, Level 1: Foyer, Level 1: Great Room, Level 1: Kitchen/Living, Level 1: Eat-in Kitchen, Level 1: Laundry Room, Level 1: Primary Bdm Ste, Level 1: Mudroom
  • Rooms: Level 2: Level 2: Bedroom, Level 2: Bonus Room
  • Rooms: Level B: Level B: 1/2 Bathroom, Level B: Family Room, Level B: Laundry Room, Level B: Media Room, Level B: Office/Study
  • Flooring: Carpet, Ceramic Tile, Hardwood, Tile, Wood
  • Heating: Propane, Solar, Heat Pump, Multi Zone, Radiant Floor
  • Cooling: None
  • Total Stories: 2.5
  • Rooms Total: 19
  • Bathrooms Full: 5
  • Bathrooms Half: 1
  • Bathrooms One Quarter: 0
  • Bathrooms Three Quarter: 0
  • Bedrooms Total: 4
  • Bathrooms Total: 6
Room Information
Room 1
  • Room Level: 1
  • Room Type: Mudroom
Room 2
  • Room Level: 1
  • Room Type: Laundry Room
Room 3
  • Room Level: 1
  • Room Type: Bathroom Half
Room 4
  • Room Level: 1
  • Room Type: Foyer
Room 5
  • Room Level: 1
  • Room Type: Eat-in Kitchen
Room 6
  • Room Level: 1
  • Room Type: Kitchen/Living
Room 7
  • Room Level: 1
  • Room Type: Dining Room
Room 8
  • Room Level: 1
  • Room Type: Great Room
Room 9
  • Room Level: 1
  • Room Type: Primary BR Suite
Room 10
  • Room Level: 2
  • Room Type: Bedroom with Bath
Room 11
  • Room Level: 2
  • Room Type: Bedroom with Bath
Room 12
  • Room Level: 2
  • Room Type: Bedroom
Room 13
  • Room Level: Basement
  • Room Type: Media Room
Room 14
  • Room Level: Basement
  • Room Type: Office/Study
Room 15
  • Room Level: Basement
  • Room Type: Bedroom with Bath
Room 16
  • Room Level: Basement
  • Room Type: Bathroom Half
Room 17
  • Room Level: Basement
  • Room Type: Family Room
Room 18
  • Room Level: Basement
  • Room Type: Laundry Room
Room 19
  • Room Dimensions: Over Garage
  • Room Level: 2
  • Room Type: Bonus Room

Property History for 816 Black Bear Road

DateEvent & SourcePriceAppreciation
Jun 26, 2026

Listed (Active)

New England Real Estate Network #5096846

$3,995,000—
May 3, 2026

Expired

New England Real Estate Network #5030672

—
Mar 1, 2025

Listed (Active)

New England Real Estate Network #5030672

$4,495,500—
DateEvent & SourcePrice
06/26/2026

Listed (Active)

New England Real Estate Network #5096846

$3,995,000
05/03/2026

Expired

New England Real Estate Network #5030672

—
03/01/2025

Listed (Active)

New England Real Estate Network #5030672

$4,495,500

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 816 Black Bear Road

Taxable ValueLand$237,300Additions$1,485,100Total$1,722,400
Tax Record2024$44,455 ($3,705 / month)
Home Facts
Beds4Baths3.5Total Finished SqFt5,595 SqFtAbove Grade Finished SqFt5,595 SqFtStories2Lot Size1,937,113 SqFtStyleSingle Family ResidenceYear Built2010CountyWINDHAMAPN(101) 00I-143Fireplace TypeHas Fireplace

Schools near 816 Black Bear Road

This home is within West River Valley Modified Union Education District #72a.
Rating
School
Type
Grades
Distance
Leland & Gray Uhsd #34
Public - 6 to 12
Rating
School
Distance
Leland & Gray Uhsd #34
Public6 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 816 Black Bear Road, Jamaica, VT 05343

816 Black Bear Road is a single family home for sale in Jamaica, VT 05343. This property was listed for sale on June 26, 2026 by Four Seasons Sotheby's Int'l Realty, it's currently listed at $3,995,000. It has been on the market for a total of 5 days and was last sold on June 16, 2015. This listing's school districts are West River Valley Modified Union Education District #72b, West River Valley Modified Union Education District #72a. Nearby schools include Leland & Gray Uhsd #34. 816 Black Bear Road is a 4-bed, 6-bath, 5,500 sqft single family home built in 2010.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Four Seasons Sotheby's Int'l Realty

Copyright 2026 PrimeMLS, 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 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 07/01/2026 02:12 PM