Sign up to get new listings emailed daily! JOIN SIGN IN
AnaSofia Hansen
REALTOR®
VCard Icon 
Refine Search

816 Black Bear Road, Jamaica, VT 05343

$3,995,000
  • Main Photo

60 Total Photos [Click to View All]

Active
BEDS4 BATHS5 full 1 partial SQUARE FEET5,500 MLS#5030672
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLWindham Central

Listing Courtesy of: Four Seasons Sothebys Intl Realty
Agency Phone: 802-464-1200
Associate Name: Betsy Wadsworth
IDX logo


Property 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-cochre 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.

816 Black Bear Road | MLS# 5030672

This single family home located at 816 Black Bear Road, Jamaica, VT 05343 is currently listed for sale with an asking price of $3,995,000. This property was built in 2010 and has 4 bedrooms and 5 full and 1 partial baths with 5500 sq. ft. Black Bear Road is located within the Windham Central school district. Search Jamaica real estate on anasofia.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Finished
Cooling: None
Garage: 6
Heating: Propane, Solar, Heat Pump, Multi Zone, Radiant Floor
Home Style: Craftsman, Post and Beam
Lot Size: 44.47 Acres
Roof Type: Metal, Standing Seam
Stories: 2.5
Taxes: $41,949
Year Built: 2010

Amenities

Blinds
Cathedral Ceiling
Ceiling Fan
Dining Area
Draperies
Wood Fireplace
Hearth
In-Law Suite
Kitchen Island
Kitchen/Living
Primary BR w/ BA
Natural Light
Natural Woodwork
Vaulted Ceiling
Walk-in Closet
Walk-in Pantry
1st Floor Laundry
Basement Laundry
Deck
Garden Space
Hot Tub
Patio
In-Ground Pool
Covered Porch

Feature Descriptions

Appliances: Dishwasher, Dryer, Microwave, Refrigerator, Washer, Dual Fuel Range, Exhaust Fan
Baths 1/2: 1
Baths Full: 5
Color: Brown
Construction: Timber Frame, Wood Siding
Construction Status: Existing
Days on Site: 420
Driveway: Paved
Electric: Circuit Breaker(s)
Equipment: Security System, Hardwired Smoke Detector, Standby Generator
Exterior: Timber Frame, Wood Siding
Flood Zone: Unknown
Flooring: Carpet, Ceramic Tile, Hardwood, Tile, Wood
Foundation: Concrete
Hot Tub: Yes
Lot: Country Setting, Landscaped, Mountain View, Orchards, Recreational, Ski Area, Trail/Near Trail, Walking Trails, Wooded, Mountain, Near Skiing, Near Snowmobile Trails
Number of Rooms: 19
Roads: Public Maintained Road
Sewer: Septic
Sq. Ft. Above Grade Finished: 5500
Sq. Ft. Total Finished: 5500
Total Stories: 2.5
Water: Drilled Well
Zoning: No zoning

Room Sizes

Bonus Room: Over Garage Level - 2

Local Schools

High School: Leland Gray
Middle School: Leland Gray Union Middle/High
Elementary School: Jamaica Village School
School District: Windham Central

Listed By / Shown By

Listed By

Agency Name: Four Seasons Sothebys Intl Realty
Agency Phone: 802-464-1200
Agent Name: Betsy Wadsworth

IDX logo

TOUR THIS HOME

Choose a date and time to see 816 Black Bear Road, Jamaica, VT 05343.
I will get in touch with you shortly.

Request a Showing
Choose your video chat app
  • Sunday April 26
  • Monday April 27
  • Tuesday April 28
  • Wednesday April 29
  • Thursday April 30
  • Friday May 1
  • Saturday May 2
  • Sunday May 3
  • Monday May 4
  • Tuesday May 5
  • Wednesday May 6
  • Thursday May 7
  • Friday May 8
  • Saturday May 9
  • Sunday May 10
  • 7:00 AM
  • 7:30 AM
  • 8:00 AM
  • 8:30 AM
  • 9:00 AM
  • 9:30 AM
  • 10:00 AM
  • 10:30 AM
  • 11:00 AM
  • 11:30 AM
  • 12:00 PM
  • 12:30 PM
  • 1:00 PM
  • 1:30 PM
  • 2:00 PM
  • 2:30 PM
  • 3:00 PM
  • 3:30 PM
  • 4:00 PM
  • 4:30 PM
  • 5:00 PM
  • 5:30 PM
  • 6:00 PM
  • 6:30 PM
  • 7:00 PM
  • 7:30 PM
  • 8:00 PM
  • 8:30 PM
  • 9:00 PM
Preferred Communication Method

Estimate Your Payment

Estimated Payment

$ 13,552.10 per month $8,891.14 Principal & Interest $3,495.75 Property Tax $1,165.21 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)
Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 04/25/2026. The listing information on this page last changed on 04/25/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 04/25/2026 12:00:03 AM EST) or MLSPIN MLS (last updated Fri 04/24/2026 11:38:35 PM EST) or Prime MLS (last updated Fri 04/24/2026 11:33:30 PM EST) or MREIS (last updated Fri 04/24/2026 11:55:24 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data compilation and photo(s) copyright © 2026 PrimeMLS, Inc. All rights reserved. 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 2026-04-24 23:33:30

Privacy Policy / DMCA Notice / ADA Accessibility

Agency License Information: Better Homes and Gardens® and the Better Homes and Gardens Real Estate Logo are registered service marks owned by Meredith Corporation and licensed to Better Homes and Gardens Real Estate LLC. The Masiello Group Limited fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each franchise is independently owned and operated. Any services or products provided by independently owned and operated franchisees are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC nor any of its affiliated companies.


Login to My Homefinder

Pixel