Sold
Last Sold Price
8 beds6,471 sqft$348/sqft
69 Upper Taylor Hill Rd, Unit D, Winhall, VT 05340
Single FamilyProperty Type
11.55 acresLot Size
2009Year Built
$348/sq ftPrice per sq ft
3 carsParking Spaces

Description

This extraordinary Stratton Mountain Retreat, just minutes to the slopes, offers glorious long range views and a very private setting. This impressive home was masterfully constructed in 2009 and includes a separate barn, 11.55 acres of land, 2 covered porches, a built in barbecue and an outdoor fireplace, hot tub and fire pit. The main level of the home features a Gourmet Kitchen, grand Great Room with stone fireplace, Dining area, Library, walk in refrigerated Wine Pantry for over 900 bottles,...This extraordinary Stratton Mountain Retreat, just minutes to the slopes, offers glorious long range views and a very private setting. This impressive home was masterfully constructed in 2009 and includes a separate barn, 11.55 acres of land, 2 covered porches, a built in barbecue and an outdoor fireplace, hot tub and fire pit. The main level of the home features a Gourmet Kitchen, grand Great Room with stone fireplace, Dining area, Library, walk in refrigerated Wine Pantry for over 900 bottles, walk in Pantry, Laundry Room, large Mudroom , and a large Primary Suite with a fireplace, private porch, and walk in closet. The Lower Level has a impressive Family/Game Room with fireplace, a Pool Table Room, walk in Game Closet, Guest Room and Bath and two additional Bunk rooms en suite. The second Floor of the Main Section of the house has two en suite - Bedrooms. Above the over-sized heated garage is another Guest Suite with its own private staircase. Exterior of the home has cedar shake siding, standing seam and wood shake roofing, beautiful stonework and mahogany doors. This Vermont property is an exceptional mountain home!

    Sold By Josiah Allen Real Estate, Inc.

    • Listed by: Sara Buckley • Josiah Allen Real Estate, Inc.
    Listing closed: 09/25/2025 12:00 AM • Source: New England Real Estate Network, MLS#: 5042856

    Recent comparable sales

    Median sold price

    $2,150,000

    Avg days on market

    202

    Sale-to-list ratio

    90.3%

    Winhall, VT

    9 comparable properties found

    $2,600,000 | 25 Mountain Haunts Road, Winhall, VT 05340
    1/56
    1

    $2,600,000

    Sold 05/01/26

    6
    Bedrooms
    6,650
    Square Feet
    40.80
    Acres
    $2,100,000 | 18 Rocky Dell Road, Winhall, VT 05340
    1/61
    2

    $2,100,000

    Sold 05/02/25

    7
    Bedrooms
    6,195
    Square Feet
    26
    Acres
    $3,025,000 | 67 High Meadow Road, Winhall, VT 05340
    1/58
    3

    $3,025,000

    Sold 03/31/26

    6
    Bedrooms
    6,437
    Square Feet
    1.35
    Acres
    $2,200,000 | 19 Old Town Road, Winhall, VT 05340
    1/45
    4

    $2,200,000

    Sold 10/14/25

    5
    Bedrooms
    7,625
    Square Feet
    21.53
    Acres
    $2,850,000 | 41 Stark Farm Road, Winhall, VT 05340
    1/2
    5

    $2,850,000

    Sold 05/22/26

    4
    Bedrooms
    5,082
    Square Feet
    7.8
    Acres
    $2,150,000 | 16 Hunter Ridge Road, Winhall, VT 05340
    1/56
    6

    $2,150,000

    Sold 02/12/26

    4
    Bedrooms
    5,000
    Square Feet
    2.66
    Acres
    $1,700,000 | 4 Stone House Road, Winhall, VT 05340
    1/38
    7

    $1,700,000

    Sold 11/22/24

    4
    Bedrooms
    4,777
    Square Feet
    1
    Acres
    $1,665,000 | 14 Old Ridge Road, Winhall, VT 05340
    1/41
    8

    $1,665,000

    Sold 03/09/26

    4
    Bedrooms
    4,270
    Square Feet
    1
    Acres
    $1,603,000 | 143 Stratton Mountain Road, Winhall, VT 05340
    1/44
    9

    $1,603,000

    Sold 01/28/26

    5
    Bedrooms
    3,688
    Square Feet
    2.1
    Acres

    Location

    Add your commute

    Payment Calculator

    $15,708 per month

    30 year fixed, 6.55% Interest

    Principal and Interest

    $11,436

    Property Taxes

    $4,272

    HOA Dues

    $0

    The Payment Calculator is for illustrative purposes only.

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    Property Information for 69 Upper Taylor Hill Road, Unit D

    Property Details
    • Taxes: $51,263 / year
    • MLS Type: Residential / Single Family
    • Zoning: Residential
    Building Information
    • Stories: 3
    • Year Built: 2009
    • Lot Size: 11.55 AC / 503,118 SF
    Summary
    Location and General Information
    • City: Winhall
    • County: VT-Bennington
    • Directions: Stratton Mountain Access Road - turn left on Upper Taylor Hill Road . Driveway is on the left just before Benson Fuller. Bear right when you turn in and you will see a sign with the house number.
    • Latitude: 43.128166764456260
    • Longitude: -72.879962925720221
    • Road Frontage: No
    • Seasonal: Unknown
    • State: VT
    • Street Designation: Road
    • Map: 12
    • Zip Code: 05340
    Taxes and HOA Information
    • SPAN Number: 771-245-12238
    • Tax Year: 2025
    • Taxes TBD: No
    Parking
    • Garage: Yes
    • Garage Capacity: 3.00
    • Driveway: Circular, Gravel, Right-Of-Way (ROW)
    Property
    Lot Information
    • Block: 02
    • Lot: 64.3
    • Lot Features: Country Setting, Landscaped, Mountain View, Ski Area, View, Near Golf Course, Near Skiing
    • Lot Size Acres: 11.55
    • Total Finished Area: 6471.0
    • Above Grade Finished Area: 4075.0
    • Above Grade Finished Area Source: Public Records
    • Above Grade Unfinished Area: 0.0
    • AboveGradeUnfinishedAreaSource: Public Records
    • Below Grade Finished Area: 2396.0
    • Below Grade Finished Area Source: Public Records
    • Below Grade Unfinished Area: 485.0
    • BelowGradeUnfinishedAreaSource: Public Records
    • Lot Size Square Feet: 503118.0
    • Total Area: 6956.0
    Property and Assessments
    • Property Class: Residential
    • Property Type: Single Family
    • Easements: Yes
    • Flood Zone: No
    • PreConstruction: No
    • Surveyed: Yes
    • Year Built: 2009
    • School District: Bennington/Rutland
    • High School: Choice
    • Middle/Jr School: Choice
    • Elementary School: Choice
    Utilities
    • Electric Company: Green Mountain Power
    • Cable Company: Xfinity/Comcast
    • Fuel Company: Suburban Propane
    • Electric: 200+ Amp Service
    • Sewer: Septic
    • Water Source: Drilled Well, Private
    • Utilities: Cable, Cable at Site, Propane, Underground Utilities
    • Internet: Cable Internet
    Interior and Exterior Features
    Exterior Features
    • Color: Tan
    • Construction Materials: Shingle Siding, Stone Exterior, Wood Siding
    • Roof: Wood Shingle, Standing Seam
    Interior Features
    • Appliances: Gas Cooktop, Dishwasher, Dryer, Range Hood, Freezer, Microwave, Mini Fridge, Double Oven, Wall Oven, Refrigerator, Washer, Warming Drawer, Water Heater
    • Basement: Yes
    • Basement Access Type: Walkout
    • Basement Description: Climate Controlled, Concrete, Concrete Floor, Finished, Full, Insulated, Storage Space, Walkout, Interior Access, Exterior Access, Basement Stairs
    • Rooms: Level 1: Level 1: Dining Room, Level 1: Great Room, Level 1: Kitchen, Level 1: Laundry Room, Level 1: Library, Level 1: Primary Bdm Ste, Level 1: Mudroom
    • Rooms: Level B: Level B: Family Room, Level B: Rec Room
    • Flooring: Carpet, Hardwood, Slate/Stone, Softwood, Tile
    • Heating: Propane, Baseboard, Radiant
    • Cooling: Central AC, Mini Split
    • Total Stories: 3
    • Rooms Total: 14
    • Bathrooms Full: 2
    • Bathrooms Half: 1
    • Bathrooms One Quarter: 0
    • Bathrooms Three Quarter: 6
    • Bedrooms Total: 8
    • Bathrooms Total: 9
    Room Information
    Room 1
    • Room Dimensions: 17 x 17
    • Room Level: 1
    • Room Type: Kitchen
    Room 2
    • Room Dimensions: 14 x 19
    • Room Level: 1
    • Room Type: Dining Room
    Room 3
    • Room Dimensions: 24 x 25
    • Room Level: 1
    • Room Type: Great Room
    Room 4
    • Room Dimensions: 15 x 14
    • Room Level: 1
    • Room Type: Library
    Room 5
    • Room Dimensions: 16 x 17
    • Room Level: 1
    • Room Type: Primary BR Suite
    Room 6
    • Room Dimensions: 11 x 15
    • Room Level: 1
    • Room Type: Mudroom
    Room 7
    • Room Dimensions: 8 x 9
    • Room Level: 1
    • Room Type: Laundry Room
    Room 8
    • Room Dimensions: 15 x 16
    • Room Level: 2
    • Room Type: Bedroom with Bath
    Room 9
    • Room Dimensions: 16 x17
    • Room Level: 2
    • Room Type: Bedroom with Bath
    Room 10
    • Room Dimensions: 25 x 26
    • Room Level: Basement
    • Room Type: Family Room
    Room 11
    • Room Dimensions: 12 x 18
    • Room Level: Basement
    • Room Type: Rec Room
    Room 12
    • Room Dimensions: 12 x 14
    • Room Level: Basement
    • Room Type: Bedroom with Bath
    Room 13
    • Room Dimensions: 12 x 13
    • Room Level: Basement
    • Room Type: Bedroom with Bath
    Room 14
    • Room Dimensions: 16 x 17
    • Room Level: Basement
    • Room Type: Bedroom with Bath
    Room 15
    • Room Dimensions: 14 x 14
    • Room Level: 2
    • Room Type: Bedroom with Bath

    Property History for 69 Upper Taylor Hill Road, Unit D

    DateEvent & SourcePriceAppreciation
    Sep 25, 2025

    Sold

    New England Real Estate Network #5042856

    $2,250,000
    May 25, 2025

    Listed (Active)

    New England Real Estate Network #5042856

    $2,950,000
    DateEvent & SourcePrice
    09/25/2025

    Sold

    New England Real Estate Network #5042856

    $2,250,000
    05/25/2025

    Listed (Active)

    New England Real Estate Network #5042856

    $2,950,000

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

    Schools near 69 Upper Taylor Hill Road, Unit D

    Rating
    School
    Type
    Grades
    Distance
    Private - K to 8
    Private - 7 to 12
    Rating
    School
    Distance
    Mountain School At Winhall
    PrivateK to 8

    Stratton Mountain School
    Private7 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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    Nearby home values

    AddressSold priceBedsBathsSqftLot (Sqft)
    This home: 69 Upper Taylor Hill Road, Unit D, Winhall, VT 05340
    $2,250,000
    8
    6,471
    503,118
    $552,500
    4
    3,552
    191,664
    4
    2
    1,736
    113,256
    3
    2
    1,848
    87,120
    3
    3.5
    2,243
    118,919
    $711,500
    2
    2
    1,600
    384,199

    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 Josiah Allen Real Estate, Inc.

    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 09/06/2026 08:08 PM