69 Upper Taylor Hill Rd, Unit D

Winhall, VT 05340

$2,250,000
Last Sold Price
8
Beds
6,471 Sq. Ft.
$348 / Sq. Ft.
6,471
Sq. Ft.
$348
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Closed 9/25/25
Closed 9/25/25

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!
  1. Listed by Sara Buckley • Josiah Allen Real Estate, Inc.

Sold By Josiah Allen Real Estate, Inc.

Property Details for 69 Upper Taylor Hill Road, Unit D

Zoning
Residential
LISTING CLOSED: 09/25/2025 12:00 AM

Property Details for 69 Upper Taylor Hill Road, Unit D

StatusClosed
MLS #5042856
Days on Market89
Taxes$51,263 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built2009
Lot Size11.55 AC / 503,118 SF
CountyBennington County
Get preapproved with Rocket Mortgage1

Location

Add your commute

Building Information for 69 Upper Taylor Hill Road, Unit D

Stories3Year Built2009Building Size-Lot Size11.55 AC / 503,118 SF

Payment Calculator

Get preapproved with Rocket Mortgage1

$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.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 69 Upper Taylor Hill Road, Unit D

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
  • Construction Status: Existing
  • Easements: Yes
  • Flood Zone: No
  • PreConstruction: No
  • Suitable Use: Residential
  • 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
Mountain School At Winhall
Private - K to 8
Stratton Mountain School
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.

Similar Homes

Nearby off-market homes

AddressSold priceBedsBathsSqftLot AC
67 Upper Taylor Hill Road, Winhall, VT 05340
$552,500
4
3,552
4.4
136 Benson Fuller Drive, Winhall, VT 05340
–
4
2
1,736
2.6
130 Benson Fuller Drive, Winhall, VT 05340
–
3
2
1,848
2
14 Hollow View Road, Winhall, VT 05340
–
3
2,243
2.73
18 Hollow View Road, Winhall, VT 05340
$400,000
3
3,787
47

Explore Nearby Homes

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 07/26/2026 03:28 AM