19 Old Town Road

Closed 10/14/25
Closed 10/14/25
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Sold
Last Sold Price
$2,200,000
5 beds7,625 sqft$289/sqft
19 Old Town Rd, Winhall, VT 05340
Single FamilyProperty Type
21.53 acresLot Size
2000Year Built
$289/sq ftPrice per sq ft
2 carsParking Spaces

Description

Experience Vermont luxury at 19 Old Town Road, Winhall—a stunning 5-bedroom, 7-bathroom estate on 21.53 private acres. Built in 2000, this meticulously designed retreat offers unobstructed views of both Stratton Mountain and Magic Mountain. The spacious great room is the heart of the home, featuring soaring ceilings, a grand stone fireplace, and walls of windows that frame breathtaking mountain vistas. A gourmet kitchen with high-end appliances, custom cabinetry, and ample workspace is perfect for...Experience Vermont luxury at 19 Old Town Road, Winhall—a stunning 5-bedroom, 7-bathroom estate on 21.53 private acres. Built in 2000, this meticulously designed retreat offers unobstructed views of both Stratton Mountain and Magic Mountain. The spacious great room is the heart of the home, featuring soaring ceilings, a grand stone fireplace, and walls of windows that frame breathtaking mountain vistas. A gourmet kitchen with high-end appliances, custom cabinetry, and ample workspace is perfect for entertaining. The den is a home office with a beautiful fireplace and built in bookcases. With five bedrooms each with their own bathroom, two half baths, thoughtfully designed living spaces, and high-end finishes throughout, this home seamlessly blends elegance and comfort. Enjoy privacy and seclusion while being just minutes from Stratton Resort, Magic Mountain, Bromley, and Manchester. This extraordinary property is a rare opportunity to own a piece of Vermont’s finest landscape.

    Sold By Berkshire Hathaway HomeServices Stratton Home

    • Listed by: Christiane Carroccio • TPW Real Estate
    Listing closed: 10/14/2025 12:00 AM • Source: New England Real Estate Network, MLS#: 5031720
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    $15,012 per month

    30 year fixed, 6.55% Interest

    Principal and Interest

    $11,182

    Property Taxes

    $3,830

    HOA Dues

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    Property Information for 19 Old Town Road

    Property Details
    • Taxes: $45,959 / year
    • MLS Type: Residential / Single Family
    • County: Bennington County
    • Zoning: Residential
    Building Information
    • Stories: 3
    • Year Built: 2000
    • Lot Size: 21.53 AC / 937,846 SF
    Summary
    Location and General Information
    • City: Winhall
    • County: VT-Bennington
    • Directions: From Manchester, take Route 30 toward Stratton. Make a left onto Old Town Road. #19 will be on your left. From Stratton, take Winhall Hollow Road to Old Town Road, #19 is on the right.
    • Latitude: 43.166169698727892
    • Longitude: -72.918822186508180
    • Road Frontage: No
    • Seasonal: No
    • State: VT
    • Street Designation: Road
    • Zip Code: 05340
    Taxes and HOA Information
    • SPAN Number: 771-245-10836
    • Tax Year: 2024
    • Taxes TBD: No
    Parking
    • Garage: Yes
    • Garage Capacity: 2.00
    • Driveway: Gravel
    Virtual Tour
    Property
    Lot Information
    • Lot Features: Country Setting, Landscaped, Mountain View, Secluded, Ski Area, View
    • Lot Size Acres: 21.53
    • Total Finished Area: 7625.0
    • Above Grade Finished Area: 6625.0
    • Above Grade Finished Area Source: Public Records
    • Above Grade Unfinished Area: 0.0
    • AboveGradeUnfinishedAreaSource: Public Records
    • Below Grade Finished Area: 1000.0
    • Below Grade Finished Area Source: Public Records
    • Below Grade Unfinished Area: 1000.0
    • BelowGradeUnfinishedAreaSource: Public Records
    • Lot Size Square Feet: 937847.0
    • Total Area: 8625.0
    Property and Assessments
    • Property Class: Residential
    • Property Type: Single Family
    • Flood Zone: No
    • PreConstruction: No
    • Surveyed: Unknown
    • Year Built: 2000
    • School District: Bennington/Rutland
    • High School: Choice
    • Middle/Jr School: Choice
    • Elementary School: Choice
    Utilities
    • Electric: Circuit Breaker(s)
    • Sewer: 1000 Gallon, Septic
    • Water Source: Drilled Well
    • Utilities: Cable at Site, Telephone at Site
    • Internet: Fiber Optic Internt Avail, High Speed Intrnt Avail
    Interior and Exterior Features
    Exterior Features
    • Color: Gray
    • Construction Materials: Shake Siding, Stone Exterior
    • Roof: Shingle
    Interior Features
    • Basement: Yes
    • Basement Access Type: Interior
    • Basement Description: Finished, Interior Stairs, Storage Space
    • Rooms: Level 1: Level 1: Den, Level 1: Dining Room, Level 1: Kitchen, Level 1: Living Room, Level 1: Primary Bedroom, Level 1: Mudroom
    • Rooms: Level 2: Level 2: Bonus Room
    • Rooms: Level B: Level B: 1/2 Bathroom, Level B: Family Room
    • Heating: Oil, Baseboard, Radiant
    • Cooling: None
    • Total Stories: 3
    • Rooms Total: 11
    • Bathrooms Full: 3
    • Bathrooms Half: 2
    • Bathrooms One Quarter: 0
    • Bathrooms Three Quarter: 2
    • Bedrooms Total: 5
    • Bathrooms Total: 7
    Room Information
    Room 1
    • Room Dimensions: 12x8
    • Room Level: 1
    • Room Type: Kitchen
    Room 2
    • Room Dimensions: 35x24
    • Room Level: 1
    • Room Type: Living Room
    Room 3
    • Room Dimensions: 18x22
    • Room Level: 1
    • Room Type: Dining Room
    Room 4
    • Room Dimensions: 20x20
    • Room Level: 1
    • Room Type: Primary Bedroom
    Room 5
    • Room Dimensions: 17x16
    • Room Level: 1
    • Room Type: Den
    Room 6
    • Room Dimensions: 16x12
    • Room Level: 2
    • Room Type: Bedroom with Bath
    Room 7
    • Room Dimensions: 16x12
    • Room Level: 2
    • Room Type: Bedroom with Bath
    Room 8
    • Room Dimensions: 20x17
    • Room Level: 2
    • Room Type: Bonus Room
    Room 9
    • Room Dimensions: 17x11
    • Room Level: 1
    • Room Type: Mudroom
    Room 10
    • Room Level: Basement
    • Room Type: Family Room
    Room 11
    • Room Level: Basement
    • Room Type: Bathroom Half

    Property History for 19 Old Town Road

    DateEvent & SourcePriceAppreciation
    Oct 14, 2025

    Sold (Public Record)

    Public Record #1917160045

    		$2,200,000—
    Oct 14, 2025

    Sold

    New England Real Estate Network #5031720

    		$2,200,000—
    Oct 14, 2025

    Pending

    New England Real Estate Network #5031720

    		—
    DateEvent & SourcePrice
    10/14/2025

    Sold (Public Record)

    Public Record #1917160045

    $2,200,000
    10/14/2025

    Sold

    New England Real Estate Network #5031720

    $2,200,000
    10/14/2025

    Pending

    New England Real Estate Network #5031720

    —

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

    Public Records for 19 Old Town Road

    Taxable ValueLand$477,200Additions$1,164,100Total$1,641,300
    Tax Record2025$34,318 ($2,860 / month)
    Home Facts
    Beds5Baths5.5Total Finished SqFt6,625 SqFtAbove Grade Finished SqFt6,625 SqFtLot Size937,847 SqFtStyleMiscellaneous ResidentialCountyBENNINGTONAPN(245)88049

    Schools near 19 Old Town Road

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

    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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    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 TPW Real Estate

    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 09/05/2026 11:06 PM