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
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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    Recent comparable sales

    Median sold price

    $2,100,000

    Avg days on market

    170

    Sale-to-list ratio

    91.2%

    Winhall, VT

    9 comparable properties found

    $2,100,000 | 18 Rocky Dell Road, Winhall, VT 05340
    1/61
    1

    $2,100,000

    Sold 05/02/25

    7
    Bedrooms
    6,195
    Square Feet
    26
    Acres

    18 Rocky Dell Road, Winhall, VT 05340

    $2,850,000 | 41 Stark Farm Road, Winhall, VT 05340
    1/2
    2

    $2,850,000

    Sold 05/22/26

    4
    Bedrooms
    5,082
    Square Feet
    7.8
    Acres

    41 Stark Farm Road, Winhall, VT 05340

    $1,603,000 | 143 Stratton Mountain Road, Winhall, VT 05340
    1/44
    3

    $1,603,000

    Sold 01/28/26

    5
    Bedrooms
    3,688
    Square Feet
    2.1
    Acres

    143 Stratton Mountain Road, Winhall, VT 05340

    $2,150,000 | 16 Hunter Ridge Road, Winhall, VT 05340
    1/56
    4

    $2,150,000

    Sold 02/12/26

    4
    Bedrooms
    5,000
    Square Feet
    2.66
    Acres

    16 Hunter Ridge Road, Winhall, VT 05340

    $975,000 | 83 Benson Fuller Drive, Winhall, VT 05340
    1/51
    5

    $975,000

    Sold 11/14/25

    5
    Bedrooms
    4,729
    Square Feet
    1.7
    Acres

    83 Benson Fuller Drive, Winhall, VT 05340

    $2,600,000 | 25 Mountain Haunts Road, Winhall, VT 05340
    1/56
    6

    $2,600,000

    Sold 05/01/26

    6
    Bedrooms
    6,650
    Square Feet
    40.80
    Acres

    25 Mountain Haunts Road, Winhall, VT 05340

    $3,025,000 | 67 High Meadow Road, Winhall, VT 05340
    1/58
    7

    $3,025,000

    Sold 03/31/26

    6
    Bedrooms
    6,437
    Square Feet
    1.35
    Acres

    67 High Meadow Road, Winhall, VT 05340

    $1,550,000 | 147 High Meadow Road, Unit 147, Winhall, VT 05340
    1/30
    8

    $1,550,000

    Sold 04/10/26

    5
    Bedrooms
    4,000
    Square Feet
    2.2
    Acres

    147 High Meadow Road, Unit 147, Winhall, VT 05340

    $1,150,000 | 35 Old Ridge Road, Winhall, VT 05340
    1/42
    9

    $1,150,000

    Sold 07/25/25

    4
    Bedrooms
    4,826
    Square Feet
    1
    Acres

    35 Old Ridge Road, Winhall, VT 05340

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    $15,575 per month

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    Principal and Interest

    $11,745

    Property Taxes

    $3,830

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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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    Nearby home values

    AddressSold priceBedsBathsSqftLot (Sqft)
    This home: 19 Old Town Road, Winhall, VT 05340
    $2,200,000
    5
    7,625
    937,846
    17 Old Town Road, Bondville, VT 05340
    –
    3
    1
    918
    204,732
    37 Old Town Road, Bondville, VT 05340
    –
    3
    3
    2,142
    453,024
    24 Old Town Road, Winhall, VT 05340
    $300,000
    3
    1,955
    431,244
    13 Old Town Road, Winhall, VT 05340
    –
    2
    2
    1,008
    69,696
    14 Old Town Road, Winhall, VT 05340
    $167,000
    3
    1,144
    43,560

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    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 09/26/2026 01:32 AM