19 Old Town Rd

Winhall, VT 05340

$2,200,000
Last Sold Price
5
Beds
7,625 Sq. Ft.
$289 / Sq. Ft.
7,625
Sq. Ft.
$289
per Sq. Ft.
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Closed 10/14/25
Closed 10/14/25

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.
  1. Listed by Christiane Carroccio • TPW Real Estate

Sold By Berkshire Hathaway HomeServices Stratton Home

Property Details for 19 Old Town Road

Zoning
Residential
LISTING CLOSED: 10/14/2025 12:00 AM

Property Details for 19 Old Town Road

StatusClosed
MLS #5031720
Days on Market191
Taxes$45,959 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built2000
Lot Size21.53 AC / 937,846 SF
CountyBennington County
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Location

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Building Information for 19 Old Town Road

Stories3Year Built2000Building Size-Lot Size21.53 AC / 937,846 SF

Payment Calculator

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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

$0

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Property Information for 19 Old Town Road

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
  • Construction Status: Existing
  • 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 Record2024$45,956 ($3,830 / month)
Home Facts
Beds5Baths5.5Total Finished SqFt6,625 SqFtAbove Grade Finished SqFt6,625 SqFtLot Size937,847 SqFtStyleMiscellaneous ResidentialCountyBENNINGTONAPN(245)88049Fireplace TypeHas Fireplace

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 07/23/2026 07:46 AM