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.
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Listed by:
Christiane Carroccio,
TPW Real Estate 802-366-1430
Bought with: Berkshire Hathaway HomeServices Stratton Home
$2,200,000
19 Old Town Road, Winhall, VT 05340
5beds
7,625sqft
Single Family Residence
Built in 2000
21.53 Acres Lot
$2,198,900 Zestimate®
$289/sqft
$7,559 Estimated rent
Home value
$2,198,900
Estimated sales range
Not available
$7,559/mo
Zestimate® history
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$12,436/mo
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Est. payment
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Zillow last checked: 8 hours ago
Listing updated: October 14, 2025 at 11:47am
Listed by:
Christiane Carroccio,
TPW Real Estate 802-366-1430
Bought with:
Lauren Behm
Berkshire Hathaway HomeServices Stratton Home
Source: PrimeMLS,MLS#: 5031720
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 7
- Full bathrooms: 3
- 3/4 bathrooms: 2
- 1/2 bathrooms: 2
Heating
- Oil, Baseboard, Radiant
Cooling
- None
Features
- Basement: Finished,Interior Stairs,Storage Space,Interior Entry
Interior area
- Total structure area: 8,625
- Total interior livable area: 7,625 sqft
- Finished area above ground: 6,625
- Finished area below ground: 1,000
Property
Parking
- Total spaces: 2
- Parking features: Gravel
- Garage spaces: 2
Features
- Levels: 3
- Stories: 3
- Has view: Yes
- View description: Mountain(s)
Lot
- Size: 21.53 Acres
- Features: Country Setting, Landscaped, Secluded, Ski Area, Views
Details
- Parcel number: 77124510836
- Zoning description: Residential
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Adirondack,Contemporary
- Property subtype: Single Family Residence
Materials
- Shake Siding, Stone Exterior
- Foundation: Poured Concrete
- Roof: Shingle
Condition
- New construction: No
- Year built: 2000
Utilities & green energy
- Electric: Circuit Breakers
- Sewer: 1000 Gallon, Septic Tank
- Utilities for property: Cable at Site, Telephone at Site, Fiber Optic Internt Avail
Community & neighborhood
Location
- Region: Bondville
Other
Other facts
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 10/14/2025 | Sold | $2,200,000-12%$289/sqft |
Source:  PrimeMLS #5031720 Report a problem | ||
| 5/19/2025 | Price change | $2,500,000-10.1%$328/sqft |
Source: PrimeMLS #5031720 Report a problem | ||
| 3/11/2025 | Listed for sale | $2,780,000$365/sqft |
Source: PrimeMLS #5031720 Report a problem | ||
| 2/26/2025 | Listing removed | $2,780,000$365/sqft |
Source: PrimeMLS #5012831 Report a problem | ||
| 1/15/2025 | Price change | $2,780,000-10.3%$365/sqft |
Source: PrimeMLS #5012831 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $1,641,300 |
| 2023 | -- | $1,641,300 |
| 2022 | -- | $1,641,300 |
Find assessor info on the county website
Neighborhood: 05340
Nearby schools
GreatSchools rating
- 6/10Flood Brook Usd #20Grades: PK-8Distance: 6.1 mi
- NABurr & Burton AcademyGrades: 9-12Distance: 7.8 mi
Schools provided by the listing agent
- District: Bennington/Rutland
Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
- Vermont
- Bennington County
- Winhall
- 05340
- 19 Old Town Road