157 Thompson Rd

$995,000
Price
4
Beds
2,772 Sq. Ft.
$359 / Sq. Ft.
2,772
Sq. Ft.
$359
per Sq. Ft.

Description

Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system, updated electrical wiring, windows designed to match the original style, and solar panels that make the...Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system, updated electrical wiring, windows designed to match the original style, and solar panels that make the home largely self-sufficient. Features a country kitchen with a spacious living room, and a generous dining room The first floor offers one bedroom and a half bath, while the second floor includes three additional bedrooms and a 3/4 bath. 33 stunning acres, the land includes a serene pond and river ideal for swimming or fishing, five outbuildings, and a magnificent 30x80 19thcentury barn. The property is dotted with apple trees with boundless possibilities— a horse farm, a dairy operation, an Airbnb retreat, or simply a peaceful and charming home in the countryside. Driveway and bridge are going to be moved by the state TBD freight train runs twice a day at lower end of the property wide pine flooring square head nails post and beam barn several outbuildings solid cherry cabinets/butcher block counter 2 pond 3 porches generator Glenwood Stove
  1. Listed by Joseph Castelluccio • Winhall Real Estate

Property Details for 157 Thompson Road

Zoning
Residential
LISTING UPDATED: 12/03/2025 03:28 PM

Property Details for 157 Thompson Road

StatusActive
MLS #5048851
Days on Market181
Taxes$9,628 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1860
Lot Size32.97 AC / 1,436,173 SF
CountyWindsor County

Location

Listing Courtesy of Winhall Real Estate
Add your commute

Building Information for 157 Thompson Road

Stories2Year Built1860Building Size-Lot Size32.97 AC / 1,436,173 SF

Payment Calculator

$5,719 per month

30 year fixed, 6.28% Interest

Principal and Interest

$4,917

Property Taxes

$802

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 157 Thompson Road

Summary
Location and General Information
  • City: Chester
  • County: VT-Windsor
  • Latitude: 43.304298577196860
  • Longitude: -72.608252999999991
  • Road Frontage: Yes
  • Seasonal: Unknown
  • State: VT
  • Street Designation: Road
  • Zip Code: 05143
Taxes and HOA Information
  • SPAN Number: 144-045-10930
  • Tax Year: 2024
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 2.00
  • Driveway: Gravel
Property
Lot Information
  • Lot Features: Agricultural, Dairy Farm, Landscaped, Mountain View, Pond, View, Near Shopping, Near Skiing, Rural, Near Railroad, Near School(s)
  • Lot Size Acres: 32.97
  • Road Frontage Length: 850.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Easements: Yes
  • Flood Zone: Yes
  • PreConstruction: No
  • Surveyed: Unknown
  • Year Built: 1860
Utilities
  • Electric: 200+ Amp Service, Generator
  • Sewer: 1000 Gallon, Concrete, Private
  • Water Source: Drilled Well, Private, Spring
  • Utilities: Cable Available, Telephone Available
  • Internet: High Speed Intrnt Avail
Interior and Exterior Features
Exterior Features
  • Construction Materials: Wood Frame, Shingle Siding
  • Roof: Asphalt Shingle
Interior Features
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Full, Gravel, Interior Stairs, Basement Stairs
  • Heating: Oil, Baseboard, Hot Water, Wood Stove
  • Cooling: None
  • Total Stories: 2

Property History for 157 Thompson Road

DateEvent & SourcePriceAppreciation
Jun 26, 2025

Listed (Active)

New England Real Estate Network #5048851

$1,249,000
Feb 27, 2025

Expired

New England Real Estate Network #5000207

Jul 29, 2024

Price Change

New England Real Estate Network #5000207

$995,000
Jun 11, 2024

Listed (Active)

New England Real Estate Network #5000207

$999,000
Apr 13, 2021

Sold (Public Record)

Public Record #1457151542

$420,000
May 9, 2006

Expired

New England Real Estate Network #867684

Sep 26, 2002

Listed (Active)

New England Real Estate Network #867684

$649,000
DateEvent & SourcePrice
06/26/2025

Listed (Active)

New England Real Estate Network #5048851

$1,249,000
02/27/2025

Expired

New England Real Estate Network #5000207

07/29/2024

Price Change

New England Real Estate Network #5000207

$995,000
06/11/2024

Listed (Active)

New England Real Estate Network #5000207

$999,000
04/13/2021

Sold (Public Record)

Public Record #1457151542

$420,000
05/09/2006

Expired

New England Real Estate Network #867684

09/26/2002

Listed (Active)

New England Real Estate Network #867684

$649,000

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

Public Records for 157 Thompson Road

Taxable ValueLand$107,700Additions$407,200Total$514,900
Tax Record2024$14,283 ($1,190 / month)
Home Facts
Beds5Total Finished SqFt2,772 SqFtAbove Grade Finished SqFt2,772 SqFtLot Size1,436,173 SqFtStyleSingle Family ResidenceYear Built1830CountyWINDSORAPN(045) 282004.100

Schools near 157 Thompson Road

This home is within Green Mountain Unified School District.
Rating
School
Type
Grades
Distance
Public - PK to 6
Public - 7 to 12
Rating
School
Distance
Chester-Andover Usd #29
PublicPK to 6

Green Mountain Uhsd #35
Public7 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

Similar Sold Homes

157 Thompson Road is a single family home for sale in Chester, VT 05143. This property was listed for sale on June 26, 2025 by Winhall Real Estate, it's currently listed at $995,000. It has been on the market for a total of 181 days and was last sold on April 13, 2021. This listing's school district is Green Mountain Unified School District. Nearby schools include Chester-Andover Usd #29 and Green Mountain Uhsd #35. 157 Thompson Road is a 4-bed, 3-bath, 2,772 sqft single family home built in 1860.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Winhall Real Estate

Copyright 2025 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 12/24/2025 11:16 PM