Single Family for Sale: 157 Thompson Road, Chester, VT 05143

4 beds
2 full, 1 half baths
2,772 sqft
$995,000
$995,000
157 Thompson Road, Chester, VT 05143
4 beds
2 full, 1 half baths
2,772 sqft
$995,000
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Price:
$995,000
$130,000 - 12/03/2025

Type Single Family
Style Farmhouse
Beds 4
Baths 2 full, 1 half baths
Square Feet 2,772 sqft
Lot Size 32.97 acres
Year Built 1860
Taxes Paid $9,627

City Chester
County Windsor
School District Chester School District

MLS 5048851
Status Active
DOM 166 days
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

Lot & Building Features

Utilities Telephone Available, Cable Available
Construction Shingle Siding, Wood Frame
Cooling None
Heating Wood Stove, Hot Water, Baseboard, Oil
Sewer Concrete, 1000 Gallon, Private
Tax Year 2024
Taxes Paid $9,627
Water Spring, Private, Drilled Well
Basement Description Gravel, Basement Stairs, Interior Stairs, Full
Foundation Fieldstone, Concrete
Lot Description Dairy Farm, Near Railroad, Agricultural, Pond, Near School(s), View, Rural, Near Shopping, Landscaped, Near Skiing, Mountain View
Roof Asphalt Shingle
Total Rooms 12
Garage Yes
Full Baths 2
Half Baths 1

Community and Schools

Elementary School Chester-Andover Elementary
Junior High School Green Mountain UHSD #35
Senior High School Green Mountain UHSD #35

Price History of 157 Thompson Road, Chester, VT

Date Name Price Difference
12/03/2025 Price Adjustment $995,000 11.56%
08/15/2025 Price Adjustment $1,125,000 9.93%
06/26/2025 Listing Price $1,249,000 N/A
*Information provided by REWS for your reference only. The accuracy of this information cannot be verified and is not guaranteed.

Map of 157 Thompson Road, Chester, VT

Location Map Street View
Photo of The Patey Team
Direct: 603-548-6392
Office
PO Box 316
Raymond, NH 03077
603-548-6392
Listed by Winhall Real Estate, Joseph Castelluccio 802-297-1550
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0.96758894472362%
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157 Thompson Road (MLS #5048851) is a farmhouse single family home located in Chester, VT. This single family home is 2,772 sqft and on a lot of 1,436,173 sqft (or 32.97 acres) with 4 bedrooms, 3 baths and is 165 years old. This property was listed on 06/26/2025 and has been priced for sale at $995,000.

Nearby zip codes are 05142, 05146, 05150, 05156 and 05495. This property neighbors other cities such as Andover, Baltimore, Cavendish, Grafton and Springfield.

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Listing Last updated . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available. Walk Score map and data provided by Walk Score. Google map provided by Google. Bing map provided by Microsoft Corporation.

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Listing information 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 display 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 12/09/2025