157 Thompson Road Chester, VT $ 995,000
157 Thompson Road
$ 995,000
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157 Thompson Road

Chester, VT, 05143
$ 995,000
Bedrooms4 Baths2.1 Sq 2,772

Monthly Estimate*

$ 6,208

Listed by Joseph Castelluccio, Winhall Real Estate, 732-979-4750, joe@winhallrealestate.com
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Single Family Home for sale in Chester, VT

for $995,000 with 4 bedrooms and 2 full baths, 1 half bath. This 2,772 square foot home was built in 1860 on a lot size of 32.97.

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

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Single Family Active

Price

$ 995,000

Bedrooms

4

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 0

Style

Farmhouse

Lot Size

32.97

Year Built

1860

Town/City

Chester

County/Region

Windsor

MLS | Web ID

5048851

Features
Interior
Basement Description Full Gravel Interior Stairs Basement Stairs
Basement Yes
Beds 4
Total Rooms 12
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General
Road Frontage Yes
Sewer 1000 Gallon Concrete Private
Heating Oil Baseboard Hot Water Wood Stove
Cooling None
Utilities Cable Available Telephone Available
Roof Asphalt Shingle
Garage Yes
Flood Zone Yes
Zoning Residential
3/4 Baths 0
Full Baths 2
Half Baths 1
Bathrooms 3
Year Built 1860
Electric 200+ Amp Service Generator
Style Farmhouse
Stories Count 2
Construction Status Existing
Type Single Family
Auction No
Tax Year 2024
Status Detail 0
Covenants Yes
Construction Materials Wood Frame Shingle Siding
High School Green Mountain UHSD #35
City Chester
School District Chester School District
Seasonal Unknown
Elementary School Chester-Andover Elementary
Middle School Green Mountain UHSD #35
DOM 169
Price Per Sq Ft Total AG 358.95
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Exterior
Lot Features Agricultural Dairy Farm Landscaped Mountain View Pond View Near Shopping Near Skiing Rural Near Railroad Near School(s)
Driveway Gravel
Lot Size Area 32.97
Water Source Drilled Well Private Spring
Garage Capacity 2
Foundation Concrete Fieldstone
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* Excluded Features
List By
Joseph Castelluccio

Listing Agent

Winhall Real Estate

Broker

(732) 979-4750

Phone

joe@winhallrealestate.com

Email

Affordability Calculator

$6,208
Per Month
100%
0%
0%
Monthly Principal & Interest
$6,208
Monthly Property Taxes
--
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4677907 Elementary School
5191489 Middle School
Green Mountain UHSD #35 High School High School
Pricing History
DatePricePrice ChangeDescription
12/3/2025$995,000 -11.56% Price Down
8/15/2025$1,125,000 -9.93% Price Down
6/26/2025$1,249,000 Listed Price

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157 Thompson Road, Chester, VT, 05143 is a Single Family Home for sale at $995,000 with 2,772 sqft and a lot size of 32.97. 157 Thompson Road has 4 bedrooms, 2.1 baths, and was built in 1860. The property's zip code is 05143 which is in Chester, VT