442 Main St, Chester, VT 05143
Property image
Property image
OFF MARKET

$339,500

Trulia Estimate
  • 4 Beds
  • 1 Bath
  • 2,264 sqft (on 0.50 acres)

442 Main St, Chester, VT 05143

Chester-Chester Depot
Est. Refi. Payment $2,453/mo*
Refinance Your Home
Currently Off Market - Sold Jul 31, 2020 for $149,000

Home Value

Trulia Estimate
$340K
Since last month
Decreased$6K (-1.7%)
Since last year
Decreased$25K (-6.9%)
Since last sale
Increased$190K (+127.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +40% in the last 10 years
MonthEstimated value
2026
September 2026$339K
August 2026$345K
July 2026$368K
June 2026$363K
May 2026$365K
April 2026$339K
March 2026$332K
February 2026$307K
January 2026$323K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
531 Main Street, Chester, VT
0.10
Single-Family Home
$359,000
05/15/26
3
1
1,608
95 Church Street, Chester, VT
0.06
Single-Family Home
$563,000
04/13/26
4
3
2,794
656 Main Street, Chester, VT
0.22
Single-Family Home
$605,000
10/02/25
3
2.5
3,040
45 Dalrymple Street, Chester, VT
0.76
Single-Family Home
$269,000
06/15/26
3
1
1,168
641 Depot Street, Chester, VT
0.67
Single-Family Home
$180,000
08/10/26
3
1.5
1,379
447 Elm Street, Chester, VT
0.72
Single-Family Home
$260,000
09/18/26
3
2
1,488
397 River Street, Chester, VT
0.61
Single-Family Home
$275,000
08/06/26
4
3
3,332
284 Flamstead Road, Chester, VT
1.01
Single-Family Home
$178,000
11/05/25
3
1.5
960
147 Pleasant View Lane, Chester, VT
0.65
Single-Family Home
$569,000
06/17/26
3
2
2,966
442 103 S, Chester, VT
1.23
Single-Family Home
$220,000
11/07/25
3
1
1,024

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
472 Main Street, Chester, VT 05143
0.03
$850,900
5
5.5
5,546
Off Market
489 Main Street, Chester, VT 05143
0.07
$357,200
4
2
2,220
Off Market
423 Main Street, Chester, VT 05143
0.06
$425,000
6
5
3,217
Recently Sold
515 Main Street, Chester, VT 05143
0.10
$144,300
Studio
4
3,024
Off Market
531 Main Street, Chester, VT 05143
0.10
$359,000
3
1
1,608
Recently Sold
95 Church Street, Chester, VT 05143
0.06
$563,000
4
3
2,794
Recently Sold
102 Church Street, Chester, VT 05143
0.08
$431,200
4
2
1,990
Off Market
115 Orcutt Drive, Chester, VT 05143
0.13
$441,000
2
1
1,360
Off Market
595 Main Street, Chester, VT 05143
0.20
$553,300
6
3
3,892
Off Market
656 Main Street, Chester, VT 05143
0.22
$624,300
3
2.5
3,040
Off Market
244 Main Street, Chester, VT 05143
0.19
$631,600
7
8
4,475
Off Market
405 Church Street, Chester, VT 05143
0.24
$552,500
3
2
1,856
Off Market

Local Information

  • Map ViewExplore the area around 442 Main St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1900
0.5 acre lot
2,264 sqft
$150/sqft
Garage

About this House

This single-family home is located at 442 Main St, Chester, VT. 442 Main St is in the Chester-Chester Depot neighborhood in Chester, VT and in ZIP code 05143. This property has 4 bedrooms, 1 bathroom and approximately 2,264 sqft of floor space. This property has a lot size of 0.50 acres and was built in 1900.
442 Main St, Chester, VT 05143 is a 4 bedroom, 1 bathroom, 2,264 sqft single-family home in Chester-Chester Depot, built in 1900. It last sold for $149,000 on Jul 31, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $339,500, with a rent estimate of $2,429/month.

Home Details for 442 Main St

Interior Features

Heating & Cooling
Heating: Forced Air, OilHeating Fuel: Forced Air
Interior Details
Types of Rooms: Dining Room, Family Room, Office

Exterior Features

Exterior Home Features
Roof: Slate
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 0.50 acres

Price and Tax history

DateEventPrice
Jul 31, 2020
Source: PrimeMLS #4799855
Sold
$149,000
Mar 31, 2020
Source: Agent Provided
Listed For Sale
$175,900

Market trends in Chester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
18
2MoM

Around this home

Neighborhood Overview

Chester-Chester Depot
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Chester-Chester Depot

At least 2 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 100 % Say they plan to stay for at least 5 years

  • 100 % Say it's walkable to restaurants

  • 100 % Say car is needed

  • 100 % Say there are sidewalks

  • 100 % Say streets are well-lit

  • 100 % Say kids play outside

  • 67 % Say yards are well-kept

  • 67 % Say it's quiet

  • 57 % Say neighbors are friendly

  • 50 % Say parking is easy

  • 50 % Say there are community events

  • 50 % Say people would walk alone at night

Sourced by Trulia users. Learn more about our methodology.
  • Kimberlee B.
    "It is safe here. I grew up here and I so grateful to be raising my family here. everybody is so nice. everybody watches out for one another. the summers are beautiful w all the flowers and green grass and the winters are festive w all the lights on the green an Santa making his big entrance every year for the local children! "
    11
    Flag
  • pissed off
    "This neighborhood is nice looking but there are some very disrespectful people. They send thier dog over to my yard to dump and will not clean up. The police can't be bothered even though there is a leash law. Town built a "pocket park" on private property which is now a drug deal location and dog toilet."
    29
    Flag
  • Georgette W.
    "Chester is a lovely quaint town in southwestern Vermont. The village has stores and restaurants and a small grocer, but is close to Springfield with a larger grocery store. It is thirty to forty-five minutes to 5 major ski areas."
    0
    Flag
  • Kz
    "We've lived in the area for almost 10 years and in this location for 2. The neighborhood is beautiful. The town is a 10 minute walk away and has many great restaurants and shopping. Close to highway. Amenities include town rec-center, banks, grocery store, skiing, biking, and hiking trails close by. And the people are super friendly."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 442 Main St

  • What is 442 Main St estimated to be worth?
    Trulia's estimated value for 442 Main St in Chester, VT is $339,500.
  • What is the price history for 442 Main St?
    442 Main St in Chester, VT last sold for $149,000 in July 2020.
  • Is Chester a buyer's or seller's market?
    Chester is currently a buyer's market, based on recent for-sale activity.
  • What are the closest schools to 442 Main St?
    The closest schools to 442 Main St in Chester, VT are Chester-Andover Usd #29 (Pre-K/Elementary, rated 6/10), Green Mountain Uhsd #35 (Middle/High, rated 7/10).
  • How big is the lot at 442 Main St?
    The lot at 442 Main St in Chester, VT is about 0.50 acres (21,780 sq ft).
  • Does 442 Main St have a garage?
    Yes, 442 Main St in Chester, VT has a garage.

Apartments for Rent

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Off Market Homes Near 442 Main St

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