Is Chester-Chester Depot, Chester, VT dog-friendly?

As of early 2026, 100% of users say it's dog friendly

Do residents of Chester-Chester Depot, Chester, VT plan to stay at least 5 years?

As of early 2026, 100% of users say they plan to stay for at least 5 years

Is Chester-Chester Depot, Chester, VT walkable to restaurants?

As of early 2026, 100% of users say it's walkable to restaurants

Is a car needed in Chester-Chester Depot, Chester, VT?

As of early 2026, 100% of users say car is needed

Does Chester-Chester Depot, Chester, VT have sidewalks?

As of early 2026, 100% of users say there are sidewalks

Are the streets well-lit in Chester-Chester Depot, Chester, VT?

As of early 2026, 100% of users say streets are well-lit

Do kids play outside in Chester-Chester Depot, Chester, VT?

As of early 2026, 100% of users say kids play outside

Are yards well-kept in Chester-Chester Depot, Chester, VT?

As of early 2026, 67% of users say yards are well-kept

Is Chester-Chester Depot, Chester, VT quiet?

As of early 2026, 67% of users say it's quiet

Are neighbors friendly in Chester-Chester Depot, Chester, VT?

As of early 2026, 57% of users say neighbors are friendly

Is parking easy in Chester-Chester Depot, Chester, VT?

As of early 2026, 50% of users say parking is easy

Are there community events in Chester-Chester Depot, Chester, VT?

As of early 2026, 50% of users say there are community events

Would people walk alone at night in Chester-Chester Depot, Chester, VT?

As of early 2026, 50% of users say people would walk alone at night

What is 501 Main St estimated to be worth?

Trulia's estimated value for 501 Main St in Chester, VT is $560,500 .

What is the price history for 501 Main St?

501 Main St in Chester, VT last sold for $465,000 in April 2022.

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 501 Main St?

The closest schools to 501 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).

Does 501 Main St have air conditioning?

Yes, 501 Main St in Chester, VT has air conditioning.

Does 501 Main St have laundry facilities?

Yes, 501 Main St in Chester, VT has in-unit laundry.

OFF MARKET

$560,500

Trulia Estimate

5 Beds
3 Baths
2,800 sqft (on 2 acres)

501 Main St, Chester, VT 05143

Chester-Chester Depot

Est. Refi. Payment $4,001/mo*

Refinance Your Home

Currently Off Market - Sold Apr 20, 2022 for $465,000

Home Value

Trulia Estimate

$561K

Since last month

$8K (-1.3%)

Since last year

$2K (+0.4%)

Since last sale

$95K (+20.5%)

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 +117% in the last 10 years

Month	Estimated value
2026
September 2026	$560K
August 2026	$568K
July 2026	$564K
June 2026	$577K
May 2026	$571K
April 2026	$555K
March 2026	$547K
February 2026	$527K
January 2026	$544K
2025
December 2025	$528K
November 2025	$537K
October 2025	$539K
September 2025	$558K
August 2025	$558K
July 2025	$562K
June 2025	$559K
May 2025	$552K
April 2025	$544K
March 2025	$537K
February 2025	$532K
January 2025	$528K
2024
December 2024	$538K
November 2024	$540K
October 2024	$539K
September 2024	$533K
August 2024	$546K
July 2024	$548K
June 2024	$552K
May 2024	$530K
April 2024	$524K
March 2024	$516K
February 2024	$511K
January 2024	$493K
2023
December 2023	$508K
November 2023	$533K
October 2023	$537K
September 2023	$537K
August 2023	$511K
July 2023	$530K
June 2023	$532K
May 2023	$357K
April 2023	$350K
March 2023	$346K
February 2023	$352K
January 2023	$357K
2022
December 2022	$360K
November 2022	$362K
October 2022	$366K
September 2022	$371K
August 2022	$376K
July 2022	$382K
June 2022	$378K
May 2022	$369K
April 2022	$360K
March 2022	$436K
February 2022	$350K
January 2022	$359K
2021
December 2021	$362K
November 2021	$365K
October 2021	$363K
September 2021	$358K
August 2021	$357K
July 2021	$353K
June 2021	$352K
May 2021	$340K
April 2021	$315K
March 2021	$318K
February 2021	$331K
January 2021	$332K
2020
December 2020	$303K
November 2020	$277K
October 2020	$266K
September 2020	$233K
August 2020	$270K
July 2020	$265K
June 2020	$248K
May 2020	$234K
April 2020	$233K
March 2020	$236K
February 2020	$233K
January 2020	$234K
2019
December 2019	$234K
November 2019	$232K
October 2019	$231K
September 2019	$229K
August 2019	$229K
July 2019	$227K
June 2019	$226K
May 2019	$227K
April 2019	$226K
March 2019	$212K
February 2019	$211K
January 2019	$215K
2018
December 2018	$224K
November 2018	$226K
October 2018	$227K
September 2018	$225K
August 2018	$225K
July 2018	$224K
June 2018	$224K
May 2018	$224K
April 2018	$224K
March 2018	$223K
February 2018	$223K
January 2018	$220K
2017
December 2017	$217K
November 2017	$218K
October 2017	$219K
September 2017	$218K
August 2017	$217K
July 2017	$217K
June 2017	$217K
May 2017	$216K
April 2017	$238K
March 2017	$238K
February 2017	$239K
January 2017	$239K
2016
December 2016	$238K
November 2016	$239K
October 2016	$239K
September 2016	$259K

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
95 Church Street, Chester, VT	0.16	Single-Family Home	$563,000	04/13/26	4	3	2,794
656 Main Street, Chester, VT	0.19	Single-Family Home	$605,000	10/02/25	3	2.5	3,040
397 River Street, Chester, VT	0.61	Single-Family Home	$275,000	08/06/26	4	3	3,332
531 Main Street, Chester, VT	0.07	Single-Family Home	$359,000	05/15/26	3	1	1,608
147 Pleasant View Lane, Chester, VT	0.60	Single-Family Home	$569,000	06/17/26	3	2	2,966
514 First Avenue, Chester, VT	0.83	Single-Family Home	$515,000	06/02/26	5	5	3,880
246 Putnam Hill Road, Chester, VT	0.81	Single-Family Home	$550,000	11/17/25	3	3.5	2,256
2651 Twenty Mile Stream Road, Proctorsville, VT	0.58	Single-Family Home	$2,000,000	01/30/26	4	3.5	3,000
447 Elm Street, Chester, VT	0.80	Single-Family Home	$260,000	09/18/26	3	2	1,488
641 Depot Street, Chester, VT	0.77	Single-Family Home	$180,000	08/10/26	3	1.5	1,379

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
489 Main Street, Chester, VT 05143	0.05	$357,200	4	2	2,220	Off Market
515 Main Street, Chester, VT 05143	0.06	$144,300	Studio	4	3,024	Off Market
423 Main Street, Chester, VT 05143	0.07	$425,000	6	5	3,217	Recently Sold
531 Main Street, Chester, VT 05143	0.07	$359,000	3	1	1,608	Recently Sold
472 Main Street, Chester, VT 05143	0.09	$850,900	5	5.5	5,546	Off Market
595 Main Street, Chester, VT 05143	0.12	$553,300	6	3	3,892	Off Market
95 Church Street, Chester, VT 05143	0.16	$563,000	4	3	2,794	Recently Sold
115 Orcutt Drive, Chester, VT 05143	0.18	$441,000	2	1	1,360	Off Market
102 Church Street, Chester, VT 05143	0.18	$431,200	4	2	1,990	Off Market
656 Main Street, Chester, VT 05143	0.19	$624,300	3	2.5	3,040	Off Market
244 Main Street, Chester, VT 05143	0.25	$631,600	7	8	4,475	Off Market
405 Church Street, Chester, VT 05143	0.33	$552,500	3	2	1,856	Off Market

Local Information

Map ViewExplore the area around 501 Main St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1805

2 acre lot

2,800 sqft

$200/sqft

Garage

About this House

What's unique:Plenty of garden spaceWalk to trailsMusic studioBeautiful five bedroomGenerous living spaceQuaint town of chester

Mini Farm with 1805 colonial farm house. Beautiful home with many original features, large hay barn, garage, workshop, in addition to 2800 sq ft of living space. Frontage on Middle Branch Williams River and 1-1/2 acre hay field.

501 Main St, Chester, VT 05143 is a 5 bedroom, 3 bathroom, 2,800 sqft single-family home in Chester-Chester Depot, built in 1805. It last sold for $465,000 on Apr 20, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $560,500, with a rent estimate of $3,475/month.

Home Details for 501 Main St

Interior Features
Interior Details BasementIn-law unitNumber of Rooms: 13Types of Rooms: Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Pantry, Recreation Room, Workshop
Heating & Cooling Heating: Heat Pump, OilAir ConditioningCooling System: WallHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 2Floors: Softwood, Hardwood, Linoleum Vinyl
Appliances & Utilities Cable ReadyDishwasherDryerRefrigeratorWasher
Fireplace & Spa Fireplace
Windows, Doors, Floors & Walls Double Paned Windows

Exterior Features
Exterior Home Features Roof: Metal, SlateExterior: Wood, BrickGardenLawnPorch
Parking & Garage GarageParking Spaces: 4Parking: Carport, Garage Attached, Off Street

Property Information
Year Built Year Built: 1805
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial

Lot Information
Lot Area: 2.00 acres

Price and Tax history

Date	Event	Price
Apr 20, 2022 Source: PrimeMLS #4899226	Sold	$465,000
Apr 20, 2022 Source: PrimeMLS #4899226	Contingent	$450,000
Feb 28, 2022 Source: PrimeMLS #4899226	Listed For Sale	$450,000
Nov 2, 2021 Source: N/A	Sold	$380,000
Apr 21, 2017 Source: PrimeMLS #4495229	Sold	$215,000
Mar 24, 2017 Source: Agent Provided	Pending	$259,000
Oct 17, 2016 Source: Agent Provided	PriceChange	$259,000 Price decreased by 7%
Sep 12, 2016 Source: Agent Provided	PriceChange	$279,000 Price decreased by 7%
Jul 12, 2016 Source: Agent Provided	PriceChange	$299,000 Price decreased by 5%
Jun 3, 2016 Source: Agent Provided	Listed For Sale	$315,000
Jul 31, 2013 Source: N/A	Sold	$205,000

Year	Property tax	Tax assessment
2025	$6,731	$231,000

Additional Cost

Market trends in Chester

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Around this home

Chester-Andover Usd #29
PK-6
Public
246 Students
Green Mountain Unified School District
6/10
GreatSchools Rating
Parent Rating Average
My experience here has been excellent. I have never met with resistance only cooperation and compassionate caring when dealing with issues concerning my child. The class sizes are small allowing for individual attention to issues. There is great collaboration among primary and secondary teachers, along with other providers. I feel very fortunate to have access to this school for my children.
Parent Review
16y ago
1 Reviews

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Chester-Chester Depot

6 Homes For You
Buy: $100k - $789k

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.
Resident
6y ago
"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
Resident
7y ago
"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.
13y ago
"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
15y ago
"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
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LGBTQ Local Legal Protections

Frequently asked questions about 501 Main St

What is 501 Main St estimated to be worth?
Trulia's estimated value for 501 Main St in Chester, VT is $560,500.
What is the price history for 501 Main St?
501 Main St in Chester, VT last sold for $465,000 in April 2022.
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 501 Main St?
The closest schools to 501 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).
Does 501 Main St have air conditioning?
Yes, 501 Main St in Chester, VT has air conditioning.
Does 501 Main St have laundry facilities?
Yes, 501 Main St in Chester, VT has in-unit laundry.