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 558 Main St estimated to be worth?

Trulia's estimated value for 558 Main St in Chester, VT is $421,900 .

What is the price history for 558 Main St?

558 Main St in Chester, VT last sold for $322,000 in August 2021.

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 558 Main St?

The closest schools to 558 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 558 Main St have laundry facilities?

Yes, 558 Main St in Chester, VT has laundry facilities.

How big is the lot at 558 Main St?

The lot at 558 Main St in Chester, VT is about 0.19 acres (8,276 sq ft).

OFF MARKET

$421,900

Trulia Estimate

4 Beds
2 Baths
2,002 sqft

558 Main St, Chester, VT 05143

Chester-Chester Depot

Est. Refi. Payment $3,030/mo*

Refinance Your Home

Currently Off Market - Sold Aug 24, 2021 for $322,000

Home Value

Trulia Estimate

$422K

Since last month

$3K (-0.8%)

Since last year

$13K (-2.9%)

Since last sale

$100K (+30.9%)

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 +72% in the last 10 years

Month	Estimated value
2026
September 2026	$422K
August 2026	$425K
July 2026	$448K
June 2026	$446K
May 2026	$447K
April 2026	$429K
March 2026	$426K
February 2026	$414K
January 2026	$422K
2025
December 2025	$409K
November 2025	$416K
October 2025	$424K
September 2025	$434K
August 2025	$434K
July 2025	$439K
June 2025	$437K
May 2025	$432K
April 2025	$432K
March 2025	$420K
February 2025	$410K
January 2025	$415K
2024
December 2024	$423K
November 2024	$422K
October 2024	$434K
September 2024	$433K
August 2024	$438K
July 2024	$436K
June 2024	$444K
May 2024	$425K
April 2024	$423K
March 2024	$417K
February 2024	$410K
January 2024	$405K
2023
December 2023	$396K
November 2023	$417K
October 2023	$418K
September 2023	$420K
August 2023	$422K
July 2023	$430K
June 2023	$423K
May 2023	$395K
April 2023	$384K
March 2023	$376K
February 2023	$370K
January 2023	$368K
2022
December 2022	$369K
November 2022	$373K
October 2022	$374K
September 2022	$377K
August 2022	$377K
July 2022	$366K
June 2022	$357K
May 2022	$351K
April 2022	$353K
March 2022	$351K
February 2022	$342K
January 2022	$340K
2021
December 2021	$336K
November 2021	$333K
October 2021	$330K
September 2021	$327K
August 2021	$293K
July 2021	$290K
June 2021	$336K
May 2021	$283K
April 2021	$276K
March 2021	$269K
February 2021	$266K
January 2021	$256K
2020
December 2020	$241K
November 2020	$239K
October 2020	$234K
September 2020	$234K
August 2020	$260K
July 2020	$268K
June 2020	$264K
May 2020	$259K
April 2020	$258K
March 2020	$259K
February 2020	$257K
January 2020	$258K
2019
December 2019	$257K
November 2019	$255K
October 2019	$255K
September 2019	$254K
August 2019	$253K
July 2019	$251K
June 2019	$250K
May 2019	$251K
April 2019	$249K
March 2019	$234K
February 2019	$233K
January 2019	$238K
2018
December 2018	$247K
November 2018	$249K
October 2018	$250K
September 2018	$247K
August 2018	$247K
July 2018	$246K
June 2018	$246K
May 2018	$246K
April 2018	$246K
March 2018	$245K
February 2018	$245K
January 2018	$242K
2017
December 2017	$240K
November 2017	$240K
October 2017	$241K
September 2017	$240K
August 2017	$239K
July 2017	$239K
June 2017	$244K
May 2017	$243K
April 2017	$244K
March 2017	$238K
February 2017	$234K
January 2017	$245K
2016
December 2016	$251K
November 2016	$249K
October 2016	$249K
September 2016	$246K

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	0.05	Single-Family Home	$359,000	05/15/26	3	1	1,608
95 Church Street, Chester, VT	0.15	Single-Family Home	$563,000	04/13/26	4	3	2,794
656 Main Street, Chester, VT	0.09	Single-Family Home	$605,000	10/02/25	3	2.5	3,040
447 Elm Street, Chester, VT	0.84	Single-Family Home	$260,000	09/18/26	3	2	1,488
641 Depot Street, Chester, VT	0.79	Single-Family Home	$180,000	08/10/26	3	1.5	1,379
397 River Street, Chester, VT	0.72	Single-Family Home	$275,000	08/06/26	4	3	3,332
45 Dalrymple Street, Chester, VT	0.79	Single-Family Home	$269,000	06/15/26	3	1	1,168
147 Pleasant View Lane, Chester, VT	0.71	Single-Family Home	$569,000	06/17/26	3	2	2,966
202 Mountain View, Chester, VT	1.39	Single-Family Home	$250,000	06/30/26	3	1.5	1,140
2651 Twenty Mile Stream Road, Proctorsville, VT	0.59	Single-Family Home	$2,000,000	01/30/26	4	3.5	3,000

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
115 Orcutt Drive, Chester, VT 05143	0.08	$441,000	2	1	1,360	Off Market
531 Main Street, Chester, VT 05143	0.05	$359,000	3	1	1,608	Recently Sold
515 Main Street, Chester, VT 05143	0.06	$144,300	Studio	4	3,024	Off Market
656 Main Street, Chester, VT 05143	0.09	$624,300	3	2.5	3,040	Off Market
472 Main Street, Chester, VT 05143	0.09	$850,900	5	5.5	5,546	Off Market
489 Main Street, Chester, VT 05143	0.08	$357,200	4	2	2,220	Off Market
595 Main Street, Chester, VT 05143	0.10	$553,300	6	3	3,892	Off Market
95 Church Street, Chester, VT 05143	0.15	$563,000	4	3	2,794	Recently Sold
423 Main Street, Chester, VT 05143	0.14	$425,000	6	5	3,217	Recently Sold
102 Church Street, Chester, VT 05143	0.18	$431,200	4	2	1,990	Off Market
405 Church Street, Chester, VT 05143	0.26	$552,500	3	2	1,856	Off Market
244 Main Street, Chester, VT 05143	0.32	$631,600	7	8	4,475	Off Market

Local Information

Map ViewExplore the area around 558 Main St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1820

2,002 sqft

$211/sqft

Garage

About this House

Lovely renovated four bedroom, two bath Chester Village home on .19 acres+/-. The charming interior has a spacious kitchen with a center island and walk-in pantry with built-ins, first floor full bath, spacious living/dining room, informal area and an office/study - perfect for working remotely from home. There is a wonderful rustic den/living area with woodstove in the back of the house that leads to the delightful rear deck and garden area as well as a handy attached storage garage. The second floor has three bedrooms in the front of the house, a spacious common area, and a private master bedroom suite with full bath and laundry area. Enjoy this wonderful location, where you can walk to the shops/restaurants, events on the Village Green and the Town Recreation Area. Close to ski resorts. 2021-07-14

558 Main St, Chester, VT 05143 is a 4 bedroom, 2 bathroom, 2,002 sqft single-family home in Chester-Chester Depot, built in 1820. It last sold for $322,000 on Aug 24, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $421,900, with a rent estimate of $2,666/month.

Home Details for 558 Main St

Interior Features
Heating & Cooling Heating: Stove, OilHeating Fuel: Stove
Interior Details Types of Rooms: Dining Room, Family Room, Office
Appliances & Utilities DishwasherDryerRefrigerator
Levels, Entrance, & Accessibility Floors: Hardwood

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

Property Information
Year Built Year Built: 1820
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 8276 sqft

Price and Tax history

Date	Event	Price
Aug 24, 2021 Source: PrimeMLS #4870838	Sold	$322,000
Jul 14, 2021 Source: Engel & Volkers #4870838	Pending	$299,000
Jul 14, 2021 Source: PrimeMLS #4870838	Contingent	$299,000
Jul 7, 2021 Source: PrimeMLS #4870838	Listed For Sale	$299,000
Jul 28, 2017 Source: PrimeMLS #4624668	Sold	$238,500
May 31, 2017 Source: Agent Provided	Pending	$257,000
Mar 31, 2017 Source: Agent Provided	Listed For Sale	$257,000
Oct 17, 2016 Source: Agent Provided	ListingRemoved	$269,000
Oct 21, 2015 Source: Agent Provided	Listed For Sale	$269,000
Oct 18, 2005 Source: N/A	Sold	$272,000
Sep 26, 2003 Source: N/A	Sold	$227,000
Aug 27, 2001 Source: N/A	Sold	$94,000
Oct 30, 1998 Source: N/A	Sold	$85,900

Year	Property tax	Tax assessment
2025	$6,875	$236,300

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 558 Main St

What is 558 Main St estimated to be worth?
Trulia's estimated value for 558 Main St in Chester, VT is $421,900.
What is the price history for 558 Main St?
558 Main St in Chester, VT last sold for $322,000 in August 2021.
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 558 Main St?
The closest schools to 558 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 558 Main St have laundry facilities?
Yes, 558 Main St in Chester, VT has laundry facilities.
How big is the lot at 558 Main St?
The lot at 558 Main St in Chester, VT is about 0.19 acres (8,276 sq ft).