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 308 Main St estimated to be worth?

Trulia's estimated value for 308 Main St in Chester, VT is $588,400 .

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 308 Main St?

The closest schools to 308 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 308 Main St?

The lot at 308 Main St in Chester, VT is about 19.5 acres .

OFF MARKET

$588,400

Trulia Estimate

Studio

308 Main St, Chester, VT 05143

Chester-Chester Depot

Est. Refi. Payment $4,197/mo*

Refinance Your Home

Home Value

Trulia Estimate

$588K

Since last month

$70K (-10.6%)

Since last year

$88K (-13%)

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 +27% in the last 10 years

Month	Estimated value
2026
September 2026	$588K
August 2026	$658K
July 2026	$615K
June 2026	$645K
May 2026	$619K
April 2026	$568K
March 2026	$630K
February 2026	$574K
January 2026	$619K
2025
December 2025	$589K
November 2025	$554K
October 2025	$610K
September 2025	$676K
August 2025	$687K
July 2025	$667K
June 2025	$675K
May 2025	$662K
April 2025	$661K
March 2025	$652K
February 2025	$626K
January 2025	$653K
2024
December 2024	$667K
November 2024	$665K
October 2024	$636K
September 2024	$661K
August 2024	$583K
July 2024	$672K
June 2024	$680K
May 2024	$647K
April 2024	$650K
March 2024	$628K
February 2024	$618K
January 2024	$634K
2023
December 2023	$605K
November 2023	$653K
October 2023	$643K
September 2023	$648K
August 2023	$655K
July 2023	$637K
June 2023	$605K
May 2023	$478K
April 2023	$478K
March 2023	$467K
February 2023	$449K
January 2023	$437K
2022
December 2022	$456K
November 2022	$458K
October 2022	$468K
September 2022	$481K
August 2022	$501K
July 2022	$511K
June 2022	$503K
May 2022	$489K
April 2022	$478K
March 2022	$452K
February 2022	$403K
January 2022	$414K
2021
December 2021	$405K
November 2021	$419K
October 2021	$432K
September 2021	$425K
August 2021	$446K
July 2021	$487K
June 2021	$489K
May 2021	$388K
April 2021	$380K
March 2021	$357K
February 2021	$338K
January 2021	$356K
2020
December 2020	$386K
November 2020	$379K
October 2020	$354K
September 2020	$423K
August 2020	$442K
July 2020	$431K
June 2020	$431K
May 2020	$420K
April 2020	$424K
March 2020	$447K
February 2020	$460K
January 2020	$450K
2019
December 2019	$418K
November 2019	$414K
October 2019	$423K
September 2019	$480K
August 2019	$477K
July 2019	$480K
June 2019	$482K
May 2019	$473K
April 2019	$469K
March 2019	$428K
February 2019	$341K
January 2019	$346K
2018
December 2018	$387K
November 2018	$391K
October 2018	$402K
September 2018	$416K
August 2018	$402K
July 2018	$404K
June 2018	$402K
May 2018	$388K
April 2018	$398K
March 2018	$420K
February 2018	$430K
January 2018	$431K
2017
December 2017	$411K
November 2017	$416K
October 2017	$430K
September 2017	$420K
August 2017	$400K
July 2017	$398K
June 2017	$404K
May 2017	$402K
April 2017	$424K
March 2017	$419K
February 2017	$437K
January 2017	$444K
2016
December 2016	$455K
November 2016	$462K
October 2016	$454K
September 2016	$463K

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	0.17	Single-Family Home	$563,000	04/13/26	4	3	2,794
514 First Avenue, Chester, VT	0.51	Single-Family Home	$515,000	06/02/26	5	5	3,880
531 Main Street, Chester, VT	0.32	Single-Family Home	$359,000	05/15/26	3	1	1,608
656 Main Street, Chester, VT	0.40	Single-Family Home	$605,000	10/02/25	3	2.5	3,040
246 Putnam Hill Road, Chester, VT	0.87	Single-Family Home	$550,000	11/17/25	3	3.5	2,256
641 Depot Street, Chester, VT	0.46	Single-Family Home	$180,000	08/10/26	3	1.5	1,379
389 Cummings Rd, Chester, VT	0.97	Single-Family Home	$640,000	02/02/26		-	-
397 River Street, Chester, VT	0.63	Single-Family Home	$275,000	08/06/26	4	3	3,332
447 Elm Street, Chester, VT	0.54	Single-Family Home	$260,000	09/18/26	3	2	1,488
45 Dalrymple Street, Chester, VT	0.59	Single-Family Home	$269,000	06/15/26	3	1	1,168

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
102 Church Street, Chester, VT 05143	0.15	$431,200	4	2	1,990	Off Market
95 Church Street, Chester, VT 05143	0.17	$563,000	4	3	2,794	Recently Sold
405 Church Street, Chester, VT 05143	0.21	$552,500	3	2	1,856	Off Market
244 Main Street, Chester, VT 05143	0.21	$631,600	7	8	4,475	Off Market
472 Main Street, Chester, VT 05143	0.25	$850,900	5	5.5	5,546	Off Market
423 Main Street, Chester, VT 05143	0.26	$425,000	6	5	3,217	Recently Sold
115 Orcutt Drive, Chester, VT 05143	0.27	$441,000	2	1	1,360	Off Market
489 Main Street, Chester, VT 05143	0.29	$357,200	4	2	2,220	Off Market
515 Main Street, Chester, VT 05143	0.31	$144,300	Studio	4	3,024	Off Market
531 Main Street, Chester, VT 05143	0.32	$359,000	3	1	1,608	Recently Sold
00 Coach Road, Chester, VT 05143	0.31	-	-	-	-	Off Market
198 Coach Road, Chester, VT 05143	0.32	$364,300	4	2.5	2,904	Off Market

Local Information

Map ViewExplore the area around 308 Main St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

19.5 acre lot

About this House

This single-family home is located at 308 Main St, Chester, VT. 308 Main St is in the Chester-Chester Depot neighborhood in Chester, VT and in ZIP code 05143. This property has a lot size of 19.50 acres.

308 Main St, Chester, VT 05143 is a studio single-family home in Chester-Chester Depot. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $588,400, with a rent estimate of $2,475/month.

Home Details for 308 Main St

Property Information
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 19.50 acres

Price and Tax history

Year	Property tax	Tax assessment
2025	$12,251	$421,100

Home facts updated by county records

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
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 308 Main St

What is 308 Main St estimated to be worth?
Trulia's estimated value for 308 Main St in Chester, VT is $588,400.
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 308 Main St?
The closest schools to 308 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 308 Main St?
The lot at 308 Main St in Chester, VT is about 19.5 acres.

Apartments for Rent

Skip to last item

$1,350/mo
1 bd
1 ba
41 Coach Rd #6,
Chester, VT 05143
$1,400/mo
1 bd
1 ba
617 Depot St #4,
Chester, VT 05143
NEW - 1 DAY AGO
PET FRIENDLY
$1,700/mo
3 bd
1 ba
644 Depot St #4,
Chester, VT 05143
See more homes for rent in
Chester
Take a look

Skip to first item

Off Market Homes Near 308 Main St

Skip to last item

SOLD
AUG 12, 2026
$510,000
2 bd
2 ba
2,016 sqft
35 Upper Bartonsville Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
JUL 7, 2026
$445,000
3 bd
2 ba
2,400 sqft
475 Flamstead Rd,
Chester, VT 05143
SOLD
JUN 17, 2026
$569,000
3 bd
2 ba
2,966 sqft
147 Pleasant View Lane,
Chester, VT 05143
PrimeMLS, Closed
SOLD
JUN 2, 2026
$515,000
5 bd
5 ba
3,880 sqft
514 First Avenue,
Chester, VT 05143
PrimeMLS, Closed
SOLD
MAY 15, 2026
$359,000
3 bd
1 ba
1,608 sqft
531 Main Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
APR 20, 2026
$379,000
2 bd
2 ba
2,751 sqft
3466 VT Route 103 N,
Chester, VT 05143
PrimeMLS, Closed
SOLD
APR 13, 2026
$563,000
4 bd
3 ba
2,794 sqft
95 Church Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
APR 2, 2026
$550,000
3,850 sqft
534 Elm Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
MAR 10, 2026
$399,000
3 bd
2 ba
1,789 sqft
187 Lacross Road,
Springfield, VT 05156
PrimeMLS, Closed
SOLD
FEB 13, 2026
$815,000
3 bd
2.5 ba
2,466 sqft
810 Quarry Road,
Chester, VT 05143
PrimeMLS, Closed
See more homes for sale in
Chester
Take a look