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 8 Pleasant St estimated to be worth?

Trulia's estimated value for 8 Pleasant St in Chester, VT is $302,800 .

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 8 Pleasant St?

The closest schools to 8 Pleasant 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 8 Pleasant St?

The lot at 8 Pleasant St in Chester, VT is about 1.1 acres .

OFF MARKET

$302,800

Trulia Estimate

Studio

8 Pleasant St, Chester, VT 05143

Chester-Chester Depot

Est. Refi. Payment $2,111/mo*

Refinance Your Home

Home Value

Trulia Estimate

$303K

Since last month

$84K (-21.5%)

Since last year

$14K (+4.7%)

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 +14% in the last 10 years

Month	Estimated value
2026
August 2026	$306K
July 2026	$389K
May 2026	$296K
April 2026	$296K
March 2026	$303K
February 2026	$386K
2025
December 2025	$313K
November 2025	$278K
October 2025	$270K
September 2025	$287K
August 2025	$292K
July 2025	$368K
June 2025	$366K
May 2025	$339K
April 2025	$382K
March 2025	$349K
February 2025	$289K
January 2025	$297K
2024
December 2024	$319K
November 2024	$312K
October 2024	$403K
September 2024	$399K
August 2024	$479K
July 2024	$451K
June 2024	$392K
May 2024	$368K
April 2024	$367K
March 2024	$349K
February 2024	$409K
January 2024	$376K
2023
December 2023	$402K
November 2023	$416K
October 2023	$501K
September 2023	$504K
August 2023	$500K
July 2023	$490K
June 2023	$527K
May 2023	$538K
April 2023	$528K
March 2023	$516K
February 2023	$502K
January 2023	$501K
2022
December 2022	$507K
November 2022	$518K
October 2022	$528K
September 2022	$524K
August 2022	$515K
July 2022	$518K
June 2022	$514K
May 2022	$499K
April 2022	$482K
March 2022	$464K
February 2022	$437K
January 2022	$439K
2021
December 2021	$444K
November 2021	$444K
October 2021	$449K
September 2021	$451K
August 2021	$462K
July 2021	$486K
June 2021	$440K
May 2021	$372K
April 2021	$338K
March 2021	$333K
February 2021	$341K
January 2021	$350K
2020
December 2020	$333K
November 2020	$332K
October 2020	$327K
September 2020	$344K
August 2020	$350K
July 2020	$351K
June 2020	$346K
May 2020	$341K
April 2020	$329K
March 2020	$325K
February 2020	$328K
January 2020	$334K
2019
December 2019	$323K
November 2019	$318K
October 2019	$328K
September 2019	$335K
August 2019	$325K
July 2019	$318K
June 2019	$311K
May 2019	$314K
April 2019	$310K
March 2019	$316K
February 2019	$304K
January 2019	$300K
2018
December 2018	$305K
November 2018	$300K
October 2018	$301K
September 2018	$292K
August 2018	$296K
July 2018	$296K
June 2018	$297K
May 2018	$296K
April 2018	$294K
March 2018	$299K
February 2018	$301K
January 2018	$294K
2017
December 2017	$290K
November 2017	$304K
October 2017	$289K
September 2017	$289K
August 2017	$283K
July 2017	$261K
June 2017	$264K
May 2017	$277K
April 2017	$251K
March 2017	$258K
February 2017	$258K
January 2017	$257K
2016
December 2016	$251K
November 2016	$287K
October 2016	$277K
September 2016	$270K
August 2016	$267K

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
397 River Street, Chester, VT	0.35	Single-Family Home	$275,000	08/06/26	4	3	3,332
230 Kevadus Circle, Chester, VT	0.16	Single-Family Home	$275,000	09/10/25	3	1	894
62 Circle Drive, Chester, VT	0.34	Single-Family Home	$389,000	09/22/25	3	2	1,196
15 Breezy Lane, Chester, VT	0.33	Single-Family Home	$239,000	06/01/26	2	1	1,026
442 State Route 103 S, Chester, VT	0.32	Single-Family Home	$220,000	11/10/25	2	1	1,088
442 103 S, Chester, VT	0.32	Single-Family Home	$220,000	11/07/25	3	1	1,024
202 Mountain View, Chester, VT	0.36	Single-Family Home	$250,000	06/30/26	3	1.5	1,140
1937 Green Mountain Turnpike, Chester, VT	0.73	Single-Family Home	$550,000	10/06/25	2	2	1,812
246 Putnam Hill Road, Chester, VT	0.32	Single-Family Home	$550,000	11/17/25	3	3.5	2,256
18 S Main St, Chester, VT	0.45	Single-Family Home	$85,000	03/30/26		-	-

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
192 Kevadus Circle, Chester, VT 05143	0.12	$291,600	3	1	1,227	Off Market
87 Kevadus Circle, Chester, VT 05143	0.15	$237,000	3	1	840	Off Market
230 Kevadus Circle, Chester, VT 05143	0.16	$284,300	3	1	894	Off Market
183 Pleasant Street, Chester, VT 05143	0.18	$392,200	4	2.5	2,686	Off Market
442 103 S, Chester, VT 05143	0.32	$220,000	3	1	1,024	Recently Sold
246 Putnam Hill Road, Chester, VT 05143	0.32	$550,000	3	3.5	2,256	Recently Sold
15 Breezy Lane, Chester, VT 05143	0.33	$239,000	2	1	1,026	Recently Sold
62 Circle Drive, Chester, VT 05143	0.34	$366,100	3	2	1,196	Off Market
468 VT Route 103 S, Chester, VT 05143	0.35	$272,700	3	1	960	Off Market
186 Mountain View, Chester, VT 05143	0.36	$259,700	3	1	966	Off Market
202 Mountain View, Chester, VT 05143	0.36	$250,000	3	1.5	1,140	Recently Sold
397 River Street, Chester, VT 05143	0.35	$275,000	4	3	3,332	Recently Sold

Local Information

Map ViewExplore the area around 8 Pleasant St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Lot Size

1.07 acres

About this House

This single-family home is located at 8 Pleasant St, Chester, VT. 8 Pleasant St is in the Chester-Chester Depot neighborhood in Chester, VT and in ZIP code 05143. This property has a lot size of 1.07 acres.

8 Pleasant 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 $302,800, with a rent estimate of $2,047/month.

Home Details for 8 Pleasant St

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

Lot Information
Lot Area: 1.07 acres

Price and Tax history

Year	Property tax	Tax assessment
2024	Unavailable	$351,700

Home facts updated by county records

Additional Cost

Market trends in Chester

Last updated July 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

7 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 8 Pleasant St

What is 8 Pleasant St estimated to be worth?
Trulia's estimated value for 8 Pleasant St in Chester, VT is $302,800.
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 8 Pleasant St?
The closest schools to 8 Pleasant 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 8 Pleasant St?
The lot at 8 Pleasant St in Chester, VT is about 1.1 acres.

Apartments for Rent

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$1,450/mo
1 bd
1 ba
41 Coach Rd #6,
Chester, VT 05143
APPLY INSTANTLY
$1,550/mo
1 bd
1 ba
9 River St #B,
Chester, VT 05143
See more homes for rent in
Chester
Take a look

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Off Market Homes Near 8 Pleasant St

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SOLD
AUG 10, 2026
$180,000
3 bd
1.5 ba
1,379 sqft
641 Depot Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
AUG 6, 2026
$275,000
4 bd
3 ba
3,332 sqft
397 River Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
JUL 20, 2026
$315,000
55 Overpass Rd,
Chester, VT 05143
SOLD
JUL 7, 2026
$445,000
3 bd
2 ba
2,400 sqft
475 Flamstead Rd,
Chester, VT 05143
SOLD
JUN 30, 2026
$250,000
3 bd
1.5 ba
1,140 sqft
202 Mountain View,
Chester, VT 05143
PrimeMLS, Closed
SOLD
JUN 15, 2026
$269,000
3 bd
1 ba
1,168 sqft
45 Dalrymple Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
JUN 1, 2026
$239,000
2 bd
1 ba
1,026 sqft
15 Breezy Lane,
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
MAY 13, 2026
$210,000
3 bd
1 ba
1,440 sqft
419 Coach Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
MAY 5, 2026
$200,000
6 bd
3 ba
3,600 sqft
45 Cobleigh St,
Chester, VT 05143
See more homes for sale in
Chester
Take a look