Is a car needed in Chester, VT?

As of early 2026, 80% of users say car is needed

Is Chester, VT quiet?

As of early 2026, 80% of users say it's quiet

Is Chester, VT dog-friendly?

As of early 2026, 80% of users say it's dog friendly

Is parking easy in Chester, VT?

As of early 2026, 75% of users say parking is easy

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

As of early 2026, 75% of users say they plan to stay for at least 5 years

Are the streets well-lit in Chester, VT?

As of early 2026, 67% of users say streets are well-lit

Do kids play outside in Chester, VT?

As of early 2026, 63% of users say kids play outside

Are yards well-kept in Chester, VT?

As of early 2026, 57% of users say yards are well-kept

Is Chester, VT walkable to restaurants?

As of early 2026, 50% of users say it's walkable to restaurants

Does Chester, VT have sidewalks?

As of early 2026, 50% of users say there are sidewalks

Are neighbors friendly in Chester, VT?

As of early 2026, 48% of users say neighbors are friendly

Would people walk alone at night in Chester, VT?

As of early 2026, 40% of users say people would walk alone at night

Is there wildlife in Chester, VT?

As of early 2026, 40% of users say there's wildlife

Does Chester, VT show holiday spirit?

As of early 2026, 40% of users say there's holiday spirit

Are there community events in Chester, VT?

As of early 2026, 17% of users say there are community events

What is 159 High estimated to be worth?

Trulia's estimated value for 159 High in Chester, VT is $312,400 .

What is the price history for 159 High?

159 High in Chester, VT last sold for $92,000 in December 2016.

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 159 High?

The closest schools to 159 High in Chester, VT are Chester-Andover Usd #29 (Pre-K/Elementary, rated 6/10), Green Mountain Uhsd #35 (Middle/High, rated 7/10).

OFF MARKET

159 High
Chester, VT 05143

3 Beds
1.5 Baths
2,000 sqft

$312,400

Trulia Estimate

as of Aug 25, 2026

Est. Refi. Payment $2,170/mo*

Refinance Your Home

$312,400

Trulia Estimate

as of Aug 25, 2026

Est. Refi. Payment $2,170/mo*

Refinance Your Home

3 Beds

1.5 Baths

2,000 sqft

Home Value

Trulia Estimate

$312K

Since last month

$13K (+4.4%)

Since last year

$44K (-12.3%)

Since last sale

$220K (+239.6%)

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 +32% in the last 10 years

Month	Estimated value
2026
August 2026	$312K
July 2026	$299K
June 2026	$314K
May 2026	$307K
April 2026	$330K
March 2026	$286K
February 2026	$304K
January 2026	$291K
2025
December 2025	$323K
November 2025	$340K
October 2025	$316K
September 2025	$345K
August 2025	$356K
July 2025	$343K
June 2025	$369K
May 2025	$369K
April 2025	$348K
March 2025	$340K
February 2025	$311K
January 2025	$308K
2024
December 2024	$325K
November 2024	$361K
October 2024	$310K
September 2024	$309K
August 2024	$304K
July 2024	$314K
June 2024	$371K
May 2024	$283K
April 2024	$286K
March 2024	$281K
February 2024	$289K
January 2024	$277K
2023
December 2023	$271K
November 2023	$287K
October 2023	$299K
September 2023	$275K
August 2023	$291K
July 2023	$307K
June 2023	$294K
May 2023	$348K
April 2023	$339K
March 2023	$328K
February 2023	$321K
January 2023	$319K
2022
December 2022	$336K
November 2022	$340K
October 2022	$347K
September 2022	$349K
August 2022	$359K
July 2022	$369K
June 2022	$373K
May 2022	$368K
April 2022	$362K
March 2022	$363K
February 2022	$292K
January 2022	$289K
2021
December 2021	$304K
November 2021	$299K
October 2021	$302K
September 2021	$300K
August 2021	$299K
July 2021	$290K
June 2021	$317K
May 2021	$286K
April 2021	$281K
March 2021	$267K
February 2021	$271K
January 2021	$269K
2020
December 2020	$272K
November 2020	$268K
October 2020	$251K
September 2020	$251K
August 2020	$250K
July 2020	$247K
June 2020	$265K
May 2020	$232K
April 2020	$208K
March 2020	$265K
February 2020	$240K
January 2020	$185K
2019
December 2019	$129K
November 2019	$100K
October 2019	$100K
September 2019	$99K
August 2019	$98K
July 2019	$98K
June 2019	$97K
May 2019	$98K
April 2019	$98K
March 2019	$92K
February 2019	$91K
January 2019	$93K
2018
December 2018	$96K
November 2018	$98K
October 2018	$98K
September 2018	$97K
August 2018	$97K
July 2018	$97K
June 2018	$97K
May 2018	$97K
April 2018	$97K
March 2018	$96K
February 2018	$96K
January 2018	$95K
2017
December 2017	$94K
November 2017	$94K
October 2017	$95K
September 2017	$95K
August 2017	$94K
July 2017	$94K
June 2017	$93K
May 2017	$93K
April 2017	$93K
March 2017	$93K
February 2017	$93K
January 2017	$92K
2016
December 2016	$92K
November 2016	$241K
October 2016	$238K
September 2016	$240K
August 2016	$237K

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
147 Pleasant View Lane, Chester, VT	0.19	Single-Family Home	$569,000	06/17/26	3	2	2,966
397 River Street, Chester, VT	0.23	Single-Family Home	$275,000	08/06/26	4	3	3,332
531 Main Street, Chester, VT	0.50	Single-Family Home	$359,000	05/15/26	3	1	1,608
246 Putnam Hill Road, Chester, VT	0.38	Single-Family Home	$550,000	11/17/25	3	3.5	2,256
641 Depot Street, Chester, VT	0.80	Single-Family Home	$180,000	08/10/26	3	1.5	1,379
230 Kevadus Circle, Chester, VT	0.62	Single-Family Home	$275,000	09/10/25	3	1	894
87 Kevadus Circle, Chester, VT	0.68	Single-Family Home	$229,000	08/29/25	3	1	840
95 Church Street, Chester, VT	0.51	Single-Family Home	$563,000	04/13/26	4	3	2,794
656 Main Street, Chester, VT	0.62	Single-Family Home	$605,000	10/02/25	3	2.5	3,040
442 103 S, Chester, VT	0.89	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
18 Mill Street, Chester, VT 05143	0.18	$304,300	4	1.5	1,380	Off Market
147 Pleasant View Lane, Chester, VT 05143	0.19	$569,000	3	2	2,966	Recently Sold
397 River Street, Chester, VT 05143	0.23	$275,000	4	3	3,332	Recently Sold
233 Dodge Road, Chester, VT 05143	0.21	$870,100	6	4.5	4,532	Off Market
50 Grafton Street, Chester, VT 05143	0.26	$409,700	4	3	2,351	Off Market
81 Main Street, Chester, VT 05143	0.28	$445,000	5	4	3,865	For Sale
17 Grafton Street, Chester, VT 05143	0.30	-	3	2	1,824	Off Market
117 South Main Street, Chester, VT 05143	0.35	$349,100	4	3	2,008	Off Market
35 Depot Street, Chester, VT 05143	0.35	-	-	-	-	Off Market
244 Main Street, Chester, VT 05143	0.36	$641,400	7	8	4,475	Off Market
246 Putnam Hill Road, Chester, VT 05143	0.38	$550,000	3	3.5	2,256	Recently Sold
423 Main Street, Chester, VT 05143	0.43	$425,000	6	5	3,217	Recently Sold

Local Information

Map ViewExplore the area around 159 High.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Living Area

2,000 sqft

Price/Sqft

$156

About this House

This single-family home is located at 159 High, Chester, VT. 159 High is in Chester, VT and in ZIP code 05143. This property has 3 bedrooms, 2 bathrooms and approximately 2,000 sqft of floor space.

159 High, Chester, VT 05143 is a 3 bedroom, 2 bathroom, 2,000 sqft single-family home. It last sold for $92,000 on Dec 16, 2016. It is currently off market. The Trulia Estimate is $312,400, with a rent estimate of $2,817/month.

Home Details for 159 High

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

Price and Tax history

Date	Event	Price
Dec 16, 2016 Source: N/A	Sold	$92,000

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.

What Locals Say about Chester

At least 4 Trulia users voted on each feature.

80 % Say car is needed
80 % Say it's quiet
80 % Say it's dog friendly
75 % Say parking is easy
75 % Say they plan to stay for at least 5 years
67 % Say streets are well-lit
63 % Say kids play outside
57 % Say yards are well-kept
50 % Say it's walkable to restaurants
50 % Say there are sidewalks
48 % Say neighbors are friendly
40 % Say people would walk alone at night
40 % Say there's wildlife
40 % Say there's holiday spirit
17 % Say there are community events

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 159 High

What is 159 High estimated to be worth?
Trulia's estimated value for 159 High in Chester, VT is $312,400.
What is the price history for 159 High?
159 High in Chester, VT last sold for $92,000 in December 2016.
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 159 High?
The closest schools to 159 High in Chester, VT are Chester-Andover Usd #29 (Pre-K/Elementary, rated 6/10), Green Mountain Uhsd #35 (Middle/High, rated 7/10).

Apartments for Rent

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$1,450/mo
1 bd
1 ba
41 Coach Rd #6,
Chester, VT 05143
$1,175/mo
1 bd
1 ba
617 Depot St #4,
Chester, VT 05143
APPLY INSTANTLY
$1,550/mo
1 bd
1 ba
9 River St #B,
Chester, VT 05143
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Chester
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Off Market Homes Near 159 High

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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
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Homes for sale near 159 High

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0.44 ACRES
$445,000
5 bd
4 ba
3,865 sqft
81 Main Street,
Chester, VT 05143
PrimeMLS, Active
0.33 ACRES
$479,000
3 bd
2 ba
1,626 sqft
3208 Green Mountain Turnpike,
Chester, VT 05143
PrimeMLS, Active
11.24 ACRES
$789,000
5 bd
3 ba
4,388 sqft
223 Coach Road,
Chester, VT 05143
PrimeMLS, Active
FOR SALE BY OWNER
0.28 ACRES
$575,000
3 bd
2 ba
1,998 sqft
296 North St,
Chester, VT 05143
7.8 ACRES
$1,200,000
4 bd
3 ba
3,308 sqft
76 Goldthwaite Road,
Chester, VT 05143
PrimeMLS, Active
14.1 ACRES
$900,000
5 bd
2.5 ba
2,800 sqft
1470 Popple Dungeon Road,
Chester, VT 05143
PrimeMLS, Active
18 ACRES
$1,490,000
5 bd
5 ba
5,400 sqft
1302 Popple Dungeon Road,
Chester, VT 05143
PrimeMLS, Active
NEW CONSTRUCTION
1.5 ACRES
$399,000
4 bd
2.5 ba
2,148 sqft
40 Fenton Road,
Chester, VT 05143
PrimeMLS, Active
7.5 ACRES
$475,000
3 bd
3 ba
2,680 sqft
175 Pleasant Valley Road,
Springfield, VT 05156
PrimeMLS, Active
See more homes for sale in
Chester
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159 High
Chester, VT 05143

$312,400

$312,400