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

OFF MARKET

159 High St
Chester, VT 05143

Studio

$319,000

Trulia Estimate

as of Aug 7, 2026

Est. Refi. Payment $2,256/mo*

Refinance Your Home

$319,000

Trulia Estimate

as of Aug 7, 2026

Est. Refi. Payment $2,256/mo*

Refinance Your Home

Studio

(on 4 acres)

Local Information

Map ViewExplore the area around 159 High 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

4 acres

About this House

This single-family home is located at 159 High St, Chester, VT. 159 High St is in Chester, VT and in ZIP code 05143. This property has a lot size of 4.00 acres.

159 High St, Chester, VT 05143 is a studio single-family home. It is currently off market. The Trulia Estimate is $319,000, with a rent estimate of $2,938/month.

Home Details for 159 High St

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

Lot Information
Lot Area: 4.00 acres

Market trends in Chester

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

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Property Tax and Assessment

Year	2024
Tax
Assessment	$145,900

Home facts updated by county records

Comparable Sales for 159 High St

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
246 Putnam Hill Road, Chester, VT	0.39	Single-Family Home	$550,000	11/17/25	3	3.5	2,256
18 S Main St, Chester, VT	0.30	Single-Family Home	$85,000	03/30/26		-	-
472 Main Street, Chester, VT	0.49	Single-Family Home	$475,000	08/27/25	5	5.5	5,546
514 First Avenue, Chester, VT	0.92	Single-Family Home	$515,000	06/02/26	5	5	3,880
95 Church Street, Chester, VT	0.51	Single-Family Home	$563,000	04/13/26	4	3	2,794
531 Main Street, Chester, VT	0.50	Single-Family Home	$359,000	05/15/26	3	1	1,608
656 Main Street, Chester, VT	0.62	Single-Family Home	$605,000	10/02/25	3	2.5	3,040
87 Kevadus Circle, Chester, VT	0.69	Single-Family Home	$229,000	08/29/25	3	1	840
230 Kevadus Circle, Chester, VT	0.63	Single-Family Home	$275,000	09/10/25	3	1	894

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $309,200
4 bd
1.5 ba
1,380 sqft
18 Mill Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
JUN 17, 2026
$569,000
3 bd
2 ba
2,966 sqft
147 Pleasant View Lane,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $865,000
6 bd
4.5 ba
4,532 sqft
233 Dodge Road,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $427,000
4 bd
3 ba
2,351 sqft
50 Grafton Street,
Chester, VT 05143
PrimeMLS, Closed
FOR SALE
3D VIEW
0.44 ACRES
$450,000
5 bd
4 ba
3,865 sqft
81 Main Street,
Chester, VT 05143
PrimeMLS, Active
OFF MARKET
Est. $298,300
3 bd
2 ba
1,824 sqft
17 Grafton Street,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $344,500
4 bd
3 ba
2,008 sqft
117 South Main Street,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
35 Depot Street,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $655,600
7 bd
8 ba
4,475 sqft
244 Main Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
NOV 17, 2025
$550,000
3 bd
3.5 ba
2,256 sqft
246 Putnam Hill Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
DEC 18, 2025
$425,000
6 bd
5 ba
3,217 sqft
423 Main Street,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $355,800
4 bd
2 ba
2,220 sqft
489 Main Street,
Chester, VT 05143
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 159 High St.

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

Apartments for Rent

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$1,450/mo
1 bd
1 ba
41 Coach Rd #6,
Chester, VT 05143
$1,275/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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Homes for sale near 159 High St

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0.44 ACRES
$450,000
5 bd
4 ba
3,865 sqft
81 Main Street,
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
0.27 ACRES
$419,900
5 bd
2 ba
1,982 sqft
176 Meadow Road,
Chester, VT 05143
PrimeMLS, Active
FOR SALE BY OWNER
0.28 ACRES
$600,000
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
3.3 ACRES
$299,000
3 bd
2 ba
1,788 sqft
1397 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
14.1 ACRES
$925,000
5 bd
2.5 ba
2,800 sqft
1470 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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Off Market Homes Near 159 High St

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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
SOLD
APR 10, 2026
$205,000
3 bd
1 ba
1,232 sqft
1876 Popple Dungeon Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
MAR 24, 2026
$186,800
3 bd
1.5 ba
1,260 sqft
252 Lacross Rd,
Springfield, VT 05156
See more homes for sale in
Chester
Take a look

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159 High St
Chester, VT 05143

$319,000

$319,000