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

27 Cross Rd
Chester, VT 05143

Studio

$277,200

Trulia Estimate

as of Aug 5, 2026

Est. Refi. Payment $1,975/mo*

Refinance Your Home

$277,200

Trulia Estimate

as of Aug 5, 2026

Est. Refi. Payment $1,975/mo*

Refinance Your Home

Studio

(on 0.25 acres)

Local Information

Map ViewExplore the area around 27 Cross Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Lot Size

0.25 acres

About this House

This single-family home is located at 27 Cross Rd, Chester, VT. 27 Cross Rd is in Chester, VT and in ZIP code 05143. This property has a lot size of 10890 sqft.

27 Cross Rd, Chester, VT 05143 is a studio single-family home. It last sold for $200,000 on Sep 13, 2021. It is currently off market. The Trulia Estimate is $277,200, with a rent estimate of $2,375/month.

Home Details for 27 Cross Rd

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

Lot Information
Lot Area: 10890 sqft

Price History for 27 Cross Rd

Date	Price	Event	Source
09/13/2021	$200,000	Sold	PrimeMLS #4869489
Recording Date 09/13/2021 County Transfer Tax N/A Total Transfer Tax N/A
04/05/2005	$103,000	Sold	N/A
Recording Date 04/05/2005 Contract Date 04/01/2005 County Transfer Tax N/A Total Transfer Tax $538
08/14/2001	$67,000	Sold	N/A
Recording Date 08/14/2001 Contract Date 08/10/2001 County Transfer Tax N/A Total Transfer Tax $335
03/01/2000	$67,500	Sold	N/A
Recording Date 03/01/2000 Contract Date 02/29/2000 County Transfer Tax N/A Total Transfer Tax $338

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	$128,900

Home facts updated by county records

Comparable Sales for 27 Cross Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
442 State Route 103 S, Chester, VT	0.03	Single-Family Home	$220,000	11/10/25	2	1	1,088
442 103 S, Chester, VT	0.03	Single-Family Home	$220,000	11/07/25	3	1	1,024
202 Mountain View, Chester, VT	0.06	Single-Family Home	$250,000	06/30/26	3	1.5	1,140
15 Breezy Lane, Chester, VT	0.06	Single-Family Home	$239,000	06/01/26	2	1	1,026
230 Kevadus Circle, Chester, VT	0.27	Single-Family Home	$275,000	09/10/25	3	1	894
62 Circle Drive, Chester, VT	0.08	Single-Family Home	$389,000	09/22/25	3	2	1,196
87 Kevadus Circle, Chester, VT	0.19	Single-Family Home	$229,000	08/29/25	3	1	840
1937 Green Mountain Turnpike, Chester, VT	0.44	Single-Family Home	$550,000	10/06/25	2	2	1,812
18 S Main St, Chester, VT	0.75	Single-Family Home	$85,000	03/30/26		-	-
246 Putnam Hill Road, Chester, VT	0.55	Single-Family Home	$550,000	11/17/25	3	3.5	2,256

Nearby homes

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

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SOLD
NOV 7, 2025
$220,000
3 bd
1 ba
1,024 sqft
442 103 S,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $368,600
3 bd
2 ba
1,196 sqft
62 Circle Drive,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $260,200
3 bd
1 ba
966 sqft
186 Mountain View,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $273,800
3 bd
1 ba
960 sqft
468 VT Route 103 S,
Chester, VT 05143
PrimeMLS, Closed
SOLD
JUN 30, 2026
$250,000
3 bd
1.5 ba
1,140 sqft
202 Mountain View,
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
OFF MARKET
Est. $237,500
3 bd
1 ba
840 sqft
87 Kevadus Circle,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $284,900
3 bd
1 ba
894 sqft
230 Kevadus Circle,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $296,800
3 bd
1 ba
1,227 sqft
192 Kevadus Circle,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $402,700
4 bd
2.5 ba
2,686 sqft
183 Pleasant Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
OCT 6, 2025
$550,000
2 bd
2 ba
1,812 sqft
1937 Green Mountain Turnpike,
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

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Additional Cost

Assigned Schools

These are the assigned schools for 27 Cross Rd.

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
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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
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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
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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."
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