Chester-Chester Depot, Chester Real Estate & Homes For Sale

7 homes

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NEW
OPEN SAT, 11-1PM
2 ACRES
$349,000
4 Beds
3 Baths
3,332 sqft
397 River Street,
Chester, VT 05143
PrimeMLS, Active
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3D VIEW
2 ACRES
$479,000
4 Beds
3 Baths
2,676 sqft
64 Maple Street,
Chester, VT 05143
PrimeMLS, Active
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1 ACRE
$390,000
3 Beds
2 Baths
1,304 sqft
663 Depot Street,
Chester, VT 05143
PrimeMLS, Active
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12.51 ACRES
$175,000
377 Coach Road Lot #15,
Chester, VT 05143
PrimeMLS, Active
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3D VIEW
0.5 ACRES
$299,000
Studio
2,702 sqft
41 VT Route 103 South,
Chester, VT 05143
PrimeMLS, Active
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0.25 ACRES
$329,000
3 Beds
2 Baths
1,488 sqft
447 Elm Street,
Chester, VT 05143
PrimeMLS, Active
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$225,000
3 Beds
1 Bath
1,327 sqft
160 Depot Street,
Chester, VT 05143
PrimeMLS, Active

Real Estate & Homes For Sale Near Chester-Chester Depot, Chester, VT

We found 9 more homes matching your filters just outside Chester-Chester Depot

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NEW - 14 HRS AGO
7.8 ACRES
$1,200,000
4 Beds
3 Baths
3,308 sqft
76 Goldthwaite Road,
Chester, VT 05143
PrimeMLS, Active
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18 ACRES
$1,690,000
5 Beds
5 Baths
5,400 sqft
1302 Popple Dungeon Road,
Chester, VT 05143
PrimeMLS, Active
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3.08 ACRES
$595,000
3 Beds
2 Baths
2,966 sqft
147 Pleasant View Lane,
Chester, VT 05143
PrimeMLS, Active
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7.95 ACRES
$129,000
0 Green Mountain Turnpike #5,
Chester, VT 05143
PrimeMLS, Active
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16.24 ACRES
$74,500
TBD Farrar Road,
Chester, VT 05143
PrimeMLS, Active
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3.3 ACRES
$349,000
3 Beds
2 Baths
1,788 sqft
1397 Popple Dungeon Road,
Chester, VT 05143
PrimeMLS, Active
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15.5 ACRES
$74,000
00 Remington Road,
Chester, VT 05143
PrimeMLS, Active
75 ACRES
$290,000
1175 Quarry Road,
Chester, VT 05143
PrimeMLS, Active
27.8 ACRES
$229,000
00 Quarry Road,
Chester, VT 05143
PrimeMLS, Active

Chester-Chester Depot, Chester, VT Real Estate Trends

Learn about the Chester-Chester Depot, Chester, VT housing market through trends and averages.

Affordability
What Locals Say

Affordability of Living in Chester-Chester Depot, Chester, VT

The median home value is $316,989

Month	Median home value
May 2025	$314k
June 2025	$316k
July 2025	$317k
August 2025	$318k
September 2025	$319k
October 2025	$319k
November 2025	$318k
December 2025	$316k
January 2026	$314k
February 2026	$316k
March 2026	$317k
April 2026	$317k

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Trends and affordability stats are provided by third party data sources.

Explore the Neighborhood

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Proctorsville
6 Homes For You
Buy: $120k - $599k
See Proctorsville homes
North Westminster
1 Home For You
Buy: $389k
See North Westminster homes
South Londonderry
1 Home For You
Buy: $1.8m
See South Londonderry homes
Harmonyville
1 Home For You
Buy: $285k
See Harmonyville homes
South Woodstock
1 Home For You
Buy: $2.95m
See South Woodstock homes
East Dorset
4 Homes For You
Buy: $150k - $565k
See East Dorset homes
West Dummerston
No homes for you
Buy: No For Sale Data
See West Dummerston homes
Manchester Center
27 Homes For You
Buy: $179k - $2.88m
See Manchester Center homes
West Woodstock
7 Homes For You
Buy: $75k - $817k
See West Woodstock homes
Quechee
9 Homes For You
Buy: $136k - $1.63m
See Quechee homes

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Neighborhood stats provided by third party data sources.

What Locals Say about Chester-Chester Depot

Kimberlee B.
Resident
6y ago
Chester-Chester Depot, Chester
"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
6y ago
Chester-Chester Depot, Chester
"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-Chester Depot, Chester
"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."
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Kz
15y ago
Chester-Chester Depot, Chester
"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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Learn more about Chester-Chester Depot

See information on schools, amenities and more.See Chester-Chester Depot Insights

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 2026-05-11 14:19:54 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.