Chester, VT Real Estate & Homes For Sale

Name: 3D View Available - 250 Fenton Road, Chester, VT 05143
Start: 2026-06-12
End: 2026-06-12

31 homes

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NEW - 23 HRS AGO
10.4 ACRES
$87,500
00 Snell Road,
Chester, VT 05143
PrimeMLS, Active
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NEW - 2 DAYS AGO
5 ACRES
$85,000
0 Linden Way,
Chester, VT 05143
PrimeMLS, Active
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0.6 ACRES
$75,000
2 Beds
1 Bath
620 sqft
1144 Potash Brook Road,
Chester, VT 05143
PrimeMLS, Active
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3D VIEW
4.7 ACRES
$153,000
250 Fenton Road,
Chester, VT 05143
PrimeMLS, Active
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3D VIEW
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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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
18 ACRES
$1,490,000
5 Beds
5 Baths
5,400 sqft
1302 Popple Dungeon Road,
Chester, VT 05143
PrimeMLS, Active
3D VIEW
2 ACRES
$479,000
3 Beds
3 Baths
2,676 sqft
64 Maple Street,
Chester, VT 05143
PrimeMLS, Active
1 ACRE
$390,000
3 Beds
2 Baths
1,304 sqft
663 Depot Street,
Chester, VT 05143
PrimeMLS, Active
1 ACRE
$169,000
1 Bed
1 Bath
200 sqft
3019 Popple Dungeon Road,
Chester, VT 05143
PrimeMLS, Active
$425,000
5 Beds
2 Baths
1,982 sqft
176 Meadow Rd,
Chester, VT 05143
Stratton Home
3.24 ACRES
$120,000
508 Mattson Road,
Chester, VT 05143
PrimeMLS, Active
7.95 ACRES
$129,000
0 Green Mountain Turnpike #5,
Chester, VT 05143
PrimeMLS, Active
12.51 ACRES
$175,000
377 Coach Road Lot #15,
Chester, VT 05143
PrimeMLS, Active
16.24 ACRES
$74,500
TBD Farrar Road,
Chester, VT 05143
PrimeMLS, Active
1.71 ACRES
$649,000
3 Beds
2 Baths
2,205 sqft
688 Hidden Heights Road,
Chester, VT 05143
PrimeMLS, Active
3.3 ACRES
$349,000
3 Beds
2 Baths
1,788 sqft
1397 Popple Dungeon Road,
Chester, VT 05143
PrimeMLS, Active
NEW CONSTRUCTION
1.5 ACRES
$399,000
4 Beds
2.5 Baths
2,148 sqft
40 Fenton Road,
Chester, VT 05143
PrimeMLS, Active
3D VIEW
0.5 ACRES
$295,000
Studio
2,702 sqft
41 VT Route 103 South,
Chester, VT 05143
PrimeMLS, Active
9 ACRES
$289,000
2 Beds
2.5 Baths
1,475 sqft
106 Contro Road,
Chester, VT 05143
PrimeMLS, Active
5 ACRES
$159,000
00 Contro Road,
Chester, VT 05143
PrimeMLS, Active
15.5 ACRES
$74,000
00 Remington Road,
Chester, VT 05143
PrimeMLS, Active
0.25 ACRES
$299,000
3 Beds
2 Baths
1,488 sqft
447 Elm Street,
Chester, VT 05143
PrimeMLS, Active
75 ACRES
$290,000
1175 Quarry Road,
Chester, VT 05143
PrimeMLS, Active
3D VIEW
6.63 ACRES
$200,000
00 Vermont Route 103,
Chester, VT 05143
PrimeMLS, Active
3D VIEW
3.35 ACRES
$115,000
00 VT Route 103 N Lot 4,
Chester, VT 05143
PrimeMLS, Active
3.28 ACRES
$115,000
00 VT Route 103 N Lot 3,
Chester, VT 05143
PrimeMLS, Active
$225,000
3 Beds
1 Bath
1,327 sqft
160 Depot Street,
Chester, VT 05143
PrimeMLS, Active
2 ACRES
$650,000
3 Beds
3 Baths
4,324 sqft
3630 Vt Route 103 N,
Chester, VT 05143
PrimeMLS, Active
84 ACRES
$249,000
000 Green Mountain Turnpike,
Chester, VT 05143
PrimeMLS, Active
27.8 ACRES
$229,000
00 Quarry Road,
Chester, VT 05143
PrimeMLS, Active

Real Estate & Homes For Sale Near Chester, VT

We found 15 more homes matching your filters just outside Chester

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NEW - 2 MIN AGO
3.99 ACRES
$85,000
00 Simonsville Road,
Chester, VT 05143
PrimeMLS, Active
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3D VIEW
10.55 ACRES
$525,000
4 Beds
2 Baths
2,232 sqft
133 Baltimore Road,
North Springfield, VT 05150
PrimeMLS, Active
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1.2 ACRES
$550,000
2 Beds
2 Baths
1,740 sqft
1043 Town Farm Road,
Ludlow, VT 05149
PrimeMLS, Active
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3.99 ACRES
$85,000
Simonsville Rd #3,
Chester, VT 05143
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51.2 ACRES
$375,000
3 Beds
2 Baths
1,352 sqft
847 Simonsville Road,
Andover, VT 05143
PrimeMLS, Active
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7.5 ACRES
$499,500
3 Beds
3 Baths
2,680 sqft
175 Pleasant Valley Road,
Springfield, VT 05156
PrimeMLS, Active
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10 ACRES
$675,000
4 Beds
2.5 Baths
2,600 sqft
518 Baltimore Road,
Baltimore, VT 05143
PrimeMLS, Active
4.97 ACRES
$279,000
5 Beds
3 Baths
1,812 sqft
2100 Baltimore Road,
Baltimore, VT 05143
PrimeMLS, Active
2.5 ACRES
$235,000
3 Beds
1 Bath
980 sqft
64 County Road,
North Springfield, VT 05150
PrimeMLS, Active
3D VIEW
10.01 ACRES
$274,500
713 South Hill Road,
Ludlow, VT 05149
PrimeMLS, Active
2 ACRES
$549,000
2 Beds
2 Baths
2,016 sqft
35 Upper Bartonsville Road,
Chester, VT 05143
PrimeMLS, Active
9.55 ACRES
$800,000
7 Beds
4.5 Baths
4,733 sqft
107-109 Baker Road,
Springfield, VT 05156
PrimeMLS, Active
0.5 ACRES
$249,000
8 Beds
4 Baths
3,312 sqft
715-717 Giddings Street,
North Springfield, VT 05150
PrimeMLS, Active
2.53 ACRES
$79,000
Lot #4 Meadow Road,
Ludlow, VT 05149
PrimeMLS, Active
3D VIEW
23.4 ACRES
$150,000
4125 Chester Road,
Grafton, VT 05146
PrimeMLS, Active

1 More Home

We found 1 more home that matches your search in other listings.

Chester, VT Real Estate Trends

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

Affordability
What Locals Say

Affordability of Living in Chester, VT

The median home value is $358,938

Month	Median home value
June 2025	$360k
July 2025	$360k
August 2025	$359k
September 2025	$359k
October 2025	$359k
November 2025	$358k
December 2025	$356k
January 2026	$356k
February 2026	$357k
March 2026	$358k
April 2026	$358k
May 2026	$359k

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

Explore Neighborhoods in Chester, VT

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Chester-Chester Depot
8 Homes For You
Buy: $175k - $479k
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Neighborhood stats provided by third party data sources.

What Locals Say about Chester

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
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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
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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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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 2026-06-12 10:04:39 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.

Chester, VT Real Estate & Homes For Sale

31 homes

We found 15 more homes matching your filters just outside Chester

Chester, VT Real Estate Trends

Affordability of Living in Chester, VT

Explore Neighborhoods in Chester, VT

What Locals Say about Chester

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