Is Chester-Chester Depot, Chester, VT dog-friendly?

As of early 2026, 100% of users say it's dog friendly

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

As of early 2026, 100% of users say they plan to stay for at least 5 years

Is Chester-Chester Depot, Chester, VT walkable to restaurants?

As of early 2026, 100% of users say it's walkable to restaurants

Is a car needed in Chester-Chester Depot, Chester, VT?

As of early 2026, 100% of users say car is needed

Does Chester-Chester Depot, Chester, VT have sidewalks?

As of early 2026, 100% of users say there are sidewalks

Are the streets well-lit in Chester-Chester Depot, Chester, VT?

As of early 2026, 100% of users say streets are well-lit

Do kids play outside in Chester-Chester Depot, Chester, VT?

As of early 2026, 100% of users say kids play outside

Are yards well-kept in Chester-Chester Depot, Chester, VT?

As of early 2026, 67% of users say yards are well-kept

Is Chester-Chester Depot, Chester, VT quiet?

As of early 2026, 67% of users say it's quiet

Are neighbors friendly in Chester-Chester Depot, Chester, VT?

As of early 2026, 57% of users say neighbors are friendly

Is parking easy in Chester-Chester Depot, Chester, VT?

As of early 2026, 50% of users say parking is easy

Are there community events in Chester-Chester Depot, Chester, VT?

As of early 2026, 50% of users say there are community events

Would people walk alone at night in Chester-Chester Depot, Chester, VT?

As of early 2026, 50% of users say people would walk alone at night

OFF MARKET

558 Main St
Chester, VT 05143

Chester-Chester Depot

4 Beds
2 Baths
2,002 sqft

$439,700

Trulia Estimate

as of Jul 29, 2026

$439,700

Trulia Estimate

as of Jul 29, 2026

4 Beds

2 Baths

2,002 sqft

Local Information

Map ViewExplore the area around 558 Main St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1820

Living Area

2,002 sqft

Price/Sqft

$220

Parking

Garage

About this House

Lovely renovated four bedroom, two bath Chester Village home on .19 acres+/-. The charming interior has a spacious kitchen with a center island and walk-in pantry with built-ins, first floor full bath, spacious living/dining room, informal area and an office/study - perfect for working remotely from home. There is a wonderful rustic den/living area with woodstove in the back of the house that leads to the delightful rear deck and garden area as well as a handy attached storage garage. The second floor has three bedrooms in the front of the house, a spacious common area, and a private master bedroom suite with full bath and laundry area. Enjoy this wonderful location, where you can walk to the shops/restaurants, events on the Village Green and the Town Recreation Area. Close to ski resorts. 2021-07-14

558 Main St, Chester, VT 05143 is a 4 bedroom, 2 bathroom, 2,002 sqft single-family home in Chester-Chester Depot, built in 1820. It last sold for $322,000 on Aug 24, 2021. It is currently off market. The Trulia Estimate is $439,700, with a rent estimate of $2,629/month.

Home Details for 558 Main St

Interior Features
Heating & Cooling Heating: Stove, OilHeating Fuel: Stove
Interior Details Types of Rooms: Dining Room, Family Room, Office
Appliances & Utilities DishwasherDryerRefrigerator
Levels, Entrance, & Accessibility Floors: Hardwood

Exterior Features
Exterior Home Features Roof: SlateExterior: Wood
Parking & Garage GarageParking Space: 1Parking: Garage Attached

Property Information
Year Built Year Built: 1820
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 8276 sqft

Price History for 558 Main St

Date	Price	Event	Source
08/24/2021	$322,000	Sold	PrimeMLS #4870838
Recording Date 08/24/2021 County Transfer Tax N/A Total Transfer Tax N/A
07/14/2021	$299,000	Pending	Engel & Volkers #4870838

07/14/2021	$299,000	Contingent	PrimeMLS #4870838

07/07/2021	$299,000	Listed For Sale	PrimeMLS #4870838

07/28/2017	$238,500	Sold	PrimeMLS #4624668
Recording Date 07/28/2017 County Transfer Tax N/A Total Transfer Tax N/A
05/31/2017	$257,000	Pending	Agent Provided

03/31/2017	$257,000	Listed For Sale	Agent Provided

10/17/2016	$269,000	ListingRemoved	Agent Provided

10/21/2015	$269,000	Listed For Sale	Agent Provided

10/18/2005	$272,000	Sold	N/A
Recording Date 10/18/2005 Contract Date 10/14/2005 County Transfer Tax N/A Total Transfer Tax $2,650
09/26/2003	$227,000	Sold	N/A
Recording Date 09/26/2003 Contract Date 09/26/2003 County Transfer Tax N/A Total Transfer Tax $2,088
08/27/2001	$94,000	Sold	N/A
Recording Date 08/27/2001 Contract Date 08/23/2001 County Transfer Tax N/A Total Transfer Tax $470
10/30/1998	$85,900	Sold	N/A
Recording Date 10/30/1998 Contract Date 10/29/1998 County Transfer Tax N/A Total Transfer Tax $430

Market trends in Chester

Last updated June 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

1MoM

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Property Tax and Assessment

Year	2024
Tax
Assessment	$236,300

Home facts updated by county records

Comparable Sales for 558 Main St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
531 Main Street, Chester, VT	0.05	Single-Family Home	$359,000	05/15/26	3	1	1,608
95 Church Street, Chester, VT	0.15	Single-Family Home	$563,000	04/13/26	4	3	2,794
656 Main Street, Chester, VT	0.09	Single-Family Home	$605,000	10/02/25	3	2.5	3,040
115 Orcutt Drive, Chester, VT	0.08	Single-Family Home	$425,000	07/30/25	2	1	1,360
312 North St, Chester, VT	0.85	Single-Family Home	$375,000	09/02/25	5	1	2,090
472 Main Street, Chester, VT	0.09	Single-Family Home	$475,000	08/27/25	5	5.5	5,546
45 Dalrymple Street, Chester, VT	0.79	Single-Family Home	$269,000	06/15/26	3	1	1,168
147 Pleasant View Lane, Chester, VT	0.71	Single-Family Home	$569,000	06/17/26	3	2	2,966
230 Kevadus Circle, Chester, VT	1.12	Single-Family Home	$275,000	09/10/25	3	1	894
202 Mountain View, Chester, VT	1.39	Single-Family Home	$250,000	06/30/26	3	1.5	1,140

Nearby homes

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

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OFF MARKET
Est. $659,400
4 bd
3 ba
2,622 sqft
548 Main Street,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $438,100
2 bd
1 ba
1,360 sqft
115 Orcutt Drive,
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
OCT 23, 2025
$140,000
4 ba
3,024 sqft
515 Main Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
OCT 2, 2025
$605,000
3 bd
2.5 ba
3,040 sqft
656 Main Street,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $916,800
5 bd
5.5 ba
5,546 sqft
472 Main Street,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $353,700
4 bd
2 ba
2,220 sqft
489 Main Street,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $581,800
6 bd
3 ba
3,892 sqft
595 Main Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
APR 13, 2026
$563,000
4 bd
3 ba
2,794 sqft
95 Church Street,
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. $427,300
4 bd
2 ba
1,990 sqft
102 Church Street,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $566,200
3 bd
2 ba
1,856 sqft
405 Church Street,
Chester, VT 05143
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 558 Main 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.

Neighborhood Overview

Chester-Chester Depot

7 Homes For You
Buy: $100k - $789k

See Local Highlights

Neighborhood stats provided by third party data sources.

What Locals Say about Chester-Chester Depot

At least 2 Trulia users voted on each feature.

100 % Say it's dog friendly
100 % Say they plan to stay for at least 5 years
100 % Say it's walkable to restaurants
100 % Say car is needed
100 % Say there are sidewalks
100 % Say streets are well-lit
100 % Say kids play outside
67 % Say yards are well-kept
67 % Say it's quiet
57 % Say neighbors are friendly
50 % Say parking is easy
50 % Say there are community events
50 % Say people would walk alone at night

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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$1,275/mo
1 bd
1 ba
617 Depot St #4,
Chester, VT 05143
$1,650/mo
2 bd
1 ba
279 Pleasant St #B,
Chester, VT 05143
$1,400/mo
2 bd
1 ba
32 S Main St #7,
Chester, VT 05143
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Chester
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Homes for sale near 558 Main St

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FOR SALE BY OWNER
0.28 ACRES
$600,000
3 bd
2 ba
1,998 sqft
296 North St,
Chester, VT 05143
0.44 ACRES
$450,000
5 bd
4 ba
3,865 sqft
81 Main Street,
Chester, VT 05143
PrimeMLS, Active
0.33 ACRES
$489,000
3 bd
2 ba
1,626 sqft
3208 Green Mountain Turnpike,
Chester, VT 05143
PrimeMLS, Active
2 ACRES
$469,000
3 bd
3 ba
2,676 sqft
64 Maple 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
7.8 ACRES
$1,200,000
4 bd
3 ba
3,308 sqft
76 Goldthwaite Road,
Chester, VT 05143
PrimeMLS, Active
3.3 ACRES
$349,000
3 bd
2 ba
1,788 sqft
1397 Popple Dungeon Road,
Chester, VT 05143
PrimeMLS, Active
14.1 ACRES
$925,000
5 bd
2.5 ba
2,850 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
See more homes for sale in
Chester
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Off Market Homes Near 558 Main St

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SOLD
JUL 9, 2026
$460,000
3 bd
2 ba
1,320 sqft
547 Williams Road,
Chester, VT 05143
PrimeMLS, Closed
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 17, 2026
$569,000
3 bd
2 ba
2,966 sqft
147 Pleasant View Lane,
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 2, 2026
$515,000
5 bd
5 ba
3,880 sqft
514 First Avenue,
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
APR 20, 2026
$379,000
2 bd
2 ba
2,751 sqft
3466 VT Route 103 N,
Chester, VT 05143
PrimeMLS, Closed
SOLD
APR 13, 2026
$563,000
4 bd
3 ba
2,794 sqft
95 Church Street,
Chester, VT 05143
PrimeMLS, Closed
See more homes for sale in
Chester
Take a look

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558 Main St
Chester, VT 05143

$439,700

$439,700