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

76 Wolf Rd
Chester, VT 05143

3 Beds
4.5 Baths
4,166 sqft (on 20.35 acres)

$996,200

Trulia Estimate

as of Jul 22, 2026

$996,200

Trulia Estimate

as of Jul 22, 2026

3 Beds

4.5 Baths

4,166 sqft

(on 20.35 acres)

Local Information

Map ViewExplore the area around 76 Wolf Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

2005

Lot Size

20.35 acres

Living Area

4,166 sqft

Price/Sqft

$239

Parking

Garage

Description

This single-family home is located at 76 Wolf Rd, Chester, VT. 76 Wolf Rd is in Chester, VT and in ZIP code 05143. This property has 3 bedrooms, 5 bathrooms and approximately 4,166 sqft of floor space. This property has a lot size of 20.35 acres and was built in 2005.

76 Wolf Rd, Chester, VT 05143 is a 3 bedroom, 5 bathroom, 4,166 sqft single-family home built in 2005. It last sold for $725,000 on Aug 28, 2020. It is currently off market. The Trulia Estimate is $996,200, with a rent estimate of $5,013/month.

Home Details for 76 Wolf Rd

Interior Features
Heating & Cooling Heating: Baseboard, Electric, Gas, OilCooling System: OtherHeating Fuel: Baseboard
Interior Details Types of Rooms: Walk In Closet, Dining Room, Family Room, Pantry
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa Fireplace
Windows, Doors, Floors & Walls Double Paned Windows
Levels, Entrance, & Accessibility Floors: Tile, Carpet, Hardwood

Exterior Features
Exterior Home Features Roof: MetalDeckExterior: WoodGardenPatioPorch
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached

Property Information
Year Built Year Built: 2005
Property Type / Style Property Type: Single Family HomeArchitecture: Contemporary

Lot Information
Lot Area: 20.35 acres

Price History for 76 Wolf Rd

Date	Price	Event	Source
08/28/2020	$725,000	Sold	PrimeMLS #4809852
Recording Date 08/28/2020 County Transfer Tax N/A Total Transfer Tax N/A
06/09/2020	$725,000	Listed For Sale	Agent Provided

04/02/2019	$697,000	ListingRemoved	Agent Provided

08/30/2018	$697,000	PriceChange	Agent Provided
Price Change $102,000 (-13%)
07/30/2018	$799,000	Listed For Sale	Agent Provided

02/02/2005	$112,000	Sold	N/A
Recording Date 02/02/2005 Contract Date 01/31/2005 County Transfer Tax N/A Total Transfer Tax $650

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	$509,600

Home facts updated by county records

Comparable Sales for 76 Wolf Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
187 Lacross Road, Springfield, VT	0.84	Single-Family Home	$399,000	03/10/26	3	2	1,789
870 Cummings Road, Chester, VT	0.77	Single-Family Home	$320,000	12/18/25	3	1.5	1,525
725 Flamstead Road, Chester, VT	1.47	Single-Family Home	$800,000	12/12/25	4	3.5	2,775
372 Lacross Rd, Springfield, VT	1.22	Single-Family Home	$470,000	09/22/25	4	3	2,900
2739 Route 11, Chester, VT	0.38	Single-Family Home	$230,000	11/07/25	1	1	1,424
1573 Flamstead Road, Chester, VT	1.37	Single-Family Home	$560,000	11/25/25	4	3	2,689
88 Pleasant Valley Road, Springfield, VT	0.91	Single-Family Home	$359,000	07/25/25	3	2	1,550
514 First Avenue, Chester, VT	1.74	Single-Family Home	$515,000	06/02/26	5	5	3,880
252 Lacross Rd, Springfield, VT	0.97	Single-Family Home	$186,800	03/24/26	3	1.5	1,260
106 Hall Road, Chester, VT	0.71	Single-Family Home	$210,000	11/20/25	1	1	528

Nearby homes

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

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OFF MARKET
Est. $350,700
3 bd
1 ba
1,500 sqft
154 Fletcher Hill Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
NOV 7, 2025
$230,000
1 bd
1 ba
1,424 sqft
2739 Route 11,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $418,600
3 bd
1.5 ba
1,800 sqft
3057 VT Route 11 East,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Hall Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
NOV 20, 2025
$210,000
1 bd
1 ba
528 sqft
106 Hall Road,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Lot 8 Jillie Lane,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Lot 6 Jillie Lane,
Chester, VT 05143
PrimeMLS, Closed
SOLD
DEC 18, 2025
$320,000
3 bd
1.5 ba
1,525 sqft
870 Cummings Road,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $331,400
3 bd
1.5 ba
2,288 sqft
9 Pleasant Valley Road,
Springfield, VT 05156
PrimeMLS, Closed
OFF MARKET
Lot 2 Jillie Lane,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
1369 Vt Route 11 E Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
MAR 10, 2026
$399,000
3 bd
2 ba
1,789 sqft
187 Lacross Road,
Springfield, VT 05156
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 76 Wolf 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
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
Contact for price
1-2 bd
1-2 ba
105 Chester Rd #776f18ccb,
Springfield, VT 05156
$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
See more homes for rent in
Chester
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Homes for sale near 76 Wolf Rd

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7.5 ACRES
$475,000
3 bd
3 ba
2,680 sqft
175 Pleasant Valley Road,
Springfield, VT 05156
PrimeMLS, Active
11.24 ACRES
$849,000
5 bd
3 ba
4,388 sqft
223 Coach Road,
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
NEW - 1 DAY AGO
$175,000
3 bd
1.5 ba
1,379 sqft
641 Depot Street,
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
0.44 ACRES
$450,000
5 bd
4 ba
3,865 sqft
81 Main Street,
Chester, VT 05143
PrimeMLS, Active
48.94 ACRES
$695,000
4 bd
2 ba
4,144 sqft
1607 Massey Road,
Springfield, VT 05156
PrimeMLS, Active
3 ACRES
$199,900
3 bd
2 ba
1,767 sqft
165 Dutton Farm Road,
Springfield, VT 05156
PrimeMLS, Active
17 ACRES
$465,000
3 bd
2 ba
1,939 sqft
105 Craigue Hill,
Springfield, VT 05156
PrimeMLS, Active
See more homes for sale in
Chester
Take a look

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Off Market Homes Near 76 Wolf Rd

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SOLD
JUN 17, 2026
$569,000
3 bd
2 ba
2,966 sqft
147 Pleasant View Lane,
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
APR 13, 2026
$563,000
4 bd
3 ba
2,794 sqft
95 Church Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
APR 2, 2026
$550,000
3,850 sqft
534 Elm Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
FEB 13, 2026
$815,000
3 bd
2.5 ba
2,466 sqft
810 Quarry Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
FEB 2, 2026
$640,000
389 Cummings Rd,
Chester, VT 05143
SOLD
JAN 22, 2026
$549,000
3 bd
1.5 ba
1,848 sqft
197 Baker Road,
Springfield, VT 05156
PrimeMLS, Closed
SOLD
DEC 19, 2025
$600,000
9 ba
9,740 sqft
2 Valley Street,
Springfield, VT 05156
PrimeMLS, Closed
SOLD
DEC 12, 2025
$800,000
4 bd
3.5 ba
2,775 sqft
725 Flamstead Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
NOV 25, 2025
$560,000
4 bd
3 ba
2,689 sqft
1573 Flamstead Road,
Chester, VT 05143
PrimeMLS, Closed
See more homes for sale in
Chester
Take a look

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76 Wolf Rd
Chester, VT 05143

$996,200

$996,200