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

FOR SALE

9 ACRES

Listed by Christine M Lewis, Brattleboro Area Realty, (802) 257-1335

106 Contro Road
Chester, VT 05143

2 Beds
2.5 Baths
1,475 sqft (on 9 acres)

$289,000

2 Beds

2.5 Baths

1,475 sqft

(on 9 acres)

Local Information

-- mins to

Commute Destination

Last check for updates: about 23 hours ago

Listing courtesy of Christine M Lewis

Brattleboro Area Realty, (802) 257-1335

Source: PrimeMLS, MLS#5069928

Also Listed on PrimeMLS.

Description

Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided from the parcel across the street and they may be purchased together. See MLS #5069927 This is a nice level to rolling lot with some open and some woods, has a 2 car garage, 2 enclosed porches and is well put together inside. The outside needs some finish work, so not likely to go a federal program. With some TLC this will be a fab get away. The town maintains the road to the house...such a benefit! This is a must see for location

Home Highlights

Parking

Garage

Outdoor

Porch

A/C

Heating only

HOA

None

Price/Sqft

$196

Listed

180+ days ago

Home Details for 106 Contro Road

Active Status
MLS Status: Active

Interior Features
Interior Details Basement: Concrete,Concrete Floor,Interior Stairs,Storage Space,Unfinished,Interior EntryNumber of Rooms: 4
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 3Number of Bathrooms (full): 1Number of Bathrooms (three quarters): 1Number of Bathrooms (half): 1
Dimensions and Layout Living Area: 1475 Square Feet
Appliances & Utilities Utilities: PropaneAppliances: Gas Range, Refrigerator, Propane Water Heater, Owned Water HeaterRefrigerator
Heating & Cooling Heating: Propane,Forced AirNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Propane
Gas & Electric Electric: Circuit Breakers
Windows, Doors, Floors & Walls Window: Double Pane WindowsFlooring: Carpet, Softwood
Levels, Entrance, & Accessibility Stories: 1.5Levels: One and One HalfFloors: Carpet, Softwood
View No View
Security Security: Carbon Monoxide Detector(s), Smoke Detector(s)

Exterior Features
Exterior Home Features Roof: MetalPatio / Porch: Enclosed PorchOther Structures: OutbuildingExterior: Building, Garden, Natural Shade, StorageFoundation: Concrete, Poured ConcreteGarden
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageParking Spaces: 2Parking: Dirt,Garage,Off Street,On Site,Unpaved,Detached
Frontage Road Frontage: Dead EndResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Gravel, Unpaved
Water & Sewer Sewer: On-Site Septic Exists
Farm & Range Frontage Length: Road frontage: 933
Finished Area Finished Area (above surface): 1475 Square Feet

Days on Market
Days on Market: 180+

Property Information
Year Built Year Built: 1985
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: Rehab NeededArchitecture: Rehab Needed
Building Construction Materials: Wood Frame, Clapboard ExteriorNot a New Construction

Price & Status
Price List Price: $289,000Price Per Sqft: $196

Location
Direction & Address City: Chester

Agent Information
Listing Agent Listing ID: 5069928

Building
Building Area Building Area: 1894 Square Feet

Lot Information
Lot Area: 9 Acres

Miscellaneous
BasementMls Number: 5069928Above Grade Unfinished Area: 1475Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 419Below Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

Market trends in Chester

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

5MoM

Price History for 106 Contro Road

Date	Price	Event	Source
11/18/2025	$289,000	Listed For Sale	PrimeMLS #5069928

03/25/2024	$180,000	Sold	N/A
Recording Date 03/25/2024 Contract Date 03/21/2024 County Transfer Tax N/A Total Transfer Tax $26

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Tax
Assessment	$224,700

Home facts updated by county records

Comparable Sales for 106 Contro Road

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
1269 Howard Hill Road, Andover, VT	1.66	Single-Family Home	$825,000	04/09/26	3	3	2,172
231 Richardson Road, Chester, VT	2.20	Single-Family Home	$360,000	10/28/25	3	1.5	1,304
1876 Popple Dungeon Road, Chester, VT	2.30	Single-Family Home	$205,000	04/10/26	3	1	1,232
938 Stigers Road, Andover, VT	1.57	Single-Family Home	$1,400,000	08/27/25	3	3.5	2,614
3091 Route 121, West Townshend, VT	2.30	Single-Family Home	$364,000	08/15/25	4	2	1,758
1342 Old Stage Road, Chester, VT	2.02	Single-Family Home	$805,000	01/13/26	2	2	1,576
2026 Stagecoach Road, Grafton, VT	2.13	Single-Family Home	$475,000	10/18/25	3	2.5	2,342
387 Weston Andover Road, Andover, VT	3.04	Single-Family Home	$399,000	07/31/25	3	2	1,402
332 Hidden Heights Road, Chester, VT	2.70	Single-Family Home	$421,833	07/10/25	4	2.5	2,868

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FOR SALE
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00 Contro Road,
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Additional Cost

Assigned Schools

These are the assigned schools for 106 Contro Road.

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
6y 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

Christine M Lewis, Brattleboro Area Realty, (802) 257-1335

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 2026-06-19 18:58:45 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.

106 Contro Road, Chester, VT 05143 is a 2 bedroom, 3 bathroom, 1,475 sqft single-family home built in 1985. This property is currently available for sale and was listed by PrimeMLS on Nov 18, 2025. The MLS # for this home is MLS# 5069928.

106 Contro Road
Chester, VT 05143

$289,000

$289,000

Local Information