Listed by Katie Ladue Gilbert, KW Vermont Woodstock, (802) 654-8500 . Bought with Southern Vermont Realty Group
$616,100
7 Beds
8 Baths
4,475 sqft (on 0.60 acres)
244 Main Street, Chester, VT 05143
Currently Off Market - Sold Sep 29, 2023 for $579,000
Home Value
Trulia Estimate
$616KSince last month
Decreased$12K (-1.9%)Since last year
Increased$5K (+0.9%)Since last sale
Increased$51K (+8.7%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +899% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $630K |
| August 2026 | $642K |
| July 2026 | $662K |
| June 2026 | $660K |
| May 2026 | $661K |
| April 2026 | $630K |
| March 2026 | $643K |
| February 2026 | $618K |
| January 2026 | $629K |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.20 | Single-Family Home | $563,000 | 04/13/26 | 4 | 3 | 2,794 | |
0.41 | Single-Family Home | $605,000 | 10/02/25 | 3 | 2.5 | 3,040 | |
0.64 | Single-Family Home | $515,000 | 06/02/26 | 5 | 5 | 3,880 | |
0.44 | Single-Family Home | $275,000 | 08/06/26 | 4 | 3 | 3,332 | |
0.28 | Single-Family Home | $359,000 | 05/15/26 | 3 | 1 | 1,608 | |
0.55 | Single-Family Home | $569,000 | 06/17/26 | 3 | 2 | 2,966 | |
0.67 | Single-Family Home | $550,000 | 11/17/25 | 3 | 3.5 | 2,256 | |
0.55 | Single-Family Home | $180,000 | 08/10/26 | 3 | 1.5 | 1,379 | |
0.80 | Single-Family Home | $269,000 | 06/15/26 | 3 | 1 | 1,168 | |
0.80 | Single-Family Home | $2,000,000 | 01/30/26 | 4 | 3.5 | 3,000 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.16 | $445,000 | 5 | 4 | 3,865 | For Sale | |
0.18 | $431,200 | 4 | 2 | 1,990 | Off Market | |
0.19 | $425,000 | 6 | 5 | 3,217 | Recently Sold | |
0.20 | $563,000 | 4 | 3 | 2,794 | Recently Sold | |
0.23 | $823,600 | 5 | 5.5 | 5,546 | Off Market | |
0.24 | $357,200 | 4 | 2 | 2,220 | Off Market | |
0.25 | $394,100 | 4 | 3 | 2,351 | Off Market | |
0.26 | $299,400 | 3 | 2 | 1,824 | Off Market | |
0.27 | - | - | - | - | Off Market | |
0.27 | $144,300 | Studio | 4 | 3,024 | Off Market | |
0.28 | $359,000 | 3 | 1 | 1,608 | Recently Sold |
Local Information
- Map ViewExplore the area around 244 Main Street.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Single-Family Home
Built in 1825
0.6 acre lot
4,475 sqft
$138/sqft
Garage
About this House
You can sometimes search a lifetime for a property like this, a home that has a story, a town that is known to be quintessential VT living, and one that you can operate as an Inn or Bed & Breakfast, or have a wonderful family compound. Seek no further than this 1800's historical Victorian. The main house has 6 bedrooms on the second floor each with it's own private bathroom. On the first floor you'll find a kitchen prime for your renovation ideas, a formal dining room, front living room and a den that's ideal for a home office with fiber optic internet. You will also find gorgeous hardwood floors, original interior oak trim and a grand stairway leading up to the second floor. There is also a 1 bedroom apartment upstairs above the barn area. The porch overlooks a gorgeous green and town setting with shopping and restaurants alike. Complete this package with a guest cottage that was just fully renovated. Being sold mostly furnished, this will not last through the Summer.
244 Main Street, Chester, VT 05143 is a 7 bedroom, 8 bathroom, 4,475 sqft single-family home in Chester-Chester Depot, built in 1825. It last sold for $579,000 on Sep 29, 2023 (3% below the $599,999 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $616,100, with a rent estimate of $3,630/month.
Home Details for 244 Main Street
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MLS Status: Closed |
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Interior Details Basement: Concrete,Concrete Floor,Full,Interior Stairs,Unfinished,Interior EntryNumber of Rooms: 15 |
Beds & Baths Number of Bedrooms: 7Number of Bathrooms: 8Number of Bathrooms (full): 1Number of Bathrooms (three quarters): 7 |
Dimensions and Layout Living Area: 4475 Square Feet |
Appliances & Utilities Utilities: Cable AvailableAppliances: Dishwasher, Dryer, Electric Range, Refrigerator, Washer, Electric Water HeaterDishwasherDryerLaundry: In BasementRefrigeratorWasher |
Heating & Cooling Heating: Oil,Baseboard,Zoned,RadiatorNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Oil |
Fireplace & Spa Fireplace: Wood BurningHas a Fireplace |
Gas & Electric Electric: 200+ Amp Service |
Windows, Doors, Floors & Walls Window: DrapesFlooring: Hardwood, Tile |
Levels, Entrance, & Accessibility Stories: 2Levels: TwoFloors: Hardwood, Tile |
View No View |
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Exterior Home Features Roof: SlatePatio / Porch: Patio, Covered PorchOther Structures: Barn(s), Guest House, OutbuildingExterior: DeckFoundation: Stone |
Parking & Garage Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageParking Spaces: 1Parking: Shared Driveway,Paved,Right-Of-Way (ROW),Storage Above,Barn,Detached |
Frontage Road Frontage: PublicRoad Surface Type: Paved |
Water & Sewer Sewer: Public Sewer |
Farm & Range Frontage Length: Road frontage: 100 |
Finished Area Finished Area (above surface): 4475 Square Feet |
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Year Built Year Built: 1825 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Victorian |
Building Construction Materials: Wood Frame, Wood SidingNot a New Construction |
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Price List Price: $599,999 |
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Direction & Address City: Chester |
School Information Elementary School: Chester-Andover ElementaryElementary School District: ChesterAndover USD 29Jr High / Middle School: Green Mountain UHSD #35Jr High / Middle School District: ChesterAndover USD 29High School: Green Mountain UHSD #35High School District: ChesterAndover USD 29 |
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Building Area Building Area: 5675 Square Feet |
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Lot Area: 0.60 acres |
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BasementMls Number: 4954502Attribution Contact: Cell: 802-299-7522Above Grade Unfinished Area: 4475Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 1200Below Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Sep 29, 2023 Source: PrimeMLS #4954502 | Sold | $579,000 |
Aug 4, 2023 Source: PrimeMLS #4954502 | Contingent | $599,999 |
May 26, 2023 Source: PrimeMLS #4954502 | Listed For Sale | $599,999 |
Feb 17, 2021 Source: PrimeMLS #4816260 | Sold | $430,000 |
May 15, 2018 Source: N/A | ListingRemoved | $470,000 |
Sep 27, 2017 Source: N/A | PriceChange | $470,000 Price decreased by 4% |
May 13, 2017 Source: N/A | PriceChange | $490,000 Price increased by 0% |
May 1, 2017 Source: N/A | PriceChange | $489,999 Price decreased by 0% |
Oct 20, 2016 Source: N/A | Listed For Sale | $490,000 |
Sep 17, 2016 Source: Agent Provided | ListingRemoved | $490,000 |
Feb 23, 2016 Source: Agent Provided | PriceChange | $490,000 Price decreased by 8% |
Sep 24, 2015 Source: Agent Provided | Listed For Sale | $535,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $3,913 | $134,300 |
Home facts updated by county records
Market trends in Chester
Last updated August 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
18
2MoM
Around this home
Neighborhood Overview
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.
LGBTQ Local Legal Protections
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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 2026-09-17 13:51:59 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.
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.
Frequently asked questions about 244 Main Street
- What is 244 Main Street estimated to be worth?Trulia's estimated value for 244 Main Street in Chester, VT is $616,100.
- What is the price history for 244 Main Street?244 Main Street in Chester, VT last sold for $579,000 in September 2023.
- Is Chester a buyer's or seller's market?Chester is currently a buyer's market, based on recent for-sale activity.
- What are the closest schools to 244 Main Street?The closest schools to 244 Main Street in Chester, VT are Chester-Andover Usd #29 (Pre-K/Elementary, rated 6/10), Green Mountain Uhsd #35 (Middle/High, rated 7/10).
- Does 244 Main Street have laundry facilities?Yes, 244 Main Street in Chester, VT has in-unit laundry.
- How big is the lot at 244 Main Street?The lot at 244 Main Street in Chester, VT is about 0.60 acres (26,136 sq ft).
Apartments for Rent
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SOLDAUG 12, 2026PrimeMLS, Closed
SOLDJUL 7, 2026
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