Listed by Katie Ladue Gilbert • KW Vermont Woodstock. Bought with Southern Vermont Realty Group.
Off Market Sep 2023 for $579K
$722,485
7
bd
•
8 ba
•
4,475
sq ft
244 Main St, Chester, VT 05143
About this home
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.
Single-familyProperty Type
1825Year Built
0.6 acresLot Size
$161Est. Price/Sq.Ft.
1 car garageParking
Listed by Katie Ladue Gilbert• KW Vermont Woodstock
Bought with Kelly Agrillo• Southern Vermont Realty Group
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Earn from this home
Rent
$2,815/mo
Redfin rental estimate
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Market trends in 05143, VT
Last updated August 2026
Buyer's Market
Seller's Market
Balanced market
Sale-to-List Price
97.2%
0.5% MoM
Median sale price
$289K
$70K MoM
Avg. days on market
58d
8 days MoM
Recently sold homes
17
8 MoM
Provided by Redfin
Sale history for 244 Main St
Date
Event
Price
PrimeMLS #4954502
Sep 29, 2023
Sold
$579,000
$129/sq ft
Aug 4, 2023
Contingent
—
May 26, 2023
Listed
$599,999
$134/sq ft
PrimeMLS #4816260
Feb 17, 2021
Sold
$430,000
$96/sq ft
Dec 8, 2020
Contingent
—
Aug 26, 2020
Relisted
—
Aug 9, 2020
Contingent
—
Jul 13, 2020
Listed
$425,000
$95/sq ft
+25
One of the most beloved properties in the town of Chester. There are very few homes that possess the history and character of this historic 1820 Victorian beauty. It has been cared for and had been run as a family owned Inn for nearly three decades. It's now ready for it's next chapter in which many possibilities exist. The main house has six bedrooms on the second floor each with it's own private bathroom. On the first floor you'll find a country kitchen, formal dining room, large 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. A classic front porch that gazes across to the town green. Connected to the house is a barn that had been used for retail space with a lovely one bedroom apartment above it. The property also features a carriage house which like the home is also on the National Historic Register. The carriage house still has the original horse stalls from back in the day. At the back of the property is a private 3 bedroom cottage ideal for a guest house. So many possibilities exist. Located across from the vibrant town green with its retail stores and restaurants. Just a short drive to several major ski areas including Okemo, Stratton, Magic and Bromley.
PrimeMLS #2
Oct 18, 2017
Price Changed
$470,000
$105/sq ft
PrimeMLS #1
Feb 23, 2016
Price Changed
$490,000
$109/sq ft
As the MLS and public records start to fill up, we'll list the details here.