Discover the perfect blend of mid-century character and modern efficiency in the heart of Chester Village. This impeccably maintained home offers a vibrant "walk-to-everything" lifestyle, just steps from award-winning dining, boutiques, and the theater. Officially a 2-bedroom home per town records, the layout offers incredible flexibility. The main level features a stunning den currently utilized as a primary suite. This light-filled space features a private, fully renovated ensuite full bath and a handsome armoire for storage, offering a sophisticated retreat for those seeking first-floor living. Note: This serves as the primary bath for the main level, enhancing the "suite" feel of the space. Upstairs, you will find two additional well-appointed rooms and a second fully renovated full bath, providing ample space for guests or a home office. The home's infrastructure has been flawlessly upgraded, featuring a new 50-year roof, on-demand propane heat/hot water, and an electric heat pump for heating and cooling (A/C on the first floor). The updated eat-in kitchen is a chef's delight, while the professional landscaping and beautiful stone patio create a private oasis for outdoor entertaining. Rarely does a home combine such high-end mechanical peace of mind with the undeniable charm of a downtown location. Turn-key and ready for its next chapter-experience the best of Chester right outside your front door.
Single-familyProperty Type
1950Year Built
6,534 sq ftLot Size
$548Price/Sq.Ft.
Listed by Susan Woods• William Pitt Sotheby's Int'l
Est. $2,499 per month, based on comparable rentals
Sale and tax history for 81 Main St
Sale History
Tax History
Date
Event
Price
Smart MLS #24172804
Jun 11, 2026
Sold
$618,000
$548/sq ft
May 16, 2026
Pending
—
May 11, 2026
Listed
$550,000
$488/sq ft
May 8, 2026
Coming Soon
$550,000
$488/sq ft
Smart MLS #G647421
Jul 18, 2013
Sold
$260,000
$230/sq ft
Apr 9, 2013
Listed
$275,000
$244/sq ft
Be part of the village..Just steps from restaurants & shopping. Artistically styled home with eat-in kitchen, den or 3rd br, dining room. Beautiful gardens with outdoor entertainment area. Move-in condition.One-of-a-kind! Not a blade of grass to mow! Planned gardens throughout with charming patio for entertaining. Parking available.
Public Records
Apr 2, 2002
Sold
$155,000
$137/sq ft
Smart MLS #M9062507
Feb 22, 2001
Listed
$175,000
$155/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$4,450 (+0.7%)
$86,190 + $63,650
$149,840
2022
$4,420
$86,190 + $63,650
$149,840
2021
$4,420 (+3.1%)
$86,190 + $63,650
$149,840
2020
$4,288 (−0.6%)
$86,190 + $63,650
$149,840
2019
$4,314 (−1.2%)
$86,190 + $63,650
$149,840
2018
$4,365 (+2.9%)
$90,720 + $70,300
$161,020
2017
$4,244 (+3.1%)
$90,720 + $70,300
$161,020
2016
$4,117 (+3.0%)
$90,720 + $70,300
$161,020
2014
$3,997 (−2.1%)
$90,720 + $70,300
$161,020
2011
$4,082
$115,380 + $70,590
$185,970
Public record
Beds
2
Baths
2
Stories
1
Lot width
—
Lot depth
—
Lot size
6,534 Sq. Ft.
Year renovated
1995
Sq. Ft.
1,128
Year built
1950
Style
Single Family Residential
County
Middlesex County
APN
940179
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 13, 2023.
Property details
Interior
Interior Information
Total Rooms: 5
Laundry Room Location: Off the kitchen and down a few stairs.
Laundry Room Info: Main Level
Interior Features: Open Floor Plan
Cooling System: Heat Pump, Window Unit
Appliances Included: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
Bathroom Information
# of Baths (Full): 2
Bedroom Information
Beds Total: 2
Room Information
Basement Description: Crawl Space
Has Attic
Attic Description: Storage Space, Access Via Hatch
Exterior
Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Wood
Exterior Features: Gutters, Garden Area, Patio
Lot Information
Lot Description: Treed, Level Lot, Professionally Landscaped
Land Information
Encumbrances Restrictions: Easements, Right of Way
Building Information
Foundation Type: Block
Construction Description: Frame
Color: Sage
Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 1128
Financial
Assessments Information
Assessed Value: $203,210
Utilities
Utility Information
Water Source: Public Water Connected
Sewer Usage Fee Annual: $750
Sewage System: Public Sewer Connected
Hot Water Description: Domestic, Tankless Hotwater
Heat Type: Heat Pump, Radiator
Heat Fuel Type: Electric, Propane
Fuel Tank Location: Above Ground
Energy Features: Storm Doors, Thermopane Windows
Location
School Information
High School: Per Board of Ed
Elementary School: Per Board of Ed
Location Information
State: Connecticut
Directions: GPS friendly.
County: Middlesex
Public facts
Beds: 2
Baths: 2.0
Sq. Ft.: 1,128
Stories: 1.0
Lot Size: 6,534 square feet
Style: Single Family Residential
Year Built: 1950
Year Renovated: 1995
County: Middlesex County
APN: 940179
Home facts updated by county records on Jul 13, 2023
Other
Documents & Disclosures
Supplement Count Public: 4
Around this home
Schools
Chester Elementary School
Public PreK-6 • Assigned • 0.5mi
7/10
John Winthrop Middle School
Public 7-8 • Assigned • 2.6mi
4/10
Valley Regional High School
Public 9-12 • Assigned • 2.2mi
7/10
Provided by GreatSchools
Climate risks
4/10 Flood Factor
Estimated 18-28% chance of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
6/10 Heat Factor
7 days above 96° expected this year, 16 days in 30 years
6/10 Wind Factor
77% chance of strong winds in next 30 years
3/10 Air Factor
2 unhealthy days expected this year, 3 days in 30 years
Provided by First Street
Historical weather
Chester, CT • 06412
Average low and high temperatures (°F)
34
21
36
22
51
33
60
42
68
51
80
60
83
66
80
59
76
57
65
47
54
38
39
25
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
82/ 100
Very good sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
8.7 hrs
4.5 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$527,000 – $638,000
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