81 Main St

Chester, CT 06412

$550,000
Price
2
Beds
1,128 Sq. Ft.
$488 / Sq. Ft.
1,128
Sq. Ft.
$488
per Sq. Ft.
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Under Contract
Under Contract
Welcome to 81 Main Street in charming Chester Village.
From the front door you'll walk into the open living and dining areas with tons of light. Plantation shutters are all through the house to provide privacy.
This first floor room, just off the living room is currently used as a primary bedroom with ensuite bath. This was previously used as a den.
The armoire serves as a closet for this room and will convey. In the background is the entrance to the first floor full bath.
First floor bath with tiled shower.
Beautifully renovated kitchen with quartz counter tops, plenty of counter seating and lots of cabinet storage.
Notice the open corner hutch and there is even a hidden ironing board behind the panel to the right of the door. Back door leads to a lovely covered porch.
Cabinets on the right have electricity for microwave and toaster.
Laundry, utilities and crawl space just steps down from the kitchen.
The second floor is light and bright with the skylight at the top of the stairs.
Bedroom or office with vaulted ceiling and a cooling ceiling fan. Central air on the first floor and window units are used on the second floor.
Another second floor bedroom or guest space with vaulted ceiling and built in drawers.
Second floor full bath with skylight.
Side of the house with the shared driveway.
A view of the back of the house with the covered porch and pathway to the "secret garden and patio".
Easy access from the driveway to the porch and into the kitchen.
Back porch leads into the kitchen.
Follow the brick path and it opens up to a lovely private patio surrounded by greenery.
A total oasis in the center of Chester Village...
An incredible detail of this charming house that still remains is the original gate post for the trolley entrance!
Just steps away from the center of Chester and all that it holds! Restaurants, theater, shops and the seasonal Farmers Market on Sundays.

Description

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...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.
  1. Listed by Susan Woods • William Pitt Sotheby's Int'l
    P: (203)-215-8676 C: (203)-215-8676 swoods@wpsir.com

Property Details for 81 Main Street

Basement Description
Crawl Space
Direct Waterfront
No
Expected Active Date
05-11-2026
Garages Number
0
Neighborhood
N/A
Style
Cape Cod
Swimming Pool
No
Expected On Market Date
05-11-2026
LISTING UPDATED: 05/16/2026 11:54 AM

Property Details for 81 Main Street

StatusUnder Contract
MLS #24172804
Days on Market4
Taxes$5,503 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1950
Lot Size0.15 AC / 6,534 SF
CountyMiddlesex County
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Location

Listing Courtesy of William Pitt Sotheby's Int'l, Susan Woods
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Building Information for 81 Main Street

Stories-Year Built1950Building Size-Lot Size0.15 AC / 6,534 SF

Payment Calculator

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$3,228 per month

30 year fixed, 6.46% Interest

Principal and Interest

$2,770

Property Taxes

$459

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 81 Main Street

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: GPS friendly.
  • Elementary School: Per Board of Ed
  • Flood Zone: No
  • High School: Per Board of Ed
  • Latitude: 41.402482
  • Longitude: -72.448793
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Sewer Usage Fee Annual: $750
  • Tax Year: July 2025-June 2026
  • Property Tax: $5,503
Interior and Exterior Features
Exterior Features
  • Exterior Features: Gutters, Garden Area, Patio
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Storage Space, Access Via Hatch
  • Cooling System: Heat Pump, Window Unit
  • Heat Type: Heat Pump, Radiator
  • Attic YN: Yes
  • Fireplaces Total: 0
  • Interior Features: Open Floor Plan
  • Laundry Room Info: Main Level
  • Laundry Room Location: Off the kitchen and down a few stairs.
  • Rooms Total: 5
Room 1
  • Room Entry Order: 1
  • Room Features: Combination Liv/Din Rm,Dining Area,Hardwood Floor
  • Room Length: 13.7
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 11.11
Room 2
  • Room Entry Order: 2
  • Room Features: Combination Liv/Din Rm,Hardwood Floor
  • Room Length: 10.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 11.0
Room 3
  • Room Entry Order: 3
  • Room Features: Remodeled,Built-In Hutch,Quartz Counters,Eating Space,Hardwood Floor
  • Room Length: 15.4
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 14.0
Room 4
  • Room Entry Order: 4
  • Room Features: Full Bath,Hardwood Floor
  • Room Length: 14.3
  • Room Level: Main
  • Room Type: Primary Bedroom
  • Room Width: 10.3
Room 5
  • Listing Key: 5108EC5628B574AAE063E201100A382E
  • Room Entry Order: 5
  • Room Features: Vaulted Ceiling,Built-Ins,Ceiling Fan,Hardwood Floor
  • Room Length: 10.6
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Room 6
  • Room Entry Order: 6
  • Room Features: Vaulted Ceiling,Ceiling Fan,Hardwood Floor
  • Room Length: 10.0
  • Room Level: Upper
  • Room Type: Office
  • Room Width: 13.0
Property
Property and Assessments
  • Color: Sage
  • Construction Description: Frame
  • Exterior Siding: Wood
  • Foundation Type: Block
  • Fuel Tank Location: Above Ground
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1950
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 1128
Lot Information
  • Lot Description: Treed, Level Lot, Professionally Landscaped
  • Parcel Number: 940179
  • Sq Ft Est Heated Above Grade: 1128.0
  • Sq Ft Total: 1128.0
  • Zoning: C
Utilities
  • Energy Features: Storm Doors, Thermopane Windows
  • Heat Fuel Type: Electric, Propane
  • Hot Water Description: Domestic, Tankless Hotwater
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 81 Main Street

DateEvent & SourcePriceAppreciation
Jul 18, 2013

Closed (Public Record)

Public Record #365243363

$260,000

+4.7% / yr

Apr 2, 2002

Closed (Public Record)

Public Record #99590065

$155,000

+17.0% / yr

Nov 22, 1994

Closed (Public Record)

Public Record #91991722

$48,925—
DateEvent & SourcePrice
07/18/2013

Closed (Public Record)

Public Record #365243363

$260,000

+4.7% / yr

04/02/2002

Closed (Public Record)

Public Record #99590065

$155,000

+17.0% / yr

11/22/1994

Closed (Public Record)

Public Record #91991722

$48,925

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 81 Main Street

Taxable ValueLand$91,490Additions$111,720Total$203,210
Tax Record2024$5,503 ($459 / month)
Home Facts
Beds2Baths2Total Finished SqFt1,128 SqFtAbove Grade Finished SqFt1,128 SqFtStories1Lot Size6,534 SqFtStyleSingle Family ResidenceYear Built1950Year Renovated1995ZoningCCountyLOWER CONNECTICUT RIVERAPNCSTR M:14 B:537

Schools near 81 Main Street

This home is within Regional School District 04.
Rating
School
Type
Grades
Distance
Chester Elementary School
Public - PK to 6
John Winthrop Middle School
Public - 7 to 8
Valley Regional High School
Public - 9 to 12
Mt Saint John
Private - 9 to 12
Rating
School
Distance
Chester Elementary School
PublicPK to 6

John Winthrop Middle School
Public7 to 8

Valley Regional High School
Public9 to 12

Mt Saint John
Private9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Pitt Sotheby's Int'l, Susan Woods

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.