81 Main St Chester, CT 06412
Estimated payment $3,442/month
Highlights
- Open Floorplan
- Cape Cod Architecture
- Thermal Windows
- Valley Regional High School Rated A-
- Attic
- Patio
About This Home
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.
Listing Agent
William Pitt Sotheby's Int'l Brokerage Phone: (203) 215-8676 License #RES.0757106 Listed on: 05/04/2026
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $5,503
Year Built
- Built in 1950
Lot Details
- 6,534 Sq Ft Lot
- Garden
Home Design
- Cape Cod Architecture
- Block Foundation
- Frame Construction
- Asphalt Shingled Roof
- Wood Siding
Interior Spaces
- 1,128 Sq Ft Home
- Open Floorplan
- Thermal Windows
- Crawl Space
- Storm Doors
Kitchen
- Gas Range
- Microwave
- Dishwasher
Bedrooms and Bathrooms
- 2 Bedrooms
- 2 Full Bathrooms
Laundry
- Laundry on main level
- Dryer
- Washer
Attic
- Storage In Attic
- Attic or Crawl Hatchway Insulated
Outdoor Features
- Patio
- Rain Gutters
Utilities
- Window Unit Cooling System
- Radiator
- Heat Pump System
- Heating System Uses Propane
- Tankless Water Heater
Listing and Financial Details
- Assessor Parcel Number 940179
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $5,503 | $203,210 | $91,490 | $111,720 |
| 2024 | $4,968 | $203,210 | $91,490 | $111,720 |
| 2023 | $4,450 | $149,840 | $86,190 | $63,650 |
| 2022 | $4,420 | $149,840 | $86,190 | $63,650 |
| 2021 | $4,420 | $149,840 | $86,190 | $63,650 |
| 2020 | $4,288 | $149,840 | $86,190 | $63,650 |
| 2019 | $4,314 | $149,840 | $86,190 | $63,650 |
| 2018 | $4,365 | $161,020 | $90,720 | $70,300 |
| 2017 | $4,244 | $161,020 | $90,720 | $70,300 |
| 2016 | $3,246 | $161,020 | $90,720 | $70,300 |
| 2015 | $4,077 | $161,020 | $90,720 | $70,300 |
| 2014 | $3,997 | $161,020 | $90,720 | $70,300 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 05/16/2026 05/16/26 | Pending | -- | -- | -- | |
| 05/11/2026 05/11/26 | For Sale | $550,000 | +111.5% | $488 / Sq Ft | |
| 07/18/2013 07/18/13 | Sold | $260,000 | -5.5% | $230 / Sq Ft | View Prior Sale |
| 05/14/2013 05/14/13 | Pending | -- | -- | -- | |
| 04/09/2013 04/09/13 | For Sale | $275,000 | -- | $244 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $260,000 | -- | |
| Warranty Deed | $260,000 | -- | |
| Warranty Deed | $155,000 | -- | |
| Warranty Deed | $155,000 | -- | |
| Quit Claim Deed | $48,925 | -- |
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $125,000 | No Value Available | |
| Closed | $125,000 | New Conventional | |
| Previous Owner | $179,000 | No Value Available |
Source: SmartMLS
MLS Number: 24172804
APN: CHES-000014-000000-000537
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