Delaney Smith
Delrose Realty LLC
(844) 487-0664
48 Total Sales
1 in Cheshire
$420,000 Price
566 W Main St Cheshire, CT 06410
Cheshire AreaEstimated Value: $201,000 - $722,000
3
Beds
1
Bath
3,730
Sq Ft
$146/Sq Ft
Est. Value
Highlights
- Colonial Architecture
- Property is near public transit and shops
- Central Air
- Darcey School Rated A-
- Porch
About This Home
As of May 2026Welcome to 566 West Main Street-where charm meets comfort with a fresh, inviting feel for the season. This well maintained 3-bedroom, 1-bath first floor space features wide plank hardwood floors, a spacious sun-filled living room, and timeless character throughout. Natural light pours into every room, creating a warm and airy atmosphere that feels just right for easy everyday living. The thoughtfully designed layout offers both comfort and functionality, while conveniences like in-unit laundry, a detached one-car garage, and additional off-street parking make life even easier. Step outside and enjoy a covered side porch-perfect for morning coffee or unwinding in the evening-overlooking a grassy yard with added privacy from the street. Ideally located in the heart of Cheshire, you're just minutes from local restaurants, shops, and major highways, making commuting and errands seamless. A perfect place to settle in and enjoy the season-welcome home. Ask about pet policy. Note the square footage reflects entire home per town record.
Last Agent to Rent the Property
Lamacchia Realty Brokerage Phone: (860) 777-5766 License #RES.0805538 Listed on: 03/21/2026
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Home Details
Home Type
- Single Family
Year Built
- Built in 1778
Lot Details
- 42,253 Sq Ft Lot
- Property is zoned R-20
Parking
- 1 Car Garage
Home Design
- Colonial Architecture
- Vinyl Siding
Interior Spaces
- 3,730 Sq Ft Home
- Basement Fills Entire Space Under The House
Kitchen
- Oven or Range
- Dishwasher
Bedrooms and Bathrooms
- 3 Bedrooms
- 1 Full Bathroom
Laundry
- Laundry on main level
- Dryer
- Washer
Schools
- Dodd Middle School
- Cheshire High School
Utilities
- Central Air
- Heating System Uses Natural Gas
Additional Features
- Porch
- Property is near public transit and shops
Community Details
Listing and Financial Details
- Assessor Parcel Number 1082631
Home Values in the Area
Average Home Value in this Area
Agents Specializing in Cheshire, CT
-
Delaney Smith
-
Chuck Ciambriello
Chuck Ciambriello
Coldwell Banker Realty
(475) 269-6877
65 Total Sales
1 in Cheshire
$805,841 Price
-
Maxwell Castrogiovanni
Maxwell Castrogiovanni
eXp Realty
(475) 255-7967
167 Total Sales
4 in Cheshire
$369K - $735K Price Range
-
Margaret Shea
Margaret Shea
William Raveis Real Estate
(401) 661-1078
53 Total Sales
9 in Cheshire
$118K - $625K Price Range
-
Amy Rio
Amy Rio
Better Homes and Gardens Real Estate Executive Real Estate
(860) 321-8567
1,025 Total Sales
3 in Cheshire
$235K - $530K Price Range
-
Cory Tyler
Cory Tyler
Berkshire Hathaway NE Prop.
(860) 406-5786
65 Total Sales
3 in Cheshire
$277K - $710K Price Range
Property 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 | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 05/09/2026 05/09/26 | Rented | $2,700 | -3.6% | -- | |
| 05/01/2026 05/01/26 | Under Contract | -- | -- | -- | |
| 03/21/2026 03/21/26 | For Rent | $2,800 | +47.4% | -- | |
| 07/01/2022 07/01/22 | Rented | $1,900 | 0.0% | -- | |
| 06/14/2022 06/14/22 | Under Contract | -- | -- | -- | |
| 06/11/2022 06/11/22 | For Rent | $1,900 | 0.0% | -- | |
| 04/29/2022 04/29/22 | Sold | $470,000 | -1.0% | $126 / Sq Ft | View Prior Sale |
| 04/06/2022 04/06/22 | Pending | -- | -- | -- | |
| 03/25/2022 03/25/22 | For Sale | $474,900 | 0.0% | $127 / Sq Ft | |
| 02/19/2022 02/19/22 | Pending | -- | -- | -- | |
| 11/19/2021 11/19/21 | Price Changed | $474,900 | -5.0% | $127 / Sq Ft | |
| 09/17/2021 09/17/21 | For Sale | $499,900 | 0.0% | $134 / Sq Ft | |
| 08/31/2018 08/31/18 | Rented | $1,700 | 0.0% | -- | |
| 08/23/2018 08/23/18 | Under Contract | -- | -- | -- | |
| 06/07/2018 06/07/18 | For Rent | $1,700 | +6.3% | -- | |
| 03/28/2013 03/28/13 | Rented | $1,600 | +6.7% | -- | |
| 03/26/2013 03/26/13 | Rented | $1,500 | -11.8% | -- | |
| 03/02/2013 03/02/13 | Under Contract | -- | -- | -- | |
| 02/04/2013 02/04/13 | Under Contract | -- | -- | -- | |
| 02/04/2013 02/04/13 | For Rent | $1,700 | +13.3% | -- | |
| 10/22/2012 10/22/12 | For Rent | $1,500 | -- | -- |
Source: SmartMLS
Tax 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.
| 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 | $9,433 | $317,170 | $56,350 | $260,820 |
| 2024 | $8,709 | $317,170 | $56,350 | $260,820 |
| 2023 | $7,586 | $216,190 | $56,340 | $159,850 |
| 2022 | $7,420 | $216,190 | $56,340 | $159,850 |
| 2021 | $7,290 | $216,190 | $56,340 | $159,850 |
| 2020 | $7,182 | $216,190 | $56,340 | $159,850 |
| 2019 | $7,182 | $216,190 | $56,340 | $159,850 |
| 2018 | $6,864 | $210,420 | $56,650 | $153,770 |
| 2017 | $6,721 | $210,420 | $56,650 | $153,770 |
| 2016 | $6,458 | $210,420 | $56,650 | $153,770 |
| 2015 | $6,458 | $210,420 | $56,650 | $153,770 |
| 2014 | $6,365 | $210,420 | $56,650 | $153,770 |
Source: Public Records
Agents Affiliated with this Home
-
Carly Kirsch
Landlord's Agent in 2026
Carly Kirsch
Lamacchia Realty
(860) 777-5766
93 Total Sales
-
Heather Dever
Tenant's Agent in 2026
Heather Dever
Showcase Realty, Inc.
(203) 528-8993
69 Total Sales
-
MM
Seller's Agent in 2022
Mary Malin
Calcagni Real Estate
-
The Sally Bowman Team
Seller's Agent in 2022
The Sally Bowman Team
Berkshire Hathaway Home Services
(203) 272-5232
160 Total Sales
-
Sally Smirnoff
Buyer's Agent in 2022
Sally Smirnoff
Calcagni Real Estate
(203) 671-4106
50 Total Sales
-
CB
Seller's Agent in 2018
Christine Baillie
Calcagni Real Estate
Map
Source: SmartMLS
MLS Number: 24161297
APN: CHES-000049-000273
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
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