Date
Details
Price
Change
Source
5/13/2026
Listed
$485,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
Set on an exceptional 2-acre parcel in the charming Connecticut River town of Chester, this 4-bedroom, 2-bath Colonial offers endless potential in a truly special setting. Being offered for the first time in 55 years, this well-loved home is filled with warmth and character throughout, featuring hardwood floors and three fireplaces, including one in the spacious primary bedroom. Mature plantings surround the property, creating a peaceful outdoor backdrop complete with a pond perfect for relaxing and enjoying nature. Additional highlights include an attached 2-car garage, two shed/barn outbuildings, and newer major mechanical updates including the roof, furnace, and oil tank. The home also offers finished space in the basement complete with a fireplace, ideal for entertaining, a home office, or flexible additional living space. Located directly across the street from Cockaponset State Forest, this property is ideal for those who appreciate outdoor recreation and nature. Whether you're looking to preserve its timeless charm or add your own finishing touches, this is an exceptional opportunity to make it your own. Enjoy all that Chester has to offer, including acclaimed restaurants, art galleries, unique local shops, and the charm of one of Connecticut's most beloved river towns.
Full Property Details
Full Property Details for 275 W Main St
General
- Price: $485,000
- Taxes: (July 2025-June 2026)
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24173958
- Updated: 5/13/2026
- Added to Site: 1 day(s) ago
Interior
- Number of Rooms: 10
- Rooms/Areas: Laundry Room
- Fireplace: Yes
- Number of Fireplaces: 3
- Appliances: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
- Full Bath: 7.5 x 11.7, Main
Bedrooms
- Total Bedrooms: 4
- Primary Bedroom: Primary Bedroom - Fireplace, Hardwood Floor, 16.1 x 11.7, Upper
- Bedroom 1: Bedroom - Hardwood Floor, 11.1 x 10.9, Upper
- Bedroom 2: Bedroom - Hardwood Floor, 11.8 x 11.7, Upper
- Bedroom 3: Bedroom - Hardwood Floor, 11.9 x 10.8, Upper
Other Rooms
- Living Room: Living Room - Fireplace, Hardwood Floor, 19.5 x 11.7, Main
- Family Room: Family Room - French Doors, Hardwood Floor, 12.1 x 10.9, Main
- Kitchen: Kitchen - Hardwood Floor, 11.5 x 10.8, Main
- Dining Room: Dining Room - Hardwood Floor, 11.6 x 10.9, Main
- Game room: Yes
- Game Room: Rec/Play Room - Fireplace, 22.11 x 22.5, Lower
- Rec Room: Fireplace, 22.11 x 22.5, Lower
- Laundry: Lower Level
- Other Room 1: Other, 9.1 x 14.6, Main
Exterior
- Exterior Features: Shed, Garden Area
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Parking: Attached Garage
Location
- County: Middlesex
- Driving Directions: GPS Friendly
School Information
- Elementary School: Chester
- Middle School: Winthrop
- High School: Valley
Heating & Cooling
- Cooling Type: Window Unit
- Heating Type: Hot Water, Oil
- Heating Fuel: Oil
- Water Heater: Domestic
Utilities
- Sewer: Septic
- Water: Private Well
Structural Information
- Architectural Style: Colonial
- Construction Status: No/Resale
- Exterior Const.: Wood
- Basement Desc.: Full, Partially Finished
- Roof: Asphalt Shingle
- Attic: Yes
- Square Feet: 1,906
- Above Ground: 1,906 Sq. Ft.
- Year Built: 1971
Lot Features
- Lot Size (Acres): 2
- Zoning: R-2
- Lot Description: Professionally Landscaped
Financial Considerations
- Assessment Amount: $275,870
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 941547
Listed by Puorro Realty Group, Kelly Puorro and Puorro Realty Group, Brandon Puorro
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agents
— 275 W Main St —
Kelly Puorro
Puorro Realty Group
Brandon Puorro
Puorro Realty Group
Agent Contact: (860) 575-8666 Office Contact: (860) 558-9740
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 275 W Main St
School Districts:Chester School District, Regional High School District 04
| Name | Grades | Distance |
|---|---|---|
Chester Elementary School, Chester, CT 23 Ridge Road, Chester, CT 06412 | K-6 | 4.4 mi |
John Winthrop Middle School 1 Winthrop Road, Deep River, CT 06417 | 7-8 | 3.6 mi |
Valley Regional High School 256 Kelsey Hill Road, Deep River, CT 06417 | 9-12 | 3.9 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 275 W Main St
Tax History
Tax History for 275 W Main St
Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,471
11%
$275,870
—
2023
$6,745
16%
$275,870
40%
2023
$5,838
1%
$196,570
—
2022
$5,799
—
$196,570
—
2021
$5,799
3%
$196,570
—
2020
$5,626
-1%
$196,570
—
2019
$5,659
5%
$196,570
-1%
2018
$5,384
3%
$198,580
—
2017
$5,235
3%
$198,580
—
2016
$5,078
1%
$198,580
—
2015
$5,028
2%
$198,580
—
2014
$4,929
2%
$198,580
-10%
2011
$4,852
—
$221,030
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 275 W Main St
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- Single Family
- Active
- Updated 7 days ago
- 5Beds
- 3Total Baths
- 1,353Sq. Ft.
- Single Family
- Active
- Updated 7 days ago
- 3Beds
- 3Total Baths
- 1,836Sq. Ft.
- Single Family
- Active
- Updated 8 days ago
- 3Beds
- 2Total Baths
- 1,790Sq. Ft.
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![[Address not provided], Deep River, CT 06417 - Photo 1](https://m.cbhomes.com/p/229/24174110/839Bf140486040a/s23cc.webp)
- Single Family
- Active
- Updated 2 days ago
- 4Beds
- 3Total Baths
- 2,774Sq. Ft.
- Single Family
- Active
- Updated 2 days ago
- 5Beds
- 4Total Baths
- 4,841Sq. Ft.
- Single Family
- Active
- Updated 20 hours ago
- 4Beds
- 3Total Baths
- 3,023Sq. Ft.
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- Single Family
- Active
- Updated 12 hours ago
- 3Beds
- 3Total Baths
- 2,000Sq. Ft.
- Mobile Home
- Active
- Updated 5 days ago
- 2Beds
- 1Total Bath
- 672Sq. Ft.
- Mobile Home
- Active
- Updated 5 days ago
- 2Beds
- 1Total Bath
- 672Sq. Ft.
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- Single Family
- Closed
- 3Beds
- 2Total Baths
- 1,408Sq. Ft.
Listed by The Full Circle Team at Coldwell Banker Realty
Sold by William Raveis Real Estate
Sold by William Raveis Real Estate
275 West Main Street, Chester, CT 06412 (MLS# 24173958) is a Single Family property with 4 bedrooms and 2 full bathrooms. 275 West Main Street is currently listed for $485,000 and was received on May 13, 2026. Want to learn more about 275 West Main Street? Do you have questions about finding other Single Family real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.