275 W Main St

Chester, CT 06412

$485,000
Price
4
Beds
1,906 Sq. Ft.
$254 / Sq. Ft.
1,906
Sq. Ft.
$254
per Sq. Ft.
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Under Contract
Under Contract

Description

Multiple offers received. Seller has asked for best and final by Monday 5/18 5pm 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,...Multiple offers received. Seller has asked for best and final by Monday 5/18 5pm 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.
  1. Listed by Kelly Puorro • Puorro Realty Group
    P: (860)-575-8666 C: (860)-575-8666 kelly@puorrorealtygroup.com
  2. Listed by Brandon Puorro • Puorro Realty Group
    P: (860)-558-9740 C: (860)-575-8799 brandon@puorrorealtygroup.com

Property Details for 275 West Main Street

Basement Description
Full, Partially Finished
Direct Waterfront
No
Garages Number
2
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Attached Garage
Swimming Pool
No
LISTING UPDATED: 05/19/2026 12:52 AM

Property Details for 275 West Main Street

StatusUnder Contract
MLS #24173958
Days on Market5
Taxes$7,471 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1971
Lot Size2.00 AC / 87,120 SF
CountyMiddlesex County
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Location

Listing Courtesy of Puorro Realty Group, Kelly Puorro; Puorro Realty Group, Brandon Puorro
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Building Information for 275 West Main Street

Stories-Year Built1971Building Size-Lot Size2.00 AC / 87,120 SF

Payment Calculator

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$3,039 per month

30 year fixed, 6.36% Interest

Principal and Interest

$2,417

Property Taxes

$623

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 275 West Main Street

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: GPS Friendly
  • Elementary School: Chester
  • High School: Valley
  • Latitude: 41.390448
  • Longitude: -72.516161
  • Middle Jr High School: Winthrop
  • Neighborhood Amenities: Golf Course, Lake, Library, Park, Shopping/Mall, Stables/Riding
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $7,471
Interior and Exterior Features
Exterior Features
  • Exterior Features: Shed, Garden Area
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Access Via Hatch
  • Cooling System: Window Unit
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 3
  • Laundry Room Info: Lower Level
  • Rooms Additional: Laundry Room
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 19.5
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 11.7
Room 2
  • Room Entry Order: 10
  • Room Features: Hardwood Floor
  • Room Length: 11.8
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 11.7
Room 3
  • Room Entry Order: 11
  • Room Length: 8.3
  • Room Level: Upper
  • Room Type: Full Bath
  • Room Width: 6.9
Room 4
  • Room Entry Order: 12
  • Room Features: Fireplace
  • Room Length: 22.11
  • Room Level: Lower
  • Room Type: Rec/Play Room
  • Room Width: 22.5
Room 5
  • Listing Key: 5150449DCC62A519E063E201100ACFCD
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Length: 11.6
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 10.9
Room 6
  • Room Entry Order: 3
  • Room Features: Hardwood Floor
  • Room Length: 11.5
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 10.8
Room 7
  • Room Entry Order: 4
  • Room Features: French Doors,Hardwood Floor
  • Room Length: 12.1
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 10.9
Room 8
  • Room Entry Order: 5
  • Room Length: 7.5
  • Room Level: Main
  • Room Type: Full Bath
  • Room Width: 11.7
Room 9
  • Listing Key: 5150449DCC62A519E063E201100ACFCD
  • Room Entry Order: 6
  • Room Length: 9.1
  • Room Level: Main
  • Room Type: Other
  • Room Width: 14.6
Room 10
  • Room Entry Order: 7
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 16.1
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 11.7
Room 11
  • Room Entry Order: 8
  • Room Features: Hardwood Floor
  • Room Length: 11.9
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 10.8
Room 12
  • Room Entry Order: 9
  • Room Features: Hardwood Floor
  • Room Length: 11.1
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 10.9
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Wood
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1971
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 1906
Lot Information
  • Lot Description: Professionally Landscaped
  • Parcel Number: 941547
  • Sq Ft Est Heated Above Grade: 1906.0
  • Sq Ft Total: 1906.0
  • Zoning: R-2
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Vacant

Public Records for 275 West Main Street

Taxable ValueLand$66,500Additions$209,370Total$275,870
Tax Record2024$7,471 ($623 / month)
Home Facts
Beds4Baths2Total Finished SqFt1,906 SqFtAbove Grade Finished SqFt1,906 SqFtUnfinished Basement SqFt593 SqFtStories2Lot Size87,120 SqFtStyleSingle Family ResidenceYear Built1971Year Renovated1993ZoningR-2CountyLOWER CONNECTICUT RIVERAPNCSTR M:16 B:51Fireplace TypeHas Fireplace

Schools near 275 West 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
Rating
School
Distance
Chester Elementary School
PublicPK to 6

John Winthrop Middle School
Public7 to 8

Valley Regional High School
Public9 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 Puorro Realty Group, Kelly Puorro; Puorro Realty Group, Brandon Puorro

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.