275 West Main Street, Chester, Connecticut

$495,000

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4

Beds

2

Baths

1,906

Square feet

2.00

Acres

About 275 West Main Street

***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.

Features of 275 West Main Street

MLS® # 24173958
Price $495,000
Bedrooms 4
Bathrooms 2.00
Full Baths 2
Square Footage 1,906
Acres 2.00
Type Single Family For Sale
Style Colonial
Status Closed

Community Information

Address 275 West Main Street
Area N/A
City Chester
County Middlesex
State Connecticut
Zip Code 06412

Amenities

Parking Attached Garage
Garage Spaces 2
Is Waterfront No
Waterfront Not Applicable
Has Pool No

Interior

Appliances Oven/Range, Refrigerator, Dishwasher, Washer, Dryer
Heating Hot Water, Oil
Cooling Window Unit
Fireplace Yes
# of Fireplaces 3

Exterior

Exterior Wood
Exterior Features Shed, Garden Area
Lot Description Professionally Landscaped
Roof Asphalt Shingle
Foundation Concrete

School Information

Elementary Chester
Middle Winthrop
High Valley

Additional Information

Date Listed May 13th, 2026
Days on Market 5
Zoning R-2
RE / Bank Owned No

Listing Details

OfficePuorro Realty Group

Listing Map

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