275 West Main Street, Chester, Connecticut

$779,999

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4

Beds

4

Baths

2,706

Square feet

2.00

Acres

About 275 West Main Street

Completely Reimagined * 4 Bedrooms * 3.5 Bathrooms * 2 Acres * Luxury Primary Suite * Finished Lower Level Welcome to 275 W Main Street, where classic New England charm meets a stunning, comprehensive renovation. Set on 2 beautiful acres directly across from Cockaponset State Forest, this exceptional Chester home has been thoughtfully transformed to deliver modern luxury, comfort, and effortless turnkey living. From the moment you step inside, you'll notice the attention to detail. Beautifully refinished hardwood floors flow throughout the home, complementing bright, open living spaces designed for both everyday comfort and entertaining. Multiple fireplaces preserve the warmth and character of the original home while the extensive upgrades bring it firmly into the modern era. At the heart of the home is a show-stopping new kitchen, beautifully appointed with quartz countertops and premium THOR Gordon Ramsay Collection appliances. Whether you're hosting family and friends or enjoying a quiet evening at home, this kitchen was designed to impress. Retreat upstairs to the luxurious primary suite, complete with a 6-foot walk-in closet and custom closet system. The spa-inspired primary bathroom creates your own private escape, featuring a custom rain shower and freestanding soaking tub-the perfect place to unwind. And the living space doesn't stop upstairs. The approximately 800-square-foot permitted finished lower level has been transformed.

Features of 275 West Main Street

MLS® # 24211368
Price $779,999
Bedrooms 4
Bathrooms 4.00
Full Baths 3
Half Baths 1
Square Footage 2,706
Acres 2.00
Type Single Family For Sale
Style Colonial
Status Active

Community Information

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

Amenities

Parking Attached Garage
# of Garages 2
Is Waterfront No
Waterfront Not Applicable
Has Pool No

Interior

Interior Features Auto Garage Door Opener, Cable - Available, Open Floor Plan, Security System
Appliances Electric Range, Microwave, Range Hood, Refrigerator, Freezer, Icemaker, Dishwasher, Disposal
Heating Zoned
Cooling Central Air
Fireplace Yes
# of Fireplaces 3
Has Basement Yes
Basement Full, Fully Finished

Exterior

Exterior Vinyl Siding
Exterior Features Shed, Deck, Gutters, Garden Area
Lot Description Professionally Landscaped
Roof Asphalt Shingle
Foundation Concrete

School Information

Elementary Per Board of Ed
High Per Board of Ed

Additional Information

Date Listed October 2nd, 2026
Days on Market 1
Zoning R-2
RE / Bank Owned No

Listing Details

OfficeGreat Estates, CT

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Listing information last updated on October 3rd, 2026 at 5:59am EDT.