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For sale
  • $779,999

    275 West Main Street, Chester, CT 06412

    4beds
    2,706sqft
    : 
    $5,804/mo
    Get pre-qualified
    Single Family Residence
    Built in 1971
    2 Acres Lot
    $761,100 Zestimate®
    $288/sqft
    $-- HOA

    What's special

    Luxury primary suiteMultiple fireplacesCustom rain showerProfessionally landscaped groundsQuartz countertopsFinished lower levelSpa-inspired primary bathroom
    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. Incredible extension of the home, featuring luxury vinyl plank flooring, a half bathroom, and its own dedicated heating and cooling zone. Create the ultimate entertainment room, home theater, game room, gym, office, or combination of them all. The renovation goes far beyond what you can see. Major improvements include a new septic system, new plumbing, complete electrical rewire with 200-amp service, hardwired security system, new windows, new siding, new gutters, and a new 3-zone central heating and air-conditioning system serving the first floor, second floor, and finished lower level. Step outside onto the new 12' 12' wood deck and enjoy the professionally landscaped grounds and peaceful surroundings of your private 2-acre property. Nearly every detail has been thoughtfully addressed. With extensive permitted renovations, luxury finishes, major new mechanical systems, generous indoor and outdoor living space, and an incredible Chester setting, 275 W Main Street isn't simply renovated-it's ready to be enjoyed. Come experience this one-of-a-kind Chester property and make it home.
    1 day
    221
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    Zillow last checked:

    Listing updated:

    Listed by:

    Shirley Tapper (475)202-2586,

    Great Estates, CT 203-200-7030

    Source: Smart MLS,MLS#: 24211368MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Primary bedroom
      • Features: Fireplace, Jack & Jill Bath
      • Level: Upper
      Bedroom
      • Level: Lower
      Bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Bathroom
      • Level: Upper
      Bathroom
      • Level: Upper
      Bathroom
      • Level: Main
      Bathroom
      • Level: Lower
      Dining room
      • Level: Main
      Kitchen
      • Level: Main
      Living room
      • Level: Main
      Heating
      • Zoned
      Cooling
      • Central Air
      Appliances
      • Included: Electric Range, Microwave, Range Hood, Refrigerator, Freezer, Ice Maker, Dishwasher, Disposal, Electric Water Heater, Water Heater
      • Laundry: Lower Level
      Features
      • Open Floorplan
      • Basement: Full,Finished
      • Attic: Pull Down Stairs
      • Number of fireplaces: 3
      Interior area
      • Total structure area: 2,706
      • Total interior livable area: 2,706 sqft
      • Finished area above ground: 1,906
      • Finished area below ground: 800
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Attached, Garage Door Opener
      • Attached garage spaces: 2
      Features
      • Patio & porch: Deck
      • Exterior features: Rain Gutters, Garden
      Lot
      • Size: 2 Acres
      • Features: Landscaped
      Details
      • Additional structures: Shed(s)
      • Parcel number: 941547
      • Zoning: R-2

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Vinyl Siding
      • Foundation: Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1971

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Cable Available

      Community & HOA

      Community
      • Features: Golf, Lake, Library, Park, Shopping/Mall, Stables/Riding
      • Security: Security System
      HOA
      • Has HOA: No
      Location
      • Region: Chester

      Financial & listing details

      • Price per square foot: $288/sqft
      • Tax assessed value: $343,420
      • Annual tax amount: $9,540
      • Date on market: 10/2/2026

        Estimated market value

        $761,100

        $723,000 - $799,000

        $4,550/mo

        Price history

        DateEventPrice
        10/2/2026Listed for sale$779,999-1.3%$288/sqft
        Source: Smart MLS #24211368 Report a problem
        9/30/2026Listing removed$789,900$292/sqft
        Source: Smart MLS #24204638 Report a problem
        9/24/2026Price change$789,900-4.2%$292/sqft
        Source: Smart MLS #24204638 Report a problem
        9/11/2026Listed for sale$824,900+66.6%$305/sqft
        Source: Smart MLS #24204638 Report a problem
        6/5/2026Sold$495,000+2.1%$183/sqft
        Source: Smart MLS #24173958 Report a problem
        5/19/2026Pending sale$485,000$179/sqft
        Source: Smart MLS #24173958 Report a problem
        5/13/2026Listed for sale$485,000$179/sqft
        Source: Smart MLS #24173958 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$7,471 +10.8%$275,870
        2024$6,745 +15.5%$275,870 +40.3%
        2023$5,838 +0.7%$196,570
        2022$5,799 $196,570
        2021$5,799 +3.1%$196,570
        2020$5,626 -0.6%$196,570
        2019$5,659 +5.1%$196,570 -1%
        2018$5,384 +2.8%$198,580
        2017$5,235 +4.1%$198,580
        2015$5,028 +2%$198,580
        2014$4,929 +1.6%$198,580 -10.2%
        2013$4,852 -2.3%$221,030
        2012$4,967 +1.6%$221,030
        2011$4,887 $221,030
        2010$4,887 +4.7%$221,030
        2009$4,666 +3.1%$221,030 +16.6%
        2008$4,526 +3.2%$189,600
        2007$4,384 +3.4%$189,600
        2006$4,241 +1.1%$189,600
        2005$4,194 +1%$189,600
        2004$4,152 +11.9%$189,600 +40.7%
        2003$3,711 +10.9%$134,800
        2001$3,347 -15.8%$134,800 -34.4%
        1995$3,975 $205,450
        Find assessor info on the county website

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        Payment breakdown

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        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 06412

        Getting around

        9 / 100
        Car-Dependent
        12 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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