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  • $559,000

    28 Deep Hollow Road, Chester, CT 06412

    3beds
    1,740sqft
    : 
    $4,159/mo
    Get pre-qualified
    Single Family Residence
    Built in 1890
    1.03 Acres Lot
    $-- Zestimate®
    $321/sqft
    $-- HOA

    What's special

    Custom moldingsHalf bath in basementBeautiful knotty alder doorsOpen floor planNew kitchen aid appliancesRattan ceiling fans
    This beautifully maintained 1890 Farm House in coveted Deep Hollow Road is a rare opportunity and has been a labor of love over the time that the sellers have lived here. This 1.04 acre property on "The Hollow" consists of a house, an oversized 24' x 24' garage/shop, antique "pony" barn with authentic outhouse and custom built service barn suited for a man cave, cigar lounge or whatever else you can envision. Walking into the front door, expect an open floor plan with beautiful knotty alder doors, custom moldings, newly refinished arctic maple flooring, 2 tongue & groove cedar ceilings (1 w/rattan ceiling fans). New Kitchen Aid appliances in a kitchen just waiting for your vision & a spacious walk-in pantry w/ample storage. Gorgeous powder room tucked away features pedestal sink and a 100+ yr old antique cabinet. 2nd floor features 3 bedrooms, 2 which have cathedral ceilings w/remotely operated skylights w/rain sensors to automatically close at first sign of precipitation. Master bedroom has been plugged & wired for stackable washer/dryer. A stand up attic includes a whole house attic fan which creates an impressive amount of air flow. Second floor is on 4 zones of radiant heat; first floor is 1 zone. Basement is walk out and 400 sq ft of newly refreshed space. New carpet, great lighting and wonderful space for a playroom for children, man cave or home office/small business as utilized by the previous owners. Half bath in basement as well. Last, but not least, living on "The Hollow" is all about living on a most beautiful dead end road that affords you access to hiking, fishing, the ability to walk into town and enjoy its old town charm or short bike ride to the Chester Hadlyme Ferry to enjoy a day of wandering the grounds of Gilette Castle. Whether you are looking for a forever home to raise your family, retiring to peaceful surrounds this home is worth a visit!
    7 days
    1,265
    81

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Tom Pentalow (860)883-9001,

    Property Shoppe, LLC 203-829-0418

    Source: Smart MLS,MLS#: 24199280MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 1
      • 1/2 bathrooms: 2
      Primary bedroom
      • Features: Remodeled, Built-in Features
      • Level: Upper
      Bedroom
      • Features: Skylight, Wall/Wall Carpet
      • Level: Upper
      Bedroom
      • Features: Skylight, Wall/Wall Carpet
      • Level: Main
      Dining room
      • Features: Remodeled, French Doors, Hardwood Floor, Wide Board Floor
      • Level: Main
      Kitchen
      • Features: Hardwood Floor, Wide Board Floor
      • Level: Main
      Living room
      • Features: Remodeled, Ceiling Fan(s), Hardwood Floor, Wide Board Floor
      • Level: Main
      Heating
      • Radiant, Oil
      Cooling
      • Window Unit(s)
      Appliances
      • Included: Oven/Range, Refrigerator, Dishwasher, Water Heater
      • Laundry: Lower Level
      Features
      • Doors: French Doors
      • Basement: Full,Partially Finished
      • Attic: Floored,Pull Down Stairs
      • Has fireplace: No
      Interior area
      • Total structure area: 1,740
      • Total interior livable area: 1,740 sqft
      • Finished area above ground: 1,740

      Property

      Parking
      • Total spaces: 2
      • Parking features: Detached
      • Garage spaces: 2
      Features
      • Patio & porch: Deck
      • Fencing: Wood,Partial,Privacy
      Lot
      • Size: 1.03 Acres
      • Features: Borders Open Space
      Details
      • Additional structures: Barn(s)
      • Parcel number: 941507
      • Zoning: R-2

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Cedar
      • Foundation: Stone
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1890

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      Community
      • Features: Shopping/Mall
      HOA
      • Has HOA: No
      Location
      • Region: Chester

      Financial & listing details

      • Price per square foot: $321/sqft
      • Tax assessed value: $182,840
      • Annual tax amount: $5,079
      • Date on market: 9/17/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        9/17/2026Listed for sale$559,000+166.2%$321/sqft
        Source: Smart MLS #24199280 Report a problem
        9/7/2001Sold$210,000$121/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$4,951 +10.8%$182,840
        2024$4,470 +10.5%$182,840 +34.2%
        2023$4,046 +0.7%$136,240
        2022$4,019 $136,240
        2021$4,019 +3.1%$136,240
        2020$3,899 -0.6%$136,240
        2019$3,922 +5%$136,240 -1.1%
        2018$3,734 +2.8%$137,750
        2017$3,631 +4.1%$137,750
        2015$3,488 +2%$137,750
        2014$3,419 -32.8%$137,750 -40.5%
        2013$5,085 -2.3%$231,680
        2012$5,206 +1.6%$231,680
        2011$5,122 0%$231,680 0%
        2010$5,123 +4.7%$231,720
        2009$4,892 -6.6%$231,720 +5.6%
        2008$5,237 -0.2%$219,400 -3.3%
        2007$5,246 +16.2%$226,900 +12.4%
        2006$4,514 +1.1%$201,800
        2005$4,464 +9.4%$201,800 +8.3%
        2004$4,080 +30.7%$186,300 +64.3%
        2003$3,122 +10.9%$113,400
        2001$2,816 +13.1%$113,400 -11.9%
        1995$2,490 $128,660
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 06412

        Getting around

        3 / 100
        Car-Dependent
        15 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Chester
        • High: Valley

        Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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