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Sold for $559,000
  • $559,000

    28 Deep Hollow Road, Chester, CT 06412

    3beds
    1,740sqft
    Single Family Residence
    Built in 1890
    1.03 Acres Lot
    $559,300 Zestimate®
    $321/sqft
    $3,429 Estimated rent

    Home value

    $559,300

    $531,000 - $587,000

    $3,429/mo

    Zestimate® history
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    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!

    Zillow last checked:

    Listing updated:

    Listed by:

    Tom Pentalow (860)883-9001,

    Property Shoppe, LLC 203-829-0418

    Bought with:

    Shelly Cumpstone, RES.0792433

    Coldwell Banker Realty

    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

    Price history

    DateEventPrice
    10/29/2026Pending sale$559,000$321/sqft
    Source: Smart MLS #24199280 Report a problem
    10/26/2026Sold$559,000$321/sqft
    Source: Smart MLS #24199280 Report a problem
    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

    Neighborhood: 06412

    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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    $559,300
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    With Zillow Showcase(estimated)

    $570,486

    Sell for more on Zillow
    Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
    $559,300
    2% more
    +$11,186
    With Zillow Showcase(estimated)

    $570,486