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For sale
  • $1,400,000

    8 Winstons Path, South Dennis, MA 02660

    3beds
    3,079sqft
    : 
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    Single Family Residence
    Built in 1976
    2.21 Acres Lot
    $1,331,100 Zestimate®
    $455/sqft
    $-- HOA

    What's special

    Gas fireplaceUpdated bathSliders to the deckCustom built-insWood floorsWet barWalk-in closet
    A One of a kind Dennis location. Pond-Front Privacy on 2+ Acres! Tucked away on a private, wooded lot sitting on Fresh Pond, this 3-bedroom, 2.5-bath Colonial offers a rare combination of space, serenity, and water views. Tucked at the end of a quiet little side street, you'll enjoy over 2 acres of privacy with direct pond frontage--perfect for kayaking, fishing, or simply relaxing in a peaceful natural setting.Inside, the home is designed to capture the pond views throughout. Highlights include a huge kitchen with cherry cabinetry, granite counters, and an 8-foot island, with sliders to the deck. The living room features a dramatic wall of windows, custom built-ins, wood floors, and a gas fireplace. Upstairs, the primary suite offers cathedral ceilings, updated bath, and a walk-in closet. Two guest bedrooms and a full bath complete the second level. The lower-level bonus room adds great space for family and friends with a wet bar and direct access to the patio and pond. This hidden retreat abutting conservation land provides unmatched privacy but is still close to everything great about owning a home in Dennis!
    7 days
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    992
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    34
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    Zillow last checked:

    Listing updated:

    Listed by:

    Leo Doyle 508-280-7951,

    Oceanside Realty Group

    Source: CCIMLS,MLS#: 22603047MLS Logo

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Heating
      • Hot Water
      Cooling
      • Central Air
      Appliances
      • Included: Electric Water Heater
      Features
      • Flooring: Hardwood, Carpet, Tile
      • Basement: Finished
      • Number of fireplaces: 3
      Interior area
      • Total structure area: 3,079
      • Total interior livable area: 3,079 sqft

      Property

      Parking
      • Total spaces: 8
      • Parking features: Garage
      • Garage spaces: 1
      Features
      • Stories: 2
      Lot
      • Size: 2.21 Acres
      Details
      • Parcel number: DENN M:000108 P:017000
      • Zoning: R-40
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Clapboard, Shingle Siding
      • Foundation: Poured
      • Roof: Asphalt
      Condition
      • Updated/Remodeled, Actual
      • New construction: No
      • Year built: 1976
      • Major remodel year: 2018

      Utilities & green energy

      • Sewer: Private Sewer

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: South Dennis

      Financial & listing details

      • Price per square foot: $455/sqft
      • Tax assessed value: $2,159,200
      • Annual tax amount: $4,631
      • Date on market: 6/23/2026
      • Cumulative days on market: 8 days

        Estimated market value

        $1,331,100

        $1.26M - $1.40M

        $4,442/mo

        Price history

        DateEventPrice
        6/23/2026Listed for sale$1,400,000+21.2%$455/sqft
        Source: CCIMLS #22603047 Report a problem
        6/13/2022Sold$1,155,000+1.8%$375/sqft
        Source: MLS PIN #72966919 Report a problem
        4/19/2022Contingent$1,135,000$369/sqft
        Source: MLS PIN #72966919 Report a problem
        4/19/2022Pending sale$1,135,000$369/sqft
        Source: CCIMLS #22201629 Report a problem
        4/13/2022Listed for sale$1,135,000+93.2%$369/sqft
        Source: CCIMLS #22201629 Report a problem
        2/6/2015Sold$587,500$191/sqft
        Source: CCIMLS #21406905 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$4,351 -2.8%$1,004,900 -1.4%
        2024$4,475 +3.7%$1,019,300 +10.3%
        2023$4,317 +5.3%$924,500 +26.3%
        2022$4,099 -0.8%$732,000 +6.9%
        2021$4,130 +6.1%$684,900 +7.4%
        2020$3,891 +1.1%$637,900 +2.3%
        2019$3,847 +7.4%$623,500 +10.4%
        2018$3,581 +3.1%$564,900
        2017$3,474 -1.8%$564,900 +4.3%
        2016$3,537 +2%$541,600
        2015$3,466 +13.4%$541,600 +12.5%
        2014$3,056 +12%$481,300 +7.4%
        2013$2,728 +2.9%$448,000 -0.7%
        2012$2,652 +0.3%$451,100 -4.6%
        2011$2,644 +3.2%$473,000 -2.7%
        2010$2,562 -2.6%$486,100 -6.3%
        2009$2,630 +9.3%$518,800 -6.2%
        2008$2,406 +3.2%$553,200 -0.3%
        2007$2,331 +22%$555,000 +23.7%
        2006$1,911 +6.8%$448,500 +14.6%
        2005$1,789 +5.2%$391,500 +12.1%
        2004$1,700 +9%$349,100 +27.9%
        2003$1,559 -9.3%$273,000 +19.8%
        2001$1,718 $227,800

        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.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: West Dennis

        Getting around

        14 / 100
        Car-Dependent
        31 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • District: Dennis-Yarmouth

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

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