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For sale
    • Price cut: $150K (6/13)
    $2,150,000

    22 Winslow Drive, Orleans, MA 02653

    5beds
    4,091sqft
    : 
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    Single Family Residence
    Built in 1968
    0.8 Acres Lot
    $2,034,000 Zestimate®
    $526/sqft
    $-- HOA

    What's special

    Overlooking a tranquil pond, 22 Winslow Drive offers a peaceful setting with a strong sense of privacy. Birds move easily through the surrounding landscape, and the quiet setting creates a calm and natural atmosphere. This gracious Cape Cod home has been cherished by four generations. Thoughtfully expanded over the years while preserving its warmth and character. Inside, more than 4,000 square feet of living space unfolds with a comfortable and natural flow. Hardwood floors, exposed beams, fireplaces, and generous gathering spaces create a welcoming environment for everyday living. A flexible fifth room within the home can be privately sectioned off and features its own exterior entrance, full bathroom, and kitchenette. The home has been carefully maintained and thoughtfully updated, including a generator for year-round living. Finished space above the carriage house provides additional options for work or hobbies. Located just moments from Pleasant Bay. This property offers convenient access to many of the Lower Cape's most loved destinations while maintaining a peaceful residential setting.
    122 days
    |
    940
    |
    65
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Whitaker Group Cape Cod 508-237-8038,

    Gibson Sotheby's International Realty

    Source: CCIMLS,MLS#: 22600770MLS Logo

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 5
      • Full bathrooms: 5
      Primary bedroom
      • Level: First
      Bedroom 2
      • Features: Bedroom 2
      • Level: First
      Bedroom 3
      • Description: Fireplace(s): Wood Burning
      • Features: Bedroom 3
      • Level: Second
      Bedroom 4
      • Features: Bedroom 4
      • Level: Second
      Primary bathroom
      • Features: Private Full Bath
      Dining room
      • Features: Dining Room
      • Level: First
      Kitchen
      • Features: Kitchen, Kitchen Island
      • Level: First
      Living room
      • Features: Cathedral Ceiling(s), Beamed Ceilings, Built-in Features
      • Level: First
      Heating
      • Has Heating (Unspecified Type)
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Washer, Refrigerator, Electric Range, Electric Dryer, Electric Water Heater
      • Laundry: Laundry Room, First Floor
      Features
      • Recessed Lighting
      • Flooring: Wood
      • Windows: Bay/Bow Windows
      • Basement: Bulkhead Access,Interior Entry,Full
      • Number of fireplaces: 3
      • Fireplace features: Wood Burning
      Interior area
      • Total structure area: 4,091
      • Total interior livable area: 4,091 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 6
      • Parking features: Garage, Open
      • Garage spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Stories: 2
      • Patio & porch: Deck
      • Exterior features: Outdoor Shower
      • Has view: Yes
      • Has water view: Yes
      • Water view: Lake/Pond
      • On waterfront: Yes
      • Body of water: Uncle Seth's Pond
      Lot
      • Size: 0.8 Acres
      Details
      • Parcel number: ORLE M:092.0 B:0006 L:0000.0
      • Zoning: R
      • Special conditions: Other - See Remarks

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Cape Cod
      • Property subtype: Single Family Residence
      Materials
      • Clapboard
      • Foundation: Poured
      • Roof: Asphalt, Pitched
      Condition
      • Updated/Remodeled, Actual
      • New construction: No
      • Year built: 1968
      • Major remodel year: 2017

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Orleans

      Financial & listing details

      • Price per square foot: $526/sqft
      • Tax assessed value: $1,520,300
      • Annual tax amount: $9,487
      • Date on market: 3/19/2026
      • Cumulative days on market: 114 days
      • Road surface type: Paved

        Estimated market value

        $2,034,000

        $1.93M - $2.14M

        $6,816/mo

        Price history

        DateEventPrice
        6/13/2026Price change$2,150,000-6.5%$526/sqft
        Source: CCIMLS #22600770 Report a problem
        3/19/2026Listed for sale$2,300,000$562/sqft
        Source: CCIMLS #22600770 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$9,487 +4.2%$1,520,300 +7.1%
        2024$9,102 +11.1%$1,419,900 +8%
        2023$8,190 +10.9%$1,314,600 +39.5%
        2022$7,388 $942,300
        2021$7,388 +4.9%$942,300 +1.1%
        2020$7,044 +3.5%$931,800 +1.4%
        2019$6,803 +31.7%$919,300 +18%
        2018$5,165 +10.7%$779,000 +5.7%
        2017$4,664 -0.6%$736,800 +1.5%
        2016$4,691 +2.4%$726,200 +1.8%
        2015$4,582 +3.5%$713,700
        2014$4,425 +12.5%$713,700 +10.7%
        2013$3,933 +1.2%$644,800 -1.9%
        2012$3,886 +6.1%$657,600
        2011$3,663 +7.5%$657,600 -0.7%
        2010$3,409 -0.3%$662,000 -5.5%
        2009$3,418 +7.3%$700,400 -0.6%
        2008$3,186 +5.8%$704,900
        2007$3,010 +1.1%$704,900 -1.5%
        2006$2,978 +13.6%$715,800 +19.8%
        2005$2,622 -16.6%$597,300 -16.2%
        2004$3,143 +13.3%$712,600 +31.5%
        2003$2,775 -2.8%$542,000 +24.1%
        2001$2,855 $436,600
        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: 02653

        Getting around

        8 / 100
        Car-Dependent
        11 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • District: Nauset

        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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