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Sold for $2,000,000
  • $2,000,000

    22 Winslow Drive, Orleans, MA 02653

    5beds
    4,091sqft
    Single Family Residence
    Built in 1968
    0.8 Acres Lot
    $2,001,700 Zestimate®
    $489/sqft
    $3,447 Estimated rent

    Home value

    $2,001,700

    $1.84M - $2.18M

    $3,447/mo

    Zestimate® history
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    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.

    Zillow last checked:

    Listing updated:

    Listed by:

    Whitaker Group Cape Cod 508-237-8038,

    Gibson Sotheby's International Realty

    Bought with:

    The Bohman Hartung Group

    Gibson Sotheby's International Realty

    Source: CCIMLS,MLS#: 22600770MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 5
    • Bathrooms: 5
    • Full bathrooms: 5
    Heating
    • Has Heating (Unspecified Type)
    Cooling
    • Central Air
    Appliances
    • Included: Dishwasher, Electric Range, Refrigerator, Washer, Electric, Water Heater
    • Laundry: Electric Dryer
    Features
    • Attic Storage, Recessed Lighting
    • Flooring: Wood
    • Basement: Full
    • Number of fireplaces: 3
    Interior area
    • Total structure area: 4,091
    • Total interior livable area: 4,091 sqft

    Property

    Parking
    • Total spaces: 6
    • Parking features: Detached, Garage Door Opener, Driveway, Paved
    • Garage spaces: 2
    • Has uncovered spaces: Yes
    Features
    • Stories: 2
    • Patio & porch: Deck
    • Exterior features: Outdoor Shower, Underground Sprinkler System
    • On waterfront: Yes
    • Waterfront features: Waterview, Waterfront, Pond
    • Body of water: Uncle Seth's Pond,Fresh
    Lot
    • Size: 0.8 Acres
    Details
    • Parcel number: ORLE M:092.0 B:0006 L:0000.0
    • Special conditions: Other - See Remarks

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence
    Materials
    • Clapboard
    • Roof: Asphalt,Pitched
    Condition
    • Year built: 1968

    Utilities & green energy

    • Water: Well, Public

    Community & HOA

    HOA
    • Has HOA: No
    Location
    • Region: Orleans

    Financial & listing details

    • Price per square foot: $489/sqft
    • Tax assessed value: $1,520,300
    • Annual tax amount: $9,487
    • Date on market: 3/19/2026
    • Cumulative days on market: 115 days

    Price history

    DateEventPrice
    9/8/2026Sold$2,000,000-7%$489/sqft
    Source: CCIMLS #22600770 Report a problem
    7/21/2026Pending sale$2,150,000$526/sqft
    Source: MLS PIN #73489022 Report a problem
    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

    Neighborhood: 02653

    Nearby schools

    GreatSchools rating
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    Estimated market value
    $2,001,700
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    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $2,001,700