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22 Winslow Drive
Orleans MA 02653 US

$2,300,000

Active Listing ID 22600770
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5 bed
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5.00 Bath (5 Full)
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Lot: 0.80 Acres
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Single Family Residence

$2,300,000

Active Listing ID 22600770
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22 Winslow Drive 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.

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Property Features

  • Facts
  • Lot Size: 0.80 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 5
  • Cooling System: Central Air
  • Exterior Finish: Underground Sprinkler System, Outdoor Shower
  • Floor Covering: Wood
  • Roof Type: Asphalt
  • Heating Fuels: Forced Air
  • Additional Features
  • Basement
  • Fireplace
  • Patio
  • Waterfront

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 2300000
  • unparsedaddress: 22 Winslow Drive
  • postalcity: Orleans
  • stateorprovince: MA
  • country: US
  • postalcode: 02653
  • bathroomsfull: 5
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.8
  • lotsizeunits: Acres
  • lotsizearea: 0.8
  • livingarea: 4091
  • livingareaunits: Square Feet
  • latitude: 41.737078
  • longitude: -69.996227
  • listagentfullname: Whitaker Group Cape Cod
  • listagentemail: Jen.Whitaker@gibsonsir.com
  • listagentkey: 3yd-CCIAORMA-T31
  • listagentmlsid: T31
  • listagentpreferredphone: 5082378038
  • listagentofficephone: 5082378038
  • listofficekey: 3yd-CCIAORMA-GSIR1
  • listofficemlsid: GSIR1
  • disclaimer: Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: CCIAORMA
  • yearbuilt: 1968
  • listingcontractdate: 2026-03-16
  • countyorparish: Barnstable
  • parcelnumber: ORLE M:092.0 B:0006 L:0000.0
  • elementaryschooldistrict: Nauset
  • middleorjuniorschooldistrict: Nauset
  • highschooldistrict: Nauset
  • appliances: Water Heater, Electric Range, Dishwasher, Refrigerator, Washer
  • cooling: Central Air
  • constructionmaterials: Clapboard
  • flooring: Wood
  • heating: Forced Air
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 2
  • parkingtotal: 6
  • parkingfeatures: Driveway, Open
  • roof: Asphalt
  • view: Lake
  • waterfrontyn: True
  • franchiseaffiliation: None
  • interiorfeatures: Attic Storage, Recessed Lighting, Kitchen Island
  • exteriorfeatures: Underground Sprinkler System, Outdoor Shower
  • rooms: Bathroom 3, Bathroom 2, Laundry Room, Basement, Dining Room, Bedroom 4, Bedroom 2, Bedroom 1, Bathroom 4, Bathroom 1, Bedroom 5, Bedroom 3, Bathroom 5
  • otherstructures: Storage
  • patioandporchfeatures: Deck
  • basement: Full
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -69.99622, 41.73708
  • openhouse: { "AppointmentRequiredYN": false, "ListingKey": "3yd-CCIAORMA-22600770", "OpenHouseEndTime": "2026-03-22 13:00:00", "OpenHouseId": "2493942", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-03-22 11:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Gibson Sotheby's International Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"Jen.Whitaker@gibsonsir.com", "ListBrokerageCity":"Brewster", "ListBrokerageCountry":"US", "ListBrokerageEmail":null, "ListBrokerageLogoUrl":null, "ListBrokerageName":"Gibson Sotheby's International Realty", "ListBrokeragePhone":"(508) 896-5000", "ListBrokeragePostalCode":null, "ListBrokerageStateOrProvince":"MA", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"2404 Main Street", "ListBrokerageWebsiteUrl":null, "ListOfficeAddress1":"6 Route 6A ", "ListOfficeAddress2":"", "ListOfficeBrokerMlsId":"GSIR1", "ListOfficeCity":"Orleans", "ListOfficeCountry":"USA", "ListOfficeEmail":null, "ListOfficePostalCode":"02653", "ListOfficeStateOrProvince":"MA", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Orleans, MA", "ListingURL":null, "MLSModificationTimestamp":"2026-03-23 06:48:30", "Neighborhoods":[{"Description":null, "Name":"Orleans"}], "PostalCode":null, "RoomCount":11, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":9487, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 3/23/2026 6:59:13 AM GMT
Source Updated Date: 3/24/2026 12:49:21 PM GMT

Courtesy of: Whitaker Group Cape Cod, Gibson Sotheby's International Realty, Jen.Whitaker@gibsonsir.com

Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.