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4 Sherwood Island Lane
Westport CT 06880 US

$15,000,000

Active Listing ID 24160355
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7 bed
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7.00 Bath (6 Full , 1 Half)
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Lot: 20.85 Acres
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Other

$15,000,000

Active Listing ID 24160355
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4 Sherwood Island Lane Hidden along a private lane in Westport's Greens Farms neighborhood, this extraordinary 20-acre waterfront estate unfolds as one of the most remarkable shoreline settings ever offered. For more than 65 years, it has been held and enjoyed by the same family as a place to gather, unwind, and take in the ever-changing views across Sherwood Island Park and Long Island Sound. Surrounded by protected open space with no immediate neighbors, the property offers a rare sense of peace and privacy-reminiscent of the Lowcountry, the Hamptons, or Nantucket, a scale and atmosphere seldom found in Westport. Beautiful in every season, the setting also offers extraordinary birdlife and nature watching. Yet it remains moments to the Post Road, train, and town centers, and just one hour from Manhattan. A collection of residences and outbuildings is thoughtfully positioned across the land, including two circa 1940s three-bedroom guesthouses with sweeping water views, creating a true family compound where generations can come together while maintaining a sense of independence. Other structures offer flexibility for staff or future use. The grounds invite a lifestyle centered around the outdoors, with a tennis court, indoor pool, pool house, and formal gardens set within expansive lawns that stretch toward the water. Whether preserved, enhanced, or reimagined, this is a once-in-a-generation opportunity to shape a legacy estate-one that will be experienced and remembered for years to come.

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Property Features

  • Facts
  • Lot Size: 20.85 Acres
  • Property Type: Residential
  • Property Sub-type: Other
  • Features
  • Full Bathrooms: 6
  • 1/2 Bathrooms: 1
  • Cooling System: Central Air
  • Heating Fuels: Zoned
  • Additional Features
  • Basement
  • Fireplace
  • Waterfront

School Information

  • School
  • Greens Farms(Elementary)
  • Staples(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Other
  • listprice: 15000000
  • unparsedaddress: 4 Sherwood Island Lane
  • postalcity: Westport
  • stateorprovince: CT
  • country: US
  • postalcode: 06880
  • bathroomsfull: 6
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 20.85
  • lotsizeunits: Acres
  • lotsizearea: 20.85
  • livingarea: 6215
  • livingareaunits: Square Feet
  • latitude: 41.118892
  • longitude: -73.330233
  • listagentfullname: Andrew Whiteley
  • listagentemail: awhiteley@bhsusa.com
  • listagentkey: 3yd-CTMLS-8005
  • listagentmlsid: 8005
  • listagentpreferredphone: 2032581595
  • listagentofficephone: 2032541500
  • listofficekey: 3yd-CTMLS-BROWN06
  • listofficemlsid: BROWN06
  • disclaimer: Copyright © 2026 SmartMLS, 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: CTMLS
  • yearbuilt: 1940
  • listingcontractdate: 2026-03-26
  • listagenturl: http://bhsusa.com
  • countyorparish: Fairfield
  • elementaryschool: Greens Farms
  • highschool: Staples
  • appliances: Wall Oven, Refrigerator, Freezer, Dishwasher, Washer, Dryer
  • cooling: Central Air
  • heating: Zoned
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • waterfrontyn: True
  • franchiseaffiliation: None
  • interiorfeatures: Audio System, Cable - Pre-wired, Sauna, Security System
  • architecturalstyle: Colonial
  • rooms: Bedroom 1, Bedroom 6, Bedroom 4, Bedroom 3, Bathroom 2, Bathroom 3, Bathroom 4, Bathroom 6, Bedroom 2, Bathroom 5, Bedroom 7, Basement, Bedroom 5, Bathroom 7, Bathroom 1
  • securityfeatures: Security System
  • basement: Partially Finished, Full
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -73.33023, 41.118893
  • openhouse: { "AppointmentRequiredYN": false, "ListingKey": "3yd-CTMLS-24160355", "OpenHouseEndTime": "2026-06-04 19:00:00", "OpenHouseId": "4911121", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-06-04 17:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Brown Harris Stevens Connecticut, LLC", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"ctinfo@halstead.com", "ListBrokerageCity":"Westport", "ListBrokerageCountry":"US", "ListBrokerageEmail":"jdicenzo@bhsusa.com", "ListBrokerageLogoUrl":"http://brokerlogos.listhub.net/CTMLS/1b8354c1dc7b11e8860f0242ac110005/20211108152830974.png", "ListBrokerageName":"Brown Harris Stevens Connecticut, LLC", "ListBrokeragePhone":"(203) 221-0666", "ListBrokeragePostalCode":"06880", "ListBrokerageStateOrProvince":"CT", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"56 Post Road East", "ListBrokerageWebsiteUrl":"http://bhsusa.com", "ListOfficeAddress1":"167 Old Post Road ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"BROWN06", "ListOfficeCity":"Southport", "ListOfficeCountry":"US", "ListOfficeEmail":"jdicenzo@bhsusa.com", "ListOfficePostalCode":"06890", "ListOfficeStateOrProvince":"CT", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Westport, CT", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/4-Sherwood-Island-Ln_Westport_CT_06880_M37987-32079?f=listhub&s=CTMLS&m=24160355&c=rexren", "MLSModificationTimestamp":"2026-06-03 11:15:48", "Neighborhoods":[{"Description":null, "Name":"Greens Farms"}], "PostalCode":null, "RoomCount":14, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":73686, "TaxDescription":null, "TaxYear":"2026"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 6/3/2026 12:05:50 PM GMT
Source Updated Date: 6/4/2026 12:54:43 AM GMT

Courtesy of: Andrew Whiteley, Brown Harris Stevens, awhiteley@bhsusa.com

Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.