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2 Windy Hill Road
Westport CT 06880 US

$4,795,000

Active Listing ID 24182984
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6 bed
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8.00 Bath (6 Full , 2 Half)
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Lot: 1.00 Acres
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Other

$4,795,000

Active Listing ID 24182984
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2 Windy Hill Road Resort-style living meets modern luxury at 2 Windy Hill Road. Set on a private landscaped acre, this newly completed 8, 100+ SF estate by HOBI Award-winning builder Cypress Development was thoughtfully designed for the way today's luxury buyer lives, entertains, and unwinds. A dramatic two-story foyer introduces light-filled interiors highlighted by soaring ceilings, white oak flooring, natural stone finishes, and walls of European windows and doors. At the heart of the home, the chef's kitchen features marble countertops and backsplash, Sub-Zero and Wolf appliances, custom oak cabinetry, dual dishwashers, and a stunning waterfall island that seamlessly connects to the home's gathering spaces. The primary suite serves as a private retreat with vaulted oak-beamed ceilings, fireplace, sitting area, private balcony overlooking the pool, custom dressing room, and spa-like bath with heated floors and dual showers. Designed for both entertaining and wellness, the lower level includes a glass-enclosed gym, custom marble-topped bar, recreation space, guest suite, and a dedicated area ready for a golf simulator or theater. Outside, enjoy a gunite pool with automatic cover, covered outdoor living area, expansive granite patios, outdoor kitchen provisions, and a large flat lawn surrounded by mature landscaping, stone walls, and privacy plantings. A rare offering that delivers the comfort of everyday living with the amenities of a private resort.

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Property Features

  • Facts
  • Lot Size: 1.00 Acres
  • Property Type: Residential
  • Property Sub-type: Other
  • Features
  • Full Bathrooms: 6
  • 1/2 Bathrooms: 2
  • Cooling System: Zoned, Central Air
  • Exterior Finish: Balcony, Gutters, Lighting, French Doors, Underground Sprinkler, Patio
  • Heating Fuels: Zoned
  • Additional Features
  • Basement
  • Fireplace
  • Patio

School Information

  • School
  • Long Lots(Elementary)
  • Staples(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Other
  • listprice: 4795000
  • unparsedaddress: 2 Windy Hill Road
  • postalcity: Westport
  • stateorprovince: CT
  • country: US
  • postalcode: 06880
  • bathroomsfull: 6
  • bathroomshalf: 2
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 1
  • lotsizeunits: Acres
  • lotsizearea: 1
  • livingarea: 8185
  • livingareaunits: Square Feet
  • latitude: 41.144377
  • longitude: -73.339806
  • listagentfullname: Jacob Bivona
  • listagentemail: jbivona.re@gmail.com
  • listagentkey: 3yd-CTMLS-844505
  • listagentmlsid: 844505
  • listagentpreferredphone: 2037058180
  • listagentofficephone: 2033276700
  • listofficekey: 3yd-CTMLS-3548
  • listofficemlsid: 3548
  • 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: 2026
  • listingcontractdate: 2026-06-10
  • listagenturl: http://www.kwcthomes.com
  • countyorparish: Fairfield
  • elementaryschool: Long Lots
  • highschool: Staples
  • appliances: Cook Top, Oven/Range, Microwave, Range Hood, Refrigerator, Subzero, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
  • cooling: Zoned, Central Air
  • heating: Zoned
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • waterfrontyn: False
  • franchiseaffiliation: Keller Williams Realty
  • interiorfeatures: Audio System, Auto Garage Door Opener, Cable - Pre-wired, Humidifier, Open Floor Plan, Security System
  • exteriorfeatures: Balcony, Gutters, Lighting, French Doors, Underground Sprinkler, Patio
  • architecturalstyle: Modern, Colonial
  • rooms: Bathroom 7, Bedroom 4, Bedroom 3, Bedroom 1, Bathroom 5, Bathroom 2, Bathroom 3, Bathroom 8, Basement, Bedroom 5, Bedroom 6, Bathroom 1, Laundry Room, Bedroom 2, Bathroom 4, Bathroom 6
  • securityfeatures: Security System
  • patioandporchfeatures: Patio
  • basement: Full
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -73.339806, 41.14438
  • openhouse: { "AppointmentRequiredYN": false, "ListingKey": "3yd-CTMLS-24182984", "OpenHouseEndTime": "2026-06-18 14:00:00", "OpenHouseId": "5618703", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-06-18 11:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Keller Williams Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"jbivona.re@gmail.com", "ListBrokerageCity":"Ridgefield", "ListBrokerageCountry":"US", "ListBrokerageEmail":"rick.scott@kw.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"Keller Williams Realty", "ListBrokeragePhone":"(203) 438-9494", "ListBrokeragePostalCode":"06877", "ListBrokerageStateOrProvince":"CT", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"404 Main Street", "ListBrokerageWebsiteUrl":"http://www.kwcthomes.com", "ListOfficeAddress1":"2777 Summer Street ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"3548", "ListOfficeCity":"Stamford", "ListOfficeCountry":"US", "ListOfficeEmail":"rick.scott@kw.com", "ListOfficePostalCode":"06905", "ListOfficeStateOrProvince":"CT", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Westport, CT", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/2-Windy-Hill-Rd_Westport_CT_06880_M49893-90131?f=listhub&s=CTMLS&m=24182984&c=rexren", "MLSModificationTimestamp":"2026-06-18 04:05:03", "Neighborhoods":[{"Description":null, "Name":"Long Lots"}], "PostalCode":null, "RoomCount":14, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":null, "TaxDescription":null, "TaxYear":"2026"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 6/18/2026 9:43:32 AM GMT
Source Updated Date: 6/20/2026 12:35:32 AM GMT

Courtesy of: Jacob Bivona, Keller Williams Prestige Prop., jbivona.re@gmail.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.