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143 Oakside Drive
Smithtown NY 11787 US

$875,000

Active Listing ID 1070587
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3 bed
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2.00 Bath (1 Full , 1 Half)
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Lot: 1.00 Acres
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Single Family Residence

$875,000

Active Listing ID 1070587
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143 Oakside Drive Historic charm meets modern farmhouse living in a tranquil setting with a view of the Nissequogue River. Perched on a full acre, this special property offers a peaceful connection to nature, with deer, wild turkeys, and other wildlife making frequent appearances. Built in the late 19th century as a servants' cottage for the Kenyon Estate, the home blends its distinctive past with extensive updates completed within the last two years. A fabulous farmhouse kitchen offers abundant counter space and opens to the dining area, while two beautifully renovated bathrooms carry the modern farmhouse style throughout. A unique third bedroom, also ideal as a separate home office, awaits finishing, with materials included in the sale. Extensive improvements include all-new plumbing, two-zone heating and central air, new 200-amp electric service, roof, and Andersen windows. A renovated inground pool adds to the outdoor enjoyment. This special location affords homeowners a peaceful retreat with everyday conveniences close by. Enjoy beach rights to multiple Town of Smithtown beaches, boat ramp access, and nearby hiking trails, parks, nature preserves, and golf courses. Main Street's restaurants and shops are just moments away, with convenient access to the LIRR and parkways. A rare opportunity to own a piece of history in a setting that feels like a retreat.

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Property Features

  • Facts
  • Lot Size: 1.00 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 1
  • 1/2 Bathrooms: 1
  • Cooling System: Central Air
  • Exterior Finish: Mailbox
  • Floor Covering: Vinyl
  • Heating Fuels: Oil, Forced Air
  • Additional Features
  • Basement
  • Patio
  • Pool

School Information

  • School
  • Smithtown Elementary School(Elementary)
  • Accompsett Middle School(MiddleSchool)
  • Smithtown High School-West(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 875000
  • unparsedaddress: 143 Oakside Drive
  • postalcity: Smithtown
  • stateorprovince: NY
  • country: US
  • postalcode: 11787
  • bathroomsfull: 1
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 1
  • lotsizeunits: Acres
  • lotsizearea: 1
  • livingarea: 0
  • livingareaunits: Square Feet
  • latitude: 40.885099
  • longitude: -73.199325
  • listagentfullname: Jessica L. Stanco AHWD PSA
  • listagentemail: jstanco@coachrealtors.com
  • listagentkey: 3yd-MLSLINY-160862
  • listagentmlsid: 160862
  • listagentpreferredphone: 6316783834
  • listagentofficephone: 6316783834
  • listofficekey: 3yd-MLSLINY-CARE07
  • listofficemlsid: CARE07
  • disclaimer: Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: MLSLINY
  • yearbuilt: 1848
  • listingcontractdate: 2026-11-06
  • listagentfax: 6317571709
  • listagenturl: http://www.coachrealtors.com
  • countyorparish: Suffolk County
  • parcelnumber: 0800-035-00-04-00-020-000
  • elementaryschool: Smithtown Elementary School
  • highschool: Smithtown High School-West
  • elementaryschooldistrict: Smithtown
  • middleorjuniorschooldistrict: Smithtown
  • highschooldistrict: Smithtown
  • appliances: Dishwasher, Dryer, Electric Range, Electric Water Heater, Refrigerator, Stainless Steel Appliance(s), Washer
  • cooling: Central Air
  • constructionmaterials: Clapboard, Frame
  • flooring: Vinyl
  • heating: Oil, Forced Air
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Driveway
  • view: River
  • waterfrontyn: False
  • franchiseaffiliation: Independent
  • interiorfeatures: Eat-in Kitchen, Open Kitchen, Quartz/Quartzite Counters, Recessed Lighting, Walk-In Closet(s), Washer/Dryer Hookup
  • exteriorfeatures: Mailbox
  • windowfeatures: Wood Frames, Skylight(s)
  • architecturalstyle: Colonial
  • rooms: Basement, Bedroom 2, Bedroom 1, Bathroom 1, Bedroom 3, Bathroom 2
  • securityfeatures: Security System
  • otherstructures: Outbuilding
  • utilities: Cable Available
  • patioandporchfeatures: Porch, Patio
  • basement: Storage Space, Unfinished
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • fencing: Chain Link
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: False
  • internetconsumercommentyn: False
  • location: -73.199326, 40.885098
  • openhouse: { "AppointmentRequiredYN": false, "ListingKey": "3yd-MLSLINY-1070587", "OpenHouseEndTime": "2026-11-14 14:00:00", "OpenHouseId": "14109485", "OpenHouseRemarks": "1st Weekend Open House for this Renovated Farmhouse Style Home! Come check out the River View too!", "OpenHouseStartTime": "2026-11-14 12:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }, { "AppointmentRequiredYN": false, "ListingKey": "3yd-MLSLINY-1070587", "OpenHouseEndTime": "2026-11-15 14:30:00", "OpenHouseId": "14143587", "OpenHouseRemarks": "1st Weekend Open House for this Renovated Farmhouse Style Home! Come check out the River View too!", "OpenHouseStartTime": "2026-11-15 12:30:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Howard Hanna | Coach Realtors", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"jstanco@coachrealtors.com", "ListBrokerageCity":"Northport", "ListBrokerageCountry":"US", "ListBrokerageEmail":"info@coachrealtors.com", "ListBrokerageLogoUrl":"http://lh.rdcpix.com/c5ababc3208c3ea801208c999cc3006bk-c1446535556r.png", "ListBrokerageName":"Howard Hanna | Coach Realtors", "ListBrokeragePhone":"(800) 321-7356", "ListBrokeragePostalCode":"11768", "ListBrokerageStateOrProvince":null, "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"66 Gilbert Street", "ListBrokerageWebsiteUrl":"http://www.coachrealtors.com", "ListOfficeAddress1":"66 Gilbert St ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"CARE07", "ListOfficeCity":"Northport", "ListOfficeCountry":"US", "ListOfficeEmail":"mls@coachrealtors.com", "ListOfficePostalCode":"11768", "ListOfficeStateOrProvince":"NY", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential, Smithtown, NY", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/143-Oakside-Dr_Smithtown_NY_11787_M48133-57283?f=listhub&s=MLSLINY&m=1070587&c=rexren", "MLSModificationTimestamp":"2026-11-14 14:49:36", "Neighborhoods":[], "PostalCode":null, "RoomCount":6, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":14136, "TaxDescription":null, "TaxYear":"2026"}], "UnitNumber":null, "UnparsedAddress":null}
  • GarageSpaces: 0
Listing Changed: 11/14/2026 3:14:57 PM GMT
Source Updated Date: 11/15/2026 12:49:26 AM GMT

Courtesy of: Jessica L. Stanco AHWD PSA, Howard Hanna Coach, jstanco@coachrealtors.com

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