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109 Oakside Drive
Smithtown NY 11787 US

$1,450,000

Active Listing ID 915379
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4 bed
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4.00 Bath (3 Full , 1 Half)
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Lot: 2.00 Acres
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Single Family Residence

$1,450,000

Active Listing ID 915379
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109 Oakside Drive Welcome to 109 Oakside Dr., your dream equestrian retreat, set on 2 scenic acres in the heart of Smithtown. This updated 4-bed, 3.5-bath ranch blends easy single-level living with true equestrian amenities. An eat-in kitchen with granite counters and stainless appliances opens to a spacious family room anchored by a stone fireplace. Throughout the home you'll find hardwood floors, custom millwork, and recessed lighting. The private main bedroom offers direct access to a low-maintenance Azek deck overlooking a serene backyard with outdoor fireplace, waterfall, and koi pond. A finished basement adds flexible recreation/storage space. For horse enthusiasts: a meticulously maintained barn with 4 heated stalls, tack room, washroom, and hayloft; plus a PVC-fenced paddock with lighting and irrigation for year-round care. Move-in ready and thoughtfully appointed-an exceptional property where comfort, convenience, and equestrian living come together.

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Property Features

  • Facts
  • Lot Size: 2.00 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 3
  • 1/2 Bathrooms: 1
  • Cooling System: Central Air
  • Exterior Finish: Fencing
  • Heating Fuels: Oil, Hot Water(Heating)
  • Additional Features
  • Basement

School Information

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

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 1450000
  • unparsedaddress: 109 Oakside Drive
  • postalcity: Smithtown
  • stateorprovince: NY
  • country: US
  • postalcode: 11787
  • bathroomsfull: 3
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 2
  • lotsizeunits: Acres
  • lotsizearea: 2
  • livingarea: 2400
  • livingareaunits: Square Feet
  • latitude: 40.879941
  • longitude: -73.203836
  • listagentfullname: George C. McKnight
  • listagentemail: george@georgemcknight.com
  • listagentkey: 3yd-MLSLINY-79159
  • listagentmlsid: 79159
  • listagentpreferredphone: (631) 269-6666
  • listagentofficephone: 6312580110
  • listofficekey: 3yd-MLSLINY-MCKN01
  • listofficemlsid: MCKN01
  • 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: 1960
  • listingcontractdate: 2025-09-20
  • listagentfax: 6312694789
  • listagenturl: http://www.C21McKnight.com
  • countyorparish: Suffolk County
  • parcelnumber: 0800-035-00-04-00-036-000
  • elementaryschool: Accompsett Elementary School
  • highschool: Smithtown High School-West
  • elementaryschooldistrict: Smithtown
  • middleorjuniorschooldistrict: Smithtown
  • highschooldistrict: Smithtown
  • appliances: Dishwasher, Dryer, Electric Cooktop, Electric Oven, Microwave, Refrigerator
  • cooling: Central Air
  • constructionmaterials: Vinyl Siding
  • heating: Oil, Hot Water(Heating)
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • waterfrontyn: False
  • franchiseaffiliation: Century 21 Real Estate
  • interiorfeatures: First Floor Bedroom, First Floor Full Bath, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters
  • architecturalstyle: Ranch
  • rooms: Dining Room, Basement, Bathroom 4, Bedroom 2, Bedroom 4, Bathroom 2, Bathroom 3, Bedroom 1, Bathroom 1, Bedroom 3
  • otherstructures: Arena
  • utilities: Cable Available
  • basement: Finished
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -73.203835, 40.87994
  • openhouse: { "AppointmentRequiredYN": false, "ListingKey": "3yd-MLSLINY-915379", "OpenHouseEndTime": "2026-01-18 15:00:00", "OpenHouseId": "870216", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-01-18 13:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }, { "AppointmentRequiredYN": false, "ListingKey": "3yd-MLSLINY-915379", "OpenHouseEndTime": "2026-01-18 15:00:00", "OpenHouseId": "870218", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-01-18 13:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }, { "AppointmentRequiredYN": false, "ListingKey": "3yd-MLSLINY-915379", "OpenHouseEndTime": "2026-01-17 15:00:00", "OpenHouseId": "870229", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-01-17 13:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }, { "AppointmentRequiredYN": false, "ListingKey": "3yd-MLSLINY-915379", "OpenHouseEndTime": "2026-01-17 15:00:00", "OpenHouseId": "870235", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-01-17 13:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Century 21 McKnight Realtors", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"george@georgemcknight.com", "ListBrokerageCity":"Kings Park", "ListBrokerageCountry":"US", "ListBrokerageEmail":"info@C21McKnight.com", "ListBrokerageLogoUrl":"http://brokerlogos.listhub.net/104/220297/20121210173333786.png", "ListBrokerageName":"Century 21 McKnight Realtors", "ListBrokeragePhone":"(631) 269-6666", "ListBrokeragePostalCode":"11754", "ListBrokerageStateOrProvince":null, "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"1 Main Street", "ListBrokerageWebsiteUrl":"http://www.C21McKnight.com", "ListOfficeAddress1":"38 Main St ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"MCKN01", "ListOfficeCity":"Kings Park", "ListOfficeCountry":"USA", "ListOfficeEmail":"george.mcknight@c21mcknight.com", "ListOfficePostalCode":"11754", "ListOfficeStateOrProvince":"NY", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Ranch - Smithtown, NY", "ListingURL":null, "MLSModificationTimestamp":"2026-01-17 20:09:42", "Neighborhoods":[], "PostalCode":null, "RoomCount":7, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":29386, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 1/17/2026 8:17:39 PM GMT
Source Updated Date: 1/20/2026 6:40:20 PM GMT

Courtesy of: George C. McKnight, George Mcknight REALTORS Inc, george@georgemcknight.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.