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131 Oakside Drive
Smithtown NY 11787 US

$1,375,000

Active Listing ID 933632
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4 bed
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3.00 Bath (3 Full)
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Lot: 1.86 Acres
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Single Family Residence

$1,375,000

Active Listing ID 933632
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131 Oakside Drive Perched atop a scenic hill in one of Smithtown's most prestigious enclaves, this architecturally distinctive ranch-style home offers an unmatched combination of total privacy, eco-conscious design, and serene natural beauty. Located within the award-winning Smithtown School District and surrounded by lush woodlands near the Nissequogue River, this Mid Century Modern home is a true retreat for those who value tranquility, style, and effortless indoor-outdoor living. From the moment you arrive, the home's striking exterior, expansive setting, and custom design features signal that this is no ordinary residence. Inside, the open-concept layout is both inviting and impressive, with a peaceful, zen vibe and a bridge over a one-of-a-kind custom koi pond. Soaring vaulted ceilings and radiant heated floors run through the main living areas. Walls of oversized sliding glass doors flood the interior with natural light and seamlessly connect the indoors to a sprawling Trex deck-perfect for entertaining on any scale. Cleverly hidden solar panels provide electricity at almost no monthly cost. At the heart of the home lies a beautifully appointed, modern kitchen featuring quartz countertops, an oversized center island, and sleek custom cabinetry. The space flows effortlessly into the expansive great room, creating a bright and airy living experience that feels both refined and relaxed. A two-sided fireplace enhances both the living and dining rooms. Step outside and discover a true entertainer's dream: a brand-new resort-style pool with a shallow sun bed lounge area, custom stone fire pit, and a vast deck ideal for hosting gatherings or simply enjoying peaceful mornings. A thoughtfully designed lower level includes a private guest suite with its own full bath and separate above-grade entrance-ideal for extended stays or multi-generational living. A fully equipped gym completes the lower level, with a ton of closets for storage. Propane generator. Unique in every sense, this residence is a rare find-a perfectly curated blend of modern comfort and natural serenity.

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Property Features

  • Facts
  • Lot Size: 1.86 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 3
  • Cooling System: Central Air
  • Floor Covering: Combination, Wood
  • Heating Fuels: Radiant Floor, Radiant, Oil
  • Additional Features
  • Basement
  • Fireplace
  • Patio
  • Pool

School Information

  • School
  • Smithtown Elementary School(Elementary)
  • Nesaquake Middle School(MiddleSchool)
  • Smithtown High School-East(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 1375000
  • unparsedaddress: 131 Oakside Drive
  • postalcity: Smithtown
  • stateorprovince: NY
  • country: US
  • postalcode: 11787
  • bathroomsfull: 3
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 1.86
  • lotsizeunits: Acres
  • lotsizearea: 1.86
  • livingarea: 3300
  • livingareaunits: Square Feet
  • latitude: 40.882999
  • longitude: -73.198866
  • listagentfullname: Kristine J. Livadas
  • listagentemail: kristine.livadas@compass.com
  • listagentkey: 3yd-MLSLINY-144477
  • listagentmlsid: 144477
  • listagentpreferredphone: 5167760039
  • listagentofficephone: 5167760039
  • listofficekey: 3yd-MLSLINY-CMPA09
  • listofficemlsid: CMPA09
  • 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: 1967
  • listingcontractdate: 2025-11-08
  • listagenturl: https://www.compass.com/
  • countyorparish: Suffolk County
  • parcelnumber: 0800-035-00-04-00-026-000
  • elementaryschool: Smithtown Elementary School
  • highschool: Smithtown High School-East
  • elementaryschooldistrict: Smithtown
  • middleorjuniorschooldistrict: Smithtown
  • highschooldistrict: Smithtown
  • appliances: Dishwasher, Dryer, Microwave, Oven, Range, Refrigerator, Washer
  • cooling: Central Air
  • constructionmaterials: Cedar
  • flooring: Combination, Wood
  • heating: Radiant Floor, Radiant, Oil
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 1
  • parkingtotal: 10
  • parkingfeatures: Driveway
  • waterfrontyn: False
  • franchiseaffiliation: None
  • interiorfeatures: First Floor Bedroom, First Floor Full Bath, Beamed Ceilings, Breakfast Bar, Cathedral Ceiling(s), Chefs Kitchen, Eat-in Kitchen, Entrance Foyer, Formal Dining, In-Law Floorplan, Open Floorplan, Open Kitchen, Primary Bathroom, Smart Thermostat, Storage
  • architecturalstyle: Ranch
  • rooms: Living Room, Bedroom 1, Bedroom 4, Dining Room, Exercise Room, Family Room, Basement, Bedroom 3, Bathroom 3, Bathroom 1, Bathroom 2, Kitchen, Bedroom 2
  • otherstructures: Storage
  • utilities: Propane
  • patioandporchfeatures: Patio, Deck
  • basement: Finished
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -73.19887, 40.883
  • openhouse: { "AppointmentRequiredYN": false, "ListingKey": "3yd-MLSLINY-933632", "OpenHouseEndTime": "2025-11-15 14:00:00", "OpenHouseId": "671720", "OpenHouseRemarks": null, "OpenHouseStartTime": "2025-11-15 12:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }, { "AppointmentRequiredYN": false, "ListingKey": "3yd-MLSLINY-933632", "OpenHouseEndTime": "2025-11-15 14:00:00", "OpenHouseId": "671754", "OpenHouseRemarks": "Send or bring buyers!", "OpenHouseStartTime": "2025-11-15 12:00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Compass Greater NY LLC", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"kristine.livadas@compass.com", "ListBrokerageCity":"New York", "ListBrokerageCountry":"US", "ListBrokerageEmail":"Support@Compass.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"Compass Greater NY LLC", "ListBrokeragePhone":"(212) 913-9058", "ListBrokeragePostalCode":"1001", "ListBrokerageStateOrProvince":null, "ListBrokerageUnitNumber":"Fl 9", "ListBrokerageUnparsedAddress":"90 5th Ave, NY", "ListBrokerageWebsiteUrl":"https://www.compass.com/", "ListOfficeAddress1":"41 The Plz ", "ListOfficeAddress2":"Fl 9", "ListOfficeBrokerMlsId":"CMPA09", "ListOfficeCity":"Locust Valley", "ListOfficeCountry":"USA", "ListOfficeEmail":"gabrielle.brower@compass.com", "ListOfficePostalCode":"11560", "ListOfficeStateOrProvince":"NY", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Ranch - Smithtown, NY", "ListingURL":null, "MLSModificationTimestamp":"2026-01-04 18:39:37", "Neighborhoods":[], "PostalCode":null, "RoomCount":7, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":20849, "TaxDescription":null, "TaxYear":"2024"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 1/8/2026 7:01:24 PM GMT
Source Updated Date: 1/10/2026 12:41:48 PM GMT

Courtesy of: Kristine J. Livadas, Compass Greater NY LLC, kristine.livadas@compass.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.