• 143 Oakside Drive, Smithtown, NY 11787 Main Photo

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New to the Market
BEDS3 BATHS1 full 1 partial MLS#1070587
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLSmithtown

Property Description

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.

143 Oakside Drive | MLS# 1070587

This single family home located at 143 Oakside Drive, Smithtown, NY 11787 is currently listed for sale with an asking price of $875,000. This property was built in 1848 and has 3 bedrooms and 1 full and 1 partial baths. Oakside Drive is located within the Smithtown school district. Search Smithtown real estate on www.laffey.com today.

Upcoming Open Houses

Open House Saturday November 14th, 12:00pm - 2:00pm
Open House Sunday November 15th, 12:30pm - 2:30pm

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Storage Space, Unfinished
Cooling: Central Air
Fenced: Yes
Heating: Forced Air, Oil
Home Style: Colonial
Lot Size: 1.00 Acres
Taxes: $14,136
Year Built: 1848

Amenities

Eat-in Kitchen
Open Kitchen
Quartz/Quartzite Counters
Recessed Lighting
Walk-In Closet(s)
Washer/Dryer Hookup
Mailbox

Feature Descriptions

Appliances: Dishwasher, Dryer, Electric Range, Electric Water Heater, Refrigerator, Stainless Steel Appliance(s), Washer
Attic: Partial, Scuttle
Days on Site: 5
Exterior: Clapboard, Frame
Fencing: Chain Link
Flooring: Laminate
Heating Zones: 2
House Faces: North
Included In Taxes: Trash
Laundry: In Basement
Lot Features: Back Yard, Front Yard, Part Wooded, Sprinklers In Front
Number Of Kitchens: 1
On Market Date: 2026-11-12
Other Structures: Barn(s), Outbuilding, Shed(s)
Parcel Number: 0800-035-00-04-00-020-000
Parking Features: Driveway
Patio And Porch: Patio, Porch
Pool Features: Fenced, In Ground, Pool Cover
Rental Term: Monthly
Road Responsibility: Public Maintained Road
Rooms Total: 6
Security: yes
Security Features: Security System, Smoke Detector(s), Video Cameras
Sewer: Septic Tank
Skylight: Y
Special View Info: River
Swimming Pool: Yes
Utilities: Cable Available, Electricity Connected, Phone Available, Trash Collection Public, Water Connected
Water: Public
Window Features: New Windows, Skylight(s), Wood Frames
Wooded: Yes

Local Schools

High School: Smithtown High School-West
Middle School: Accompsett Middle School
Elementary School: Smithtown Elementary School
School District: Smithtown

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Estimated Payment

$ 3,380.58 per month $1,947.37 Principal & Interest $1,178.00 Property Tax $255.21 Homeowner's Insurance

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Listed By / Shown By

Listing By

Agency Name: Howard Hanna Coach
Agency Contact: 631-757-4000

Shown By

Agency Title: Laffey Real Estate
Agency Phone: 1-888-289-6902

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 11/12/2026. The listing information on this page last changed on 11/12/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 11/12/2026 12:03:46 AM EST) or OneKey MLS (last updated Thu 11/12/2026 12:00:22 AM EST). Real estate listings held by brokerage firms other than Laffey Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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