Property photo 1
Property photo 2
3 Beds
2 Baths

$875,000

143 Oakside Drive, Smithtown NY, 11787

Price per sqftN/A
Built in1848
Property typeResidential
Courtesy of Howard Hanna Coach, Jessica L. Stanco AHWD PSA Listing Contact: 631-757-4000

Overview

Coming soon

Listed Nov 12, 2026

Updated 10h ago

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. ** PROFESSIONAL PHOTOS COMING SOON**

$5,821/mo

Est. mortgage payment based on a $875,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
1070587

Interior Features

Bedrooms
3
Bathrooms
2
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
1 Acre

Other Property Details

Taxes
$14,136
Tax Frequency
Annually
View
Yes
Pool
Yes
55+/Senior Community
No

Listings courtesy of OneKey MLS as distributed by MLS GRID

All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) nor Marc Gerber shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Properties displayed may be listed or sold by various participants in the MLS.

Based on information submitted to the MLS GRID as of 4:18 AM UTC on 11/8/2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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