143 Oakside Drive, Smithtown, NY 11787

$875,000 · 3 bed · 2 bath · built 1848 · MLS# 1070587 · Coming Soon

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…

Single-family homes in the Smithtown Central School District sold for a median of $840,000 (typically $735,000–$985,000) across 441 recorded sales between Nov 5, 2025 and Nov 2, 2026, up 3.1% on the 12 months before. This home's $875,000 list price sits in the mid-market single-family tier for the Smithtown Central School District.

ZIP 11787 has about 2.5 months of single family inventory — seller's market. Demand is outpacing supply, so homes sell quickly with firm pricing and limited room to negotiate.

At about $14,136 a year, this home's property tax is in line with the roughly $15,000 typical for Smithtown Central School District. Suffolk bills combine town, school and special-district levies, so two homes at the same price in neighboring districts can carry materially different taxes. Exemptions such as STAR, Senior or Veteran move the number as well — a new owner's bill is often not the same as the seller's.

OneKey MLS (recorded LI sales, trailing 12mo) + actual tax