149 Grassy Pond Drive S, Smithtown, NY 11787

$765,000 · 3 bed · 3 bath · 1,891 sq ft · built 1955 · MLS# 1036970 · Active

Welcome to Smithtown Pines! I am excited to share this beautifully maintained 3-Bedroom, 2.5-Bathroom Colonial home which was totally rebuilt from the foundation up in 2003 with a full basement. The exterior features a charming covered porch and a deep backyard complete with a large deck and a pond, perfect for outdoor relaxation. Inside, the first floor boasts a Living Room with a dual-sided gas fireplace that opens into the Dining area, which features sliding glass doors. The large Kitchen comes equipped with stainless steel appliances and leads to a…

Single-family homes in the Hauppauge Union Free School District sold for a median of $850,000 (typically $750,000–$1,000,000) across 144 recorded sales between Oct 6, 2025 and Sep 30, 2026, up 8.3% on the 12 months before. This home's $765,000 list price sits in the mid-market single-family tier for the Hauppauge Union Free School District.

ZIP 11787 has about 2.7 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 $12,406 a year, this home's property tax is in line with the roughly $12,000 typical for Hauppauge Union Free 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