64A N Midway Road, Shelter Island, NY 11964

$2,199,000 · 5 bed · 4 bath · 2,642 sq ft · built 1977 · MLS# 1029569 · Active

A rare turnkey Shelter Island retreat with two distinct homes tucked away on nearly an acre in the heart of Shelter Island, 64A North Midway Road presents a truly unique opportunity to own two homes on one private property. Surrounded by mature trees, expansive lawns, and a picturesque pond next door, this exceptional estate blends privacy, flexibility, and timeless charm. This rare property offers remarkable versatility to fit your lifestyle. The welcoming ranch-style main home offers a comfortable living space with 3 bedrooms and two full bathrooms. A spacious kitchen…

Single-family homes in the Shelter Island Union Free School District sold for a median of $1,900,000 (typically $1,450,000–$2,800,000) across 22 recorded sales between Oct 10, 2025 and Aug 27, 2026, up 11.8% on the 12 months before.

At about $7,216 a year, this home's property tax is in line with the roughly $8,000 typical for Shelter Island 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