20 Baldwin Road, Shelter Island, NY 11964

$2,500,000 · 4 bed · 3 bath · 3,097 sq ft · built 1900 · MLS# 1062621 · Active

Discover a one-of-a-kind Shelter Island retreat where historic farmhouse charm meets inspired modern living. Set amid 1.8 acres of mature trees, tall privets, sun-drenched edged lawns, and open green space, this circa-1900 property offers a rare combination of character, privacy, and flexibility. The original 2-story residence showcases beautiful period details, including traditional moldings, hand-hewn beams, wood floors, and distinctive vintage glass windows. Inside, 3 bedrooms and 2 baths are complemented by comfortable living and dining rooms, a thoughtfully updated chef’s kitchen with a casual dining area, and a screened porch…

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 $10,022 a year, this home's property tax runs roughly 25% above the $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