64a N Midway Road • Shelter Island, NY 11964

$2,199,000 Beds: 5 • Baths: 4 full • Sq. Feet: 2642 • MLS ID: 1029569 • Subdivision:School Dist: Shelter Island
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 with abundant cabinetry flows seamlessly into the dining area, creating an inviting setting for everyday living and entertaining. The living room, anchored by a wood-burning fireplace, provides a warm and cozy gathering place throughout the seasons.Step outside to the expansive rear deck, complete with a hot tub overlooking a large, private backyard with room for a pool, an ideal setting for entertaining, relaxing, or enjoying peaceful evenings. A welcoming front porch, an attached one-car garage, and a carport.Privately positioned toward the rear of the property, the stunning barn-style home feels like a secluded retreat. Overlooking a tranquil pond, this approx. The residence is filled with warmth, character, and natural light. The dramatic main room features soaring vaulted ceilings with exposed beams, a gas fireplace, and an impressive wall of windows that captures beautiful views while flooding the home with sunshine. French doors that open onto an expansive 500 square foot mahogany deck with built-in storage, creating the perfect place to enjoy morning coffee, outdoor dining, or simply unwind.The barn home also features two spacious bedrooms, two full bathrooms, a large loft, and a well-appointed kitchen. The oversized lower-level garage offers exceptional storage for vehicles, recreational equipment, bicycles, tools, and more, while additional facilities and energy-efficient solar panels further enhance the home's appeal.The beautifully landscaped .95 acre property provides an uncommon sense of privacy while remaining just minutes from the Shelter Island beaches, marinas, restaurants, shops, farm stands, and nature preserve. 64A North Midway Road offers possibilities that are rarely available on Shelter Island. View this listing at: http://irisbluth.laffey.com/mls=1029569

Property Features

  • Garage: 3
  • Taxes: $7,216
  • Basement: Yes
  • Exterior: Batts Insulation,Cedar,Frame,HardiPlank Type
  • Lot Size: 1.00 Acres
  • Heating: Ducts,Forced Air,Hot Water,Oil
  • Cooling: Central Air
  • Year Built: 1977
  • Water: Well
  • Sewer: Septic Tank
  • On Market Date: 2026-07-22
  • Appliances: Convection Oven,Dishwasher,Dryer,Electric Cooktop,Electric Range,Electric Water Heater,Exhaust Fan,Freezer,Microwave,Refrigerator,Stainless Steel Appliance(s),Washer,Tankless Water Heater
  • Basement: Bilco Door(s),Full
  • Fireplace Features: Gas,Living Room,Masonry,Wood Burning
  • Fireplace Y/N: Yes
  • Flooring: Ceramic Tile,Combination,Hardwood
  • GarageY/N: Yes
  • Interior Features: First Floor Bedroom,First Floor Full Bath,Beamed Ceilings,Cathedral Ceiling(s),Ceiling Fan(s),Central Vacuum,Crown Molding,Eat-in Kitchen,Granite Counters,High Ceilings,Open Floorplan,Open Kitchen,Pantry,Primary Bathroom,Recessed Lighting,Soaking Tub,Storage,Walk Through Kitchen
  • Attic: Partial
  • Number Of Kitchens: 2
  • Heating Zones: 2
  • Other Structures: Residence
  • Parcel Number: 0700-014-00-04-00-007-004
  • Parking Features: Private
  • Rental Term: Monthly
  • Rooms Total: 10
  • Utilities: Electricity Connected,Phone Connected,Propane,Water Connected
  • Waterfront Features: Pond

School Information

  • High School: Shelter Island School
  • Middle School: Shelter Island School
  • Elementary School: Shelter Island School
  • School District: Shelter Island
Printed July 29, 2026


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