A rare 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 1,316 square feet of comfortable living space with 3 comfortable 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, 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. A 1,330-square-foot 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.

Last Updated	7/22/2026	Year Built	1977
Garage Spaces	3.0	County	Suffolk

SCHOOLS

Elementary School	Shelter Island School
Jr. High School	Shelter Island School
High School	Shelter Island School

Additional Details

AIR	Central Air
AIR CONDITIONING	Yes
APPLIANCES	Convection Oven, Dishwasher, Dryer, Electric Cooktop, Electric Range, Electric Water Heater, Exhaust Fan, Freezer, Microwave, Refrigerator, Stainless Steel Appliance(s), Tankless Water Heater, Washer
BASEMENT	Full
CONSTRUCTION	Batts Insulation, Cedar, Frame, HardiPlank Type
FIREPLACE	Yes
GARAGE	Yes
HEAT	Forced Air, Hot Water, Oil
INTERIOR	Beamed Ceilings, Cathedral Ceiling(s), Ceiling Fan(s), Central Vacuum, Crown Molding, Eat-in Kitchen, Granite Counters, High Ceilings, Open Floorplan, Pantry, Recessed Lighting, Soaking Tub, Storage
LOT	1 acre(s)
PARKING	Private
SEWER	Septic Tank
STYLE	Barndominium, Ranch
TAXES	7216
UTILITIES	Electricity Connected, Phone Connected, Propane, Water Connected
WATER	Public, Private, Well
WATERFRONT DESCRIPTION	Pond

Location

 

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