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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.
Property Type(s):
Single Family
| 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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Listed with Douglas Elliman Real Estate
Copyright 2026 Hudson Gateway Multiple Listing Service, Inc. All rights reserved.
The data relating to real estate for sale or lease on this web site comes in part from HGMLS. Real estate listings held by brokerage firms other than Suburban Realty are marked with the HGMLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker. Information deemed reliable but not guaranteed.
Date Last Updated: 7/22/26 4:26 PM PDT
This IDX solution is (c) Diverse Solutions 2026.
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