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.
For sale
$2,199,000
64 N Midway Rd #A, Shelter Island, NY 11964
5beds
2,646sqft
Multi Family
Built in 1977
-- sqft lot
$2,055,400 Zestimate®
$831/sqft
$-- HOA
What's special
Gas fireplaceLarge loftTwo spacious bedroomsAttached one-car garagePicturesque pond next doorExpansive rear deckSurrounded by mature trees
- 51 days
- 93
- 4
Zillow last checked:
Listed by:
Douglas Elliman Real Estate 631-354-8100,
Christine Beckwith - Real Estate Sales Person 631-365-6091
Source: Out East,MLS#: 396749
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 4
Cooling
- Central Air
Features
- Basement: Yes
- Has fireplace: Yes
Interior area
- Total structure area: 2,646
- Total interior livable area: 2,646 sqft
Property
Parking
- Parking features: None
Features
- Stories: 1
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
Lot
- Size: 0.95 Acres
Construction
Type & style
- Home type: MultiFamily
- Property subtype: Multi Family
Condition
- New construction: No
- Year built: 1977
Community & HOA
Location
- Region: Shelter Island
Financial & listing details
- Price per square foot: $831/sqft
- Date on market: 7/21/2026
- Lease term: Contact For Details
Estimated market value
$2,055,400
$1.95M - $2.16M
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 7/21/2026 | Listed for sale | $2,199,000$831/sqft |
Source: Out East #396749 Report a problem | ||
Public tax history
Tax history is unavailable.





