Set on the gentle slope of a spring-fed pond, this Shelter Island residence, similar in ways to a duplex, reveals itself not all at once, but in a series of calm, considered gestures. One enters by way of a circular drive that curves around an old maple and up a short path to a home that understands the value of sunlight, privacy, and practicality. Inside, the main floor offers a living room where light from the west falls generously across books, armchairs, and a raised stone fireplace. A modest kitchen, thoughtfully arranged, adjoins a small breakfast area, a fine place for morning coffee and a quiet view. Down the hall, the primary bedroom includes its own bath, set apart in a way that grants quiet. At the rear of the house, a library lined with built-ins opens to a deck overlooking the water, where the pond's surface shifts with wind and the passage of sunlight. Below, the lower level is wholly its own space - not merely an extension of the upstairs, but a dwelling with purpose. A living room, dining nook, full kitchen (one of two legally established in the house), bedroom, and bath occupy this floor, with sliding doors that open to a hidden stretch of land and a view that belongs almost entirely to ducks, frogs, turtles, and the birds that stop in from nearby Sachem's Woods. The pond has its own rhythm; Spring-fed and self-sustaining, it hums with life. And while the property is not far from the ferry, from shops, or from the beach, it feels content to exist slightly apart, offering its new owner not just a house, but a setting in which to think, observe, and live quietly among living things.
For sale
$1,675,000
66 N Midway Rd #A, Shelter Island, NY 11964
2beds
1,488sqft
Single Family Residence
Built in 1976
1 Acres Lot
$1,671,000 Zestimate®
$1,126/sqft
$-- HOA
What's special
Hidden stretch of landSmall breakfast areaDeck overlooking the waterModest kitchenCircular driveLibrary lined with built-ins
- 89 days
- on Zillow |
- 328 |
- 12 |
Zillow last checked: 7 hours ago
Listing by:
Saunders & Associates 631-749-5801,
Penelope Moore - Associate Real Estate Broker 917-208-5519
Source: Out East,MLS#: 388843
Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 3
- Full bathrooms: 3
Rooms
- Room types: Family Room, Laundry, Library, Office
Features
- Has fireplace: Yes
Interior area
- Total structure area: 1,488
- Total interior livable area: 1,488 sqft
Property
Parking
- Parking features: GarageAttached
- Has attached garage: Yes
Features
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront
- Frontage type: Waterfront
Lot
- Size: 1 Acres
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Condition
- New construction: No
- Year built: 1976
Community & HOA
Location
- Region: Shelter Island
Financial & listing details
- Price per square foot: $1,126/sqft
- Date on market: 5/25/2025
- Lease term: Contact For Details
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