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
$1,545,000
66-A N Midway Rd, Shelter Island, NY 11964
2beds
1,488sqft
Single Family Residence
Built in 1976
1 Acres Lot
$1,456,700 Zestimate®
$1,038/sqft
$-- HOA
What's special
Spring-fed pondOld mapleRaised stone fireplaceDeck overlooking the waterModest kitchen thoughtfully arrangedCircular driveLibrary lined with built-ins
- 25 days |
- 440 |
- 12 |
Zillow last checked:
Listing updated:
Listed by:
SAUNDERS & ASSOCIATES,
Penelope Moore 917-208-5519
Source: NY State MLS,MLS#: 11502807
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 3
- Full bathrooms: 3
Rooms
- Room types: Bonus Room, Breakfast Room, Den, Dining Room, En Suite, Family Room, First Floor Bathroom, First Floor Master Bedroom, Formal Room, Great Room, Kitchen, Laundry Room, Library, Living Room, Master Bedroom, Media Room, Private Guest Room, Study
Kitchen
- Features: Separate, Laminate Counters
Heating
- Baseboard
Cooling
- Wall/Window Unit(s)
Appliances
- Included: Dishwasher, Dryer, Refrigerator, Oven, Washer, Water Heater
Features
- Flooring: Hardwood, Tile
- Basement: Full,Finished,Kitchen,Walk-Out Access
- Number of fireplaces: 2
Interior area
- Total structure area: 1,488
- Total interior livable area: 1,488 sqft
- Finished area above ground: 1,488
Property
Parking
- Total spaces: 2
- Parking features: Driveway, Attached
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Patio & porch: Patio, Open Porch, Deck
- Fencing: Fenced
- Has view: Yes
- View description: Pond, Private, Scenic, Street, Water, Wooded
- Has water view: Yes
- Water view: Pond,Water
- Waterfront features: Pond
- Frontage length: 0
Lot
- Size: 1 Acres
- Features: Trees
Details
- Parcel number: 0700014.00004000.060
- Lease amount: $0
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch
- Property subtype: Single Family Residence
Materials
- Frame, Wood Siding
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1976
- Major remodel year: 2017
Utilities & green energy
- Electric: Amps(0)
- Sewer: Private Septic
- Water: Well
Community & HOA
HOA
- Has HOA: No
Location
- Region: Shelter Island
Financial & listing details
- Price per square foot: $1,038/sqft
- Tax assessed value: $1,157,000
- Annual tax amount: $3,658
- Date on market: 6/12/2026
- Date available: 05/21/2025
- Listing agreement: Exclusive
Estimated market value
$1,456,700
$1.38M - $1.53M
$5,950/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/12/2026 | Listed for sale | $1,545,000$1,038/sqft |
Source: NY State MLS #11502807 Report a problem | ||
| 6/5/2026 | Listing removed | $1,545,000$1,038/sqft |
Source: NY State MLS #11502807 Report a problem | ||
| 5/22/2026 | Listed for sale | $1,545,000$1,038/sqft |
Source: NY State MLS #11502807 Report a problem | ||
| 12/18/2025 | Listing removed | $1,545,000$1,038/sqft |
Source: NY State MLS #11502807 Report a problem | ||
| 8/28/2025 | Price change | $1,545,000-7.8%$1,038/sqft |
Source: NY State MLS #11502807 Report a problem | ||
| 5/22/2025 | Listed for sale | $1,675,000+544.2%$1,126/sqft |
Source: NY State MLS #11502807 Report a problem | ||
| 10/2/1998 | Sold | $260,000$175/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $1,157,000 +103% |
| 2024 | -- | $570,000 |
| 2023 | -- | $570,000 |
| 2022 | -- | $570,000 |
| 2021 | -- | $570,000 +1.8% |
| 2020 | -- | $560,000 +0.2% |
| 2019 | -- | $559,000 +0.4% |
| 2018 | -- | $557,000 +13% |
| 2017 | $1,401 | $493,000 +3.1% |
| 2016 | -- | $478,000 +3.9% |
| 2015 | -- | $460,000 +1.1% |
| 2014 | -- | $455,000 +2.2% |
| 2013 | -- | $445,000 -1.5% |
| 2012 | -- | $452,000 -4.6% |
| 2011 | -- | $474,000 +0.9% |
| 2010 | -- | $470,000 -10.8% |
| 2009 | -- | $527,000 -1.2% |
| 2008 | -- | $533,200 +6.5% |
| 2007 | $1,904 -12.9% | $500,500 +39.1% |
| 2005 | $2,185 +6.5% | $359,800 +14.1% |
| 2004 | $2,052 +0.3% | $315,200 +3.3% |
| 2003 | $2,046 -17.4% | $305,000 +29.8% |
| 2002 | $2,476 | $235,000 |
| 2001 | -- | $235,000 |
| 2000 | $2,408 | $235,000 |
Find assessor info on the county website
Monthly payment
Estimated monthly payment$1,822
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 11964
Nearby schools
GreatSchools rating
- 6/10Shelter Island SchoolGrades: PK-12Distance: 0.7 mi
A local agent can set up tours, give advice and negotiate with sellers.
- New York
- Suffolk County
- Shelter Island
- 11964
- 66-A N Midway Rd





