66A North Midway Road

Shelter Island | New York

The Romance of

Country Life

View Photos Watch Film 360° VTour Open House

Penelope Moore

Presented At

$1,545,000

Bedrooms

Bathrooms

Living

1,488

SQFT

66A North Midway Road, Shelter Island, New York, United States. - Photo 1

66A North Midway Road, Shelter Island, New York, United States. - Photo 2

66A North Midway Road, Shelter Island, New York, United States. - Photo 3

66A North Midway Road, Shelter Island, New York, United States. - Photo 4

66A North Midway Road, Shelter Island, New York, United States. - Photo 5

66A North Midway Road, Shelter Island, New York, United States. - Photo 6

66A North Midway Road, Shelter Island, New York, United States. - Photo 7

66A North Midway Road, Shelter Island, New York, United States. - Photo 8

66A North Midway Road, Shelter Island, New York, United States. - Photo 9

66A North Midway Road, Shelter Island, New York, United States. - Photo 10

66A North Midway Road, Shelter Island, New York, United States. - Photo 11

66A North Midway Road, Shelter Island, New York, United States. - Photo 12

66A North Midway Road, Shelter Island, New York, United States. - Photo 13

66A North Midway Road, Shelter Island, New York, United States. - Photo 14

66A North Midway Road

Shelter Island | New York

66A North Midway Road, Shelter Island, New York, United States. , Shelter Island , New York

Ranch in Shelter Island

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

Gallery

3D Street View Tour

Property Location

66A North Midway Road, Shelter Island, New York, United States., Shelter Island New York

Local Weather & Climate

Shelter Island, New York

Current Conditions Updated recently

30 °F

Clear sky

Feels Like 27°F

Humidity 62%

Wind 3 mph

Visibility 6.2 mi

Sunrise 10:56 AM

Sunset 10:58 PM

5-Day Forecast

Thu 19 Mar

Clouds

High 38°

Low 31°

Fri 20 Mar

Clouds

High 44°

Low 35°

Sat 21 Mar

Rain

High 46°

Low 41°

Sun 22 Mar

Clouds

High 47°

Low 39°

Mon 23 Mar

Clouds

High 49°

Low 43°

Data from OpenWeatherMap

Walkability & Transit Scores

How easy is it to get around Shelter Island?

Walkability and transit scores for this address come from the EPA National Walkability Index.

Mortgage Calculator

Estimate your monthly payments for this property

Home Price

Down Payment

$100,000

Interest Rate

Loan Term

Estimated Monthly Payment $3,160

Monthly Payment Breakdown

Principal & Interest $2,528

Loan Amount $400,000

Total Interest $337,621

Total Cost $737,621

Potential Tax Benefits (United States)

$0 Est. First Year Interest Deduction

$0 Est. Annual Tax Savings

*Based on post-2017 tax law. Actual deductions depend on filing status, itemization, and current tax laws.

Ready to explore financing?

Connect with trusted mortgage partners

Important Information

This calculator is for illustrative purposes only and does not constitute a loan offer, pre-approval, or commitment to lend.
Monthly payment estimates do not include property taxes, homeowner's insurance, HOA fees, or other applicable costs which may significantly increase your actual payment.
Interest rates shown are for demonstration only. Actual rates depend on your credit score, down payment, loan type, property location, and current market conditions.
This tool provides estimates only. Consult with a licensed mortgage professional for accurate quotes and personalized advice.
Tax benefit calculations are simplified estimates based on general assumptions for United States. Actual deductions depend on your specific tax situation, filing status, and current tax laws.
Tax Year Information: Tax data shown is based on United States tax year 2025 (fiscal year: January-December), rules effective from 2018 through 2025. Tax laws change frequently and may have been amended since this data was compiled.

Tax Information Disclaimer

The tax benefit information displayed on this page is provided for general informational and educational purposes only. This information:

Does not constitute tax advice and should not be relied upon as such. Tax laws are complex and vary by jurisdiction, individual circumstances, and are subject to change without notice.
May not be current or accurate for your specific situation. Tax rules are updated frequently by governments, and the information shown may not reflect the most recent changes.
Uses simplified assumptions that may not apply to your circumstances, including filing status, total income, other deductions, alternative minimum tax considerations, and local tax variations.
Should not be used as the basis for any tax planning decisions or financial strategies without consulting a qualified tax professional licensed in your jurisdiction.

Before making any decisions based on potential tax benefits, you should consult with a qualified tax advisor, certified public accountant (CPA), or licensed tax professional who can evaluate your specific circumstances and provide advice tailored to your situation.

Limitation of Liability: By using this calculator, you acknowledge that all results are approximations and should not be relied upon for financial, legal, or tax decisions. openluxe, its affiliates, officers, directors, employees, and agents expressly disclaim all liability for any damages, losses, or consequences arising from the use of or reliance on this calculator or the information provided herein. openluxe is not a lender, financial advisor, or tax professional and does not provide mortgage loans, financial advice, or tax advice. Use of this calculator does not create any professional relationship.

Frequently Asked Questions

Common questions about this property

How many bedrooms and bathrooms does 66A North Midway Road, Shelter Island, New York, United States have?

This other at 66A North Midway Road, Shelter Island, New York, United States features 2 bedrooms with 1,488 square feet of living space.

What is the size of 66A North Midway Road, Shelter Island, New York, United States?

This property offers 1,488 square feet of living space.

What is the listing price for 66A North Midway Road, Shelter Island, New York, United States?

This property is listed at $154,500,000, which equals $103831 per square foot.

What type of property is 66A North Midway Road, Shelter Island, New York, United States?

This is a other located in Shelter Island, New York. The property is situated in an established neighborhood with convenient access to local amenities and services.