Dickerson Drive

Shelter Island | New York

Trophy Home

Premier Living

View Photos Watch Film 360° VTour Open House

Penelope Moore

Presented At

$4,450,000

Bedrooms

Bathrooms

Living

3,187

SQFT

Fireplace

Library

Washer Dryer

Bar

Walk In Closet

Sauna

Garage

Garden

Pool

Water View

Privacy

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 1

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 2

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 3

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 4

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 5

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 6

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 7

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 8

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 9

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 10

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 11

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 12

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 13

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 14

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 15

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 16

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 17

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 18

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 19

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 20

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 21

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 22

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 23

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 24

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 25

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 26

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 27

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 28

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 29

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 30

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 31

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 32

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 33

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 34

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 35

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 36

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 37

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 38

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 39

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 40

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 41

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 42

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 43

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 44

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 45

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 46

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 47

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 48

11 Dickerson Drive, Shelter Island, New York, United States. - Photo 49

Dickerson Drive

Shelter Island | New York

11 Dickerson Drive, Shelter Island, New York, United States. , Shelter Island , New York

Residential in Shelter Island

Set on 1.3 private acres on a peninsula at the end of a long driveway, this sleek modern has been masterfully reimagined through a high-end renovation. Upon entering the foyer, expansive water views immediately capture the eye. With gentle elevations over approximately 300 feet of shoreline along Menantic Creek, the home is perfectly positioned to maximize natural light and scenic vistas. Dramatic double-height ceilings and floor-to-ceiling windows define the main living and dining areas, which feature a stone fireplace and radiant heat floors. The custom kitchen is equipped with Viking Professional Series appliances, Borghini Gold Quartz countertops, and a breakfast bar, seamlessly connected to a striking sunroom that opens to expansive outdoor entertaining decks. The main level includes two bedrooms: an en-suite primary suite that spans nearly the entire southern length of the home, with a lounge area, private deck access, walk-in closet, and a spa-inspired bath . A guest en-suite bedroom is located near the front of the home, offering privacy and convenience. Upstairs, a lofted library overlooks both the water and the living area below. A second en-suite primary bedroom offers a walk-in closet, sitting area, and a spacious bath, echoing the design and comfort of the first-floor suite. A fourth bedroom with oversized western-facing windows enjoys pool and garden views, and is serviced by an adjacent full bath. The finished lower level adds approximately 800 square feet of living space, including a game area, media room, full bath, and a well-equipped mechanical room with water filtration and softener system, LG Professional Series washer/dryer, Generac generator, and a pantry area. Outdoor amenities make this property a true summer retreat: A deep-water dock with power and freshwater hookups providing easy boating access to open waters; a 16' x 36' Gunite pool with long porcelain tile, a Coverstar automatic cover, and Letro autofill system, complemented by an Evolution 8-person spa and a 4-person Almost Heaven sauna overlooking the water, and a two-car garage with custom storage. Nearly every modern amenity has been addressed in the renovation: underground power, full perimeter fencing, retaining walls, high R-factor insulation, new roof, shingles, and skylights, new hardwood floors, a comprehensive low heat/flood/theft central station security system, NEST thermostats, and expanded electrical capacity. Lush landscaping-featuring crepe myrtle, hydrangeas, beach grass, boundary evergreens, and native trees-add colorful, finishing touches of natural beauty to this special property.

Gallery

3D Street View Tour

Property Location

11 Dickerson Drive, Shelter Island, New York, United States., Shelter Island New York

Local Weather & Climate

Shelter Island, New York

Current Conditions Updated recently

31 °F

Light snow

Feels Like 24°F

Humidity 45%

Wind 7 mph

Visibility 6.2 mi

Sunrise 10:56 AM

Sunset 10:58 PM

5-Day Forecast

Wed 18 Mar

Clouds

High 32°

Low 31°

Thu 19 Mar

Clouds

High 38°

Low 27°

Fri 20 Mar

Clouds

High 44°

Low 35°

Sat 21 Mar

Rain

High 44°

Low 42°

Sun 22 Mar

Clouds

High 47°

Low 41°

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 11 Dickerson Drive, Shelter Island, New York, United States have?

This house at 11 Dickerson Drive, Shelter Island, New York, United States features 4 bedrooms with 3,187 square feet of living space.

What is the size of 11 Dickerson Drive, Shelter Island, New York, United States?

This property offers 3,187 square feet of living space.

What is the listing price for 11 Dickerson Drive, Shelter Island, New York, United States?

This property is listed at $445,000,000, which equals $139630 per square foot.

What type of property is 11 Dickerson Drive, Shelter Island, New York, United States?

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