Coldwell Banker Home Page
Local Realty Service Provided By: Coldwell Banker Phillips
Property view
Listing view 2
Listing view 3

21 Thompson Road, 
Shelter Island, NY 11964

$6,345,000


2

Beds


2

Baths


1,504

Sq Ft


Single Family


Virtual Tour

Active

Listed by

Debra L. Von Brook Binder Cbr

Daniel Gale Sothebys Intl Rlty

Last updated:

October 8, 2025, 03:58 PM

MLS#

906564

Source:

OneKey MLS

About This Home

21 Thompson Road

Perched 59 feet above sea level for commanding views and peace of mind, this exceptional contemporary estate—designed by noted architect Kenton van Boer—rests on 9.4 private acres, of which 2.7 acres are buildable, and offers 561 feet of premier waterfront on Smiths Cove. Sweeping panoramic vistas of the Sound and the tranquil yacht anchorage set the scene for direct beachfront access and creek frontage along the serene Miss Annie’s Creek—plus the rare opportunity to create your own private dock and mooring. The 1,504-square-foot residence features 2 bedrooms, a study and 2 spa-inspired full baths. A chef’s kitchen anchors the open layout, flowing into a light-filled living room with a stone-accented fireplace and a custom built-in dining area. Thoughtful architectural details by Kenton van Boer. Quartzite flagstone masonry patios and walkways add an additional 1,120 square feet of outdoor living, seamlessly extending the home’s footprint and immersing you in the surrounding natural beauty. Nestled in a serene coastal setting of wood shingles, flagstone patios, and unspoiled shoreline, this property offers unmatched privacy while being just moments from the Shelter Island Ferry to Sag Harbor. A rare blend of seclusion, convenience, and timeless design.

Home Facts

Single Family

2 Baths

2 Bedrooms

Built in 2022

Price Summary

6,345,000

$4,218 per Sq. Ft.

MLS #:

906564

Last Updated:

October 8, 2025, 03:58 PM

Added:

a month ago


Rooms & Interior

Bedrooms

Total Bedrooms:

2

Bathrooms

Total Bathrooms:

2

Full Bathrooms:

2

Interior

Living Area:

1,504 Sq. Ft.


Structure

Structure

Architectural Style:

Contemporary

Building Area:

1,504 Sq. Ft.

Year Built:

2022


Lot

Lot Size (Sq. Ft):

409,464


Finances & Disclosures

Finances

Price:

$6,345,000

Price per Sq. Ft:

$4,218 per Sq. Ft.

Source:OneKey MLS
Copyright 2025 OneKey MLS. All rights reserved. Listings courtesy of OneKey MLS as distributed by MLS GRID . OneKey MLS provides content displayed here (“provided content”) on an “as is” basis and makes no representations or warranties regarding the provided content, including, but not limited to those of non-infringement, timeliness, accuracy, or completeness. Individuals and companies using information presented are responsible for verification and validation of information they utilize and present to their customers and clients. OneKey MLS will not be liable for any damage or loss resulting from use of the provided content or the products available through Portals, IDX, VOW, and/or Syndication. Recipients of this information shall not resell, redistribute, reproduce, modify, or otherwise copy any portion thereof without the expressed written consent of OneKey MLS.

Contact an Agent

Yes, I would like more information from Coldwell Banker. Please use and/or share my information with a Coldwell Banker agent to contact me about my real estate needs.

By clicking Contact I agree a Coldwell Banker Agent may contact me by phone or text message including by automated means and prerecorded messages about real estate services, and that I can access real estate services without providing my phone number. I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

 

Contact an Agent

Yes, I would like more information from Coldwell Banker. Please use and/or share my information with a Coldwell Banker agent to contact me about my real estate needs.

By clicking Contact I agree a Coldwell Banker Agent may contact me by phone or text message including by automated means and prerecorded messages about real estate services, and that I can access real estate services without providing my phone number. I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.