Property photo 1
2 Beds
2 Baths
1,504 sqft

$5,700,000

21 Thompson Road, Shelter Island NY, 11964

Price per sqft$3,789.89
Built in2022
Property size1,504 sqft
Property typeResidential
Courtesy of Daniel Gale Sothebys Intl Rlty, Debra L. Von Brook Binder CBR Listing Contact: 631-749-1155

Overview

Sold

Listed Aug 30, 2025

Updated Aug 21

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.

Additional information

MLS® ID
906564

Interior Features

Bedrooms
2
Bathrooms
2
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
9.4 Acres

Other Property Details

Taxes
$19,523
Tax Frequency
Annually
Association Fee Frequency
Yearly
View
Yes
Waterfront
Yes
55+/Senior Community
No

Listings courtesy of OneKey MLS as distributed by MLS GRID

All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) nor Jennifer Friedberg shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Properties displayed may be listed or sold by various participants in the MLS.

Based on information submitted to the MLS GRID as of 9:49 PM UTC on 8/21/2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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