855.375.4001
Listing Courtesy of: Debra Von Brook Binder - Daniel Gale Sothebys Intl Rlty 631-749-1155
$5,875,000 affordable loan icon Calculate Payment

21 Thompson Rd Shelter Island, NY 11964

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Single Family Residence
2 Beds
2 Baths
... Bed/Bath
1,504 Sq. Ft.

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Last updated on 12/10/2025 9:43 PM
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 o...f 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. Continue reading
MLS#
906564
Property Type
Single Family
Bedrooms
2
Bathrooms
2 Full
Year Built
2022
HOA Fee
$225 Annually
Square Feet
1,504 sq. ft
Lot Size
9.4
Stories
2.0
Sewer
Cesspool, Holding Tank

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Listing Courtesy of: Debra Von Brook Binder - Daniel Gale Sothebys Intl Rlty 631-749-1155
Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067


Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. 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. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2025, OneKey MLS, Inc. All Rights Reserved.
This content last refreshed on 12/10/2025 9:43 PM. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
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