21 Thompson Road • Shelter Island, NY 11964

$5,875,000 • Beds: 2 • Baths: 2 full • Sq. Feet: 1504 • MLS ID: 906564 • Subdivision: • School Dist: Shelter Island
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. View this listing at: http://kathleenmyers.laffey.com/mls=906564

Property Features

  • Taxes: $19,523
  • Basement: Yes
  • Wooded: Yes
  • Exterior: Batts Insulation,Cedar,Frame,Shake Siding,Shingle
  • Special View Info: Open,Panoramic,Skyline,Trees/Woods,Water
  • Lot Size: 9.40 Acres
  • Heating: ENERGY STAR Qualified Equipment,Forced Air,Heat Pu
  • Cooling: Central Air,ENERGY STAR Qualified Equipment
  • Year Built: 2022
  • Fireplaces: 1
  • Water: Well
  • Sewer: Cesspool,Septic Tank
  • On Market Date: 2025-08-30
  • Appliances: Dishwasher,Dryer,Electric Oven,Electric Range,Electric Water Heater,Exhaust Fan,Microwave,Refrigerator,Washer,Water Softener Owned
  • Association Fee: $225/Annually
  • Association Fee Includes: Other
  • Basement: Bilco Door(s),Full,Storage Space,Unfinished
  • Exterior Features: Balcony,Fire Pit,Lighting,Rain Gutters
  • Fireplace Features: Living Room,Masonry,Wood Burning
  • Fireplace Y/N: Yes
  • Flooring: Hardwood
  • Interior Features: First Floor Bedroom,Built-in Features,Cathedral Ceiling(s),Chefs Kitchen,Eat-in Kitchen,ENERGY STAR Qualified Door(s),Entrance Foyer,High Ceilings,Kitchen Island,Marble Counters,Natural Woodwork,Open Floorplan,Open Kitchen,Pantry,Primary Bathroom,Master Downstairs,Soaking Tub,Washer/Dryer Hookup
  • Laundry: Electric Dryer Hookup,In Hall,Laundry Room,Washer Hookup
  • Lot Features: Back Yard,Front Yard,Part Wooded,Private,Restrictions,Secluded,Views,Waterfront
  • Attic: Pull Stairs
  • Number Of Kitchens: 1
  • Heating Zones: 3
  • Parcel Number: 0700-024-00-01-00-018-000
  • Parking Features: Driveway,Private
  • Patio And Porch: Deck,Patio
  • Rental Term: Monthly
  • Road Responsibility: Public Maintained Road
  • Rooms Total: 6
  • Security Features: Smoke Detector(s)
  • Utilities: Cable Connected,Electricity Connected,Propane,Underground Utilities
  • Waterfront Features: Beach Access,Beach Front,Creek,Sound,Waterfront
  • Beach Rights: Y
  • Window Features: Casement

School Information

  • High School: Shelter Island School
  • Middle School: Shelter Island School
  • Elementary School: Shelter Island School
  • School District: Shelter Island
Printed March 04, 2026

Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 03/04/2026. The listing information on this page last changed on 03/04/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 03/04/2026 4:47:39 AM EST) or OneKey MLS (last updated Wed 03/04/2026 1:45:01 AM EST). Real estate listings held by brokerage firms other than Laffey Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data and photos distributed by MLSGRID
Member Participants (and their affiliated licensees, if applicable) shall indicate on their websites that IDX information is provided exclusively for consumers’ personal non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability.
Based on information submitted to the MLS GRID. 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.



Privacy Policy / DMCA Notice / ADA Accessibility
Federal Housing Equal Opportunity Realtor
This site is hosted, designed and copyright © 1994 - 2026 by Delta Media Group, Inc. -- Patent Pending --