Price Reduced 12.96%
Price History
$6,750,000
8/30/2025
$6,345,000
10/8/2025
$5,875,000
11/6/2025
21 Thompson Road, Shelter Island, NY, 11964
6 rooms
2 beds
2 Full baths
2022
Contemporary
1,504 sqft
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.
Status:
Active
Type:
Single-family residential
Laundry Remarks:
Electric Dryer Hookup, In Hall, Laundry Room, Washer Hookup
Heating:
ENERGY STAR Qualified Equipment, Forced Air, Heat Pump
Cooling:
Central Air, ENERGY STAR Qualified Equipment
Basement:
Bilco Door(s), Full, Storage Space, Unfinished
Parking:
Driveway, Private
Common Charge:
$225 Annually
Acreage:
9.4
Est. Taxes:
$19,523
HOA Fee
$225
Construction
Batts Insulation, Cedar, Frame, Shake Siding, Shingle Siding
Utilities
Cable Connected, Electricity Connected, Propane, Underground Utilities
Lot Description:
Back Yard, Front Yard, Part Wooded, Private, Restrictions, Secluded, Views, Waterfront
View Description:
Open, Panoramic, Skyline, Trees/Woods, Water
Waterfront:
Yes
Elementary School:
Shelter Island School
Middle School:
Shelter Island School
High School:
Shelter Island School
School District:
Shelter Island
Days on Market:
77
Appliances:
Dishwasher, Dryer, Electric Oven, Electric Range, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Water Softener Owned
MLS #:
906564
Community Info
School Info
Walk Score
Mass Transit
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Listing courtesy of Daniel Gale Sothebys Intl Rlty 631-749-1155