About 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.
Features of 21 Thompson Road
| MLS® # | 906564 |
|---|---|
| Price | $6,345,000 |
| Bedrooms | 2 |
| Bathrooms | 2.00 |
| Full Baths | 2 |
| Square Footage | 1,504 |
| Square Footage | 409464 |
| Acres | 9.40 |
| Year Built | 2022 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Contemporary |
| Status | Active |
Community Information
| Address | 21 Thompson Road |
|---|---|
| City | Shelter Island |
| County | Suffolk County |
| State | NY |
| Zip Code | 11964 |
Amenities
| Utilities | Cable Connected, Electricity Connected, Propane, Underground Utilities |
|---|---|
| Parking | Driveway, Private |
| View | Open, Panoramic, Skyline, Trees/Woods, Water |
| Is Waterfront | Yes |
| Waterfront | Beach Access, Beach Front, Creek, Sound, Waterfront |
| Has Pool | No |
Interior
| Interior | 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 |
| Appliances | Dishwasher, Dryer, Electric Oven, Electric Range, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Water Softener Owned |
| Heating | ENERGY STAR Qualified Equipment, Forced Air, Heat Pump |
| Cooling | Central Air, ENERGY STAR Qualified Equipment |
| Fireplace | Yes |
| # of Fireplaces | 1 |
| Fireplaces | Living Room, Masonry, Wood Burning |
| Has Basement | Yes |
| Basement | Bilco Door(s), Full, Storage Space, Unfinished |
Exterior
| Exterior Features | Balcony, Fire Pit, Lighting, Rain Gutters |
|---|---|
| Lot Description | Back Yard, Front Yard, Part Wooded, Private, Restrictions, Secluded, Views, Waterfront |
| Windows | Casement |
| Construction | Batts Insulation, Cedar, Frame, Shake Siding, Shingle Siding |
School Information
| District | Shelter Island |
|---|---|
| Elementary | Shelter Island School |
| Middle | Shelter Island School |
| High | Shelter Island School |
Additional Information
| Date Listed | August 29th, 2025 |
|---|---|
| Days on Market | 54 |
| Short Sale | No |
| RE / Bank Owned | No |
| HOA Fees | 225 |
| HOA Fees Freq. | Annually |
Listing Details
| Office | Daniel Gale Sothebys Intl Rlty |
|---|---|
| Contact Info | 631-749-1155 |