21 Thompson Road, Shelter Island, NY 11964

• 2 beds |
• 2 baths |
• 1,504 sqft

Property Description

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.

Listing Status:

Pending

Data Last Updated:

February 9, 2026 at 1:22AM

Listing Office:

Daniel Gale Sothebys Intl Rlty : 631-749-1155

MLS ID:

906564

Interior

• General: First Floor BedroomBuilt-in FeaturesCathedral Ceiling(s)Chefs KitchenEat-in KitchenENERGY STAR Qualified Door(s)Entrance FoyerHigh CeilingsKitchen IslandMarble CountersNatural WoodworkOpen FloorplanOpen KitchenPantryPrimary BathroomMaster DownstairsSoaking TubWasher/Dryer Hookup
• Appliances: DishwasherDryerElectric OvenElectric RangeElectric Water HeaterExhaust FanMicrowaveRefrigeratorWasherWater Softener Owned
• Laundry: Electric Dryer HookupIn HallLaundry RoomWasher Hookup
• Basement: Bilco Door(s)FullStorage SpaceUnfinished
• Flooring: Hardwood
• A/C: Central AirENERGY STAR Qualified Equipment
• Heating: ENERGY STAR Qualified EquipmentForced AirHeat Pump
• Fireplace: Living RoomMasonryWood BurningFireplaceFireplaces: 1

Exterior

• General: BalconyFire PitLightingRain Gutters
• Style: Contemporary
• Other Structures: DeckPatio
• Parking: DrivewayPrivate

Construction

• Windows: Casement
• General: Two

Location

• Road/Access: Municipal
• HOA Amenities: Other225.0Annually
• Originating MLS: onekey2
• School District: Shelter Island
• County: Suffolk County

Lot

• Zoning: 0700-024-00-01-00-018-000
• View: OpenPanoramicSkylineTrees/WoodsWater

Utilities

• Utilities: Cable ConnectedElectricity ConnectedPropaneUnderground Utilities
• Water: Well
• Sewer: CesspoolSeptic Tank

Financial

• Source: onekey2