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575 MADISON AVENUE, NEW YORK, NY 10022. 212.891.7000 © 2025 DOUGLAS ELLIMAN REAL ESTATE. EQUAL EMPLOYMENT OPPORTUNITY PROVIDER. ALL MATERIAL PRESENTED HEREIN IS INTENDED FOR INFORMATION PURPOSES ONLY. WHILE THIS INFORMATION IS BELIEVED TO BE CORRECT, IT IS REPRESENTED SUBJECT TO ERRORS, OMISSIONS, CHANGES, OR WITHDRAWAL WITHOUT NOTICE. ALL PROPERTY INFORMATION, INCLUDING, BUT NOT LIMITED TO SQUARE FOOTAGE, ROOM COUNT, NUMBER OF BEDROOMS, AND THE SCHOOL DISTRICT IN PROPERTY LISTINGS SHOULD BE VERIFIED BY YOUR OWN ATTORNEY, ARCHITECT, OR ZONING EXPERT. EQUAL HOUSING OPPORTUNITY.LISTING DATA REFRESHED ON OCT 09 2025 AT 7:36 AM.

DOUGLAS ELLIMAN IS A LICENSED REAL ESTATE BROKER IN CALIFORNIA WITH LICENSE # 01947727, COLORADO WITH LICENSE # EC100053892, CONNECTICUT WITH LICENSE # REB.0314827, THE DISTRICT OF COLUMBIA WITH LICENSE # REO40000160, FLORIDA WITH LICENSE # CQ1020232, MARYLAND WITH LICENSE # 645270, MASSACHUSETTS WITH LICENSE # 422764, NEVADA WITH LICENSE # 1454643, NEW JERSEY WITH LICENSE # 0572105, NEW YORK WITH LICENSE # 10991211812, TEXAS WITH LICENSE # 9008706, AND VIRGINIA WITH LICENSE # 0226035659.

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21 Thompson Rd

shelter island, NY 11964

$6,345,000

  • 2 BR
    2 BA
    APPROX. 1,504 SF

INTERESTED? LET'S CONNECT

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.

Details

1,504 Sq Ft

9.4 Private Acres Lot Size

Single Family Home

$225 Annually Maintenance/CC

$19,523 Annual Tax

Built in 2022

MLS/Listing ID 906564

Amenities & Features

Electric Oven

Electric Range

Exhaust Fan

Casement Windows

Water View

Electric Water Heater

Water Softener Owned

Construction - Batts Insulation

Construction - Frame

Parking - Private

Deck

Patio

Panoramic View

Skyline View

Trees Woods View

Beach Access

Beach Front

Creek

Sound

Waterfront

Eat-in Kitchen

Chef's Kitchen

Cathedral Ceilings

Built-in Features

Heating - Forced Air

Heating - ENERGY STAR Qualified Equipment

Concrete Perimeter

Hardwood

Wood Burning Fireplace

Open View

Heating - Heat Pump

Construction - Shake Siding

Entrance Foyer

High Ceilings

Kitchen Island

Marble Countertops

Natural Woodwork

Open Floor Plan

Open kitchen

Pantry

Master Downstairs

Soaking Tub

Washer/Dryer Hookup

Electric Dryer Hookup

Laundry Room

Washer Hookup

Lot - Back Yard

Lot - Front Yard

Lot - Private

Lot - Restrictions

Lot - Secluded

Lot - Views

Lot - Waterfront

Parking - Driveway

Microwave

Refrigerator

Washer

Style - Contemporary

Construction - Cedar

Construction - Shingle Siding

Cooling - Central Air

Cooling - ENERGY STAR-qualified Equipment

Balcony

Fire Pit

Lighting

Rain Gutters

Living Room Fireplace

Masonry Fireplace

Dishwasher

Dryer

ONEKEY

Source of Data: ONEKEY MLS

estimate my mortgage

TOTAL MONTHLY COST

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  • PRINCIPAL & INTEREST

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  • PROPERTY TAXES

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  • COMMON CHARGES

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HOME PRICE
DOWN PAYMENT
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INTEREST

Interested in 21 Thompson Rd?