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.
Sold for $5,700,000
$5,700,000
21 Thompson Road, Shelter Island, NY 11964
2beds
1,504sqft
Single Family Residence, Residential
Built in 2022
9.4 Acres Lot
$5,745,400 Zestimate®
$3,790/sqft
$6,971 Estimated rent
Home value
$5,745,400
$5.17M - $6.38M
$6,971/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
Debra L. Von Brook Binder CBR 631-872-2889,
Daniel Gale Sothebys Intl Rlty 631-749-1155
Bought with:
Debra L. Von Brook Binder CBR, 10401210622
Daniel Gale Sothebys Intl Rlty
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 906564
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Description: Primary bedroom with built in closets, en-suite bathroom, water-view with sliding doors to deck
- Level: First
Bedroom 2
- Description: Bedroom with sliders to deck and beautiful waterview
- Level: First
Primary bathroom
- Description: Primary bathroom with marble counters and tile Soaking tub/shower
- Level: First
Bathroom 2
- Description: Hall bath with glass enclosed shower and marble counter and tile
- Level: First
Den
- Description: Second Floor bedroom/library with balcony deck out sliding doors
- Level: Second
Kitchen
- Description: Custom kitchen with wood cabinetry, high end appliances, counter seating and built in banquet dining
- Level: First
Laundry
- Level: First
Living room
- Description: Vaulted living room with wood burning fireplace and stunning views of Smith Cove
- Level: First
Heating
- ENERGY STAR Qualified Equipment, Forced Air, Heat Pump
Cooling
- Central Air, ENERGY STAR Qualified Equipment
Appliances
- Included: Dishwasher, Dryer, Electric Oven, Electric Range, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Water Softener Owned
- Laundry: Washer/Dryer Hookup, Electric Dryer Hookup, In Hall, Laundry Room, Washer Hookup
Features
- First Floor Bedroom, Built-in Features, Cathedral Ceiling(s), Chefs Kitchen, Eat-in Kitchen, Entrance Foyer, Kitchen Island, Marble Counters, Natural Woodwork, Open Floorplan, Open Kitchen, Pantry, Primary Bathroom, Master Downstairs, Soaking Tub
- Flooring: Hardwood
- Doors: ENERGY STAR Qualified Doors
- Windows: Casement
- Basement: Bilco Door(s),Full,Storage Space,Unfinished
- Attic: Pull Stairs
- Number of fireplaces: 1
- Fireplace features: Living Room, Masonry, Wood Burning
Interior area
- Total structure area: 1,504
- Total interior livable area: 1,504 sqft
Property
Parking
- Parking features: Driveway, Private
- Has uncovered spaces: Yes
Features
- Levels: Two
- Patio & porch: Deck, Patio
- Exterior features: Fire Pit, Lighting, Rain Gutters
- Has view: Yes
- View description: Open, Panoramic, Skyline, Trees/Woods, Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Beach Access, Beach Front, Creek, Sound, Waterfront
Lot
- Size: 9.40 Acres
- Features: Back Yard, Front Yard, Private, Restrictions, Secluded, Views
- Residential vegetation: Partially Wooded
Details
- Parcel number: 0700024000100018000
- Special conditions: None
- Other equipment: Fuel Tank(s), Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence, Residential
Materials
- Batts Insulation, Cedar, Shake Siding, Shingle Siding
- Foundation: Concrete Perimeter
Condition
- New Construction
- New construction: Yes
- Year built: 2022
Utilities & green energy
- Sewer: Cesspool, Septic Tank
- Utilities for property: Cable Connected, Electricity Connected, Propane, Underground Utilities
Community & neighborhood
Security
- Security features: Smoke Detector(s)
Location
- Region: Shelter Island
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $225 annually
- Services included: Other
Other
Other facts
- Listing agreement: Exclusive Right To Sell
- Listing terms: 1031 Exchange,Cash,Conventional
Price history
| Date | Event | Price |
|---|---|---|
| 4/7/2026 | Sold | $5,700,000-3%$3,790/sqft |
Source:  OneKey® MLS as distributed by MLS GRID #906564 Report a problem | ||
| 12/23/2025 | Pending sale | $5,875,000$3,906/sqft |
Source: OneKey® MLS as distributed by MLS GRID #906564 Report a problem | ||
| 11/6/2025 | Price change | $5,875,000-7.4%$3,906/sqft |
Source: OneKey® MLS as distributed by MLS GRID #906564 Report a problem | ||
| 10/8/2025 | Price change | $6,345,000-6%$4,219/sqft |
Source: OneKey® MLS as distributed by MLS GRID #906564 Report a problem | ||
| 8/30/2025 | Listed for sale | $6,750,000+1250%$4,488/sqft |
Source: OneKey® MLS as distributed by MLS GRID #906564 Report a problem | ||
| 11/12/1999 | Sold | $500,000-76.2%$332/sqft |
Source: Public Record Report a problem | ||
| 9/8/1999 | Sold | $2,100,000$1,396/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $4,225,000 +51% |
| 2024 | -- | $2,797,200 |
| 2023 | -- | $2,797,200 +29.5% |
| 2022 | -- | $2,160,000 |
| 2021 | -- | $2,160,000 |
| 2020 | -- | $2,160,000 |
| 2019 | -- | $2,160,000 +7.4% |
| 2018 | -- | $2,011,300 |
| 2017 | $11,929 | $2,011,300 +0% |
| 2016 | -- | $2,011,000 +21.3% |
| 2015 | -- | $1,657,700 +2% |
| 2014 | -- | $1,625,200 |
| 2013 | -- | $1,625,200 |
| 2012 | -- | $1,625,200 -9.1% |
| 2011 | -- | $1,788,000 |
| 2010 | -- | $1,788,000 -10% |
| 2009 | -- | $1,986,000 |
Find assessor info on the county website
Neighborhood: 11964
Nearby schools
GreatSchools rating
- 6/10Shelter Island SchoolGrades: PK-12Distance: 1.5 mi
Schools provided by the listing agent
- Elementary: Shelter Island School
- Middle: Shelter Island School
- High: Shelter Island School
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$5,745,400
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$5,745,400
- New York
- Suffolk County
- Shelter Island
- 11964
- 21 Thompson Road
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