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$5,875,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 2 Beds
  • 2 Full Baths
See This Home
Save This Home
See This Home
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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.

Full Property Details for 21 Thompson Rd

General

  • Price: $5,875,000
  • HOA FEE: $19/month
  • HOA FEE FREQ.: Annually
  • Taxes: $19,523
  • Status: Pending
  • Type: Single Family
  • Source: Long_Island
  • MLS ID: 906564
  • Updated: 12/23/2025
  • Added to Site: 141 day(s) ago

Interior

  • Number of Rooms: 6
  • 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
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Living Room, Masonry, Wood Burning
  • Appliances: Dishwasher, Dryer, Electric Oven, Electric Range, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Water Softener Owned
  • Laundry Facilities: Yes
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Laundry: Electric Dryer Hookup, In Hall, Laundry Room, Washer Hookup

Additional Information

  • Security/Safety: Smoke Detector(s)

Exterior

  • Exterior Features: Balcony, Fire Pit, Lighting, Rain Gutters
  • Porch/Patio/Deck: Deck, Patio

Parking

  • Parking Features: Driveway, Private

Location

  • County: Suffolk County
  • Cross Streets: Irene Lane

School Information

  • High School District: Shelter Island
  • Elementary School: Shelter Island School
  • Middle School: Shelter Island School
  • High School: Shelter Island School

Community

  • Association: Yes
  • Assoc. Fees Include: Other

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central Air, ENERGY STAR Qualified Equipment
  • Heating Type: ENERGY STAR Qualified Equipment, Forced Air, Heat Pump
  • Heating Zones: 3

Utilities

  • Sewer: Cesspool, Septic Tank
  • Water: Well
  • Utility Description: Cable Connected, Electricity Connected, Propane, Underground Utilities

Structural Information

  • Architectural Style: Contemporary
  • Detached/Attached: Detached
  • Construction: Batts Insulation, Cedar, Frame, Shake Siding, Shingle Siding
  • Basement: Yes
  • Basement Desc.: Bilco Door(s), Full Basement, Storage Space, Unfinished
  • Windows: Casement
  • Sq. Ft. Source: Public Records
  • Year Built: 2022

Lot Features

  • Property View: Open, Panoramic, Skyline, Trees/Woods, Water
  • Lot Size (Acres): 9.4
  • Lot Size (Sq. Ft.): 409,464
  • Frontage: Municipal
  • Road Maintenance: Public Maintained Road
  • Lot Features: Back Yard, Front Yard, Part Wooded, Private, Restrictions, Secluded, Views, Waterfront

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front View: Beach Access, Beach Front, Creek, Sound, Waterfront

Financial Considerations

  • Association Fee: Yes
  • Association Fee: $225
  • Assoc Fee Freq.: Annually
  • Tax Amount: $19,523.32

Disclosures and Reports

  • Special Conditions: None
  • Property ID: 0700-024-00-01-00-018-000
  • Block: 1
  • Lot Number: 18

Listed by Daniel Gale Sothebys Intl Rlty

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Listing agent

— 21 Thompson Rd —

  • Daniel Gale Sothebys Intl Rlty

631-749-1155

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 21 Thompson Rd

School District:Shelter Island Union Free School District
NameGradesDistance
Shelter Island School
33 North Ferry Road, Shelter Island, NY 11964
PK-121.5 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 21 Thompson Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/06/2025
Price Reduced
$5,875,000
-7.41%
MLS
10/08/2025
Price Reduced
$6,345,000
-6%
MLS
8/30/2025
Listed
$6,750,000
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 21 Thompson Rd

Year
Property Taxes
Change
Tax Assessment
Change
2020
-100%
$2,797,200
30%
2022
$13,595
1%
$2,160,000
—
2021
$13,400
2%
$2,160,000
—
2020
$13,176
10%
$2,160,000
7%
2017
$11,991
-2%
$2,011,300
—
2016
$12,251
22%
$2,011,000
21%
2015
$10,067
—
$1,657,700
2%
2015
$10,079
—
$1,625,200
—
2014
$10,064
2%
$1,625,200
—
2013
$9,819
—
$1,625,200
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 21 Thompson Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Listed by Daniel Gale Sothebys Intl Rlty

21 Thompson Road, Shelter Island, NY 11964 (MLS# 906564) is a Single Family property with 2 bedrooms and 2 full bathrooms. 21 Thompson Road is currently listed for $5,875,000 and was received on August 30, 2025. Want to learn more about 21 Thompson Road? Do you have questions about finding other Single Family real estate for sale in Shelter Island? You can browse all Shelter Island real estate or contact a Coldwell Banker agent to request more information.

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