21 Thompson Rd

Shelter Island, NY 11964

$5,875,000
Price
2
Beds
1,504 Sq. Ft.
$3,906 / Sq. Ft.
1,504
Sq. Ft.
$3,906
per Sq. Ft.
PendingVirtual Tour
PendingVirtual Tour
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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...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.
  1. Listed by Debra L. Von Brook Binder CBR • Daniel Gale Sothebys Intl Rlty
    P: (631)-749-1155 C: (631)-872-2889 debravonbrookbinder@danielgale.com

Property Details for 21 Thompson Road

City/Township
Shelter Island
View
Open, Panoramic, Skyline, Trees/Woods, Water
Architectural Style
Contemporary
Waterfront
Yes
Section Area
Irene Lane
LISTING UPDATED: 12/23/2025 04:22 PM

Property Details for 21 Thompson Road

StatusPending
MLS #906564
Days on Market115
Taxes$19,523 / year
HOA Fees$225 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family
Year Built2022
Lot Size9.40 AC / 409,464 SF
CountySuffolk County

Location

Listing Courtesy of Daniel Gale Sothebys Intl Rlty, Debra L. Von Brook Binder CBR
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Building Information for 21 Thompson Road

Stories-Year Built2022Building Size-Lot Size9.40 AC / 409,464 SF

Payment Calculator

$30,279 per month

30 year fixed, 6.15% Interest

Principal and Interest

$28,634

Property Taxes

$1,627

HOA Dues

$19

The Payment Calculator is for illustrative purposes only.

Property Information for 21 Thompson Road

Summary
Location and General Information
  • Senior Community YN: No
  • MLS District Code: 700
  • Tax Block: 1
  • Tax Lot: 18
  • Property Attached: No
  • Structure Type: false
  • Levels: Two
  • Property Condition: New Construction
  • State Or Province: NY
  • Water Access YN: Yes
School Information
  • School District: Shelter Island
  • Elementary School District: Shelter Island
  • Elementary School: Shelter Island School
  • Middle Or Junior School District: Shelter Island
  • Middle Or Junior School: Shelter Island School
  • High School District: Shelter Island
  • High School: Shelter Island School
Rental
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Room Information
Room 1 Information
  • Room Level: First
  • Room Type: Living Room
  • RoomDescription 1: Vaulted living room with wood burning fireplace and stunning views of Smith Cove
Room 2 Information
  • Room Level: First
  • Room Type: Kitchen
  • Room Description: Custom kitchen with wood cabinetry, high end appliances, counter seating and built in banquet dining
Room 3 Information
  • Room Level: First
  • Room Type: Primary Bedroom
  • Room Description: Primary bedroom with built in closets, en-suite bathroom, water-view with sliding doors to deck
Room 4 Information
  • Room Level: First
  • Room Type: Primary Bathroom
  • Room Description: Primary bathroom with marble counters and tile Soaking tub/shower
Room 5 Information
  • Room Level: First
  • Room Type: Bedroom 2
  • Room Description: Bedroom with sliders to deck and beautiful waterview
Room 6 Information
  • Room Level: First
  • Room Type: Bathroom 2
  • Room Description: Hall bath with glass enclosed shower and marble counter and tile
Room 7 Information
  • Room Level: Second
  • Room Type: Den
  • Room Description: Second Floor bedroom/library with balcony deck out sliding doors
Room 8 Information
  • Room Level: First
  • Room Type: Laundry
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 0700-024-00-01-00-018-000
  • Association Fee: $225.00
  • Association Fee Includes: Other
  • Association Fee Frequency: Annually
  • Association: Yes
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, Balcony, Beach Access, Beach Front, Built-in Features, Casement, Cathedral/Vaulted/High Ceiling, Chefs Kitchen, Contemporary, Creek, Deck, ENERGY STAR Qualified Door(s), Eat in Kitchen, Electric Dryer Hookup, Entrance Foyer, Fire Pit, Hardwood Floors As Seen, High Ceilings, In Hall, Kitchen Island, Laundry Room, Lighting, Living Room, Marble Counters, Masonry, Natural Woodwork, Open, Open Floorplan, Open Kitchen, Panoramic, Pantry, Patio, Primary Bathroom, Rain Gutters, Skyline, Smoke Detector(s), Soaking Tub, Sound, Trees/Woods, Washer Hookup, Washer/Dryer Hookup, Water View, Waterfront, Well, Wood Burning
  • 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, 1st Fl Master Bedroom, Soaking Tub, Washer/Dryer Hookup
  • Appliances: Dishwasher, Dryer, Electric Oven, Electric Range, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Water Softener Owned
  • Number Of Kitchens: 1.0
  • Total Rooms: 6
  • Primary on Main: Yes
  • Basement: Bilco Door(s), Full, Storage Space, Unfinished
  • Attic Description: Pull Stairs
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Fireplace Features: Living Room, Masonry, Wood Burning
  • Location Amenities: Balcony, Hardwood Floors As Seen, 1st Fl Master Bedroom, Cathedral/Vaulted/High Ceiling, Chef's Kitchen, Eat in Kitchen, Entry Foyer, Foyer, High Ceilings, Island Kitchen, Marble Countertops, Open Kitchen, Pantry, Soacking Tub, WD Hookup, Privacy, Scenic View, Waterfront, Deck, Patio, Open View, Skyline View, Water View, Casement Windows
  • Laundry Features: Electric Dryer Hookup, In Hall, Laundry Room, Washer Hookup
  • Security Features: Smoke Detector(s)
  • Window Features: Casement
  • Flooring: Hardwood
  • Living Area: 1,504.00
  • Foundation Details: Concrete Perimeter
  • Basement: Yes
Exterior Features
  • Exterior Features: Balcony, Fire Pit, Lighting, Rain Gutters
  • Exterior Property Features: Balcony, Fire Pit, Lighting, Rain Gutters, Deck, Patio, Driveway, Private, Casement, Back Yard, Front Yard, Part Wooded, Restrictions, Secluded, Views, Waterfront
  • Elevation Certificate: No
  • Patio And Porch Features: Deck,Patio
  • Construction Materials: Batts Insulation, Cedar, Frame, Shake Siding, Shingle Siding
  • Road Frontage Type: Municipal
  • Road Responsibility: Public Maintained Road
  • Waterfront Features: Beach Access, Beach Front, Creek, Sound, Waterfront
  • Pool Private: No
Lot Information
  • Lot Features: Back Yard, Front Yard, Part Wooded, Private, Restrictions, Secluded, Views, Waterfront
  • Additional Parcel: No
  • Site Features: Back Yard, Front Yard, Part Wooded, Private, Restrictions, Secluded, Views, Waterfront
  • Building Area Units: Square Feet
Parking
  • Parking Features: Driveway, Private
  • Garage: No
  • Carport: No
Utilities
  • Cooling: Central Air, ENERGY STAR Qualified Equipment
  • Heating: ENERGY STAR Qualified Equipment, Forced Air, Heat Pump
  • Heat Fuel Type: ENERGY STAR Qualified Equipment, Forced Air, Heat Pump
  • Number Of Heating Zones: 3
  • Sewer: Cesspool, Septic Tank
  • Water Source: Well
  • Utilities: Cable Connected, Electricity Connected, Propane, Underground Utilities
Green Features
  • Green Features: Casement, Dishwasher, Dryer, Electric Oven, Electric Range, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Water Softener Owned, ENERGY STAR Qualified Equipment, Forced Air, Heat Pump, Balcony, Fire Pit, Lighting, Rain Gutters
Agent
Payment and Rate
  • Down Payment Resource: No

Public Records for 21 Thompson Road

Taxable ValueLand$2,274,700Additions$522,500Total$2,797,200
Home Facts
Beds2Total Finished SqFt1,506 SqFtAbove Grade Finished SqFt1,506 SqFtStories2Lot Size409,464 SqFtStyleSingle Family ResidenceYear Built2022ZoningAACountySUFFOLKAPN0700-024.00-01.00-018.000Fireplace TypeHas Fireplace

Schools near 21 Thompson Road

This home is within Shelter Island Union Free School District.
Rating
School
Type
Grades
Distance
Shelter Island School
Public - PK to 12
Rating
School
Distance
Shelter Island School
PublicPK to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Daniel Gale Sothebys Intl Rlty, Debra L. Von Brook Binder CBR

Based on information submitted to the MLS GRID as of 12/23/2025 04:22 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.