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Photo slider slide 1 of 42, , Aerial of 9.4 acre Property looking towards Mashomack Preserve and surrounding waterfront
 Aerial of 9.4 acre Property looking towards Mashomack Preserve and surrounding waterfront
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21 Thompson Rd, Shelter Island, NY 11964

$5,875,000
  • Beds
    2
  • Baths
    2
  • Acres
    9.4
  • Sq. ft.
    1,504 1.5K
Listing by Daniel Gale Sotheby's International Realty (11 Grand Avenue, Shelter Island Heights NY 11965)

Last Verified:

Nov 12, 2025

Highlights

A Kenton van Boer Masterpiece on Smiths Cove

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, p

Home Details

Construction

Property type: Single-family

Property style: Contemporary

New construction: Yes

Year built: 2022

Interior Details

Sq. ft: 1,504

Price per square foot: $3,906/sqft

Basement type: Full

Stories: 2

Floors: Hardwood, Tile

Fireplaces: 1

Bedrooms & Bathrooms

Bedrooms: 2

Full bathrooms: 2

Bathroom on first floor: Yes

Primary bedroom on first floor: Yes

Other Rooms

Breakfast area, Laundry room

Utilities

Water source: Well

Heat type: Electric

Central air conditioning: Yes

Tv/cable/satellite: Yes

Financial Details

Price: $5,875,000

Taxes: $19,523/yr

Outdoor Details

Pool & Spa

Pool: No

Room for a pool: Yes

Parking

Garage: No

Outdoor Amenities

Tennis: No

Room for a tennis court: Yes

Water frontage/View: Harborfront

Outdoor Shower(s): Yes

Rights & Access

Water access: Yes

Beach rights: Yes

Lot Details

Lot size: 9.4 Acres

South of highway: No

Zoning: AA Residential

Location

  • Nearby Beaches

    • 1 mile
      Wades Beach
    • 2 miles
      Shell Beach
    • 3 miles
      Crescent Beach
  • Nearby Transportation

    • 3 miles
      Shelter Island - Shelter Island Seaplane Base
    • 4 miles
      Sag Harbor - Hampton Jitney
    • 4 miles
      Greenport - Hampton Jitney

Listing info

21 Thompson Rd,   Shelter Island
$5,875,000
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