Property photo 1
Property photo 2
Property photo 3
Property photo 4
Property photo 5
4 Beds
3 Baths
3,097 sqft

$2,500,000

20 Baldwin Road, Shelter Island NY, 11964

Price per sqft$807.23
Built in1900
Property size3,097 sqft
Property typeResidential

Overview

Active

Listed Oct 14, 2026

Updated 2h ago

Discover a one-of-a-kind Shelter Island retreat where historic farmhouse charm meets inspired modern living. Set amid 1.8 acres of mature trees, tall privets, sun-drenched edged lawns, and open green space, this circa-1900 property offers a rare combination of character, privacy, and flexibility. The original 2-story residence showcases beautiful period details, including traditional moldings, hand-hewn beams, wood floors, and distinctive vintage glass windows. Inside, 3 bedrooms and 2 baths are complemented by comfortable living and dining rooms, a thoughtfully updated chef’s kitchen with a casual dining area, and a screened porch perfect for long summer evenings. A remarkable addition completed in 2005 is the approximately 1,300-square-foot artist’s atelier, featuring radiant-heated floors and an upper-level primary suite that opens onto a spacious rooftop deck. A detached guest cottage adds another dimension to the property, offering independent accommodations with a large bedroom, full bath, kitchen, living room, and its own garden and lawn. A charming outbuilding provides yet another opportunity, whether envisioned as a reading nook or hobby space. With its blend of historic architecture, dedicated studio space, separate guest quarters, and generous grounds, the property invites a variety of possibilities, including the potential for a swimming pool. Equally suited to relaxed summer gatherings or comfortable year-round living, this is a distinctive island sanctuary with room to create something truly your own.

$16,633/mo

Est. mortgage payment based on a $2,500,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
1062621
Available since
October 14, 2026

Interior Features

Bedrooms
4
Bathrooms
3
Basement
No

Exterior Features

Lot Size
1.8 Acres

Other Property Details

Taxes
$10,022
Tax Frequency
Annually

 Courtesy of Tina Marika Kaasik | Daniel Gale Sotheby's International Realty

Based on information from DASH - Sotheby's International Realty (SIR) as of 10/15/2026. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. The display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent. 

©2026 DASH - Sotheby's International Realty (SIR). All rights reserved. 

Data last updated 2:14 PM UTC, 10/15/2026

Powered by Luxury Presence