20 Baldwin Road
Shelter Island, NY 11964

$2,500,000

Beds: 4
Baths: 3 full
Sq. Feet: 3097
MLS ID: 1062621
Subdivision:
School Dist: Shelter Island
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. View this listing at: http://www.laffey.com/lid=190141590

Property Features

School Information

Printed October 15, 2026


Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 10/15/2026. The listing information on this page last changed on 10/15/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 10/15/2026 12:01:36 AM EST) or OneKey MLS (last updated Wed 10/14/2026 11:53:25 PM EST). Real estate listings held by brokerage firms other than Laffey Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

mls logo
Listing data and photos distributed by MLSGRID
Member Participants (and their affiliated licensees, if applicable) shall indicate on their websites that IDX information is provided exclusively for consumers’ personal non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability.
Based on information submitted to the MLS GRID. 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.



Privacy Policy / DMCA Notice / ADA Accessibility