20 Baldwin Road , Shelter Island, NY 11964

$2,500,000
  • 20 Baldwin Road , Shelter Island, NY 11964 Main Photo

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New to the Market
BEDS4 BATHS3 full SQUARE FEET3,097 MLS#1062621
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLShelter Island

Property Description

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.

20 Baldwin Road | MLS# 1062621

This single family home located at 20 Baldwin Road , Shelter Island, NY 11964 is currently listed for sale with an asking price of $2,500,000. This property was built in 1900 and has 4 bedrooms and 3 full baths with 3097 sq. ft. Baldwin Road is located within the Shelter Island school district. Search Shelter Island real estate on www.laffey.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Partial
Cooling: None
Heating: Hot Water, Propane
Home Style: Farmhouse
Lot Size: 1.80 Acres
Taxes: $10,021
Year Built: 1900

Amenities

First Floor Full Bath
Formal Dining
Sauna

Feature Descriptions

Appliances: Dishwasher, Dryer, Gas Cooktop, Gas Oven, Washer
Attic: Unfinished
Building Area Total: 3097
Exterior: Cedar
Formal Dining: Yes
On Market Date: 2026-10-14
Parcel Number: 0700-019-00-01-00-073-001
Parking Features: Driveway
Rental Term: Monthly
Rooms Total: 9
Sauna: Yes
Sewer: Septic Tank
Utilities: See Remarks
Water: Well

Local Schools

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

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Estimated Payment

$ 7,128.17 per month $5,563.92 Principal & Interest $835.08 Property Tax $729.17 Homeowner's Insurance

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Listed By / Shown By

Listing By

Agency Name: Daniel Gale Sothebys Intl Rlty
Agency Contact: 631-749-1155

Shown By

Agency Title: Laffey Real Estate
Agency Phone: 1-888-289-6902

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