Private Retreat with Separate Studio & Pool PotentialTucked away on Shelter Island's coveted southern peninsula, 5 Osprey Lane offers a rare combination of privacy, flexibility, and natural beauty within the sought-after Shorewood Farm enclave. Set on approximately 0.78 acres of beautifully landscaped grounds with room to add a pool, the property is designed for relaxed island living and effortless entertaining. Surrounded by the waters of Peconic Bay, Shorewood Farm is known for its exceptional waterfront setting and outdoor lifestyle. Residents enjoy access to a private association beach, community tennis courts, nearby boat launches at Wade's Beach, and convenient proximity to the South Ferry. Just moments away, the protected 2,350-acre Mashomack Preserve offers miles of scenic trails, tidal creeks, and old-growth forest, preserving the area's natural beauty for generations to come. The approximately 1,750-square-foot main residence features three bedrooms, two-and-a-half baths, a flexible bonus room, and a separate laundry room. Thoughtfully updated, the home is highlighted by a renovated kitchen and an inviting primary suite, blending modern comfort with timeless Shelter Island charm. Complementing the main house is a separate one-bedroom triplex studio offering approximately 1,390 square feet of additional living space. With multiple levels of wraparound decking overlooking the surrounding landscape, the studio provides exceptional versatility and privacy, making it ideal as a guest house, home office, artist's studio, or wellness retreat. Mature plantings and thoughtfully designed outdoor living spaces create a seamless connection between the homes and their natural surroundings. A wraparound bluestone patio anchors the outdoor setting, while the generous grounds provide ample opportunity for future enhancements, including the addition of a pool. Offering two distinct structures, exceptional privacy, and access to one of Shelter Island's most desirable waterfront communities, 5 Osprey Lane presents a unique opportunity to create a lasting island retreat.
5 Osprey Lane | MLS# 1023936
This single family home located at 5 Osprey Lane , Shelter Island, NY 11964 is currently listed for sale with an asking price of $1,850,000. This property was built in 1974 and has 4 bedrooms and 4 full and 1 partial baths with 1608 sq. ft. Osprey Lane is located within the Shelter Island school district. Search Shelter Island real estate on www.laffey.com today.
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 07/11/2026. The listing information on this page last changed on 07/11/2026. 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 Sat 07/11/2026 12:02:44 AM EST) or OneKey MLS (last updated Sat 07/11/2026 12:00:25 AM 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.
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.
If you're searching for your next home, or just curious about the market there is no better tool to help you quickly find homes that meet your needs and wants.
With an account you can:
Save your favorite listings
Save searches with your important parameters
Be emailed about new listings that meet your criteria
Be notified of changes to your saved listings such as a price reduction or when a property goes off the market
5 Osprey Lane | MLS# 1023936
This single family home located at 5 Osprey Lane , Shelter Island, NY 11964 is currently listed for sale with an asking price of $1,850,000. This property was built in 1974 and has 4 bedrooms and 4 full and 1 partial baths with 1608 sq. ft. Osprey Lane is located within the Shelter Island school district. Search Shelter Island real estate on www.laffey.com today.