BEDS4
BATHS3 full 1 partial
SQUARE FEET3,484
MLS#1010703
STATUSActive
PROPERTY TYPERental - Single Family
SUBDIVISIONSherwood Farms
SCHOOLShelter Island
Property Description
Welcome to 23 Osprey Road, Shelter Island-a beautifully renovated retreat offering privacy, tranquility, and the best of island living. Available for summer or year-round rental, this exceptional property sits on over an acre of landscaped grounds with peaceful pond views and direct adjacency to Dusty Boots Farm, where horses can often be seen grazing nearby. A charming front porch welcomes you into the foyer, complete with a convenient powder room. Beyond, you'll find a chef-inspired eat-in kitchen designed for both everyday living and entertaining. The spacious living room features a wood-burning fireplace and opens to the backyard, creating a seamless indoor-outdoor experience. The main level also includes a primary suite with its own en-suite bathroom, while a screened porch provides the perfect place to relax and enjoy the surrounding natural beauty throughout the seasons. An attached two-car garage adds convenience and ample storage. Upstairs, a versatile sitting area or salon is accompanied by a laundry closet with washer and dryer. Two additional bedrooms offer generous closet space, including a second en-suite bedroom ideal for guests or extended family. The unfinished basement provides abundant storage space for seasonal belongings, recreational equipment, and more. Residents enjoy access to a private beach and tennis court just down the block, while Wades Beach, the South Ferry, and many of Shelter Island's beloved destinations are less than five minutes away. Professional Photography Coming Soon! MD-LD: $70K, Two Weeks: $20K, Y/R: $86K, June: $10K, July: $25K; July-LD: $60K; August: $23K, August-LD: $25K; September: $8K - [[Rental Registration # 2026-L-0067]]
Property Features
Property Type: Rental - Single Family
Basement: Yes
Basement: Full, Unfinished
Cooling: Central Air
Fireplaces: 1
Garage: 2
Heating: Oil
Home Style: Ranch
Lot Size: 1.10 Acres
Year Built: 2005
Amenities
First Floor Bedroom
First Floor Full Bath
Breakfast Bar
Chefs Kitchen
Crown Molding
Eat-in Kitchen
Entrance Foyer
Formal Dining
Granite Counters
High Ceilings
High Speed Internet
His and Hers Closets
In-Law Floorplan
Pantry
Primary Bathroom
Master Downstairs
Soaking Tub
Storage
Walk Through Kitchen
Walk-In Closet(s)
Washer/Dryer Hookup
Feature Descriptions
Appliances: Dishwasher, Dryer, Gas Oven, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer
Building Area Total: 4009
Days on Site: 1
Exterior: Shake Siding
Fireplace Features: Living Room
Fireplace Y/N: Yes
Flooring: Ceramic Tile, Wood
Formal Dining: Yes
Furnished: Furnished
Furnished: Yes
GarageY/N: Yes
Laundry: Common Area, In Hall, Inside
Lot Features: Back Yard, Front Yard, Landscaped, Part Wooded, Sloped, Views, Waterfront, Wooded
On Market Date: 2026-06-08
Parcel Number: 0700-023-00-02-00-078-000
Parking Features: Driveway, Garage
Permit Number: 2026-L-0067
Permit Required Y/N: Yes
Pets Allowed: Call
Rental Term: Monthly
Rooms Total: 10
Sewer: Septic Tank
Utilities: Cable Connected, Electricity Connected, Phone Connected, Propane, Water Connected
Water: Well
Waterfront Features: Pond
Wooded: Yes
Local Schools
High School: Shelter Island School
Middle School: Shelter Island School
Elementary School: Shelter Island School
School District: Shelter Island
Listed By / Shown By
Listing By
Agency Name: Douglas Elliman Real Estate
Agency Contact: 631-329-9400
Shown By
Agency Title: Coldwell Banker Choice Properties
Agency Phone: 833-88-CHOICE (2-4642)
Broker Headquarters, 621 Columbia St. Suite 800, Cohoes, NY 12047
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23 Osprey Road | MLS# 1010703
This property located at 23 Osprey Road, Shelter Island, NY 11964 is currently listed for rent with an asking price of $86,000 / Monthly. Osprey Road is located within the Shelter Island school district. Search Shelter Island real estate on www.coldwellbankerchoice.com today.