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]]
- Heating System:
- Oil
- Cooling System:
- Central Air
- Basement:
- Full, Unfinished
- Appliances:
- Dishwasher, Oven, Refrigerator, Microwave, Stainless Steel Appliance(s), Dryer, Washer, Range, Gas Oven
- Fireplace Features:
- Living Room
- Fireplaces Total:
- 1
- Flooring:
- Ceramic Tile, Wood
- Garage Spaces:
- 2
- Interior Features:
- Eat-in Kitchen, Master Downstairs, Entrance Foyer, Granite Counters, High Ceilings, Pantry, Storage, Walk-in Closet(s), Chefs Kitchen, Walk Through Kitchen, Washer/dryer Hookup, High Speed Internet, Soaking Tub, Formal Dining, First Floor Bedroom, In-law Floorplan, Primary Bathroom, First Floor Full Bath, His And Hers Closets, Breakfast Bar, Crown Molding
- Laundry Features:
- In Hall, Inside, Common Area
- Lot Features:
- Wooded, Sloped, Views, Waterfront, Part Wooded, Back Yard, Landscaped, Front Yard
- Parking Features:
- Driveway, Garage
- Sewer:
- Septic Tank
- Utilities:
- Propane, Cable Connected, Water Connected, Electricity Connected, Phone Connected
- City:
- Shelter Island
- State:
- NY
- Street:
- Osprey
- Street Number:
- 23
- Street Suffix:
- Road
- Postal Code:
- 11964
- Floor Number:
- 0
- Longitude:
- W73° 40' 27.4''
- Latitude:
- N41° 2' 56.4''
- Subdivision Name:
- Sherwood Farms
- Directions:
- Use Google Maps
- PostalCity:
- Shelter Island
- Architectural Style:
- Ranch
- Construction Materials:
- Shake Siding
- Elementary School:
- Shelter Island School
- High School:
- Shelter Island School
- Levels:
- Three Or More
- Agent MlsId:
- 187996
- MiddleOrJunior School:
- Shelter Island School
- PhotosCount:
- 1
- Special Listing Conditions:
- No
- Water Source:
- Well
- Office MlsId:
- DERE45
Residential Lease - MLS# 1010703
23 Osprey Road, Shelter Island, NY
- Property Type :
- Residential Lease
- Property SubType :
- Single Family Residence
- Listing Type :
- For Rent
- Listing ID :
- 1010703
- Price :
- $86,000
- Rooms :
- 10
- Bedrooms :
- 4
- Bathrooms :
- 3
- Half Bathrooms :
- 1
- Bathrooms Total :
- 4
- Square Footage :
- 3,484 Sqft
- Building Area :
- 4,009 Sqft
- Lot Area :
- 1.07 Acre
- Year Built :
- 2005
- Status :
- Active
- Listing Agent :
- Joseph Flynn
- Listing Office :
- Douglas Elliman Real Estate
