Single Family
23 Osprey Road
Active · Shelter Island · Suffolk County, NY 11964
- Bedrooms
- 4 Beds
- Bathrooms
- 4 Baths
- Year built
- 2005
0 of 18 photos ready
About this home
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. Two Weeks: $20K or Year Round: $86K - [[Rental Registration # 2026-L-0067]]
Listing snapshot
- Days on site
- 59 days
- Listed on MLS
- Jun 8, 2026
- Full baths
- 3
- Half baths
- 1
- Area source (MLS)
- Plans
- Listing brokerage
- Douglas Elliman Real Estate
- MLS ID
- KEY1010703
- Last updated
- Oct 1, 2026
General features
- Property type
- Single Family
- Property subtype
- Single Family Residence
- Year built
- 2005
- Garage
- Yes
- Garage spaces
- 2
- Parking
- Driveway, Garage
- Water source
- Well
- Sewer
- Septic Tank
- Utilities
- Cable Connected, Electricity Connected, Phone Connected, Propane, Water Connected
Interior features
- Basement
- Full, Unfinished
- Heating
- Oil
- Cooling
- Central Air
- Interior
- 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
- Appliances
- Dishwasher, Dryer, Gas Oven, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer
- Flooring
- Ceramic Tile, Wood
- Fireplace
- Yes
- Fireplaces
- 1
Exterior features
- Architectural style
- Ranch
- Construction materials
- Shake Siding
- Private pool
- No
Schools (MLS)
- Elementary school
- Shelter Island School
- Elementary school district
- Shelter Island
- Middle school
- Shelter Island School
- Middle school district
- Shelter Island
- High school
- Shelter Island School
- High school district
- Shelter Island
School information is provided by the MLS. Confirm attendance eligibility with the school district.
Recent activity
- Listing updated from MLS
- First seen on this site
- MLS status changed
Location
Listing data is supplied by the MLS and may change without notice.