Last Updated: 1 Day Ago

Monthly Rent

$86,000

Beds

4

Baths

3.5

* Price shown is base rent. Excludes user-selected optional fees and variable or usage-based fees and required charges due at or prior to move-in or at move-out. View Fees and Policies for details. Price, availability, fees, and any applicable rent special are subject to change without notice.

Note: Prices and availability subject to change without notice.

Lease Terms

Contact office for Lease Terms

Fees and Policies

The fees below are based on community-supplied data and may exclude additional fees and utilities.

  • One-Time Basics
    • Due at Move-In
      • Security Deposit - Refundable
        Charged per unit.
        $8,000
        Charged per unit.

Property Fee Disclaimer: Based on community-supplied data and independent market research. Subject to change without notice. May exclude fees for mandatory or optional services and usage-based utilities.

About 23 Osprey Rd

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; September: $8K; YR: $86K - [[Rental Registration # 2026-L-0067]] MLS ID KEY1010703

23 Osprey Rd is located in Shelter Island, New York in the 11964 zip code.

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$24,835 / month $3,795,000 Listing Price
5 Beds |5 Baths | 3,072 Sq Ft
$14,692 / month $2,245,000 Listing Price
4 Beds |3 Baths | 2,300 Sq Ft
$12,165 / month $1,850,000 Listing Price
4 Beds |3 Baths | 2,600 Sq Ft

Floorplan Amenities

  • Air Conditioning

Commuter Rail

  • Greenport

    Drive: 25 min 5.6 mi
  • Bridgehampton

    Drive: 35 min 9.7 mi
  • Southold

    Drive: 33 min 9.9 mi
  • East Hampton

    Drive: 38 min 11.7 mi
  • Amagansett

    Drive: 45 min 15.1 mi

Parks & Recreation

  • East End Seaport Maritime Museum

    Drive: 24 min 5.5 mi
  • Red House Nature Center

    Drive: 28 min 6.9 mi
  • Elizabeth A. Morton National Wildlife Refuge

    Drive: 30 min 7.4 mi
  • Custer Institute Observatory

    Drive: 35 min 10.9 mi
  • Cedar Point County Park

    Drive: 48 min 12.9 mi

Shopping Centers & Malls

Schools

Data provided by GreatSchools.org 2025 © 2025. All rights reserved.

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Ratings

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Transit

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Bikeability

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