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. 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]] MLS ID KEY1010703 Based on information submitted to the MLS GRID as of [see last changed date above]. 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. Some IDX listings have been excluded from this website. Prices displayed on all Sold listings are the Last Known Listing Price and may not be the actual selling price.

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

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$11,520 / month $1,995,000 Listing Price
4 Beds |3.5 Baths | 3,484 Sq Ft
$13,697 / month $2,395,000 Listing Price
4 Beds |3 Baths
$10,839 / month $1,850,000 Listing Price
4 Beds |3 Baths | 2,600 Sq Ft

Floorplan Amenities

  • Air Conditioning

Commuter Rail

  • Greenport Station

    Drive: 25 min 5.6 mi
  • Bridgehampton Station

    Drive: 35 min 9.7 mi
  • Southold Station

    Drive: 33 min 9.8 mi
  • East Hampton Station

    Drive: 38 min 11.7 mi
  • Amagansett Station

    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

Walkability

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Transit

NR
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Bikeability

NR
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