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$86,000 /month

23 Osprey Rd, Shelter Island, NY 11964

Last Updated:

What This House Offers

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.

Unit

  • $86,000 / month
  • 4 Beds
  • 3.5 Baths
  • 3484 sq. ft.
  • Available Jun 15

Home Features

  • Air Conditioning

23 Osprey Rd is a single-family home for rent in Shelter Island, NY

Fees and Policies

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

One-Time Basics

  • Security Deposit - Refundable
    $8,000

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.

Explore Commute Options

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What's nearby 23 Osprey Rd

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Get In Touch

Property Address:
23 Osprey Rd,
Shelter Island, NY 11964
Listed by
Joseph Flynn | Douglas Elliman Real Estate
Phone Number: (516) 320-9540
MLSLongIsland#NY

Information Copyright 2026, OneKey® MLS. All Rights Reserved. The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.

Area Scores

Walkability

Somewhat walkable20 / 100

Driveability

Exceptionally drivable90 / 100

Bikeability

Fairly bikeable50 / 100

Scores provided by

Travel and Transit

Commuter Rail
25 min Drive
Long Island Rail Road
Commuter Rail
32 min Drive
Long Island Rail Road

Local Education

Primary and Secondary Schools

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HARBOR WALDORF SCHOOL

Grades PK-5

Private

6 rating

Shelter Island School

Grades PK-12

Public

Data provided by GreatSchools.org © 2026. All rights reserved.

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