• Primary Photo - 23 Osprey Rd
  • Primary Photo - 23 Osprey Rd
$86,000 / Month

23 Osprey Rd

,

Shelter Island, NY 11964

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516-320-9540

  • Bedrooms

    4

  • Bathrooms

    3.5

  • Square Feet

    3,484 sq ft

  • Available

    Available Jun 15

Highlights

  • Home fronts a pond
  • Gourmet Galley Kitchen
  • Partially Wooded Lot
  • 3-Story Property
  • Wood Flooring
  • Main Floor Primary Bedroom
23 Osprey Rd
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About This Home

$8,000 deposit, Available Jun 15

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 a house located in Suffolk County and the 11964 ZIP Code.

* 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. Price, availability, fees, and any applicable rent special are subject to change without notice.
* Square footage definitions vary. Displayed square footage is approximate.

Home Details

Home Type

Single Family Detached Home

Year Built

Built in 2005

Bedrooms and Bathrooms

Primary Bedroom on Main In-Law or Guest Suite Soaking Tub Dual Closets Walk-In Closet Bathroom on Main Level En-Suite Primary Bedroom 3.5 Bathrooms 4 Bedrooms

Flooring

Wood Ceramic Tile

Home Design

3-Story Property Shake Siding Entry on the 1st floor

Interior Spaces

Living Room with Fireplace High Ceiling Furnished Formal Dining Room Crown Molding Entrance Foyer Storage 3,484 Sq Ft Home

Kitchen

Gourmet Galley Kitchen Granite Countertops Stainless Steel Appliances Breakfast Bar Gas Oven Range Microwave Dishwasher

Laundry

Dryer Laundry in Hall Washer

Listing and Financial Details

12-Month Minimum Lease Term Assessor Parcel Number 0700-023-00-02-00-078-000

Lot Details

1.07 Acre Lot Home fronts a pond Partially Wooded Lot Landscaped Back and Front Yard Sloped Lot

Parking

2 Car Garage Driveway

Schools

Shelter Island Elementary And Middle School Shelter Island High School

Unfinished Basement

Basement Fills Entire Space Under The House

Utilities

Central Air High Speed Internet Propane Cable TV Available Well Septic Tank Heating System Uses Oil

Community Details

Amenities

Laundry Facilities

Pet Policy

Call for details about the types of pets allowed

Fees and Policies

The fees listed below are community-provided and may exclude utilities or add-ons. All payments are made directly to the property and are non-refundable unless otherwise specified. Use the Cost Calculator to determine costs based on your needs.

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

Contact

  • Listed by Joseph Flynn | Douglas Elliman Real Estate
  • Phone Number
  • Contact
  • Source
    OneKey® MLS
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.
Location Get Directions
| Edit
Edit Commute

Under 30 minutes

Commute Time is calculated at rush hour.
City - Shelter Island

Nicknamed “the un-Hamptons,” Shelter Island is a peaceful island community situated on the eastern end of Long Island. Shelter Island is only accessible by ferry and sits just five minutes from its bustling neighbor, the Hamptons. Adorned with old-fashioned buildings along tree-lined streets, Shelter Island exudes small-town charm and tranquil luxury in equal measure.

The community’s secluded feel is a part of its allure, despite being within close reach of wine country and the Hamptons. Shelter Island is also roughly a two-hour drive from New York City. Shelter Island’s rental homes generally offer quick access to the community’s many beaches as well as the locally owned shops and restaurants that line Ferry Road.

Learn more about living in Shelter Island 
Amenities
  • Air Conditioning
Education
Colleges & Universities Distance
Colleges & Universities Distance
SUNY Suffolk Co., Eastern
Drive: 71 min 31.8 mi
Connecticut College
Drive: 136 min 34.3 mi
University of Connecticut
Drive: 144 min 38.0 mi
23 Osprey Rd is within 71 minutes or 31.8 miles from SUNY Suffolk Co., Eastern. It is also near Connecticut College and University of Connecticut.
Transportation

23 Osprey Rd is near Tweed/New Haven, located 77.5 miles or 191 minutes away.

Commuter Rail Distance
Commuter Rail Distance
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
Airports Distance
Airports Distance
Tweed/New Haven
 Drive: 191 min 77.5 mi
Getting Around
Somewhat Walkable
Walkability
20 / 100
Exceptionally Drivable
Drivability
90 / 100
Fairly Bikeable
Bikeability
50 / 100

Scores provided by

What do Walkability, Transit, Drivability, and Bikeability mean? Walkability measures the walking distance to day-to-day needs. Transit measures access to public transportation. Drivability measures congestion, parking availability, and access to major roads. Bikeability measures the suitability for cycling. How It Works
-
Soundscore™
- / 100

Traffic

-

Airport

-

Businesses

-

Scores provided by

HowLoud What is a Sound Score Rating? A Sound Score Rating aggregates noise caused by vehicle traffic, airplane traffic and local sources. How It Works
Points of Interest

Time and distance from 23 Osprey Rd.

Shopping Centers Distance
Shopping Centers Distance
Bridgehampton Village
Drive: 34 min 9.5 mi
Southold Square
Drive: 33 min 9.8 mi
Village Of Southold
Drive: 33 min 9.8 mi
23 Osprey Rd has 3 shopping centers within 9.8 miles, which is about a 33-minute drive. The miles and minutes will be for the farthest away property.
Parks and Recreation Distance
Parks and Recreation Distance
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
23 Osprey Rd has 5 parks within 12.9 miles, including East End Seaport Maritime Museum, Red House Nature Center, and Elizabeth A. Morton National Wildlife Refuge.
Hospitals Distance
Hospitals Distance
Stony Brook Eastern Long Island Hospital
Drive: 27 min 6.1 mi
23 Osprey Rd is 6.1 miles and a 27 minute drive from Stony Brook Eastern Long Island Hospital.
Military Bases Distance
Military Bases Distance
Fort Trumbell US Navy
Drive: 136 min 33.8 mi
New London Naval Sub Base
Drive: 144 min 37.8 mi
Naval & Marine Reserve Center
Drive: 201 min 79.9 mi
23 Osprey Rd has 3 military bases within 79.9 miles, the nearest is Fort Trumbell US Navy which is 33.8 miles away and a 136 minute drive.

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