- 4BR, 3.5BA Home
- $86,000 Pricing
- 3,484 Square Feet
- 06-15-2026 Availability
Unit Rent and Fees
Unit Price
- $86,000
Deposit
- $8,000 deposit
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.
Property Contact Info
- Listed by:
- Agency:
- Vendor Logo:
- Website:
- View Property Website
- Call Us:
- (516) 320-9540
- Disclaimer:
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.
Required Fees
One-Time Basics
- Due at Move-In
- Security Deposit - RefundableiCharged Per Unit.$8000
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.
Features and Amenities
On-Site Services
- Garden Style
Interior Features
- Air Conditioning

Map
- Shopping
- Schools
- Grocery
- Medical
- Transportation

Map
Frequently Asked Questions about 23 Osprey Rd
What type of rental is available at 23 Osprey Rd?
There is currently a 4 Bed 3 Bath Home for rent with 3,484 sq ft listed at 23 Osprey Rd. It is Available June 15, 2026.
How much is the rent at 23 Osprey Rd?
The rental at 23 Osprey Rd is currently listed at $86,000.
What area of town is 23 Osprey Rd located in?
Located in the Outlying Eastern Suffolk Neighborhood, 23 Osprey Rd is in the 11964 Zip Code of Shelter Island, NY.
Points of Interest
Time and distance from 23 Osprey Rd.
Big Box and Retail
Homegoods
Sleepy's
Groceries
Iga
Stop & Shop
Hospitals
Shopping Centers
23 Osprey Rd has 5 shopping centers within 8.3 miles.
Transit Stations
Greenport Station-Greenport Branch
Southold Station-Greenport Branch
Bridgehampton Station-Montauk Branch
Nearby Neighborhoods
Rental Price Ranges in the Area
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Shelter Island Studio Apartments | $1,692 | $1,350 | $2,768 |
| Shelter Island 1 Bedroom Apartments | $2,010 | $1,100 | $3,255 |
| Shelter Island 2 Bedroom Apartments | $2,242 | $1,200 | $4,212 |
| Shelter Island 3 Bedroom Apartments | $2,801 | $1,400 | $3,815 |
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