Updated 5+ Days Ago
Highlights
- Tennis court
- Wood-burning fireplace
- Spacious living room
- Chef-inspired eat-in kitchen
- En-suite bathroom
- Laundry closet
Location
23 Osprey Rd, Shelter Island, NY 11964, USA
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Amenities for 23 Osprey Rd
Features
| Central Air | Den |
| Fireplace | High Ceilings |
| Three Floors | Walk-in Closet |
Appliances
| Dishwasher | In-Unit Laundry |
Community
| Exterior Type: Shake Siding | Onsite Laundry |
Grounds
| Garage Parking | Outdoor Space |
| Storage |
Other
| Architecture Style: Ranch | Oil |
| Ten Rooms |
Units, floor plans, amenities, dimensions, details, availability, and prices may be approximate and subject to change. Please contact a community representative for more information.
Policies and fees
Applicants
Applicants
One-time.
Contact Property
REQUIRED FEES
Security Deposit
One-time. Refundable.
Contact Property
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About 23 Osprey Rd
Property Status: Active 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]] Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Property highlights
We compared every listing in the surrounding area to determine which amenities are most common. If a building lacks an amenity that most others in the area have, it is a con. If a building has an amenity most others in the area do not, it is a pro. Similarly, price, schools, and size are calculated relative to the size, price, and distance to schools of the other properties nearby.How 23 Osprey Rd compares to other nearby properties.
Positives
- More space
- The 4-bedroom is 880 sqft larger than other listings nearby
- Fireplace
- Upgraded in-unit features
- Images Available
- There are at least 10 photos of this address
- Laundry available on site
- Washers and dryers are available in-building or in-unit
Address details
| Zip code | 11964 |
|---|---|
| Type | House for rent |
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Rent trends in Shelter Island
4-bedroom apartments at 23 Osprey Rd cost about 300% more than the average rent price for 4-bedroom apartments in Shelter Island.
Median rents as of Sep 5 2026.
Shelter Island
| Month | Median Rent |
|---|---|
| March 2025 | $30,000 |
| April 2025 | $30,000 |
| May 2025 | $30,000 |
| June 2025 | $30,000 |
| July 2025 | $30,000 |
| August 2025 | $30,000 |
| September 2025 | $30,000 |
| October 2025 | $30,000 |
| December 2025 | $30,000 |
| January 2026 | $30,000 |
| February 2026 | $30,000 |
| March 2026 | $30,000 |
| April 2026 | $28,750 |
| May 2026 | $21,400 |
| June 2026 | $24,375 |
| July 2026 | $28,437 |
| August 2026 | $21,500 |
| September 2026 | $21,500 |
Affordability calculator
Can I afford to live at 23 Osprey Rd?
Bedrooms
4+ bedroomsRent-to-income ratio
30%
Slide to adjust the percentage of your monthly income you are willing to spend on rent.
The general rule of thumb is to spend around 30% or less of your income on rent.
Recommended income
$3,440,000/yr
With your selected rent-to-income ratio, you'd ideally want to make $3,440,000 annually to afford this 4-bedrooms monthly rent price of $86,000.
For more information on rent affordability, visit our rent calculator.
Schools near 23 Osprey Rd
Shelter Island School
33 n ferry rd
shelter island, NY, 11964
PK, K-12Public
B+
Oysterponds Elementary School
23405 main rd
orient, NY, 11957
PK, K-6Public
B
Wainscott School
47 main st
wainscott, NY, 11975
K-3Public
Springs School
48 school st
east hampton, NY, 11937
PK, K-8Public
B
Amagansett School
320 main street
amagansett, NY, 11930
PK, K-6Public
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Internet available near 23 Osprey Rd
Neighborhood
Getting around Shelter Island near 23 Osprey Rd
Walking
2/10
You’ll need another mode of transportation for getting around. Scooter, anyone?
Driving
9/10
Commuting is easy with multiple accessible routes and plenty of parking.
Cycling
5/10
More spots are within biking distance and some roads are cyclist-friendly.
Points of interest for 23 Osprey Rd, Shelter Island
Groceries
4/10
Some groceries within a short drive
Shopping
2/10
Few or no shops within a short drive
Cafes
1/10
Few or no cafés within a short drive
Restaurants
3/10
Some restaurants within a short drive
Primary schools
0/10
Closest elementary school further than a 30-minute walk
High schools
0/10
Closest high school further than a 30-minute walk
Nightlife
2/10
Few or no bars within a short drive
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