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23 Osprey Rd, Shelter Island, NY 11964

Memorial Day - Labor Day 2026 $70,000
June 2026$10,000
July - Labor Day 2026 $60,000

Beds

4
Baths

3.5
Acres

1.07
Sq. ft.

3,484 3.48K

Listing by Douglas Elliman Real Estate (20 Main Street, East Hampton NY 11937)

Last Verified:

Jun 9, 2026

Highlights

Available Year-Round & Seasonally!

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

Home Details

Construction

Property type: Single-family

Property style: Ranch

New construction: No

Year built: 2005

Interior Details

Sq. ft: 3,484

Basement type: Full

Stories: 2

Fireplaces: 1

Furnished: Yes

Bedrooms & Bathrooms

Bedrooms: 4

Full bathrooms: 3

Half bathrooms: 1

Bathroom on first floor: Yes

Primary bedroom on first floor: Yes

Linens: Yes

Other Rooms

Bonus room, Breakfast area, In-law suite/private guest quarters, Loft

Utilities

Water source: Well

Heat type: Oil hot air

Central air conditioning: Yes

Tv/cable/satellite: Yes

House Rules

Pet policy: Pets considered

Smoking policy: Not allowed

Outdoor Details

Pool & Spa

Pool: No

Room for a pool: No

Parking

Garage: Yes

Spaces in garage: 2

Outdoor Amenities

Tennis: No

Room for a tennis court: No

Water frontage/View: Pondfront

Outdoor Shower(s): No

Rights & Access

Water access: Yes

Beach rights: Yes

Lot Details

Lot size: 1.07 Acres

Lot with trees: Yes

South of highway: No

Location

Nearby Beaches
- 0 miles
  Wades Beach
- 1 mile
  Shell Beach
- 3 miles
  Crescent Beach
Nearby Transportation
- 3 miles
  Shelter Island - Shelter Island Seaplane Base
- 4 miles
  Sag Harbor - Hampton Jitney
- 4 miles
  Greenport - LIRR