• Primary Photo - 100 W Shore Dr
  • Building Photo - 100 W Shore Dr
    Building Photo - 100 W Shore Dr
  • Building Photo - 100 W Shore Dr
    Building Photo - 100 W Shore Dr
$14,950 / Month

100 W Shore Dr

,

Southold, NY 11971

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212-671-1112

  • Bedrooms

    6

  • Bathrooms

    3.5

  • Square Feet

    3,500 sq ft

  • Available

    Available Sep 1

Highlights

  • Water Views
  • Property Fronts a Bay or Harbor
  • Gourmet Kitchen
  • Panoramic View
  • Cape Cod Architecture
  • Cathedral Ceiling
100 W Shore Dr
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About This Home

$5,000 deposit, Available Sep 1

Set in the highly sought-after Reydon Shores community,100 W Shore Dr,Southold is a rare dog-friendly North Fork waterfront seasonal rental with your own private,sandy beach and sweeping bay views to Shelter Island. This renovated classic offers three levels of living with a great room and sunroom,6 bedrooms,3.5 baths,two wood-burning fireplaces,and a huge Trex deck built for sunset dinners and effortless entertaining. The walk-out lower level opens directly to the backyard and shoreline,featuring a waterfront family room plus an entertainment/bonus room with a bar and fireplace. For true North Fork ease,you can moor your boat right off the private beach,with an additional private marina option for effortless boating days; arrive,depart,and live on the water all season long. Monthly Pricing September: $14,950 Available October thru April as a off season rental. price/ month dependant on amount of months rented. MLS ID KEY968304 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.

100 W Shore Dr is a house located in Suffolk County and the 11971 ZIP Code. This area is served by the Shelter Island Union Free School District attendance zone.

* 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 1930

Bedrooms and Bathrooms

Main Floor Bedroom Bathroom on Main Level 3.5 Bathrooms 6 Bedrooms

Finished Basement

Basement Storage

Home Design

Cape Cod Architecture Entry on the 1st floor

Interior Spaces

Cathedral Ceiling 2 Fireplaces 3,500 Sq Ft Home 3-Story Property

Kitchen

Gourmet Kitchen Stainless Steel Appliances Gas Cooktop Oven Microwave Dishwasher

Laundry

Dryer Laundry in Hall

Listing and Financial Details

6-Month Minimum Lease Term Assessor Parcel Number 1000-080-00-05-00-006-001

Lot Details

Property Fronts a Bay or Harbor 21,344 Sq Ft Lot

Parking

Driveway 6 Parking Spaces

Schools

Southold Elementary School Southold Junior-Senior High Middle School Southold Junior-Senior High School

Utilities

Forced Air Heating and Cooling System High Speed Internet Natural Gas Connected Septic Tank Vented Exhaust Fan

Views

Water Panoramic

Community Details

Pet Policy

Dogs 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.
        $5,000

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 Basil Boziotis | Compass Greater NY LLC
  • 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
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Edit Commute

Under 30 minutes

Commute Time is calculated at rush hour.
City - Southold

The small hamlet of Southold is located at the far northeastern end of Long Island. Most of the community is residential, with upscale suburban-style homes composing most of the rental market. Main Road serves as the commercial backbone of Southold, lined with quaint local favorites like the Blue Duck Bakery and Founder’s Tavern.

Boating and fishing are major pastimes among the locals, with numerous marinas and boat launches all around the area providing easy access to Long Island Sound, Peconic Bay, and beyond. In addition to the local beaches, this region is packed with vineyards that are quite popular among visitors and locals alike.

Learn more about living in Southold 
Amenities
  • Air Conditioning
  • Smoke Free
Education
Colleges & Universities Distance
Colleges & Universities Distance
SUNY Suffolk Co., Eastern
Drive: 46 min 24.6 mi
Connecticut College
Drive: 127 min 36.7 mi
University of Connecticut
Drive: 135 min 40.4 mi
Yale University, Main Campus
Drive: 177 min 76.9 mi
100 W Shore Dr is within 46 minutes or 24.6 miles from SUNY Suffolk Co., Eastern. It is also near Connecticut College and University of Connecticut.
Schools
Shelter Island School
Public Elementary, Middle & High School
Grades PK-12
183 Students
Nearby
The Hayground School
Private Elementary & Middle School
Grades PK-8
87 Students
Nearby
Our Lady Of Mercy Regional School
Private Elementary School
Grades PK-5
92 Students
Nearby
School data provided by The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.

View GreatSchools Rating Methodology

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

100 W Shore Dr is near Tweed/New Haven, located 80.0 miles or 182 minutes away.

Commuter Rail Distance
Commuter Rail Distance
Southold Station
Drive: 9 min 3.8 mi
Greenport Station
Drive: 18 min 8.3 mi
Mattituck Station
Drive: 19 min 10.9 mi
Southampton Station
Drive: 61 min 38.4 mi
Bridgehampton Station
Drive: 72 min 43.7 mi
Airports Distance
Airports Distance
Tweed/New Haven
 Drive: 182 min 80.0 mi
Getting Around
Not Walkable
Walkability
10 / 100
Minimal Public Transit
Transit
0 / 100
Exceptionally Drivable
Drivability
90 / 100
Fairly Bikeable
Bikeability
40 / 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 100 W Shore Dr.

Shopping Centers Distance
Shopping Centers Distance
Lighthouse Center
Drive: 10 min 3.9 mi
Southold Square
Drive: 11 min 4.4 mi
Village Of Southold
Drive: 11 min 4.5 mi
100 W Shore Dr has 3 shopping centers within 4.5 miles, which is about a 11-minute drive. The miles and minutes will be for the farthest away property.
Parks and Recreation Distance
Parks and Recreation Distance
Custer Institute Observatory
 Drive: 7 min 3.1 mi
Red House Nature Center
 Drive: 16 min 7.9 mi
East End Seaport Maritime Museum
 Drive: 18 min 8.3 mi
Elizabeth A. Morton National Wildlife Refuge
 Drive: 70 min 20.0 mi
South Fork Natural History Museum & Nature Center
 Drive: 72 min 20.9 mi
100 W Shore Dr has 5 parks within 20.9 miles, including Custer Institute Observatory, Red House Nature Center, and East End Seaport Maritime Museum.
Hospitals Distance
Hospitals Distance
Stony Brook Eastern Long Island Hospital
Drive: 19 min 9.2 mi
100 W Shore Dr is 9.2 miles and a 19 minute drive from Stony Brook Eastern Long Island Hospital.
Military Bases Distance
Military Bases Distance
Fort Trumbell US Navy
Drive: 127 min 36.2 mi
New London Naval Sub Base
Drive: 135 min 40.2 mi
100 W Shore Dr is 36.2 miles from Fort Trumbell US Navy, and is convenient to other military bases, including New London Naval Sub Base.

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