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4 Glynn Drive, Shelter Island, NY 11964

Suffolk County

Key Facts

4Beds
3Baths
3,037Sq Ft
1999Year Built
0.50Lot (acres)
1Garage

Description

This Shelter Island home is the kind of summer rental people wait all year to find-turnkey, stylish, and effortlessly comfortable. Recently renovated and designer-furnished, the home is ready for immediate enjoyment. Bright, sun-filled interiors and multiple inviting living spaces create an easy flow for summer living, whether it's slow mornings with coffee, afternoons by the pool, or relaxed evenings entertaining friends and family. The backyard and pool area offer a private, resort-like setting that makes it easy to settle in and stay awhile. Shelter Island delivers a unique Hamptons experience-more peaceful and private, yet still deeply connected to the water and surrounding towns. Boating is a central part of life here, with quick access to Peconic and Gardiners Bay for day trips, sunset cruises, and dock-and-dine outings. The restaurant scene adds to the appeal, with favorites like Sunset Beach for a lively, waterfront atmosphere, along with SALT and the Rams Head Inn for classic coastal dining. Sag Harbor is just a short trip away, offering even more restaurants, shops, and marinas. For summer renters, homes like this-fully updated, beautifully furnished, and ready to go-are in especially high demand. This is a seamless, elevated way to experience Shelter Island and the Hamptons at their best.

Property Information

Property Type

Residential Lease

Sub-Type

Single Family Residence

Style

Post Modern

Year Built

1999

Living Area

3,037 sq ft

Lot Size

0.50 acres

Garage Spaces

1

Days on Market

85

MLS® Listing#

975096

Property Features

Appliances

Other

Cooling

Central Air

Heating

Other

Basement

Unfinished

Parking

Driveway

Construction

Other

Utilities

See Remarks

Sewer

None

Water Source

Other

Schools

Elementary:
Shelter Island School
Middle:
Shelter Island School
High:
Shelter Island School

Financial Details

Parcel Number

0700-017-00-01-00-098-000

Affordability Calculator

$2,400

Estimated monthly payment

$64/mo

Principal $9,600 · Est. interest $13,393 over 30 yrs

Neighborhood Market Statistics

How this home compares to active listings in Shelter Island, NY

$842,857
Median Listing Price
53
Median Days on Market
1,600
Median Sq Ft
$482
Median Price / Sq Ft
594
Active Listings
  • This home’s price is 99% below the area median.
  • Its price per sq ft is 99% below the area median.

Market statistics compiled from active EXIT Realty® and MLS listings in Shelter Island, NY.

Location

  • 4 Glynn Drive, Shelter Island, NY 11964

Points of Interest in Shelter Island, NY

Showing the Shelter Island area map.

Nearby Schools

  • Shelter Island School

    School · 1.6 mi away

  • Greenport Elementary School

    Elementary · 2.6 mi away

  • Southold Elementary School

    Elementary · 3.3 mi away

  • Southold Junior Senior High School

    Secondary · 3.3 mi away

  • Head Start

    School · 3.8 mi away

  • Cutchogue East Elementary School

    Elementary · 6.0 mi away

  • Sag Harbor Elementary School

    Elementary · 6.2 mi away

  • Sag Harbor Union Free School District Page

    School · 6.3 mi away

  • Pierson High School

    Secondary · 6.3 mi away

  • Harbor Waldorf School

    School · 6.4 mi away

  • Our Sons and Daughters

    School · 6.4 mi away

  • Oysterponds Elementary School

    Elementary · 6.6 mi away

  • Mattituck-Cutchogue School Dist

    School · 7.0 mi away

  • Our Lady of Mercy Elementary School

    Elementary · 7.2 mi away

  • New Suffolk School

    Elementary · 7.4 mi away

  • Ross Lower School

    School · 8.1 mi away

  • Hayground School

    School · 8.9 mi away

  • The Green School

    School · 9.0 mi away

  • Ross School

    Elementary · 9.3 mi away

  • Bridgehampton School

    School · 9.5 mi away

Commute Calculator

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Nearby Homes

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Similar Home Values

Comparable nearby listings and their asking prices.

Moving Cost Estimate

EXIT Agents in Shelter Island

Listing Courtesy: Douglas Elliman Real Estate - 6316686565

Presented by: Joseph T. Van Asco

The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright ©2026 OneKey MLS. All Rights Reserved
Fair Housing Notice

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of one or more Multiple Listing Services (MLS). Listing information is deemed reliable but is not guaranteed accurate. Copyright © EXIT Realty® and respective MLS providers.

Data provided by LIBOR. MLS® Listing#975096. © 2026EXIT Realty®. All rights reserved.