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253 Windward Drive, Port Jefferson, NY 11777

The Highlands · Suffolk County

Key Facts

2Beds
2Baths
1,173Sq Ft
1993Year Built
1Garage
3Stories

Description

Enjoy all the amenities of Port Jefferson without the responsibilities of homeownership. This well-maintained residence features beautiful new hardwood floors and an updated kitchen with white shaker-style cabinetry. Residents enjoy access to Port Jefferson Village amenities, including private beaches, private parking, and country club privileges. Conveniently located near the train station, St. Charles Hospital, Mather Hospital, Stony Brook University Hospital, as well as local shopping, dining, and waterfront attractions. A wonderful opportunity to enjoy the Port Jefferson lifestyle in a prime location—this is a must-see!

Property Information

Property Type

Residential Lease

Sub-Type

Condominium

Style

Other

Year Built

1993

Stories

3

Living Area

1,173 sq ft

Lot Size

1,097 sq ft

Garage Spaces

1

Days on Market

13

MLS® Listing#

1007518

Property Features

Interior

Eat-in Kitchen

Exterior

Balcony

Appliances

DishwasherMicrowaveRefrigeratorWasherGas Water Heater

Cooling

Central Air

Heating

Forced AirNatural Gas

Flooring

HardwoodTile

Basement

Partially Finished

Parking

AttachedDrivewayGarage

Laundry

In Basement

Patio

DeckPatio

Lot Features

Near Public Transit

Construction

Frame

Community

ClubhouseFitness CenterPlaygroundPoolTennis Court(s)

Utilities

Cable Available

Sewer

Public Sewer

Water Source

Public

Schools

Elementary:
Terryville Road School
Middle:
John F Kennedy Middle School - Suffolk
High:
Comsewogue High School

Financial Details

Parcel Number

0206-022-00-04-00-253-000

Directions

Highland Blvd to Windward Drive

Affordability Calculator

$640

Estimated monthly payment

$17/mo

Principal $2,560 · Est. interest $3,571 over 30 yrs

Neighborhood Market Statistics

How this home compares to active listings in Port Jefferson, NY

$607,692
Median Listing Price
42
Median Days on Market
1,800
Median Sq Ft
$332
Median Price / Sq Ft
232
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 Port Jefferson, NY.

Location

Map showing the location of 253 Windward Drive, Port Jefferson, NY 11777

Points of Interest in Port Jefferson, NY

Showing the Port Jefferson area map.

Nearby Schools

  • Port Jefferson School District

    School · 0.7 mi away

  • Port Jefferson Elementary School

    Elementary · 0.8 mi away

  • Maryhaven Center of Hope

    School · 0.9 mi away

  • Primarily 2's and 3's

    School · 0.9 mi away

  • Harbor View Nursery School

    School · 1.1 mi away

  • Mount Sinai High School

    Secondary · 1.1 mi away

  • Port Jefferson Middle School

    Secondary · 1.2 mi away

  • Earl L. Vandermeulen High School

    Secondary · 1.2 mi away

  • John F Kennedy Middle School

    Secondary · 1.3 mi away

  • Mount Sinai Middle School

    Secondary · 1.3 mi away

  • Mount Sinai Elementary School

    Elementary · 1.4 mi away

  • Mount Sinai School District

    School · 1.4 mi away

  • Norwood Avenue School

    Elementary · 1.7 mi away

  • Terryville Road Elementary School

    Elementary · 1.8 mi away

  • Ward Melville High School

    Secondary · 1.9 mi away

  • Three Village Central School District

    School · 1.9 mi away

  • Clinton Avenue Elementary School

    Elementary · 2.1 mi away

  • Play Groups School

    School · 2.2 mi away

  • Arrowhead Elementary School

    Elementary · 2.3 mi away

  • Kids of Miller Place

    School · 2.5 mi away

Commute Calculator

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Nearby Homes

Similar Homes Nearby

Similar Home Values

Comparable nearby listings and their asking prices.

Moving Cost Estimate

EXIT Agents in Port Jefferson

Listing Courtesy: Douglas Elliman Real Estate - 6317516000

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#1007518. © 2026EXIT Realty®. All rights reserved.