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Back 249 Windward Court North
Off Market

249 Windward Court North

Port Jefferson NY 11777

2
3
1
1179 sq. ft.
1179 sq. ft.
Condo
Last sold for $440,000
Jonathan GuercioJonathan Guercio, last sold this property on 27 March 2026 after 57 days on market.

Overview

Welcome to 249 Windward Drive, a well-maintained 2-bedroom, 2.5-bath condominium located in The Highlands, one of Port Jefferson’s most established and amenity-rich communities. Offering a smart layout, generous storage, and access to resort-style amenities, this home presents an excellent opportunity for comfortable, low-maintenance living. The main level features an open living and dining area with abundant natural light, an eat-in kitchen, and a convenient half bath. Upstairs, the primary suite includes a private full bath, while the second bedroom is served by an additional full bath. Laundry is located within the unit on the second floor, and the home includes an attached garage plus additional storage, providing functionality rarely found in condominium living. The Highlands community offers a wide range of amenities, including a clubhouse, outdoor pool, fitness center, tennis and basketball courts, playground, professionally landscaped grounds, and a scenic community pond with walking paths. Monthly HOA fees cover exterior maintenance, snow removal, landscaping, trash service, water, and basic cable/internet, allowing for simplified homeownership. Ideally located just a short distance from Port Jefferson Village, residents enjoy access to harbor front parks, dining, shopping, Theatre Three, the Port Jefferson Ferry, and the LIRR station, providing convenient options for travel and recreation. Additional benefits include resident-only beach access, village parking privileges, and discounted country club membership. This property combines location, community amenities, and everyday practicality, making it a compelling option within today’s market.

Features

2 bedrooms
3 bathrooms
1 carspace
1 garage space
1179 sq. ft. floor area
1179 sq. ft. lot size
Condo

Estimated Value

Based on this property and similar 2 bedroom condos sold in Port Jefferson over the last 12 months, the estimated median property value of 249 Windward Court North is $500.5k.

Median value
$500.5k
Estimated value range
$415k - $610k
Median days on market
19
Estimated value trend
3%
increase over the last 12 months
Average days on market is based on recent, comparable sales in Port Jefferson. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 249 Windward Court North

2026
Sold
$440,000
27 Mar 2026 by Jonathan Guercio, of Signature Premier Properties

Happy sellers in Port Jefferson

~%

We have insufficient information to provide an overview of customer satisfaction for Port Jefferson. Viewing the agent profiles, reviews and sales for Port Jefferson can provide insights for this location.

Local market activity for 2 bedroom condos in Port Jefferson

In the last 12 months, 11 two-bedroom condos similar to 249 Windward Court North, have been sold.

This represents a 50% decrease in two-bedroom condos sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Port Jefferson

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Maria Palmar

Maria Palmar is a recommended agent for Port Jefferson.  They have 2 local sales and collected 2 local reviews across the last 12 months.

  •   5   (14 reviews)
  •  2 Reviews in Port Jefferson
  •  2 Sales in Port Jefferson
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Melissa Martins

Melissa Martins is a recommended agent for Port Jefferson.  They have 1 local sale and collected 1 local review across the last 12 months.

  •   5   (2 reviews)
  •  1 Review in Port Jefferson
  •  1 Sale in Port Jefferson
View profile
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Julie Poidomani

Julie Poidomani is an award winning recommended agent for Port Jefferson.  They have 1 local sale and collected 1 local review across the last 12 months.

  •   5   (38 reviews)
  •  1 Review in Port Jefferson
  •  1 Sale in Port Jefferson
View profile
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Kristen Toffales

Kristen Toffales is a recommended agent for Port Jefferson.  They have 3 local sales across the last 12 months.

  •  3 Sales in Port Jefferson
View profile
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