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149 Windward Court S, 
Port Jefferson, NY 11777

$649,990

3

Beds

3

Baths

1,900

Sq Ft

Condo

Active

Listed by

Patricia Massimo, Toni Romano
Coldwell Banker American Homes

Last updated:

October 26, 2026, 01:22 AM

MLS#

1030359

Source:

OneKey MLS

Company Logo

About This Home

149 Windward Court S

Welcome to the largest unit in the highly desirable Highlands community! This beautifully updated corner unit offers exceptional space, privacy, and an impressive list of upgrades throughout. The bright and inviting interior features gleaming hardwood floors on the first level, a stunning renovated kitchen, and a spacious primary suite complete with a dedicated vanity area and an elegant frameless glass shower door. Thoughtful storage abounds with three linen closets, while new Andersen windows with a transferable warranty provide energy efficiency and peace of mind. Custom blinds are included with the home. Additional recent improvements include a new roof, a 2022 hot water heater and boiler, a new storm door, outdoor electrical outlets in both the front and rear of the home, and a beautiful Nicolock patio—perfect for relaxing or entertaining. Residents of The Highlands enjoy an outstanding resort-style lifestyle with exclusive amenities, including a private beach, clubhouse with fitness center, saltwater in-ground pool, tennis courts, and Port Jefferson Country Club golfing privileges. Additional benefits include free parking in Port Jefferson Village, making it easy to enjoy the area's renowned waterfront, dining, shopping, entertainment, and community events. Ideally located near St. Charles Hospital and Mather Hospital, this exceptional home combines comfort, convenience, and an unbeatable location. Don't miss this rare opportunity to own the largest unit in one of Port Jefferson's most sought-after communities!

Home Facts

Condo

3 Baths

3 Bedrooms

Built in 1998

Subdivision & Development:

The Highlands

Price Summary

649,990

$342 per Sq. Ft.

MLS #:

1030359

Last Updated:

October 26, 2026, 01:22 AM

Added:

3 month(s) ago

Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

2

Interior

Living Area:

1,900 Sq. Ft.

Structure

Structure

Building Area:

1,900 Sq. Ft.

Year Built:

1998

Lot

Lot Size (Sq. Ft):

1,727

Finances & Disclosures

Finances

Price:

$649,990

Price per Sq. Ft:

$342 per Sq. Ft.

Source:OneKey MLS
Copyright 2026 OneKey MLS. All rights reserved. Listings courtesy of OneKey MLS as distributed by MLS GRID . OneKey MLS provides content displayed here (“provided content”) on an “as is” basis and makes no representations or warranties regarding the provided content, including, but not limited to those of non-infringement, timeliness, accuracy, or completeness. Individuals and companies using information presented are responsible for verification and validation of information they utilize and present to their customers and clients. OneKey MLS will not be liable for any damage or loss resulting from use of the provided content or the products available through Portals, IDX, VOW, and/or Syndication. Recipients of this information shall not resell, redistribute, reproduce, modify, or otherwise copy any portion thereof without the expressed written consent of OneKey MLS.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.