249 Windward Drive, Port Jefferson, NY 11777

Local realty services provided by:Bon Anno Realty ERA Powered
249 Windward Drive,Port Jefferson, NY 11777
$424,999
  • 2 Beds
  • 3 Baths
  • 1,179 sq. ft.
  • Condominium
  • Active
Listed by: jonathan guercio sres abr, elijah rivas
Office: signature premier properties
MLS#:954933
Source:OneKey MLS

Price summary

  • Price:$424,999
  • Price per sq. ft.:$360.47
  • Monthly HOA dues:$647

About this home

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

Contact an agent

contact an agent

Yes, I would like more information. Please use and/or share my information with an ERA®  affiliated agent to contact me about my real estate needs. By clicking Send message, 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 an ERA®  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® , Coldwell Banker® , Corcoran® , Sotheby's International Realty® ). I acknowledge that I have read and agree to theTerms of useandPrivacy notice

Home facts

  • Year built:1991
  • Listing ID #:954933
  • Added:5 day(s) ago
  • Updated:February 03, 2026 at 11:47 AM

Rooms and interior

  • Bedrooms:2
  • Total bathrooms:3
  • Full bathrooms:2
  • Half bathrooms:1
  • Living area:1,179 sq. ft.

Heating and cooling

  • Cooling:Central Air
  • Heating:Forced Air, Natural Gas

Structure and exterior

  • Year built:1991
  • Building area:1,179 sq. ft.
  • Lot area:0.03 Acres

Schools

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

Utilities

  • Water:Public

Finances and disclosures

  • Price:$424,999
  • Price per sq. ft.:$360.47
  • Tax amount:$5,329 (2025)
Copyright 2026 OneKey MLS. All rights reserved. Listings courtesy of OneKey MLS as distributed by MLS GRID <lastMLSCheckTimestamp>. 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.

New listings near 249 Windward Drive