249 Windward Drive, Port Jefferson, NY 11777

Local realty services provided by:Better Homes and Gardens Real Estate Dream Properties
249 Windward Drive,Port Jefferson, NY 11777
$424,999
  • 2 Beds
  • 3 Baths
  • 1,179 sq. ft.
  • Condominium
  • Active
Upcoming open houses
  • Sat, Jan 31
    10:00 am - 01:00 pm
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

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Home facts

  • Year built:1991
  • Listing ID #:954933
  • Added:1 day(s) ago
  • Updated:January 30, 2026 at 11:53 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)
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