New Listing - 01/28/2026
249 Windward Drive, Port Jefferson, NY, 11777
5 rooms
2 beds
2 Full / 1 Half baths
1991
1,179 sqft
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.
Status:
Active
Type:
Condo
Laundry Remarks:
In Hall
Garage:
1-car
Heating:
Forced Air, Natural Gas
Cooling:
Central Air
Basement:
See Remarks
Levels:
2
Parking:
Garage, Parking Lot
Common Charge:
$647 Monthly
Acreage:
0.03
Est. Taxes:
$5,329
HOA Fee
$647
Construction
Vinyl Siding
Utilities
Natural Gas Connected
Amenities:
Children's Playroom, Concierge, Playground, Pool, Snow Removal, Tennis Court(s), Trash
Waterfront:
Yes
Elementary School:
Terryville Road School
Middle School:
John F Kennedy Middle School - Suffolk
High School:
Comsewogue High School
School District:
Brookhaven-comsewogue
Days on Market:
3
Pet Policy:
Yes
Appliances:
Dishwasher, Gas Range, Microwave, Refrigerator
Pool:
Community, In Ground, Salt Water
MLS #:
954933
Community Info
School Info
Walk Score
Mass Transit
Yelp
Listing courtesy of Signature Premier Properties 516-459-0977