249 Windward Drive, Port Jefferson, NY 11777

• 2 beds |
• 3 baths |
• 1,179 sqft

Property Description

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.

Listing Status:

Active

Data Last Updated:

February 8, 2026 at 5:21AM

Listing Office:

Signature Premier Properties : 516-459-0977

MLS ID:

954933

Interior

• General: Eat-in KitchenEntrance FoyerPrimary BathroomStorage
• Appliances: DishwasherGas RangeMicrowaveRefrigerator
• Laundry: In Hall
• Basement: See Remarks
• Flooring: CarpetCeramic Tile
• A/C: Central Air
• Heating: Forced AirNatural Gas

Exterior

• General: Balcony
• Pool: CommunityIn GroundSalt Water
• Parking: GarageParking Lot

Construction

• General: Tri-Level

Location

• HOA Amenities: Children's PlayroomConciergePlaygroundPoolSnow RemovalTennis Court(s)TrashCable TVCommon Area MaintenanceGrounds CareInternetPool ServiceSewerSnow RemovalTrash647.0Monthly
• Originating MLS: onekey2
• School District: Brookhaven-Comsewogue
• County: Suffolk County

Lot

• Zoning: 0206-022-00-04-00-249-000

Utilities

• Utilities: Natural Gas Connected
• Water: Public
• Sewer: Shared

Financial

• Source: onekey2