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.
Property Features
Bedrooms
- Bedrooms: 2
- Primary Bedroom Level: Second
- Bedroom 2 Level: Second
- Primary Bedroom Description: Upper-level primary bedroom with vaulted ceiling, generous floor space, and his-and-hers closets. Direct access to a private en-suite bath.
- Bedroom 2 Description: Well-proportioned second bedroom with closet storage and natural light, located near a full bathroom.
Other Rooms
- Total Rooms: 5
- Auxiliary Room Level: Lower
- Auxiliary Room Description: Additional storage space behind the garage with utility access.
- Laundry Level: Second
- Laundry Description: Laundry located on the second floor, positioned near both bedrooms for convenience and efficient daily use.
- Living Room Level: First
- Living Room Description: Open living and dining area with strong natural light and recessed lighting. The layout accommodates both living and dining furniture without crowding and maintains clear sightlines throughout the main level. Sliders lead to the private balcony overlooking landscaped community grounds and pond. Accessible from the main living area and sized for seating.
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- 1/2 Bathrooms: 1
- Primary Bathroom Level: Second
- Bathroom 1 Level: First
- Bathroom 2 Level: Second
- Primary Bathroom Description: En-suite bathroom featuring a walk-in shower and a dedicated linen closet for additional storage.
- Bathroom 1 Description: Powder room ideally located for guest usage.
- Bathroom 2 Description: Full bathroom with single-sink vanity, tile flooring, and a tub/shower combination enclosed by glass sliding doors. Clean, functional layout with mirrored wall and ample counter space.
Interior Features
- Eat-in Kitchen
- Entrance Foyer
- Primary Bathroom
- Storage
- Flooring: Carpet, Ceramic Tile
Appliances
- Dishwasher
- Gas Range
- Microwave
- Refrigerator
- Laundry Features: In Hall
Heating and Cooling
- Cooling Features: Central Air
- Heating Features: Forced Air, Natural Gas
- Heating: Yes
Kitchen and Dining
- Kitchen Description: Eat-in kitchen with wood cabinetry, ample counter space, and a built-in cushioned window seat that adds functional seating and natural light. Practical layout with clear connection to the main living areas.
- Kitchen Level: First
Exterior and Lot Features
Land Info
- Additional Parcels: No
- Lot Size Acres: 0.0271
- Lot Size Square Feet: 1179
Pool and Spa
- Pool Features: Community, In Ground, Salt Water
Waterfront and Water Access
Garage and Parking
- Garage Spaces: 1
- Parking Features: Garage, Parking Lot
Homeowners Association
- Association: Yes
- Association Amenities: Children's Playroom, Concierge, Playground, Pool, Snow Removal, Tennis Court(s), Trash
- Association Fee: 647
- Association Fee Frequency: Monthly
- Association Fee Includes: Cable TV, Common Area Maintenance, Grounds Care, Internet, Pool Service, Sewer, Snow Removal, Trash
- Calculated Total Monthly Association Fees: 647
- Association Name: The Highlands
- Pets Allowed: Yes
School Information
- Elementary School: Terryville Road School
- Elementary School District: Brookhaven-Comsewogue
- High School: Comsewogue High School
- High School District: Brookhaven-Comsewogue
- Middle School: John F Kennedy Middle School - Suffolk
- School District: Brookhaven-Comsewogue
- Middle or Junior School District: Brookhaven-Comsewogue
Amenities and Community Features
- Children's Playroom
- Concierge
- Playground
- Pool
- Snow Removal
- Tennis Court(s)
- Trash
Other Property Info
- Annual Tax Amount: 5329
- Source Listing Status: Active
- County: Suffolk County
- Directions: 25A to Perry St. to Oakland Ave to Highlands Blvd. to Windward Drive
- Tax Year: 2025
- Source Property Type: Residential
- Property Subtype: condo
- Parcel Number: 0206-022-00-04-00-249-000
- Postal City: Port Jefferson
- Postal Code Plus 4: 2322
- Property Subtype: Condominium
Building and Construction
- Total Square Feet Living: 1179
- Year Built: 1991
- Attic: Partial
- Common Walls: Center, No One Above, No One Below
- Construction Materials: Vinyl Siding
- Entry Level: 2
- Levels: Tri-Level
- Living Area Source: Public Records
- Property Age: 35
- Property Attached: Yes
- Property Condition: Actual
- Levels or Stories: Tri-Level
- Building Total Stories: 2
- Structure Type: Townhouse
- Total Area Sqft: 1179
- Year Built Effective: 1991
Utilities
- Sewer: Shared
- Natural Gas Connected
- Water Source: Public
