249 Windward Drive, Port Jefferson, NY 11777
- $440,000
- 2
- BD
- 3
- BA
- 1,179
- SqFt
- Sold Price
- $440,000
- Days on Market
- 17
- Closing Date
- Mar 27, 2026
- MLS#
- 954933
- Status
- CLOSED
- Property Type
- Condominium
- Year Built
- 1991
- Property Tax
- $5,329
- Monthly Maintenance
- $647
- School District
- Brookhaven-Comsewogue
- High School
- Comsewogue High School
- Jr. High
- John F Kennedy Middle School - Suffolk
- Elementary School
- Terryville Road School
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.
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Additional Information
- Bedrooms
- 2
- Bathrooms
- 3
- Full Baths
- 2
- Half Baths
- 1
- Square Footage
- 1,179
- Acres
- 0.03
- Parking
- Garage, Parking Lot
- Stories
- 2
- Basement
- See Remarks
- Laundry
- In Hall
- Pets
- Yes
- Heating
- Forced Air, Natural Gas
- Cooling
- Central Air
- Water
- Public
- Sewer
- Shared
- Amenities
- Children's Playroom, Concierge, Playground, Pool, Snow Removal, Tennis Court(s), Trash
Mortgage Calculator
Listing courtesy of Listing Agent: Jonathan Guercio SRES ABR (jguercio@signaturepremier.com) from Listing Office: Signature Premier Properties.
Selling Office: Compass Greater NY LLC.Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.