Nicholas Falcone
Licensed Real Estate Salesperson
REALTOR®
Stamford, NY
Office: (607) 652-2220
(631) 384-1507
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.
249 Windward Drive | MLS# 954933
This condo located at 249 Windward Drive, Port Jefferson, NY 11777 is currently listed for sale with an asking price of $424,999. This property was built in 1991 and has 2 bedrooms and 2 full and 1 partial baths with 1179 sq. ft. Windward Drive is located within the Brookhaven-Comsewogue school district. Search Port Jefferson real estate on nicholas-falcone.timberlandproperties.com today.
Gallery
Property Features
Property Type: Residential - Condominium
Basement: See Remarks
Cooling: Central Air
Garage: 1
Heating: Forced Air, Natural Gas
Lot Size: 0.03 Acres
Stories: 2.0
Taxes: $5,329
Year Built: 1991
Amenities
Eat-in Kitchen
Entrance Foyer
Primary Bathroom
Storage
Balcony
Feature Descriptions
Appliances: Dishwasher, Gas Range, Microwave, Refrigerator
Association Amenities: Childrens Playroom, Concierge, Playground, Pool, Snow Removal, Tennis Court(s), Trash
Association Fee: $647/Monthly
Association Fee Includes: Cable TV, Common Area Maintenance, Grounds Care, Internet, Pool Service, Sewer, Snow Removal, Trash
Attic: Partial
Common Walls: Center, No One Above, No One Below
Days on Site: 33
Exterior: Vinyl Siding
Flooring: Carpet, Ceramic Tile
GarageY/N: Yes
Included In Taxes: Trash, Water
Laundry: In Hall
On Market Date: 2026-01-28
Parcel Number: 0206-022-00-04-00-249-000
Parking Features: Garage, Parking Lot
Pets Allowed: Yes
Pool Features: Community, In Ground, Salt Water
Property Attached Y/N: 1
Rental Term: Monthly
Rooms Total: 5
Sewer: Shared
Utilities: Natural Gas Connected
Water: Public
Waterfront Features: Pond
Local Schools
High School: Comsewogue High School
Middle School: John F Kennedy Middle School - Suffolk
Elementary School: Terryville Road School
School District: Brookhaven-Comsewogue
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249 Windward Drive, Port Jefferson, NY 11777
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Estimated Payment
$ 1,513.91 per month $945.87 Principal & Interest $444.08 Property Tax $123.96 Homeowner's InsuranceChange Payment Information
Demographics
Listed By / Shown By
Listing By
Agency Name: Signature Premier Properties
Agency Contact: 516-459-0977
Shown By
Agent Name: Nicholas Falcone
Agent Phone: (631) 384-1507
Agency Title: Timberland Properties
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249 Windward Drive, Port Jefferson, NY 11777
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