Date
Details
Price
Change
Source
1/28/2026
Listed
$424,999
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$424,999 Sale Pending
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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.
Full Property Details
Full Property Details for 249 Windward Dr
General
- Price: $424,999
- HOA FEE: $647/month
- Taxes: $5,329
- Status: Pending
- Type: Condo
- Source: Long_Island
- MLS ID: 954933
- Updated: 2/12/2026
- Added to Site: 23 day(s) ago
Interior
- Number of Rooms: 5
- Interior Features: Eat-in Kitchen, Entrance Foyer, Primary Bathroom, Storage
- Appliances: Dishwasher, Gas Range, Microwave, Refrigerator
- Laundry Facilities: Yes
- Flooring: Carpet, Ceramic Tile
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 2
Other Rooms
- Laundry: In Hall
Additional Information
- Shared Amenities: Children's Playroom, Concierge, Playground, Pool, Snow Removal, Tennis Court(s), Trash
- Pool: Yes
- Pool Description: Community, In-Ground, Salt Water
Exterior
- Exterior Features: Balcony
Parking
- Garage: Yes
- Garage Spaces: 1
- Parking Features: Garage, Parking Lot
Location
- County: Suffolk County
- Driving Directions: 25A to Perry St. to Oakland Ave to Highlands Blvd. to Windward Drive
School Information
- High School District: Brookhaven-Comsewogue
- Elementary School: Terryville Road School
- Middle School: John F Kennedy Middle School - Suffolk
- High School: Comsewogue High School
Community
- Association: Yes
- Assoc. Fees Include: Cable TV, Common Area Maintenance, Grounds Care, Internet, Pool Service, Sewer, Snow Removal, Trash
- Pets Allowed: Yes
- Pet Restrictions: Yes
Heating & Cooling
- Central air: Yes
- Cooling Type: Central Air
- Heating Type: Forced Air, Natural Gas
Utilities
- Sewer: Shared
- Water: Public
- Utility Description: Natural Gas Connected
Structural Information
- Detached/Attached: Attached
- Construction: Vinyl Siding
- Basement: Yes
- Basement Desc.: See Remarks
- Common Walls: Center, No One Above, No One Below
- Entry Floor Number: 2
- Stories/Levels: 2
- Stories in Building: 2
- Sq. Ft. Source: Public Records
- Year Built: 1991
Lot Features
- Lot Size (Acres): 0.0271
- Lot Size (Sq. Ft.): 1,179
Water Features
- Water Front View: Pond
Financial Considerations
- Association Fee: Yes
- Association Fee: $647
- Assoc Fee Freq.: Monthly
- Taxes Include: Trash, Water
- Tax Amount: $5,329.24
Disclosures and Reports
- Special Conditions: None
- Property ID: 0206-022-00-04-00-249-000
Listed by Signature Premier Properties
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Listing agents
— 249 Windward Dr —
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516-459-0977
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Schools
Schools serving 249 Windward Dr
School District:Brookhaven-Comsewogue Union Free School District
| Name | Grades | Distance |
|---|---|---|
John F Kennedy Middle School, Port Jefferson Station, NY 200 Jayne Boulevard, Port Jefferson Station, NY 11776 | 6-8 | 1.3 mi |
Terryville Road School 401 Terryville Road, Port Jefferson Station, NY 11776 | 3-5 | 1.8 mi |
Clinton Avenue School, Port Jefferson Station, NY 140 Clinton Avenue, Port Jefferson Station, NY 11776 | PK-2 | 2.1 mi |
Comsewogue High School 565 North Bicycle Path, Port Jefferson Station, NY 11776 | 9-12 | 1.9 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 249 Windward Dr
Tax History
Tax History for 249 Windward Dr
Year
Property Taxes
Change
Tax Assessment
Change
2020
100%
$1,323
—
2022
-100%
$1,323
—
2016
$492
-55%
$1,323
—
2020
$1,101
119%
$1,323
—
2018
$502
3%
$1,323
—
2017
$489
-3%
$1,323
—
2016
$504
3%
$1,323
—
2015
$491
3%
$1,323
—
2015
$479
1%
$1,323
—
2014
$472
—
$1,323
—
2013
$471
—
$1,323
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 249 Windward Dr
249 Windward Drive, Port Jefferson, NY 11777 (MLS# 954933) is a Condo property with 2 bedrooms, 2 full bathrooms and 1 partial bathroom. 249 Windward Drive is currently listed for $424,999 and was received on January 28, 2026. Want to learn more about 249 Windward Drive? Do you have questions about finding other Condo real estate for sale in Port Jefferson? You can browse all Port Jefferson real estate or contact a Coldwell Banker agent to request more information.