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$440,000

  • Sold
  • Closed
  • Condo
  • 2 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1 Car Garage
  • Updated 2 days ago
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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 for 249 Windward Dr

General

  • Sold For: $440,000
  • HOA FEE: $647/month
  • Taxes: $5,329
  • Status: Closed
  • Type: Condo
  • Source: Long_Island
  • MLS ID: 954933
  • Added to Site: 70 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
Sold by Compass Greater NY LLC

Listing agents

— 249 Windward Dr —

  • Signature Premier Properties

  • Signature Premier Properties

516-459-0977

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 249 Windward Dr

School District:Brookhaven-Comsewogue Union Free School District
NameGradesDistance
John F Kennedy Middle School, Port Jefferson Station, NY
200 Jayne Boulevard, Port Jefferson Station, NY 11776
6-81.3 mi
Terryville Road School
401 Terryville Road, Port Jefferson Station, NY 11776
3-51.8 mi
Clinton Avenue School, Port Jefferson Station, NY
140 Clinton Avenue, Port Jefferson Station, NY 11776
PK-22.1 mi
Comsewogue High School
565 North Bicycle Path, Port Jefferson Station, NY 11776
9-121.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 249 Windward Dr

Date
Details
Price
Change
Source
3/27/2026
Sold
$440,000
3.53%
MLS
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.

Listed by Signature Premier Properties
Sold by Compass Greater NY LLC

249 Windward Drive, Port Jefferson, NY 11777 (MLS# 954933) is a Condo property that was sold at $440,000 on March 27, 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.