NY
Suffolk
Port Jefferson
11777
249 Windward Drive
249 Windward Drive, Port Jefferson, NY 11777
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Listing Type
Condo/Townhome
Listing Status
Pending
34
$424,999

Home Details for 249 Windward Drive

Price
$424,999
Type
Residential
Bedrooms
2
Total Bathrooms
3
Full Bathrooms
2
Half Bathrooms
1
Square feet
1179
Year built
1991
Lot size acres
0.0271
County
Suffolk
Total rooms
5
Garage
1
Days on site
60
MLS Listing#
954933
Hoa
647
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.

Property Features
  • House Interior
    • Eat-in Kitchen
    • Entrance Foyer
    • Storage
  • Heating Information
    • Forced Air
    • Natural Gas
  • Utilities
    • Natural Gas Available
    • Natural Gas Connected
  • Parking
    • Garage
    • Parking Lot
  • Waterfront and Water Access
    • Pond
  • Cooling Information
    • Central Air
  • Water Features
    • Public
School Information
School Information for 249 Windward Drive, Port Jefferson, NY 11777
Elementary School
Terryville Road School
Middle School
John F Kennedy Middle School - Suffolk
High School
Comsewogue High School
Listing Courtesy: Signature Premier Properties - 631-360-2800
Presented by: Jonathan Guercio SRES ABR
The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright ©2026 OneKey MLS. All Rights Reserved
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Median Listing Price
Median Days on Site
Median Square Feet
Market statistics compiled from data from OneKey MLS.
EXIT REALTY DKC
3825 East Tremont Ave, Bronx, NY 10465
Justin Simmons
Associate Broker
Office
718 676 1371
Agent
917 254 2103
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