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Sold for $440,000
  • $440,000

    249 Windward Drive, Port Jefferson, NY 11777

    2beds
    1,179sqft
    Condominium, Residential
    Built in 1991
    -- sqft lot
    $447,300 Zestimate®
    $373/sqft
    $3,418 Estimated rent

    Home value

    $447,300

    $403,000 - $497,000

    $3,418/mo

    Zestimate® history
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    What's special

    Outdoor poolTennis and basketball courtsProfessionally landscaped groundsResident-only beach accessConvenient half bathSmart layoutGenerous storage
    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.

    Zillow last checked:

    Listing updated:

    Listed by:

    Jonathan Guercio SRES ABR 516-459-0977,

    Signature Premier Properties 631-360-2800,

    Elijah Rivas 631-681-6931,

    Signature Premier Properties

    Bought with:

    Thomas Kennelly, 10401335143

    Compass Greater NY LLC

    Source: OneKey® MLS as distributed by MLS GRID,MLS#: 954933MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 2
    • Bathrooms: 3
    • Full bathrooms: 2
    • 1/2 bathrooms: 1
    Primary bedroom
    • Description: Upper-level primary bedroom with vaulted ceiling, generous floor space, and his-and-hers closets. Direct access to a private en-suite bath.
    • Level: Second
    Bedroom 2
    • Description: Well-proportioned second bedroom with closet storage and natural light, located near a full bathroom.
    • Level: Second
    Primary bathroom
    • Description: En-suite bathroom featuring a walk-in shower and a dedicated linen closet for additional storage.
    • Level: Second
    Bathroom 1
    • Description: Powder room ideally located for guest usage.
    • Level: First
    Bathroom 2
    • Description: Full bathroom with single-sink vanity, tile flooring, and a tub/shower combination enclosed by glass sliding doors. Clean, functional layout with mirrored wall and ample counter space.
    • Level: Second
    Other
    • Description: Additional storage space behind the garage with utility access.
    • Level: Lower
    Kitchen
    • Description: Eat-in kitchen with wood cabinetry, ample counter space, and a built-in cushioned window seat that adds functional seating and natural light. Practical layout with clear connection to the main living areas.
    • Level: First
    Laundry
    • Description: Laundry located on the second floor, positioned near both bedrooms for convenience and efficient daily use.
    • Level: Second
    Living room
    • Description: Open living and dining area with strong natural light and recessed lighting. The layout accommodates both living and dining furniture without crowding and maintains clear sightlines throughout the main level. Sliders lead to the private balcony overlooking landscaped community grounds and pond. Accessible from the main living area and sized for seating.
    • Level: First
    Heating
    • Forced Air
    Cooling
    • Central Air
    Appliances
    • Included: Dishwasher, Gas Range, Microwave, Refrigerator
    • Laundry: In Hall
    Features
    • Eat-in Kitchen, Entrance Foyer, Primary Bathroom, Storage
    • Flooring: Carpet, Ceramic Tile
    • Basement: See Remarks
    • Attic: Partial
    • Has fireplace: No
    • Common walls with other units/homes: Center,No One Above,No One Below
    Interior area
    • Total structure area: 1,179
    • Total interior livable area: 1,179 sqft

    Property

    Parking
    • Total spaces: 1
    • Parking features: Garage
    • Garage spaces: 1
    Features
    • Levels: Tri-Level
    • Pool features: Community, In Ground, Salt Water
    • On waterfront: Yes
    • Waterfront features: Pond
    Lot
    • Size: 1,179 Square Feet
    Details
    • Parcel number: 0206022000400249000
    • Special conditions: None

    Construction

    Type & style
    • Home type: Condo
    • Property subtype: Condominium, Residential
    • Attached to another structure: Yes
    Materials
    • Vinyl Siding
    Condition
    • Actual
    • Year built: 1991
    • Major remodel year: 1991

    Utilities & green energy

    • Water: Public
    • Utilities for property: Natural Gas Connected

    Community & HOA

    HOA
    • Has HOA: Yes
    • Amenities included: Concierge, Playground, Pool, Snow Removal, Tennis Court(s), Trash
    • Services included: Cable TV, Common Area Maintenance, Maintenance Grounds, Internet, Pool Service, Sewer, Snow Removal, Trash
    • HOA fee: $647 monthly
    • HOA name: The Highlands
    Location
    • Region: Port Jefferson

    Financial & listing details

    • Price per square foot: $373/sqft
    • Tax assessed value: $249,623
    • Annual tax amount: $5,329
    • Date on market: 1/28/2026
    • Cumulative days on market: 13 days
    • Listing agreement: Exclusive Right To Sell

    Price history

    DateEventPrice
    3/27/2026Sold$440,000+3.5%$373/sqft
    Source: OneKey® MLS as distributed by MLS GRID #954933 Report a problem
    2/12/2026Pending sale$424,999$360/sqft
    Source: OneKey® MLS as distributed by MLS GRID #954933 Report a problem
    2/10/2026Listing removed$424,999$360/sqft
    Source: OneKey® MLS as distributed by MLS GRID #954933 Report a problem
    1/29/2026Listed for sale$424,999+229.5%$360/sqft
    Source: OneKey® MLS as distributed by MLS GRID #954933 Report a problem
    7/11/1995Sold$129,000$109/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025-- $1,323
    2024-- $1,323
    2023-- $1,323
    2022-- $1,323
    2021-- $1,323
    2020-- $1,323
    2019-- $1,323
    2018-- $1,323
    2017$502 $1,323
    2016-- $1,323
    2015-- $1,323
    2014-- $1,323 -30.6%
    2001$653 -5.9%$1,907
    2000$694 $1,907
    Find assessor info on the county website

    Neighborhood: 11777

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Terryville Road School
    • Middle: John F Kennedy Middle School - Suffolk
    • High: Comsewogue High School

    Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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    Estimated market value
    $447,300
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $447,300