249 Windward Drive, Port Jefferson, NY 11777
Home value
$447,300
$403,000 - $497,000
$3,418/mo
Owner options
$3,418/mo
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$3,418/mo
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$3,661/mo
Est. payment
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$3,661/mo
Est. payment
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Zillow last checked:
Listing updated:
Jonathan Guercio SRES ABR 516-459-0977,
Signature Premier Properties 631-360-2800,
Elijah Rivas 631-681-6931,
Signature Premier Properties
Thomas Kennelly, 10401335143
Compass Greater NY LLC
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
| Date | Event | Price |
|---|---|---|
| 3/27/2026 | Sold | $440,000+3.5%$373/sqft |
Source: | ||
| 2/12/2026 | Pending sale | $424,999$360/sqft |
Source: | ||
| 2/10/2026 | Listing removed | $424,999$360/sqft |
Source: | ||
| 1/29/2026 | Listed for sale | $424,999+229.5%$360/sqft |
Source: | ||
| 7/11/1995 | Sold | $129,000$109/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax 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 |
Neighborhood: 11777
Nearby homes
- $464,000-- bd-- ba-- sqft248 Windward Dr, Port Jefferson, NY 11777Off Market
- $491,800-- bd-- ba-- sqft250 Windward Dr, Port Jefferson, NY 11777Off Market
- $500,300-- bd-- ba-- sqft251 Windward Dr, Port Jefferson, NY 11777Off Market
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- $---- bd-- ba-- sqft247 Windward Dr, Pt Jefferson, NY 11777Off Market
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- $440,7002 bd2 ba-- sqft252 Windward Dr, Port Jefferson, NY 11777Off Market
Nearby schools
GreatSchools rating
- 2/10Terryville Road SchoolGrades: 3-5Distance: 1.8 mi
- 2/10John F Kennedy Middle SchoolGrades: 6-8Distance: 1.3 mi
- 6/10Comsewogue High SchoolGrades: 9-12Distance: 2 mi
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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- New York
- Suffolk County
- Port Jefferson
- 11777
- 249 Windward Drive