149 Windward Court S, Port Jefferson, NY, 11777
About This Home
Welcome to the largest unit in the highly desirable Highlands community! This beautifully updated corner unit offers exceptional space, privacy, and an impressive list of upgrades throughout. The bright and inviting interior features gleaming hardwood floors on the first level, a stunning renovated kitchen, and a spacious primary suite complete with a dedicated vanity area and an elegant frameless glass shower door. Thoughtful storage abounds with three linen closets, while new Andersen windows with a transferable warranty provide energy efficiency and peace of mind. Custom blinds are included with the home. Additional recent improvements include a new roof, a 2022 hot water heater and boiler, a new storm door, outdoor electrical outlets in both the front and rear of the home, and a beautiful Nicolock patio—perfect for relaxing or entertaining. Residents of The Highlands enjoy an outstanding resort-style lifestyle with exclusive amenities, including a private beach, clubhouse with fitness center, saltwater in-ground pool, tennis courts, and Port Jefferson Country Club golfing privileges. Additional benefits include free parking in Port Jefferson Village, making it easy to enjoy the area's renowned waterfront, dining, shopping, entertainment, and community events. Ideally located near St. Charles Hospital and Mather Hospital, this exceptional home combines comfort, convenience, and an unbeatable location. Don't miss this rare opportunity to own the largest unit in one of Port Jefferson's most sought-after communities!
Getting Around
Car-Dependent
Very Limited Transit
Somewhat BikeableSchools
Construction
Condition
- Year built: 1998
Materials
- Construction materials: Vinyl Siding
Other
- Builder model: Schooner
Type & Style
- Home type: Condo
- Property subType: Condominium,Residential
Interior
Appliances
- Appliances included: Dishwasher,Dryer,Gas Range,Microwave,Refrigerator,Stainless Steel Appliance(s),Washer,Gas Water Heater
- Laundry features: Washer/Dryer Hookup,Gas Dryer Hookup,In Hall,Inside
Bedrooms & Bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Features
- Open Kitchen,Pantry,Walk-In Closet(s)
- Flooring: Carpet,Hardwood
- Attic: Scuttle
- Common walls with other units/homes: 1 Common Wall
Heating & Cooling
- Heating features: Hot Air,Natural Gas
- Cooling features: Central Air
Interior Area
- Total structure area: 1,900
- Total interior livable area: 1,900 sqft
Other
- Level: First
Other
- Level: Second
Property
Accessibility
- Accessibility features: Accessible Entrance,Grip-Accessible Features
Details
- Parcel number: 0206022000400149000
- Attached to another structure: Yes
- Special condition: None
- Exclusions: Garage Refrigerator
Lot
- Lot size: 1,727 sqft
Parking
- Total spaces: 2
- Parking features: Driveway
- Has garage: Yes
- Attached garage spaces: 1
- Covered spaces: 1
- Has uncovered spaces: Yes
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Winter Weather
- Tsunami
How This Home’s Risks Compare
FEMA Declared Disasters in Suffolk County and New York
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $3,438 | $41,256 |
| Home Insurance * | $299 | $3,588 |
| Property Taxes | $918 | $11,016 |
| Electricity | $313 | $3,767 |
| Total | $4,968 | $59,616 |
Income You'd Need if You Spent...
New York FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-08-16 | Price change | $670,000 |
| 2026-07-24 | Listed for sale | $680,000 |
| 2013-12-03 | Sold | $335,000 |
| 2008-05-29 | Sold | $345,000 |
| 2001-06-05 | Sold | $261,000 |
| 1997-08-11 | Sold | $81,000 |
For Sale by Agent
View on Zillow