Published September 29, 2026 in Market Update

What I Wish Every Windermere Seller Knew Before Listing

By Marlon Persaud

Real estate, windermere market update clean

Back in the summer of 2025, Windermere homes were moving. July 2025 was the strongest month in the file: 51 homes sold, and the typical one closed at $1,175,000 in just 35 days. Sellers who priced right found buyers fast.

A lot has changed since then.

The market slowed down, and sellers who did not adjust paid for it.

From May 2025 through January 2026, the typical sold price was $985,500. From January 2026 through September 2026, it slipped to $915,000. The typical home in the first half closed $70,500 higher than the typical home in the second half.

The time it took to sell crept up too. The first half averaged 50 days. The second half averaged 52 days. That gap looks small, but March 2026 tells the real story: 125 days to find a buyer, the slowest month in the file.

And right now, as of September 28, 2026, 107 of the 181 homes for sale have already dropped their price. That is 59.1% of everything on the market. The typical drop is $100,000.

What I wish every Windermere seller knew before they listed.

The first thing is this: cutting your price does not put you back on equal footing. Homes that found a buyer in the first month closed at 97.8% of what they first asked. Homes that took five or six months closed at 87.5%. That is a 10.3-point gap. On a $1,000,000 home, that is $103,000 left behind.

The price you start with sets the ceiling. Every week that passes pushes the floor down.

The second thing: homes that gave up entirely started higher than homes that sold. The typical first asking price for a home that came off the market with no sale was $1,200,000. The typical first asking price for a home that sold was $998,000. That $202,000 gap at the start is the single clearest signal in the data.

The third thing is about the high end. At $2.75M and up, nearly 3 in 10 homes gave up entirely: 29.5% of that group came off the market without a sale. The lower end is more forgiving. Under $750K, that share was 17.9%.

The fourth thing is about size. Larger homes sit longer and close lower. Homes between 1,500 and 2,500 square feet sold in 28 days and got 96.9% of their first asking price. Homes over 7,000 square feet took 113 days and got only 90% of what they first asked.

The fifth thing is the one sellers least expect: even homes that sold at or over asking sometimes paid money back. Across the whole market, 32.1% of sellers paid money back to the buyer after the contract was signed. The typical amount was $10,000. Sixty-four homes sold at or over asking and still paid back $20,000 or more.

What this means for you right now.

If you are selling, the number that matters most is your first asking price. The data is clear: homes priced right from the start close closer to full price and close faster. The typical Windermere home sold for 93.9% of what it first asked. But homes that lingered past five months settled for 87.5%. Pricing sharp on day one is not leaving money behind. It is keeping more of it. The 30-year fixed mortgage averaged 7.03% as of September 24, 2026, up from 6.95% the week before, according to Freddie Mac's weekly rate survey. That is also up from 6.30% a year ago. Buyers are already stretched. A price that needs defending is a price that will get cut.

If you are buying, the supply picture is worth understanding. There are 4.1 months of homes for sale at the current pace, which sits between the range that favors sellers and the range that favors buyers. Nationally, existing-home sales in August 2026 ran at a rate of 3.98 million, with 4.9 months of supply across the country, according to NAR. Windermere's 4.1 months is tighter than that national figure. More than half the homes on the market here have already dropped their price, and 59.1% of sellers are signaling they will negotiate. The typical home still closed at 100% of its last asking price, so the negotiating happens before the final price is set, not after. The Orlando area added 11,900 jobs in August 2026, second only to Tampa among Florida metros, according to Florida Commerce and the Bureau of Labor Statistics, which means the local job base is still growing even as the housing market cools.