Market Report · September 2026
The Winter Park market, read honestly.
Is now a good time to sell? Should I buy now or wait? These are the questions behind every market report, and the honest answer is that it depends on your goals far more than the headlines. Here is what the data says, what the luxury tier looks like, and what I actually watch from week to week.
What the latest data says
These are ZIP level public figures for 32789, the historic core of Winter Park, reported by Redfin and Zillow and current as of this report.
$890K
Median sale price (Redfin), roughly flat year over year
$970K
Average sale price (Redfin), up sharply year over year
$431
Median price per square foot (Redfin) · 32789
~35 days
Typical time to pending (Zillow), a balanced pace
+4.7%
Average home value growth over the past year (Zillow), near $810K
Sources: Redfin, 32789 housing market and Zillow, 32789 home values. A balanced to warm market: stable sale prices, low inventory pressure, and premium pricing in the historic core.
Where I work
Why the top of the market is a different game.
I work across a typical range of $500K to $2.5M+, with my focus on luxury and $1M+ properties and an average target around $1.2M. At that level, ZIP medians stop being useful. A $1.5M lakefront estate does not move with the town's median price; it moves with the handful of comparable lakefront sales in the region, adjusted for each property's one of one character.
That is why pricing at the top is a judgment call built on evidence: the lot, the finish quality, the renovation history, the scarcity of the address, and the story the home tells. It is also why a house that sits for months at an aspirational price can end up selling for less than it would have with an honest start. I price to the right buyer, then make sure the right buyer hears the story.
What I watch
Days on market
The single most honest signal in a luxury market. Homes priced well sell in the first weeks; the ones that linger tell a story about the price, not the market.
Price per square foot
More stable than median prices, and better at revealing the direction of the market beneath the noise of a few big sales.
Inventory at the top
Lakefront and luxury inventory in Winter Park is durably scarce, and scarcity is the quiet engine behind the values clients count on. When it loosens, it shows up here first.
The seasonal rhythm
Winter Park has its own calendar. The spring and early summer months are typically the liveliest for premium sales, while the lakefront market stays warm almost year round. Timing a listing around the rhythm matters more than timing the headlines.
The data is a map. Your goals are the destination.
Bring me your situation and I will give you a personal read: what your home is worth, what the market says about your timing, and what I would consider if it were mine.