If you're buying, selling, or just keeping an eye on home values in Windermere, Florida, here's your mid-year snapshot of exactly what happened in our local market through the end of June 2026. I pulled the numbers straight from the MLS — 363 closed home sales across Windermere and the surrounding 34786 zip code,  so this isn't a national headline or a guess. It's what actually sold, for what price, and how fast.

I'm Andy Neal, a local Realtor who lives and works right here in Windermere. I track these numbers every month because my neighbors, clients, and future clients deserve real data, not recycled national news. Here's what the first half of 2026 tells us.

Windermere FL Real Estate Market at a Glance (H1 2026)

• 363 homes closed in Windermere from January through the end of June 2026
• Median sale price: $800,000 (average sale price: $1,256,534 — more on why that gap matters below)
• Homes sold for a median of 97.2% of list price, meaning most sellers gave up only a few cents on the dollar
• Median 35 days on market before going under contract
• 1 in 4 homes (25.6%) sold at or above asking price
• More than a third of homes (34.4%) went under contract in two weeks or less
• Sale prices ranged from $285,000 for a Lakeside condo to $13.2 million for an estate in Keenes Pointe

Windermere continues to be one of the widest-ranging markets in Central Florida, everything from starter condos in the $280,000s to nine-figure lakefront compounds trade hands here, which is part of why the "average" price looks so different from the "median" price. More on that below.

Median vs. Average: Why the Gap Is So Big

This is the single most important thing to understand about our market right now. The median sale price, the true middle of the market, sits at $800,000. But the average sale price is $1,256,534, nearly $450,000 higher.

That gap exists because Windermere includes guard-gated luxury enclaves like Isleworth and Keenes Pointe, where multiple homes closed well north of $5 million (including one Isleworth estate that sold for $11.5 million and a Keenes Pointe home that closed at $13.2 million). Those sales pull the average up dramatically, even though they represent a small slice of total transactions.

The takeaway for most buyers and sellers: trust the median more than the average. If you're shopping in the $500,000–$900,000 range, which is where the bulk of Windermere's activity actually happens, the average price tells you almost nothing useful about your specific price point.

As the chart above shows, the $400,000–$800,000 range accounted for the largest share of activity, 69 of the 363 total sales, while sales above $3 million, though headline-grabbing, made up just 27 transactions.

Spring Momentum: Q2 Outpaced Q1

Breaking the first half of the year into quarters tells a clear story:

Sales volume jumped roughly 43% from Q1 to Q2, median prices rose, and homes went under contract nearly 40% faster. Buyers who waited out the winter for a slower market didn't get one — if anything, the spring buying season brought more competition and quicker closings, especially in the $600,000–$1 million range where inventory tends to move fastest.

Where the Volume Is: Windermere's Busiest Communities

Here's how the most active Windermere neighborhoods performed through June 2026:

A few things stand out:

Summerport is the market's fastest mover. With a median of just 7 days on market and homes closing at nearly 98% of asking price, this family-friendly community near the town center continues to be one of the tightest pockets of the Windermere market.

Palms at Windermere is the new-construction story of 2026. Homes here, many built in 2024–2026, are commanding a median price over $1 million and moving in just 13 days, reflecting steady demand for new builds with modern floor plans.

Keenes Pointe drives the luxury numbers. With 39 closings and a median price just under $1.9 million, it's both the highest-volume and highest-value established community in Windermere, though its 94% sale-to-list ratio shows more negotiating room exists at the top of the market than in the entry-level segment.

Isleworth remains the ceiling. Only 8 sales, but a median price of nearly $4.4 million, including that $11.5 million closing, confirms Isleworth's status as Windermere's most exclusive address.

The Other Side of the Market: 124 Homes That Didn't Sell

Every closed sale tells half the story. The other half is the listings that came off the market without a buyer, canceled, expired, or withdrawn. Through the same period, 124 Windermere-area listings failed to sell, compared to 363 that closed. That means roughly 1 in 4 listings that reached a conclusion in 2026 did not result in a sale.

Two things jump out immediately when you compare this to the sold data:

Unsold listings sat more than 3x longer than sold homes. The median time on market for homes that eventually sold was 35 days. The median time on market for homes that were pulled, expired, or withdrawn was 119.5 days, before the seller gave up. Several sat for well over a year: listings in the Reserve at Lake Butler Sound, Down Point Sub, Waterstone, Windsor Hill, and Wauseon Ridge languished for 617 to 851 days before coming off the market unsold.

Unsold listings skew heavily toward the luxury tier. 71 of the 124 unsold listings (57%) were priced above $1 million, versus only about 39% of actual closed sales. In the sub-$1 million range specifically, 53 listings failed to sell at a median list price of $625,000 and a median of 96 days on market,  still roughly triple the market-wide sold median of 35 days.

What this tells us: the "hot market, quick sale" story earlier in this post is true, but it's true for correctly priced homes. Overpriced listings, especially in the $1M+ estate and luxury-lakefront segment, are sitting for months or years rather than selling. If you're pricing a home above $1 million in Windermere right now, the data says buyers in that tier are far more selective and far more patient than buyers shopping in the $500,000–$900,000 range.

What This Means If You're Selling

With a median 97.2% sale-to-list ratio and over a third of homes going under contract within two weeks, well-priced, well-presented homes are still moving efficiently, especially in the sub-$1 million range. Communities like Summerport, Belmere, and Lake Sawyer South are seeing some of the fastest turnaround times in all of Central Florida.

If your home has been sitting for more than 45–60 days, it's very likely a pricing or presentation issue rather than a "the market is slow" issue, the data shows buyers are active and closing quickly when a home is positioned correctly. The 124 listings that canceled, expired, or withdrew this year (median 119.5 days on market before coming off) are the clearest evidence of this: it's not that these homes couldn't sell, it's that most were priced for a different market than the one buyers are actually shopping in.

What This Means If You're Buying

Competition hasn't disappeared. One in four homes sold at or above asking price in the first half of 2026, and that share climbs in the most in-demand pockets like Summerport and Lake Sawyer South. If you're house hunting in Windermere this summer, come prepared to move quickly and make a strong first offer in the communities with sub-20-day median market times.

That said, the luxury tier (Keenes Pointe, Isleworth, and estate-lot neighborhoods) is showing more room to negotiate, with sale-to-list ratios in the low-to-mid 90s and a few notable price reductions on the way to closing, a more favorable environment for buyers targeting $1.5 million-plus homes.

Looking Ahead to the Second Half of 2026

If Q2's momentum holds, expect continued competition in the $500,000–$900,000 range as summer buyers close on deals before the new school year, while the luxury market likely continues to move at its own, more negotiated pace. Inventory levels, mortgage rate movement, and the usual seasonal slowdown into late summer will all be worth watching, I'll have an updated report as we move through Q3.

Windermere FL Real Estate FAQ

What is the median home price in Windermere, FL in 2026?
Through the end of June 2026, the median home sale price in Windermere was $800,000, based on 363 closed MLS transactions.

Are homes in Windermere selling above asking price?
About 1 in 4 homes (25.6%) sold at or above their list price in the first half of 2026, with the fastest-moving communities like Summerport seeing even higher rates of over-asking offers.

How long do homes stay on the market in Windermere?
The median time on market was 35 days across all of Windermere in H1 2026, though several communities, including Summerport (7 days) and Belmere (13 days) — moved significantly faster.

Is Windermere, FL a buyer's or seller's market right now?
Conditions vary by price point. The sub-$1 million market is leaning toward sellers, with quick sales and prices holding near asking. The luxury market above $1.5 million is more balanced, with more room for buyer negotiation.

How many Windermere home listings fail to sell?
In the first half of 2026, 124 Windermere-area listings were canceled, expired, or withdrawn without selling, roughly 1 in 4 of all listings that reached a conclusion. These unsold listings sat a median of 119.5 days, more than three times longer than the 35-day median for homes that sold, and were disproportionately priced above $1 million.

About Andy Neal
Andy Neal is a Realtor based in Windermere, Florida, specializing in residential real estate throughout Windermere, Winter Garden, and the greater 34786 area. If you're thinking about buying or selling a home in Windermere and want a personalized breakdown of what's happening in your specific neighborhood, reach out anytime — I'm happy to run a free, no-obligation comparative market analysis for your home. Contact me here.