Windermere Real Estate Market Update — September 2026 - The Results!

Windermere’s September Market: Buyers Have More Leverage, but Demand Remains Strong for the Right Home

The Windermere real estate market is showing a clear divide between homes that are positioned correctly and those that are not.

Based on my activity in the market, buyers are taking longer to make decisions, showing activity is down, and offers are generally coming in at a lower percentage of asking price. Sellers are also facing more pressure to price competitively from the beginning rather than listing high simply to “test the market.”

At the same time, this is not a market where every home is struggling. Updated homes, new construction, and especially waterfront properties continue to attract strong buyer interest. The difference is that buyers are becoming much more selective about where they are willing to spend their money.

The September MLS report covering 42 sold listings showed an average sale price of $996,504 and a median sale price of $692,500. The average sale-to-list price ratio was 96.2%, the median was 97.1%, and the average days on market was 61, compared with a median of 27 days.

Those numbers tell only part of the story, however. The experience of buying and selling in Windermere right now depends heavily on the individual property.

What Changed in the Windermere Market?

From what I am seeing, there is less overall activity than there was previously.

I am seeing fewer new buyers entering the market, less activity on my listings, fewer showings, and buyers taking considerably longer to decide whether they want to move forward with a property.

I am also seeing offers come in at a lower percentage of asking price.

That creates an important distinction for sellers: being on the market does not necessarily mean being competitive in the market.

The supplemental MLS report I reviewed also provides a broader look at properties that have not resulted in a closed sale. It includes 17 canceled listings, four expired listings, and 48 pending listings, including a pending Windermere Town property listed at $7.5 million.

That broader picture reinforces an important point: there is still activity at a variety of price points, but the properties attracting buyers are not necessarily doing so simply because they are available.

Buyers Are Becoming More Selective

One of the biggest changes I am seeing is that buyers increasingly want a home they can move into without immediately taking on a major renovation.

The homes that are getting attention tend to be updated or new construction.

That makes sense from a buyer's perspective. If a buyer is already facing higher financing costs, particularly at lower price points, they may be less willing to purchase a home that also requires substantial additional money and effort after closing.

I am hearing and seeing more buyers who would rather pay for a home that is already finished than take on a renovation project themselves.

This doesn't mean homes that need updating cannot sell. It means buyers are becoming more conscious of the total cost of ownership and are comparing the finished product more carefully.

Interest Rates Are Still a Bigger Issue at Lower Price Points

Interest rates continue to be a concern, particularly among buyers at lower price points.

At the higher end of the Windermere market, I am seeing more cash buyers.

That creates a somewhat different dynamic across the market. Financing costs can have a significant effect on a buyer's purchasing power and monthly payment at lower price points, while a cash buyer at the higher end is not facing that same mortgage-rate consideration.

The result is a market that cannot always be understood by looking at one overall statistic.

Waterfront Homes Continue to Stand Out

If there is one segment of the Windermere market where I continue to see particularly strong demand, it is waterfront.

Waterfront homes are definitely in demand.

I recently had a waterfront listing where we made significant price adjustments, first $150,000 and then another $140,000 in order to ultimately accept an offer. That experience illustrates an important distinction: even desirable waterfront property still has to be priced correctly.

At the same time, I recently saw a waterfront property around $7.5 million go under contract, demonstrating that buyers are still willing to pursue exceptional waterfront homes at the luxury end of the market.

The MLS report also shows the depth of the high-end market currently being pursued, with a pending Windermere Town property listed at $7.5 million.

So I would not describe the current market as a lack of demand for waterfront. Instead, I would describe it as strong demand for the right waterfront property at a price buyers consider justified.

Property went under contract after significant reductions. 

What the September Sales Numbers Tell Us

The September sold data provides some useful context.

Among the 42 sold listings in the report:

• Average sale price: $996,504

• Median sale price: $692,500

• Average sale-to-list ratio: 96.2%

• Median sale-to-list ratio: 97.1%

• Average days on market: 61

• Median days on market: 27

• Sale price range: $319,600 to $4,000,000

The averages also hide a significant amount of variation.

Some properties are selling quickly and, in the right circumstances, above asking price. Others are taking substantially longer and selling below the original asking price.

That is particularly important in the luxury market, where a small number of sales can create a very wide range of outcomes.

Multiple Offers Are Rare

Multiple-offer situations are currently the exception rather than something I am routinely seeing.

In my own experience during September, I saw only one clear multiple-offer situation.

It involved a lake home listed around $1.6 million that needed updates. My buyer made an offer, but the property ultimately sold for approximately $50,000 over asking.

That is an important reminder that buyers will still compete when they believe a property represents the right opportunity.

The lesson isn't that every waterfront or lake property will generate multiple offers. It is that the right property, in the right location, at a compelling price, can still move very quickly.

Casa Bella Shows How Competition Can Affect Sellers

Inventory is also changing within individual Windermere communities.

I am currently seeing significantly more luxury inventory in Casa Bella than I would normally expect. There are five homes for sale there right now, whereas I would typically expect to see one or two.

I have a client who wants to sell in Casa Bella but is currently waiting because of the amount of competing inventory.

This is a good example of why looking only at broad Windermere statistics isn't enough.

A seller's actual competition is often much more specific: the homes competing for the same buyer, in the same community, with similar size, condition, views, amenities, and price.

What Sellers Need to Know

The biggest message I am giving sellers right now is simple:

Be competitive from the beginning.

The days of listing high simply to see whether someone will pay the price are gone, at least based on what I am experiencing in the current market.

One of the biggest conversations I am having with sellers involves updates.

Sellers who have renovated their homes understandably feel that their property should command a premium compared with homes that have not been updated.

That is often a legitimate distinction.

But an updated home still needs to be priced in relation to the alternatives a buyer has available.

The goal isn't simply to have the nicest house in a particular group of listings. The goal is to make the home compelling enough that a buyer chooses it over the other options.

I have personally seen this play out through significant price adjustments, including a waterfront listing where I reduced the price by $150,000 and subsequently another $140,000 in order to reach an acceptable offer.

That is why I believe pricing correctly at the beginning is more important than testing the market and hoping buyers will validate a higher price.

What Buyers Need to Know

For buyers, September's market presents an opportunity to be selective.

You do not necessarily have to rush into a decision simply because a property is available.

At the same time, buyers should recognize that not every home will be equally negotiable.

An updated home, new construction, or desirable waterfront property can still attract significant attention.

If a property checks the boxes for location, condition, and price, waiting solely because you assume the seller will eventually make a large reduction could mean missing the opportunity.

The key is understanding which properties are genuinely competing for your attention and which ones may have been priced ahead of the market.

The Windermere Market Is Not One Market 

Perhaps the most important takeaway from September is that there isn't one single Windermere market.

The experience can vary considerably based on:

• Waterfront vs. non-waterfront

• Updated vs. needing renovation

• New construction vs. older resale

• Entry-level vs. luxury

• Cash vs. financed buyers

• Individual community and competing inventory

• The initial asking price

A home can still sell quickly if it offers something buyers strongly want.

But properties that are dated, overpriced, or competing against better-presented alternatives may take considerably longer.

My Takeaway for Windermere Sellers

If you're considering selling in Windermere, I would not base your pricing strategy simply on what your neighbor received for their home or what you invested in improvements.

Instead, the question should be:

What will make today's buyer choose my home over the alternatives they can buy right now?

If the answer is waterfront, updated condition, new construction, a great location, or some combination of those factors, that can create a meaningful advantage.

But even a desirable property needs to be positioned correctly.

The September market is rewarding sellers who understand their competition and price accordingly.

My Takeaway for Windermere Buyers

For buyers, this is a market where patience can be valuable, but so can recognizing a good opportunity when it appears.

If you want a move-in-ready home, updated property, or waterfront home, you may still face competition for the right property.

The broader market may provide negotiating opportunities, but those opportunities won't necessarily apply equally to every home.

The best strategy is to evaluate each property individually rather than assuming that every seller is willing to make a major concession.

Frequently Asked Questions

Is Windermere a buyer's market right now?

Based on my firsthand experience in September, I believe buyers currently have more leverage than they did previously. I am seeing less activity, longer decision times, fewer showings, and more pressure on sellers to adjust pricing.

That is my market observation rather than a formal classification based on a specific months-of-inventory calculation.

Are Windermere home prices going down?

The September sold data shows that the average sale price was $996,504 and the median was $692,500, with an average sale-to-list ratio of 96.2%.

Those figures do not, by themselves, establish a market-wide price trend. What I am seeing firsthand is more negotiation around asking prices and more price reductions on individual listings.

Are waterfront homes still in demand?

Yes. Waterfront remains one of the areas where I am seeing strong buyer demand. However, waterfront does not eliminate the importance of pricing correctly. I have seen significant price adjustments on waterfront property as well as strong demand for desirable waterfront homes.

Are buyers still purchasing luxury homes?

Yes. There is still activity at the luxury end. I am also seeing more cash buyers among higher-end buyers. The current MLS snapshot includes a pending $7.5 million Windermere Town property.

What type of Windermere home is attracting buyers?

From what I am seeing, buyers are showing the most interest in homes that are updated, move-in ready, new construction, or offer desirable waterfront locations.

Should Windermere sellers wait to list?

There is no universal answer, because timing depends on the individual property and the seller's circumstances. But if a seller is ready to move forward, I would focus heavily on pricing and positioning rather than listing high simply to test the market.

How long are Windermere homes taking to sell?

The September MLS report showed an average of 61 days on market and a median of 27 days among the 42 sold listings. Individual properties vary considerably, particularly at higher price points.

The Bottom Line

September's Windermere market is selective.

Sellers need to be more competitive with pricing, while buyers are becoming more selective about condition and value.

Updated homes, new construction, and waterfront properties continue to stand out. But even desirable homes need to be positioned correctly, and sellers should not assume that improvements automatically justify any particular asking price.

For buyers, the opportunity is to take advantage of greater selectivity without assuming every property will be heavily negotiable.

For sellers, the message is even simpler: price to compete, not to test the market.

Market statistics in this article are from the MLS reports provided for this September 2026 market update. Firsthand observations and examples are identified as such. The MLS report is a Comparative Market Analysis and is not an appraisal.