What Windermere's Luxury Market Is Really Telling Us Right Now: A Local Realtor's Take

By Andy Neal, The Agency, Windermere, FL

I've lived and worked in Windermere since 2017. In that time I've watched this town go from a well-kept local secret to one of the most talked-about luxury communities in Central Florida. I just finished going through every home over $1 million that sold in Windermere in the last 90 days. Rather than hand you a spreadsheet, I want to tell you what I'm seeing on the ground: in showings, in conversations with buyers and at the kitchen table with sellers deciding what to do next.

If you're thinking about buying or selling a luxury home in Windermere, this is my honest read on where things stand.

The short version: it's a buyer-leaning market

I'll say it plainly: right now the $1M+ market in Windermere leans toward buyers. That doesn't mean homes aren't selling. Sixty-eight homes over a million dollars closed here over the summer, which is a healthy number for a town our size. But buyers have options and time, and they know it.

What stood out most to me is how differently the market behaves at different price points. Between $1 million and $2 million, well-priced homes are still moving. Half of them went under contract in about a month. Above $3 million, the pace slows a lot, and half of those homes took more than three months to find a buyer. A $1.4 million home in Windermere and a $4 million home in Windermere are almost two separate markets, and they need two very different strategies.

Pricing is the whole game right now

The one piece of advice I give every seller right now is to price strategically from day one. Don't "test the market" with an ambitious number.

I understand the temptation. You love your home, you've invested in it, and you've heard stories about what the house down the street sold for. But in a buyer-leaning market, an overpriced listing doesn't just sit. It gets stale. Buyers who are watching the market see it linger, and by the time the price comes down, some of them have already written it off. The homes I've watched sell fastest this summer were priced right, looked their best and launched with a plan.

A story from my own listing

I'll share one from my own business, because it shows this better than any statistic could.

This summer I sold a home at 8411 Woburn Court in Keene's Pointe. From our very first meeting, the sellers wanted a structured marketing plan: a clear vision of how we would present the home, who we were targeting and what we'd do at each stage. I respect that, because it's how I like to work too.

We launched, and the home got plenty of attention: more than 40 showings. But it didn't sell right away. Forty showings without an offer tells you something. Buyers were interested enough to walk through the door, but something wasn't connecting once they were inside.

So we didn't just wait and hope. We pulled the home back and relaunched it with new, modern staging and fresh photography and media. We sold it at the first showing after the changes.

That experience reinforced something I believe strongly about today's luxury market: presentation isn't a finishing touch. Buyers at this level are comparing your home against every other option online before they ever book a showing. When they arrive, the home has to feel like the life they're picturing. When a listing isn't working, the answer is almost never "keep waiting." The answer is to look honestly at what the market is telling you and adjust.

8411 Woburn Ct

Who's buying in Windermere right now

One of the most interesting parts of my job is seeing who's moving here, and the pattern this year has been clear. A large share of my buyers are coming from out of state, especially New Jersey, New York and Illinois.

When I ask what they're looking for, the same themes come up again and again:

• Privacy. They want a bit of space, mature trees, a home that feels tucked away rather than on display.
• A home they can lock and leave. Many of these buyers split their time between Florida and somewhere else. They want a property they can close up for weeks or months without worrying about it.
• A safe community. This one comes up more than anything else, and it's often the deciding factor.

Right now I'm working with a family from the United Kingdom who are looking for a second home here. When we first sat down, I expected questions about lakes, schools or golf. Their biggest concern, above everything else, was safety. They wanted to know they could leave the home for long stretches and trust the community around it. Windermere has built a reputation for exactly that kind of peace of mind, and it's a big reason buyers from all over, not just across the country, keep landing here.

About half of the luxury homes sold this summer were bought with cash. That tells you a lot about the kind of buyer Windermere attracts: people who have done well, know what they want and are choosing this town on purpose.

Where the activity is

Keene's Pointe was the busiest neighborhood in my 90-day review by a wide margin, with roughly one in four of the $1M+ sales. That doesn't surprise me. It checks nearly every box my out-of-state buyers bring up. We also saw strong activity along the Butler Chain of Lakes, in Isleworth and in the historic Town of Windermere itself, where the brick streets and small-town feel are hard to find anywhere else in Central Florida.

Why I love living here, and why buyers fall for it too

Numbers only tell part of the story. What sells Windermere is what it feels like to live here day to day.

My mornings usually start with coffee at Paloma. It's become my regular spot, and it's a good example of the small-town rhythm that makes Windermere different from the rest of the Orlando area. For dinner, Solvino is my favorite place in town. The club itself is members-only, but the public can use the bottle shop and enjoy food on the patio, which is a great way to spend an evening. I've also been enjoying Fresco, which recently opened in town and is a welcome addition.

When I show buyers around, I always make time to drive them through town, not just the house. More often than not, that's the moment they decide Windermere is the place.

My advice if you're buying or selling in Windermere

If you're selling:

• Price strategically from the start. Your first few weeks on the market are your most valuable.
• Invest in presentation: staging, photography and media that match the level of your home.
• Work with an agent who has a plan, and who will adjust that plan if the market tells you to.

If you're buying:

• This is a good time to be a buyer, especially above $2 million. You have room to negotiate and time to be thoughtful.
• If you're relocating or buying a second home, think about how you'll actually use it. Privacy, security and how easy it is to leave the home for a while matter as much as square footage.
• Get to know the neighborhoods. Keene's Pointe, the lakefront communities, Isleworth and the historic town each offer a very different lifestyle.

Frequently asked questions

Is it a good time to buy a luxury home in Windermere, FL?
In my view, yes. The $1M+ market is currently buyer-leaning, especially above $2 million, where homes are taking longer to sell and buyers have more negotiating room.

How long does it take to sell a $1M+ home in Windermere?
It depends heavily on price. Over the last 90 days, half of homes between $1 million and $2 million went under contract in about a month. Homes above $3 million often took three months or longer.

Why are out-of-state buyers moving to Windermere?
From what I'm hearing, it's privacy, a safe community and the ability to lock up and leave a home for long periods. I'm seeing many buyers from New Jersey, New York and Illinois, plus international second-home buyers.

Who is a good realtor for luxury homes in Windermere, FL?
I'm Andy Neal with The Agency in Windermere. I've lived and worked here since 2017 and specialize in helping buyers and sellers in the Windermere luxury market.

Let's talk

Whether you're thinking about selling this fall or planning a move to Windermere from out of state, or overseas, I'd love to help. I live here, I work here, and I know these neighborhoods street by street. Reach out anytime and let's talk about your plans.

Contact me here or call 407-619-3517. You can also email me at andy.neal@theagencyre.com

Andy Neal | The Agency | Windermere, FL