Windermere Housing Market Update 2025

Windermere Housing Market Update 2025: Is Now a Good Time to Buy or Sell?

August 15, 2025

Story Highlights:

• Inventory remains low: 215 active listings vs. historical norms of 300–400.
• Median prices are stable, generally hovering between $750K and $900K.
• Buyer activity is stronger than last year, but still below pre-pandemic levels.
• 36% of listings are seeing price cuts, mainly due to overpricing.
• Windermere remains in demand, but buyers are more value-focused.

Windermere Housing Market Update 2025: Is Now a Good Time to Buy or Sell?

If you’re keeping tabs on one of the most talked-about real estate markets in Central Florida—Windermere—this one’s for you. Whether you already live in this lakeside gem or are dreaming of moving into a luxury estate with a view, let’s break down what’s actually happening in the market (and not just what headlines are saying).

What's the real deal with Florida's housing market right now?

You’ve probably seen the flashy headlines—”Florida hits 11-year high in housing inventory” or “Builders slashing prices left and right.” But here’s the thing: real estate is local, and Windermere isn’t following the national script.

While some areas are flooded with listings and slow sales, Windermere is holding its own.

Is Windermere real estate crashing like the rest of Florida?

While Central Florida’s inventory is up 15% year-over-year, that’s still way below national numbers. And fewer homes are being listed right now, which means unsold inventory is likely to shrink even more.

So, despite all the doom-and-gloom, Windermere isn’t spiraling—it’s stabilizing.

That growth has been anything but random. Osceola County, where Kissimmee sits, is one of the fastest-growing counties in Florida—adding over 15,000 residents in just one recent year. As a result, the area has seen major investment in schools, roads, neighborhoods, and commercial development. Kissimmee is no longer a pass-through—it’s a place people are choosing to live.

What are home prices doing in Windermere?

Across Central Florida, average sale prices are down about 3%. But Windermere, with its luxury price point, dances to a different beat.

• Median prices are holding steady—hovering near or above $800K.

• Prices have dipped slightly from early 2024, but we’re still well above pre-pandemic numbers.

• Like any luxury market, Windermere sees wild monthly swings. One month it’s $900K, next it’s $750K. The key? Look at the yearly trend: flat to stable.

Are buyers still interested in Windermere?

Pending sales are up year-over-year in 2025. But compared to pre-pandemic summers, buyer activity is still below historical levels.

Why? There’s just less inventory. In the past, 300–400 homes were available during peak months. This summer? Around 215 active listings.

Buyers want in. But when they can’t find the right house, they look elsewhere.

Why are 36% of homes seeing price cuts in Windermere?

This stat feels dramatic, but here’s what’s actually happening:

• Sellers are starting too high.

• Then reality (and savvy buyers) force a price reduction.

That 36% of listings with price cuts? It doesn’t mean values are plummeting. It just means pricing correctly matters more than ever.

Sellers can’t bank on 2021 energy anymore. Overpricing leads to extended time on market, multiple reductions, and buyer hesitation.

How does new construction compare to resale homes right now?

Nationally, the price gap between new construction and resale homes is at a record low—under 8%.

In Windermere, this matters because:

Builders are motivated and offering big incentives.

Buyers are comparing new vs. resale more aggressively.

Bottom line: Resale sellers have to be competitive. Gone are the days of ignoring new build competition.

Is Windermere still in high demand?

Executives relocating for new opportunities, growing families upgrading their lifestyle, and out-of-state buyers looking for that Florida dream all continue to have Windermere at the top of their wish list.

But today’s buyers? They’re not messing around. They’re smart, they’re patient, and they’re focused on value over hype. They’ll fall in love with your lakefront view—but only if the price tag makes sense.

That’s why homes priced right are still moving. Windermere isn’t cooling off—it’s just getting smarter.

FAQs About the Windermere Housing Market

Is now a good time to buy in Windermere?
Yes—if you’re prepared. With fewer listings and motivated sellers, buyers who act quickly and strategically can still land a great deal.

Are Windermere home prices dropping?
Not significantly. Prices are stable overall, with monthly fluctuations typical of a luxury market.

Why are there so many price reductions?
Many sellers are still pricing like it’s 2021. Buyers today are savvy and will wait or walk away.

How competitive is the Windermere market right now?
Less competitive than during the peak frenzy, but good homes still move quickly. There’s just less to choose from.

Should I wait until 2026 to buy or sell?
It depends on your situation, but waiting doesn’t guarantee better deals. The current market is balanced and healthy.

Are condos in Windermere struggling to sell?
Statewide, condos have more supply (around 10 months), but single-family homes in Windermere remain strong.

How does Windermere compare to nearby areas?
It’s still considered a top-tier market due to schools, location, and community lifestyle. But price-wise, buyers are comparing it closely with places like Winter Garden and Dr. Phillips.

Are builders in Windermere offering incentives?
Yes—many are, especially if they have standing inventory to clear before year-end.

Is inventory expected to rise in Windermere?
Unlikely. New listings are down year-over-year, and delisting trends are increasing.

What’s the biggest mistake sellers make in Windermere?
Overpricing. Starting too high leads to more time on market, multiple price cuts, and a weaker final offer.

Why Choose Jared Jones?

As a top real estate agent with nearly 4,000 homes sold and over 20 years of experience in the Florida real estate market, I have the expertise needed to help you navigate today’s evolving landscape. Whether you’re looking to buy or sell, my deep understanding of market trends and personalized approach will provide you with the insights and strategies required for success.

Best Realtor in Windermere - Reach Out Today!

If you’re ready to make a move in Florida’s real estate market, don’t hesitate to reach out. Contact Jared Jones at 407-706-5000 (call or text) or email info@jaredjones.com for professional guidance and personalized service that will help you achieve your real estate goals.