Windermere Real Estate Market Report — February 2026

Is the Windermere housing market up or down in February 2026?

Luxury continues to set the tone for Windermere’s real estate market in February 2024. The market recorded a median sold price of just above the million-dollar mark, one of the strongest signals of upper-tier strength in recent memory. Yet, homes are taking an average of almost three months to secure a contract, and over a dozen sellers have trimmed their asking prices, often by a significant margin. The February market has cooled from last year’s more frenzied pace, but it remains fundamentally steady — substantial cash deals are still getting done, and well-presented homes at the right price do move. For both sides, last month’s patterns underline the importance of sharp pricing and a clear understanding of the current negotiation environment. Here’s what the numbers mean for Windermere buyers and sellers as we head toward spring.

What the Numbers Are Telling Us

The Windermere market is firmly in luxury territory this February, with a median sold price clocking in at one million twenty-five thousand dollars and a solid price per square foot at three hundred forty-five dollars. Sellers are seeing homes take close to three months from list to contract, making patience essential for those entering the market. With twenty-one sales completed and twenty-five homes pending, the pace is measured — yet still shows an undercurrent of active demand in Windermere’s coveted communities.

Most homes are closing at ninety-six cents on the dollar relative to the list price. This signals that buyers expect some negotiation room, but not fire-sale discounts — especially on well-prepared listings. The vibrancy in Windermere’s market isn’t just about price, but about strategic positioning. The presence of seven cash buyers among February’s closed deals — one-third of the month’s closings — confirms that well-heeled, quick-moving buyers remain in play, particularly for luxury homes.

The Price Reduction Picture

Thirteen out of the thirty-one active listings saw price reductions during February, with the typical reduction amounting to seventy-nine thousand dollars. This isn’t just a fleeting trend — it suggests that sellers, especially in the top price ranges, are encountering real pushback from buyers, who are leveraging longer market times to negotiate. These reductions signal a recalibration in seller expectations and reflect the reality that overpricing can lead to extended days on market and, sometimes, expired listings. When a home sits for over 200 days and ultimately expires, as we saw in February, it’s a clear message: Windermere buyers are patient and willing to wait for true market value.

What This Means for Sellers

For sellers, the data underlines the critical importance of getting the pricing and presentation right straight out of the gate. With most homes taking close to three months to go under contract — and some listing agents needing to make substantial price corrections — overpricing can translate into longer holding periods and increased carrying costs. The ninety-six-to-one sale-to-list ratio means buyers are coming in below ask, but strong, buttoned-up listings in this market can still justify premium positioning. Sellers who move quickly on price feedback and market signals are more likely to secure timely and profitable deals.

What This Means for Buyers

Buyers in Windermere see a window of opportunity in a market with healthy inventory and a measured sales pace. The presence of twenty-five pending listings, twelve of which spent over sixty days on the market before going under contract, tells prospective buyers that patience and strategic negotiation can pay off — especially in the million-dollar range. With nearly a third of February’s sales closing with cash, buyers relying on financing should be prepared for stiff competition on turnkey, well-staged luxury homes. However, those willing to do their homework and act where sellers have shown flexibility can secure excellent value in the current environment.

Construction Lens — What’s Happening on the Ground

Builders in Windermere are in a delicate balancing act, pulling small numbers of premium-spec homes to meet the steady, but not overheated, demand. Lot releases remain conservative, particularly in established luxury enclaves. New construction is competing sideways with veteran resales — buyers are weighing newer features and builder incentives against the emotional value and mature landscaping of resale properties. Construction delays have eased, but with longer resale market times, some sellers are holding out on major refreshes, hoping well-crafted pricing will bridge the gap. Local code changes and finishes continue to shape buyer expectations on both sides of the new-versus-resale equation.

What to Watch Next Month

Looking into March, expect continued measured activity, with buyers focused on real value and sellers deciding between pricing-in-place or strategic reductions. If active inventory holds steady and more sellers get aggressive on price, we may see average market times contract slightly as pent-up, ready buyers materialize. Keep an eye on the size and speed of new price reductions on unsold luxury listings — these changes are likely to influence how quickly the market moves in early spring.

Field Insights

The Friction: Sellers are hesitating to lower prices quickly enough, leading to listings sitting longer than buyers are willing to wait, particularly at the higher end.

The Strategy: Secure the sale by professionally prepping the home early and pricing within the neighborhood’s true range, not at the top; leverage fresh paint, deep cleaning, and subtle feature upgrades to stand out from both newer and existing competition.

Frequently Asked Questions

Are Windermere homes still selling with cash this month? Yes, seven of twenty-one sales closed with cash in February, showing luxury demand is still present.

Are homes in Windermere selling above list price right now? No, the typical Windermere home is selling at ninety-six cents on the dollar compared to the asking price.

Is the high days on market a sign of low demand? No, the average days on market reflects more price sensitivity and negotiation rather than a lack of buyer interest.

Windermere’s housing market in February 2024 offers unique opportunities whether you’re aiming to buy or sell in the area. The market is steady but disciplined, with luxury pricing, active negotiation, and a mix of new construction and resale homes shaping results. Florida Homes Group combines deep Windermere expertise with construction-savvy advice to maximize your outcome, whether you’re strategizing a sale or looking to buy the perfect property. If you want real-time insight and a tailored plan for Windermere’s evolving market, now is the time to talk. Reach out to Florida Homes Group today for a no-obligation conversation about your next move.

About the Author: Sol Simpson is a licensed Florida real estate agent with Florida Homes Group (Brokerage License #CQ1073198, Agent License #SL3644140), specialising in listing homes across Horizon West, Winter Garden, and Windermere. With seven years of residential construction experience and deep knowledge of new construction across builders including Pulte, Ashton Woods, Toll Brothers, and DRB Homes, Sol helps West Orange County homeowners position and sell their properties competitively in a new construction market.