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2021 Windermere Year Summary

Welcome to RTR’s Windermere Real Estate Market Report 2021 Year in review. The only place on the internet to get this much accurate data regarding the Windermere Housing market along with in-depth breakdown and predictions from Windermere resident and unprecedented 4-year running #1 REMAX Realtor in the State of Florida, RTR.

Windermere continues to be sought after due to its proximity to the theme parks, Downtown Orlando and the famed Butler Chain of Lakes. Exclusive manned gated communities lined with mature oaks attract high net worth families to call 34786 their home. The Town’s dedication to keeping the charm of the area allows for one of the only places in Central Florida not bustling with 4 lane highways and neon signs on every corner.

The sought after schools and close proximity to Sand Lakes restaurant row, International Drive and booming Winter Garden allow the residents endless shopping and dining options.

Lets Look At How 2021 Finished Compared To 2020….. All Data Derived From The ORRA MLS


Average Sale Price


Average Days on Market


ave $/ft

2021 Windermere

2021 treated Windermere better than it has ever been treated ! One for the record books, experiencing largest year to year spikes on all 4 major metrics ever witnessed.  Unprecedented 18% spike in average sale price, climbing $150,000 over 2020 average, average $/ft climbing 15% to $234.51 a foot and a median sale price sailing past the 500k mark.
What is even more impressive is that during what was the lowest inventory ever on record, Windermere experienced a 27% surge of units sold in 2021… 1,319 up from 961 in 2020.
Let’s shave off the condos and townhomes and look at the single-family market to get the whole picture before we get into the RTR breakdown of the why and how.

2021 Windermere Single-Family


Average Sale Price


Average Days on Market


ave $/ft


Listings SOLD


13 Estates purchased topping just over $25,000,000 in closed volume

Looking at the single-family market of Windermere is crucial because, for the zip code of 34786, THAT IS THE MARKET… the real market.

Central Florida witnessed the greatest migration of owner-occupant buyers it has ever seen in 2021. With some studies guestimating 1,000 new families a week flocking to the area to call their new home.

Windermere has long been known as the place to be in Central Florida, a close tie with Winter Park. With the new remote work environment in the country and lessening demand on commuting, Windermere has become the hotbed for demand for the luxury buyer.

So much so that the average sale price soared to almost $1,000,000 and just shy of $250 / ft. Representing a 21% spike in ave sale price from the 2020s $785,000.

An increase of just over 250 more homes sold in 2021 than 2020 and the days on the market improved by almost 50% to 44 days!


The 2021 market statistics are like ones we have never seen in the area. Like all data, you need to read between the lines to get the real picture of the market. Without knowing the why you can not accurately forecast what is on the horizon.
Windermere had the most incredible 4th quarter it has ever had… Closing not 1 but 2 $11,000,000 estates, one for $7,125,000 ( RTRs doing ) and a total of 96 estates over 2 million price tag.
When you go back and analyze 2020… only 41 estates eclipsed the 2m mark and only 2 barely closed over the 5m price tag.
Please keep in mind you also have to understand the 2020 market was full of uncertainty… the entire state and the largest employer in 34786 backyards shut its doors for almost 2 months, several democrats run cities were smoldering under the feet of rioters left to run free unchecked and the country was in the heat of the largest presidential election in its history.  All factors of uncertainty led to the unprecedented 2021 results.
Affluent residents of liberal-run cities decided to cash out and flock to Florida. These housing markets were and are substantially higher than Central Florida, when they started to come to the area and research where to call home, Windermere was the obvious choice. Buying and setting new records almost every week, driving up prices, and buying even homes that sat on the market for years.
With more sales, even more, buyers became comfortable at the new heights of the property values… continuing to drive the cycle upwards all the way through to the record 4th quarter. Those that read the RTR 4h Quarter Windermere report know that single-family home sales spiked over 30% from the 2020 4th quarter and the average sale price soared to over $1,200,000 !!!

What is in store for 2022 ?

2022 Market Predictions
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