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2023 Winter Garden Year Summary

Welcome to Ron the Realtor’s Windermere Real Estate Market Report 2023 Year in review. The only place on the internet to get this much accurate data regarding the Windermere Real Estate market along with in-depth breakdown and predictions from Windermere resident and #1 REMAX Realtor in State of Florida 6 consecutive years..

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 the booming Winter Garden allow the residents endless shopping and dining options.

Lets dive right into the report a year in the making….



Average Sale Price

16% Increase


ave $/ft

12% Increase


Average Days on Market



Median Sale Price

14% Increase

Windermere is truly an amazing market. In a sea of doom and gloom headlines, record inflation and largest spike in interest rates our country has ever seen. The Windermere real estate market experienced another well over double digit spike in all major market metrics. It is truly remarkable how 34786 continues to prove the truth that location is everything in real estate.
Another economic fact that is easily witnessed with this data is Supply and Demand. We had over a 10% drop-in closed units from 2022 to 2023 yet we have seen unmatched spikes in average sale price and $/ft year over year.
Let us do what we do here in the RTR ARMY and put in the extra effort and dive into what really matters , the single-family market on its own.


Average Sale Price

16% Increase


ave $/ft

11% Increase


Average Days on Market

48% increase


Median Sale Price

13% Increase

Another record setting year with Windermere blowing past the $1,300,000 average and fast approaching $350/ ft . Even more impressive is the median sale price soaring to almost $1m.
FULL DISCLOSURE,  in the spirit of selfishness and wanting to understand the true metric Data, I have omitted a RECORD CLOSED SALE from the charts. Windermere experienced a record breaking $35,000,000 closing behind the manned gates of Isleworth in 2023. It was just such a huge number it was skewing all the data with a 3-4% impact to sale price and $/ft.
I did keep the other equally impressive $12M closing and is an obvious contributing factor to these unexpected gains.
Lets look at what was predicted to Reality


Wow, way off.  I am form once happy I was wrong, these gains were some unexpected and every quarter as the reports were produced and toiled over, the double digit gains were there every single quarter.
In 2023 Windermere experienced record breaking sales volume at all major price points, we discussed the $35m and $12… But 13 estates sold of $5m , 106 over $2m and a record 258 over $1m.  In 2022 Windermere had one amazing sale over $15m , one over $10m , only 5 over $5m , only 69 over $2m and 224 that topped over $1m
Lets go one step deeper into this remarkable run. 2020 was a great year with under 3% rates and Florida experiencing the “Covid Migration” due to our  States adherence to our Constitutional Rights.
In 2020 there were 50% MORE closed units than in 2023 and the average sale price was $683,856 , and the average $/ft was $198.72… In 3 short years these 2 data metrics have soared 40% !!!!! Never seen anything like it in my 26 years of this business.
I will say it again, I am even more impressed with the performance of 2023. I was predicting a modest 5% jump, I could not have been further from reality.
I truly misjudged the desirability and lack of Supply in 34786. Unlike the Winter Garden to the west, Windermere is at capacity. If you want to build new the choices are almost NIL, zilch , nada… and  will take 2-3 years to complete. Resale is the only option. Tear down to remodeling seems to be occurring on practically every block.

What is in store for 2024.... click below and find in the Ron the Realtor Crystal Ball forecast.

Thank you for taking time to read and follow. I do not require a subscription, registration or even a sign up to access this data and analysis I provide. Most of the local Realtors read this report too. I am happy to provide this for all. I don’t feel, I have any competition and truly believe that knowledge is power. I want everyone around me to succeed…. why I do this every quarter and every year for literally decades, these report take a lot of time and energy so I love that you spent your time here, I hope you obtained an amazing return on investment (ROI)
When it does come time for your family to buy and sell, I hope that I am the one your family turns to for representation. Thank you for being apart of the RTR ARMY. Phone is always on 407 592 SOLD
All the very best in 2024 to you and yours.
God Bless our troops overseas and the families they leave behind , I for one will never forget that FREEDOM IS NEVER FREE.




What is in store for Windermere in 2024…. click the link below to find out.


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