If you are a family considering a move to Orlando, there is a neighborhood that stands out even before the theme parks: Windermere, nestled by the Butler Chain of Lakes, and its gated community, Isleworth. At the center of this area is a championship golf course designed by the well-known Arnold Palmer.

As of June 2026, the median sale price in Isleworth is around $3.7 million, reflecting an increase of approximately 127% over the ten years from 2015 to 2025, making it one of the gated communities with the highest price growth in the Windermere area.

When looking at Windermere as a whole, there is a significant mix of ultra-high-end communities like Isleworth and more typical single-family home areas, resulting in considerable price variation. Overall, it is estimated that prices range from $900,000 to $1.1 million. The history of famous athletes and businesspeople residing in this area is often cited as a reason for its growing recognition.

Shifting focus to Lake Nona reveals a different kind of upscale residential area. With a strong planned community character, it features a medical cluster and corporate facilities like the KPMG training center. Despite being a recently developed area, it has established a market price range of $600,000 to $700,000, attracting young professional asset holders.

The median sale price for all of Orange County has recently been recorded at around $440,000 over the past three months, while the greater Orlando area remains at about $385,000. When comparing Isleworth alone, it shows a difference of more than nine times the average of the greater area, indicating that the market experience can vary significantly even within the same name of Orlando.

This widening gap appears to be influenced by the scarcity of land near lakes, the combination of private schools and golf communities, and the brand effect created by celebrity residents.

Among Korean families moving to Orlando, there is a growing trend of choosing areas near Lake Nona for reasons related to children's education and medical professions. It may be more realistic to consider relatively accessible upscale residences like Lake Nona or Doctor Phillips rather than areas with very high entry barriers like Isleworth.

Ultimately, regardless of which neighborhood you choose, it is important to consider school districts, community management fees, and future resale demand, as these are often overlooked aspects in the decision to relocate.