Isleworth's median sale price is $4,998,261 — four times the next community in Orlando. And it is still not the address producing the region's largest transactions.
Source: Redfin market data, three months ending June 2026, retrieved 17 August 2026. Isleworth and Keene's Pointe are neighborhood-level areas; Windermere, Bay Hill, Winter Park and Dr. Phillips are city-level. Isleworth's median rests on 3 June sales — at that volume treat it as directional. For context, the Orlando Regional REALTOR® Association reported a $416,308 median for June 2026 across Orange, Osceola, Lake, Seminole and Volusia counties.
No portal maintains a market page for the residential community inside Walt Disney World Resort, so it has no median and appears on no ranking of Orlando neighborhoods. Per the Orlando Sentinel, eight of the ten highest home sales in Central Florida in 2025 were in Golden Oak. The top sale that year closed in August at $23 million. In March 2026 a Golden Oak estate on Enchanted Oak Drive sold for $14 million.
By median sale price, Isleworth in Windermere at $4,998,261 for the three months ending June 2026. By actual transaction size, Golden Oak inside Walt Disney World Resort, which produced eight of Central Florida's ten highest sales in 2025 per the Orlando Sentinel but has no published median.
Windermere's 34786 ZIP, which contains Isleworth, Keene's Pointe and Lake Butler Sound. By median household income, Baldwin Park's 32814 is higher at $140,274 against Windermere's $134,214 (ACS 2024 five-year), which shows why income by ZIP is a poor measure of wealth.
The median sale price is $4,998,261 for the three months ending June 2026, at $784 per square foot. That median rests on a small number of sales, so treat it as directional. The community record is $35,000,000, set in February 2023.
No real estate portal maintains a market page for it, so it has no median for a ranking to use. Rankings measure what aggregates easily.
Windermere, by a wide margin at the median. Winter Park is more expensive per square foot than Windermere — $498 against $365 — because you are buying a smaller house closer to Park Avenue. Winter Park's ceiling competes: the Isle of Sicily and the Vias have produced $9.7M and $13M sales.
At the median, yes — $1,041,933 against $1,924,331. Per square foot, no: Bay Hill is $493 and Keene's Pointe is $467. The difference is house size, not address quality, and Bay Hill takes 68 days to sell against Keene's Pointe's 39.
$416,308 in June 2026, across the five-county area of Orange, Osceola, Lake, Seminole and Volusia reported by the Orlando Regional REALTOR® Association. ORRA added Volusia County in April 2026, so figures before that date are not comparable to figures after it.
Adams Equities is a boutique luxury real estate brokerage serving Windermere, Isleworth, Dr. Phillips, Bay Hill, Winter Park, Golden Oak, and the greater Orlando area. Edgar Adams, Founder & Managing Broker. Alexander Adams, Principal & Market Strategist.
Office: 9100 Conroy Windermere Road, Suite 200, Windermere, FL 34786. Phone: +1 407-448-3757.
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