Orlando's most expensive homes sit in golf communities. Of the 39 single-family sales of $10 million or more recorded in Orange County since 2000, 29 were in Golden Oak, Isleworth or Keene's Pointe, each beside a championship golf course.
Ask about the club before you ask about the house. At Isleworth, membership is by invitation and the club keeps a waiting list.
Isleworth: six hundred acres on the Butler Chain, built around a course Arnold Palmer and Ed Seay opened in 1986. Steve Smyers rebuilt it and the club reopened it in December 2003. It holds the county's record sale, $32,000,000 in February 2023.
Bay Hill: Dick Wilson laid it out in 1961, and Arnold Palmer refined it for decades. The Challenger/Champion course plays par 72 at 7,466 yards and hosts the Arnold Palmer Invitational. Its median sale price was $1,041,933 over the three months ending June 2026, against Isleworth's $4,998,261 (Redfin).
Keene's Pointe and the Golden Bear Club: Jack Nicklaus' Signature course opened in 1999. Keene's Pointe recorded its highest sale in June 2026: $13,200,000 for a 4.4-acre lakefront estate on Tibet Pointe Circle.
Tom Fazio's course opened in 1992 as Disney's Osprey Ridge and reopened in 2014 after Fazio's firm reworked it. Nineteen of Orange County's 39 single-family sales of $10 million or more since 2000 were in Golden Oak.
Lake Nona Golf & Country Club, a Tom Fazio design from the mid-1980s, hosted the first Solheim Cup in 1990. Interlachen Country Club in Winter Park is a Joe Lee course from 1985. Alaqua Country Club in Longwood is a Gary Player course from 1988. Heathrow Country Club's Ron Garl course dates to 1983. Windermere Country Club closed in 2016.
For a private club on the Butler Chain, Isleworth: a Palmer course rebuilt by Steve Smyers, membership by invitation and the county's record sale. For the deepest market at $10 million and up, Golden Oak, with 19 of the county's 39 such sales since 2000. For a PGA Tour course on the chain at roughly a fifth of Isleworth's median price, Bay Hill.
Bay Hill hosts the Arnold Palmer Invitational on the PGA Tour. Lake Nona hosted the LPGA Tournament of Champions from 2022 to 2024 and in 2026. Isleworth hosted the Hero World Challenge in 2014, and the Four Seasons course in Golden Oak hosted a PGA Tour Champions event in 2017 and 2018.
The club describes membership as by invitation, with a waiting list. Treat the house and the club as separate decisions, and settle the club question before you sign.
Isleworth, Bay Hill and Keene's Pointe, home of the Golden Bear Club.
No. It closed in 2016 and the property sold in 2024.
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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