Keith Chubb

Keith “Chubby” Chubb is a Realtor with Realty Executives in The Villages, Florida — the largest and, without question, coolest 55+ community in the U.S.
Chubby works alongside his wife and business partner, Jude Hamilton, under their musical brand: Your Musical Realtors. Together, they bring heart, harmony, and hustle to every transaction — and yes, they’ve been known to hit many high notes with their clients. They work with other members as a team and can be found on Facebook and their website under Herd Of The Villages.

Before diving into real estate, Chubby earned a degree in accounting from Bowling Green State University (1977) and spent 15 years in the business world. But his journey took a more entertaining turn when he became the CD+G karaoke product line manager for Sound Choice, helping design, launch and market the most successful karaoke software line in U.S. history. In 1989, he founded Chubby’s Karaoke, which later grew into Chubby’s Entertainment — a business that is still thriving TODAY, including an 18-year exciting expansion in Cancún, Mexico (2001–2019).

While in Cancún, Chubby didn’t just host karaoke shows — he also held weekly live medical presentations, officiated over 40 beach weddings and vow renewals, and even stepped into the ring 5 times as a guest referee for Lucha Libre (professional Mexican wrestling).

In 2023, Chubby and Jude were awarded Rookies of the Year with Realty Executives in The Villages. Today, they continue to grow their business by building real relationships, providing expert guidance, and showing that buying or selling a home doesn’t have to be stressful — it can be fun, rewarding, and maybe even a little musical.