Woody Allen – Manhattan, $26 Million

Unlike Ron, Woody Allen began as a writer during his college years, making a living out of writing jokes for newspaper columnists. Not long after, he eventually found his way to bigger gigs, creating scripts for programs like The Ed Sullivan Show, The Tonight Show, and Stanley. Over six decades since, Woody has received major credit for his work in film, which includes Award-winning titles like Annie Hall, Bullets over Broadway, Midnight in Paris, and Blue Jasmine.

Despite being known for his comedic work, Woody doesn’t joke around when it comes to his home – an English country-style townhouse. Besides this humble abode’s astounding class and beauty, it’s also conveniently located in the same street Woody filmed Annie Hall years before. Although different from Ron’s lakeside estate, both properties provided their residents with many fond memories. Plus, they’re both valuable, albeit a million and a half dollars apart.