9 Things You May Not Know About Hollywood’s Fascinating History

Nestled between the famed locales of Fort Lauderdale and Miami lies Hollywood, Florida—a picturesque beach town with a story all its own to tell. One of the Sunshine State’s most thoughtfully planned communities, Hollywood has a century-long history that’s full of surprises, delights, and a legacy that defines the city to this day.

1. It Was Modeled After Hollywood, California 

Hollywood was the brainchild of Joseph Wesley Young, a real estate developer with big dreams and bold ideas. Inspired by Hollywood, California, Young envisioned a glamorous, welcoming city where everyone from movie stars to working families could thrive.

Starting with just one square mile in the early 1920s, Young got to work developing the marshland and pine forests. Today, that dream has become a thriving, 28.87-square-mile city with over 153,000 residents. It’s now the second-most populous city in Broward County and the ninth largest in Florida.

2. It’s One of Florida’s First Master-Planned Communities

Long before planned communities were the norm, Joseph Young laid out Hollywood as a carefully designed city, with areas for living, working, and gathering—a concept that was revolutionary at the time. 

One of his most iconic features was the creation of three major circular parks along Hollywood Boulevard:

• Young Circle (originally Harding Circle): Now home to ArtsPark, a cultural and community hub with fountains, an amphitheater, and art installations.
• Watson Circle: The site of City Hall and key municipal buildings.
• Presidential Circle (formerly Academy Circle): Now a prominent office and commercial center, once the location of a military academy.

Many of Hollywood’s most desirable neighborhoods, like Hollywood Lakes, Downtown, and Hollywood Hills, were also part of Young’s original vision. The broad medians, palm-lined streets, and proximity to parks and water are still major selling points for homebuyers looking for a balance of charm, convenience, and beauty.

3. Mediterranean Style Helped Shape the City

Young’s development overlapped with the peak of the Mediterranean Revival and Spanish Colonial Revival movements in Florida architecture. These styles became Hollywood’s signature, with stucco exteriors, terracotta roofs, arched windows, wrought iron details, and lush tropical landscaping.

These historic homes remain among the most sought-after in the area, and many have been lovingly preserved or updated, blending Old Florida elegance with modern comfort.

Walk these neighborhoods and you’ll see why buyers prize Hollywood’s historic districts, thanks to the timeless style and a deep connection to the city’s roots.

4. Hollywood’s “Broadwalk” Isn’t a Typo

There’s a story behind the spelling of Hollywood’s oceanfront promenade. While it was inspired by the iconic boardwalks of Atlantic City, founder Joseph Young opted for a wider, more elegant version, thus giving it the unique name of “broadwalk.”

Stretching nearly 2.5 miles, the Broadwalk is lined with boutique hotels, beachfront condos, and family-run cafes, offering a blend of scenery and fun. It’s also been named one of the top beach boardwalks in America by USA Today, TripAdvisor, Travel + Leisure, and Fodor’s Travel Guides.

5. The Hollywood Beach Hotel Trained WWII Radar Operators

Opened in 1926, the Hollywood Beach Hotel was once the crown jewel of the city—a luxurious oceanfront retreat known for its grand architecture and glamorous guests.

But during World War II, the hotel took on a new role as a U.S. Navy radar training school, where thousands of servicemen trained in cutting-edge technology.

Today, the building still stands as part of the Hollywood Beach Resort, offering a rare glimpse into the city’s layered past. It’s one of the few places in South Florida where you can walk through a piece of WWII history, steps from the sand—or even own a condo inside a building that helped shape both Hollywood and history.

6. A Colorful Mid-Century Chapter

In the 1950s and 60s, Hollywood gained a quieter reputation as a haven for organized crime figures seeking refuge from law enforcement scrutiny up north. Notably, infamous mobsters like Meyer Lansky were rumored to frequent the area, with some even owning property or operating businesses.

Many of the retro hotels and motels along Hollywood Beach have whispered legends about mobsters, underground gambling, and secret meetings. While that chapter has faded, the influence lingers in vintage neon signs, Art Deco architecture, and the nostalgic, mid-century vibe of North Beach and Downtown.

7. A City of Canals and Waterways

Part of Joseph Young’s original vision was to create a city inspired by Venice—complete with canals, lakes, and waterfront living. Today, areas like South Lake, North Lake, and East Hollywood offer direct water access, making them ideal for boaters, paddleboarders, and anyone who loves a coastal lifestyle.

These scenic canals are lined with Spanish Revival estates, mid-century ranches, and modern waterfront homes, many with private docks and views of passing boats or the occasional manatee. Originally built to manage marshland, the canals now offer some of Hollywood’s most desirable real estate, blending beauty, function, and that unmistakable South Florida vibe.

8. The City Grew—And So Did Its Real Estate Potential

Hollywood has grown into a dynamic city with over $25 billion in taxable property value. Its real estate market is one of the most diverse in South Florida, offering everything from:

• Historic Mediterranean villas near Young Circle
• Midcentury homes in neighborhoods like Hollywood Hills
• Luxury high-rises and Intracoastal estates near the beach and canals
• New developments that bring modern design to a city rich in tradition

For buyers and investors, this means options for every lifestyle and budget, all within a city rooted in visionary design.

9. Celebrating 100 Years in 2025

It’s safe to say that Joseph Young would have been proud to see Hollywood turn 100 in the year 2025, a testament to his dream vision that not only turned into a reality, but cemented his legacy and opened the door for so many families to call this wonderful place home.

And in fact, the celebration isn’t just about the past. As part of the centennial, Hollywood is investing in green infrastructure, public spaces, transportation upgrades, and long-term sustainability, continuing Joseph Young’s vision of a city designed for the future.

Ready to Own a Piece of History? 

If you’re captivated by Hollywood’s rich past and timeless homes, let us help you find the perfect place to live your own Florida story. From canal-front properties to historic Spanish villas, Hollywood offers a unique blend of heritage, beauty, and community—all within reach.