2024’s Best Main Streets: Spotlight on 11 Central Florida Communities

A family explores downtown Mount Dora.

Principal photography by Roberto Gonzalez

There’s just something about the allure of a Main Street. It can be a nostalgic world that takes you back to another time; a contemporary, master-planned district; a down-to-earth enclave where all feel free to express themselves; or a mix of all the above. But what all these walkable areas have in common is a sense of community and good cheer. Discover what our 32nd president Franklin D. Roosevelt meant when he said, “The whole world is one neighborhood.” 

Clermont: The Choice of Champions

Downtown Clermont’s walkable Montrose Street and food hall Montrose Street Market.

Known as the “Choice of Champions,” Clermont has a reputation as a training ground for athletes, from high school athletes and regional record-breakers to Olympians; among those who have lived or trained here are Shane Greene, an MLB pitcher for the Atlanta Braves who was named an All Star in 2019; Nina Kraft, the oldest professional female Ironman winner; and Noah Lyles, an Olympic Gold Medalist and world record-holding sprinter. Read more.

Deland: Our Own “Mayberry”

Athens Theatre, which dates to 1921, is one of the few existing examples of a classic American theater in Central Florida.

DeLand is the “Mayberry” of Central Florida cities, with a downtown seemingly stuck in time, with older architecture dating back to the 1920s. Read more.

Ivanhoe Village: An indie Darling

Lake Ivanhoe is an anchor to Ivanhoe Village. Here, kayakers enjoy a day on the lake, with Orlando’s skyline providing a backdrop.

As part of the Main Street America initiative, Ivanhoe Village is part of an inclusive, grassroots movement dedicated to revitalizing the economies of historic districts. It’s also part of Orlando’s Main Streets, a program that strengthens and defines commercial districts in The City Beautiful. Read more.

Kissimmee: An Independent Spirit

Businesses on Broadway Avenue in Historic Downtown Kissimmee.

Long before European settlers came to Central Florida, the land was inhabited by a Native American tribe called the Jororo. It is from this tribe’s language that the name Kissimmee, or “long water” can be traced. At the time, Central Florida was swampland and the headwaters of the Everglades extended as far north as Lake Tohopekaliga (Lake Toho for short), the largest lake in Osceola County and one of the country’s most famous lakes for bass fishing. Read more.

Lake Mary: Marvelous microcosm

People enjoy a relaxed shopping experience and al fresco dining on 4th Street.

There are rare times suburban sprawl creates a workable, livable city. Lake Mary, north of Longwood in Seminole County is one of these rare gems. Most of Lake Mary seems eerily like the vast majority of Central Florida; chains, small sidewalks and car-focused infrastructure and design. But skip down to 4th Street and you’ll see something different. Mom-and Pop-businesses, a strong sense of self and a bonded community ready to make their city one of the best. This microcosm of a main street is no less so, reveling in stability over the last two decades of intense change. Read more.

Lake Nona: The future of cities

A bird’s-eye view of container/food truck park Boxi Park. ©Boxi Park

Lake Nona, referred to as “the Future of Cities” by Fortune magazine, ranks among the fastest-growing, best-selling communities in America. “There’s more than people think” says Rob Adams, senior vice president of residential for Tavistock, a diversified real estate firm specializing in planning, design, finance, construction and development in Central Florida. Perhaps their largest and most ambitious project, home to Lake Nona Medical City, a Sports & Performance District, world-class educational institutions and unique and vibrant residential communities, the 17-square-mile master-designed community is recognized for excellence in diverse industry clusters, residential and commercial design and human performance. Read more.

Mills 50: Cultural convergence

The intersection of Mills Avenue and State Road 50, aka Colonial Drive.

One of Orlando’s oldest neighborhoods, Mills 50, just a mile northeast of Downtown Orlando, is known for its many bright and cheerful murals that pay homage to living in Orlando—more than any other district in the city.  Its name is derived from its main thoroughfares: Mills Avenue and State Road 50, aka Colonial Drive. Read more.

Mount Dora: Out of a Hallmark movie

Full of history and charm, Mount Dora is known for its small-town atmosphere. A city with an expansive tree cover, opportunities to connect with nature are also prevalent.

We sat down with Mount Dora Mayor Chrissy Stile to discuss what makes Mount Dora unique, and why it’s such a great neighborhood with a unique main street. Read more.

Park Avenue: A Year-Round “Wintering” Destination

Park Avenue is one of the most walkable main streets in the state.

Designed around a central park and its main street, Park Avenue, Winter Park was born as a “wintering” destination for wealthy Northerners and became the first planned community in Florida when it was chartered in 1887. That same year, construction began on the Orlando and Winter Park Railroad, which brought affluent tourists to Central Park, at the heart of Park Avenue. Among those first travelers to Winter Park were presidents Grover Cleveland and Benjamin Harrison. Read more.

Sanford: Where community comes alive

Hollerbach’s Willow Tree Café is part of Sanford’s fabric, serving up authentic and expertly-prepared German cuisine.

Downtown Sanford offers a delightful mix of historical ambiance and modern amenities, making it a captivating destination for both locals and tourists. Characterized by its picturesque setting on the shores of Lake Monroe, the heart of the town is its vibrant main street, locally known as First Street. This historic thoroughfare is the lifeblood of Downtown Sanford, lined with beautifully preserved buildings that speak to the area’s rich history. Read more.

Winter Garden: An ode to urban renewal

Families and couples at play in downtown Winter Garden. A local farmers market, ranked among the top in the state, beckons nearby.

Once a humble agricultural town by Lake Apopka, Winter Garden has transformed into a vibrant hub for business and community life. Pollution and harsh weather nearly devastated the area, but dedicated local efforts have revitalized its environment, economy, and historic charm, turning it into a model for urban renewal. Read more.