Tropical Streets of Sarasota: A Local Love Letter

Author's note: The photos in this article don’t reflect all the places, links, or names mentioned — they were taken during a casual walk through the city.

My love for Sarasota began when I took photos of its historic buildings and wandered the neighborhoods near my home on Oak Street, a historic part of central Sarasota known for its old homes and long-standing local character. But what captured my imagination the most were the street names themselves: Cocoanut Avenue, Palm Avenue, Orange Avenue, Pineapple Avenue, Lemon Avenue, and Fruitville Road. 

 I was born in the Far East of Russia, where winters are long and life moves differently. Even after living in tropical countries for many years, I still find something deeply emotional about places where palm trees line the sidewalks, which stir something playful and childlike within me, as if I were living in a postcard.

This article has lived in my mind for a long time. One day, I grabbed my camera and began walking the streets I had long admired, wanting to understand more about them, not just their charm, but also their history. What I discovered made me fall in love with Sarasota all over again.

Cocoanut Avenue: Where the Old Soul of Sarasota Lives

Cocoanut Avenue likely takes its name from the coconut palms (fun fact: Cocoanut vs. Coconut) that early settlers began planting in Sarasota in the early 1900s. The street name appeared on city maps as early as 1915 and may have been inspired by developers wanting to promote Sarasota’s tropical identity to prospective buyers from the north.

Located just steps from the heart of downtown, Cocoanut Avenue's southern end shares with Palm Avenue. This district is home to cultural landmarks, including Florida Studio Theatre and its historic Keating building, which dates back to 1915. A few blocks north, contemporary spaces like Art Ovation Hotel and its rooftop bar overlook the Avenue, blending performance, design, and hospitality in one frame. I also liked the pink building (in the photo), I couldn't identify the story behind it.

Cocoanut Avenue becomes more residential as you move toward 10th and 12th Street. This stretch is part of the Central–Cocoanut Historic District, listed on the National Register of Historic Places. Here, small bungalows and early 20th-century cottages tell the story of Sarasota’s modest beginnings. It's quiet, a little wild, and filled with personality—gardens spilling onto the sidewalks, trees that don’t match, homes that feel loved.

The Avenue also borders the Rosemary District—once a historically Black neighborhood, now undergoing a creative rebirth. Independent galleries, design studios, and new restaurants have moved in, yet traces of its past still shape the place's rhythm.

Cocoanut Avenue is layered, mixed, and unpredictable, and maybe that's precisely what makes it so Sarasota.

Palm Avenue: Art and Architecture

Palm Avenue, which appears on official maps dating back to the 1920s, was named after the ubiquitous palm trees that define the city’s landscape. Palm trees were heavily featured in early promotional materials, presenting Sarasota as a subtropical paradise to tourists and snowbirds.

Today, Palm Avenue is the city’s contemporary art corridor, lined with art galleries, restaurants, and creative business offices that reflect Sarasota’s modern look. It intersects with Cocoanut Avenue at a roundabout adorned with public art, most notably, the “Jumping Fish” sculpture by Jeffrey Laramore, part of Sarasota’s “Art in the Roundabouts” initiative.

Palm Avenue is Sarasota’s gallery row, home to refined spaces like MARA Art Studio, Define Art Gallery, and Palm Avenue Fine Art—each showcasing a mix of regional and national artists.

Architecturally, Palm Avenue offers a thoughtful blend: a few preserved Mediterranean Revival buildings, such as the historic Mira Mar Plaza, alongside a growing number of sleek, contemporary structures.

In addition to the Mira Mar Plaza, two other notable Mediterranean Revival buildings grace Palm Avenue:

• Frances-Carlton Apartments: Located at 1221–1227 North Palm Avenue, this 1924 building was designed by architects Francis James and Alex Browning. Opened initially as furnished apartments, it became Florida’s first cooperative apartment building in 1952 and was added to the National Register of Historic Places in 1984. 

• L.D. Reagin House: Situated at 1213 North Palm Avenue, was designed by architect Thomas Reed Martin in 1926. It exemplifies the Mediterranean Revival style and was added to the National Register of Historic Places in 1984. 

Orange Avenue: Urban and Unexpected

Orange Avenue, established in the early 1900s, honored Florida’s citrus-growing legacy. It was named in the early 1900s during significant development in the region. The naming was influenced by the Florida Mortgage and Investment Company of Scotland, pivotal in promoting Sarasota's growth. Today, it stands as a lane of contrasts, stretching from historic Burns Square to the edge of Newtown, blending old bungalows, art spaces, refined boutique stores, restaurants, and contemporary businesses.

One standout is the elegant Italica Boutique, located at 441 N. Orange Avenue, which offers a curated selection of Italian women’s clothing in a refined, European-style space that brings a touch of Milan to Sarasota.

Next door, Summer + Company, located at 431 N. Orange Avenue, offers upscale interior décor. For its exceptional interior design, it has been featured in publications such as Coastal Living and Southern Living.

The newly opened The Breakfast Company delivers polished brunch fare with Greek roots across the Street at 411 N. Orange Avenue.

A few doors down, Pazzo on Orange, at 481 N. Orange Avenue, remains a favorite for Italian dining in an intimate setting.

I’ve always liked the building of St. Martha Catholic Church, located at 200 N. Orange Avenue. Built in 1941, it features Spanish Mission Revival architecture with stucco walls and a red tile roof, reflecting Sarasota’s historic character.

Further south, the Sarasota Herald Building (known these days as the Woman's Exchange)

City Waterworks is a preserved Mediterranean Revival landmark, each repurposed with care. North of downtown, Orange Avenue shifts again—it becomes more residential and local but still carries the layered, creative energy that defines this Street.

Pineapple and Lemon Avenues: Whimsy and Flavor

Pineapple and Lemon Avenues took shape during Sarasota’s real estate boom in the 1910s and 1920s, when developers used tropical fruit names to brand Florida as exotic, fertile, and full of promise. The Florida Mortgage and Investment Company of Scotland and local developers like Owen Burns helped define the city grid and deliberately chose names like Pineapple, Orange, and Lemon to attract northern buyers with a sense of charm and abundance.

These two short, cheerful avenues branch off Main Street and feel like part of a European village—walkable, lively, and filled with personality. The cut through the Burns Square area is architecturally significant and culturally vibrant. It hosts events such as the Sarasota Chalk Festival, an annual celebration of pavement art that attracts artists and visitors from around the world. One of Sarasota's most architecturally distinct districts, it features buildings dating back to the 1920s, designed by Thomas Reed Martin in the Mediterranean Revival style.

Historic landmarks anchor the area. The Sarasota Opera House, located at 61 N. Pineapple Avenue, originally opened in 1926 as the Edwards Theatre and still showcases world-class productions in a meticulously restored space listed on the National Register of Historic Places.

Other preserved gems include the Russell Building (27 N. Lemon Ave.), a 1925 commercial property designed by W.B. and W.D. Talley, and several mixed-use storefronts from the same era that now house creative businesses and boutique restaurants.

The Burns Square Hotel, located at 531 South Pineapple Avenue, was previously featured on my blog.

Here's an interesting article I wrote about unique businesses on Pineapple Avenue.

During the monthly “Fresh Fridays” and the year-round Saturday Farmers Market (which extends beyond Lemon Avenue, including parts of Main Street and State Street), these streets turn into open-air salons—full of live music, design lovers, foodies, and families. Pineapple and Lemon Avenues capture Sarasota's downtown core's playful yet elevated spirit: a place where creativity, history, and community intersect beautifully.

Fruitville Road: Where the Name Meets the Journey

Fruitville is one of the oldest street names in the region. The name originates from the Fruitville settlement, founded in the late 1800s by pioneers from Georgia. The area was once home to numerous fruit and citrus farms, and the name "Fruitville" reflected the region’s agricultural abundance. Early Sarasota maps from the 1890s referred to the district and road as Fruitville.

Today, Fruitville Road is one of the city’s main east-west arteries, stretching from downtown to I-75 and beyond. The most interesting stretch, however, is the one closest to downtown—especially just east of Washington Blvd—where small, colorful cottages host local cafes, bakeries, and design studios. I featured a bit of this here.

The Reserve Retreat is one I wrote about before, and it has become a community favorite.

Further east, Fruitville becomes more commercial, but the roots of its name—and its journey from farmland to freeway—remain part of Sarasota’s evolving story.

To those born here, these names may seem ordinary. But for someone like me, coming from far colder places, they still feel like little miracles. And maybe you, who were born here or have lived here a long time, still found something new between the lines.

Photos: iruphotos.com