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The U.S. Post Office 鈥� Federal Building is one of the city鈥檚 architectural treasures and a proud symbol of civic refinement. Completed in 1934 during the Great Depression, the structure was built under the Works Progress Administration and designed by architects George Albree Freeman and Louis A. Simon. It marked Freeman鈥檚 final monumental project and reflected the federal government鈥檚 goal of creating enduring public buildings that embodied stability and confidence. On March 22, 1984, the building was added to the U.S. National Register of Historic Places for its outstanding craftsmanship and architectural merit.

The building鈥檚 design exemplifies the Neoclassical Revival style, distinguished by its stylized ornamentation and academic precision. The west fa莽ade features a graceful colonnade with Corinthian capitals, their acanthus leaves carved with exceptional detail. Traditional Neoclassical motifs such as string courses, modillioned entablatures, and columns in antis are faithfully executed, while certain elements鈥攍ike the implied pediment above the nine-bay loggia鈥攐ffer a modern interpretation of classical form. Even the metal grilles, though made from contemporary materials, retain the structure鈥檚 classical elegance, blending innovation with tradition.

Inside, visitors encounter a space that mirrors the artistry of its exterior. The lobby showcases terrazzo floors, brass fixtures, and marble detailing that speak to the craftsmanship of the 1930s. Beyond its architectural beauty, the Federal Building reflects Sarasota鈥檚 evolution from a small coastal resort into a flourishing civic and cultural centre.

Welcome to Sarasota鈥檚 historic heart, where the American National Bank Building (also known by its later name, the Orange Blossom Hotel) commands attention on Main Street. Though relatively modest in scale, this building holds outsized significance鈥攈aving borne witness to the city鈥檚 boom, bust, and reinvention through nearly a century of change.

Completed in 1926, the structure was designed by Francis Palmer Smith in a Classical Revival / Neoclassical style鈥攁n architectural choice less common than the Mediterranean motifs popular in Florida at the time. Originally intended to serve as the headquarters of the then-new American National Bank, the building鈥檚 first floor housed the banking operations, while the upper stories offered office suites to a variety of local professionals. Although the bank failed in 1928 amid the collapse of the Florida real estate boom, the building鈥檚 life was far from over.

In the 1930s, responding to Sarasota鈥檚 growing tourist traffic, the building was transformed into the Orange Blossom Hotel, offering 125 rooms, modern conveniences, and a popular cocktail lounge called the 鈥淎ztec Room.鈥� For more than three decades, it welcomed visitors and locals alike鈥攈osting famous guests and becoming part of Sarasota鈥檚 instrumental shift toward tourism. In 1967, the building was repurposed again, this time as a retirement residence, and later underwent extensive renovation and restoration under private ownership.

Today, the American National Bank Building stands as a proud contributing property in the Downtown Sarasota Historic District, reflecting the city鈥檚 layered past. Visitors walking Main Street will see in its facade and proportions both the aspirations of Sarasota鈥檚 1920s boom era and the adaptive spirit that has kept the building alive across cycles of change.

Florida Studio Theatre (FST) is a premier non-profit theater company. Founded in 1973 by Jon Spelman, it has since grown to become a prominent institution for the performing arts in Florida.

FST's architecture is unique and has become an iconic feature of the theater. The building itself is a collection of five historic buildings that have been renovated and connected to create a unified space for the theater's performances and programs.

The main entrance to the theater is through the Hegner Theatre Wing, a large, modern structure that houses the 173-seat Gompertz Theatre and the 109-seat John C. Court Cabaret. The Hegner Theatre Wing is a contemporary addition to the historic buildings that make up the rest of the complex. Its sleek, angular design stands in contrast to the traditional architecture of the surrounding buildings.

The historic buildings that make up the rest of the FST complex include the Keating Theatre, the Goldstein Cabaret, and the renovated Woman's Club building. These buildings have been restored to their original grandeur and have been adapted to serve the theater's needs.

The Keating Theatre is a converted church that seats 237 people. It has a traditional proscenium stage and is used for larger productions. The Goldstein Cabaret is a smaller, more intimate space that seats 109 people. It has a flexible stage that can be adapted to different types of performances, from cabaret to musicals to plays.

The Woman's Club building, which was originally built in 1916, has been renovated to serve as FST's administrative headquarters. The building also houses rehearsal spaces and a costume shop.

Overall, the architecture of FST is a blend of traditional and modern elements. The historic buildings that make up the majority of the complex provide a sense of history and character, while the Hegner Theatre Wing adds a contemporary edge to the overall design. The result is a unique and dynamic space that has become an important cultural hub in the Sarasota community.

The Frances-Carlton Apartments, completed in 1924, remain one of Sarasota鈥檚 most refined examples of Mediterranean Revival architecture from the city鈥檚 Jazz Age boom. Designed by Tampa architect Francis James in collaboration with Sarasota鈥檚 own Alex Browning, the building was conceived as furnished rental apartments for well-to-do northerners seeking winter refuge. Its vintage wrought-iron gate still bears the original name, 鈥淔rances Carlton Apartments,鈥� evoking the glamour of the Roaring Twenties when Sarasota was just beginning to emerge as a cosmopolitan coastal retreat.

Architecturally, the Frances-Carlton stands out for its stucco walls, arched openings, and red barrel-tile roof. The design draws on Spanish-Moresque and Italian villa influences, with the 1924 press describing it as 鈥渞esembling the ancient hostelry of the Pyrenees along the Spanish border of southern France.鈥� The three-story, twenty-unit structure features a U-shaped plan with four interconnected blocks and stairway 鈥渉yphens,鈥� giving every apartment windows on multiple sides鈥攁n ingenious design for cross-ventilation before the age of air conditioning. The third-floor observatory, topped with a small mirador, adds a touch of Mediterranean romance to the skyline.

Located on Palm Avenue鈥擲arasota鈥檚 historic boulevard lined with boutiques, galleries, and theaters鈥攖he Frances-Carlton sits at the cultural heart of downtown. Its neighbors include acclaimed restaurants like Sage and Cas鈥橝ntica, both housed in similar 1920s landmarks, while the Sarasota Opera House and Florida Studio Theatre are just steps away.

Listed on the National Register of Historic Places since 1984, the Frances-Carlton Condominium remains a prized residence鈥攁 perfect blend of Jazz Age heritage and enduring coastal sophistication.

The F. A. DeCanizares Residence stands as one of Sarasota鈥檚 architectural gems, representing the city鈥檚 early 20th-century transformation from a quiet Gulf Coast settlement into a flourishing resort community. Built in 1926 during the height of the Florida Land Boom, the house was commissioned by Frank A. DeCanizares, a businessman and civic leader who contributed to Sarasota鈥檚 commercial development. Its construction reflected both the optimism of the era and the desire to create homes that embodied Mediterranean grace and coastal elegance.

Architecturally, the residence is a fine example of the Mediterranean Revival style that dominated Sarasota in the 1920s. Designed by architect Thomas Reed Martin鈥攐ne of the most influential figures in the region鈥檚 early architectural history鈥攖he home features stucco walls, red tile roofing, arched windows, and ornamental detailing that echo the influence of Spanish and Italian villas. The property鈥檚 symmetrical fa莽ade and carefully proportioned design illustrate Martin鈥檚 skill in blending aesthetic refinement with Florida鈥檚 climate and landscape.

Over the decades, the DeCanizares Residence has retained much of its original charm and remains an enduring symbol of Sarasota鈥檚 Golden Age of architecture. The structure鈥檚 preservation contributes to the city鈥檚 historic fabric, standing alongside other landmarks that define the Palm Avenue Historic District. For visitors, viewing the residence offers a glimpse into Sarasota鈥檚 early vision of sophistication and style鈥攁 reminder of the artistry that helped shape its unique architectural identity.

The L. D. Reagin House, built in 1926, stands as a fine example of Sarasota鈥檚 Mediterranean Revival architecture and the creative vision that flourished during the city鈥檚 land boom years. Designed by noted architect Thomas Reed Martin, the two-story residence was commissioned by Lucius D. Reagin, the owner and editor of the Sarasota Times newspaper. Its construction coincided with a transformative period in Sarasota鈥檚 history, when the once-sleepy Gulf Coast town was evolving into a thriving resort community defined by elegance, ambition, and architectural experimentation.

Reagin鈥檚 home reflects both his status as a civic leader and his appreciation for refined design. Martin鈥檚 use of stucco walls, red barrel-tile roofing, and arched openings demonstrates the hallmarks of the Mediterranean Revival style that swept across Florida in the 1920s. These details, inspired by Spanish and Italian villas, were intended to harmonize with Sarasota鈥檚 subtropical setting鈥攃ombining European sophistication with the relaxed atmosphere of coastal living. The house鈥檚 symmetrical proportions and handcrafted detailing further emphasize the craftsmanship and optimism of the Roaring Twenties.

Today, the L. D. Reagin House endures as more than a private residence鈥攊t represents a lasting chapter in Sarasota鈥檚 architectural and cultural heritage. Its preservation contributes to the city鈥檚 reputation for distinctive design and creative spirit, qualities that continue to attract artists, historians, and visitors alike.

The Sarasota Times Building is a significant historical site that was added to the U.S. National Register of Historic Places on March 22, 1984. The three-story, Mediterranean Revival structure was designed by architect Dwight James Baum and is known for its architectural merits as well as its role as the headquarters of the Sarasota Times newspaper, which was established in 1899. The newspaper was later purchased by L.D. Reagin in March 1924 and the new plant and offices were constructed at the current site, indicative of the shift in commercial development away from lower Main Street.

The Sarasota Times Building is significant for its architectural style, which is in keeping with other Baum-designed projects under construction or planned for the Broadway area, including the Burns Realty Company, the El Vernona Hotel (later called John Ringling Towers, now demolished), and the El Vernona Apartment (currently called Belle Haven Apartments).

Baum was responsible for many of the most significant buildings constructed in Sarasota in the 1920s, including John Ringling's palatial home, the Ca da'Zan, the Sarasota County Courthouse, and the four Mediterranean Revival Style buildings in the Broadway area.

The Times Building features a variety of architectural elements, including the use of three different door types and enframements on the ground floor elevation, which is particularly effective on a relatively small-scaled building. Following the crash of land prices and the onset of the Depression, the Sarasota Times newspaper went into receivership, and the Times Building was subsequently used as the office of the "Tree-Ripe Citrus Products, Inc.," which was owned and operated by Mr. Owen Burns.

In 2014, Ataraxia LLC, a Nokomis company managed by Sharon Carole, purchased the historic downtown building and began renovations for the new restaurant that opened in 2019, "Sage." The restaurant aims to bring a global culinary experience to the artsy town of Sarasota using the highest quality and freshest ingredients as possible. The chef at Sage, Christopher Covelli, is a graduate of the French Culinary Institute in New York City and specializes in Classic French, Italian, and Spanish cuisine as well as American Haute Cuisine.

The Sarasota Times Building was locally designated by the City of Sarasota in 1985 and continues to be an important historical and architectural landmark in the area.

The Gompertz Theatre in downtown Sarasota has a story that mirrors the city鈥檚 own evolution from a small coastal town to a thriving arts hub. Built in 1920, the building first opened as the Park-Seventh Movie House, offering silent films and early talkies to Sarasota audiences. Like many entertainment venues of its time, it struggled during the Great Depression and closed its doors, standing vacant through much of the 1930s. By the 1940s, however, the theatre revived as a home for road shows and traveling acts, welcoming performers such as Tom Mix and his Wonder Horse, and the All-Girls鈥� Orchestra.

Over the decades, the theatre changed names and identities several times, known variously as the Garden Theater, the Art Theater, and the Palm Tree Playhouse. Its modern chapter began when Florida Studio Theatre (FST) purchased the property, renaming it the Gompertz Theatre in honor of Leila Gompertz, whose generous contribution made the acquisition possible.

Architecturally, the Gompertz Theatre maintains the early 20th-century charm of Sarasota鈥檚 Classical Revival style while integrating contemporary stage design, lighting, and acoustics. Today, it serves as FST鈥檚 largest venue, featuring 237 seats and hosting the theatre鈥檚 Winter and Summer Mainstage productions. Past performances have included acclaimed titles such as Buddy: The Buddy Holly Story, The Play That Goes Wrong, Bright Star, American Son, and Million Dollar Quartet.

For visitors, the Gompertz Theatre offers an intimate, engaging setting where every performance feels close and personal. Surrounded by Sarasota鈥檚 downtown caf茅s, galleries, and boutiques, it remains a cornerstone of the city鈥檚 cultural life鈥攑roof that nearly a century later, the old Park-Seventh still knows how to draw a crowd.

Your evenings in Sarasota can be as spectacular as your days. To experience pure elegance in the heart of downtown Sarasota, catch an opera or a live concert at the Sarasota Opera House. Have dinner in a nearby restaurant, walk to the opera house, and enjoy a wonderful evening. You can also have drinks in the outdoor courtyard.

The Opera House, previously known as the Edwards Theatre, opened to the public in 1926. The place became a popular entertainment venue with famous performers of the day, such as the vaudeville performer and actor Will Rogers and Ziegfeld Follies Broadway shows. Elvis Presley performed a concert there in 1956. Over the years, it changed management, and it finally closed in 1973.

By the late 1970s, however, opera started to take off in Sarasota. And in 1979, the Asolo Opera Guild decided to purchase Edwards Theatre, renovate it, and rename it the Sarasota Opera House.

Today, the Opera House seats 1,119 in an intimate setting. The Sarasota Opera has performed all of Giuseppe Verdi鈥檚 operas, the works of Italian composer Giacomo Puccini and French composer Georges Bizet. And for visitors worried about not understanding Italian or French opera, there are English subtitles above the stage.

Besides opera, you can also watch ballet performances, rock concerts, or orchestra renditions.

The Dr. Joseph Halton House is one of Sarasota鈥檚 most notable early residences, representing the city鈥檚 formative years in the early 20th century. Built between 1909 and 1910 for Dr. and Mrs. Joseph Halton, the home was added to the U.S. National Register of Historic Places on March 22, 1984. Dr. Halton, one of Sarasota鈥檚 first physicians, was part of the city鈥檚 early professional class whose work helped shape its growing community and civic identity during a time of optimism and expansion along Florida鈥檚 Gulf Coast.

Located on Coconut Avenue, the two-story residence was constructed by Joseph S. Maus and is designed in the Transitional Queen Anne style鈥攁 blend of late Victorian detail and emerging early-20th-century symmetry. The house stands out for its artificial pressed stone fa莽ade, one of the earliest examples in Sarasota to make extensive use of this modern material. Its elegant columns, balanced fa莽ade, and generous verandas reflect a thoughtful adaptation of northern architectural traditions to Florida鈥檚 subtropical environment, combining formality with comfort.

Beyond its architectural significance, the Halton House captures the spirit of an era when Sarasota was evolving from a small coastal settlement into a refined residential community. Its enduring craftsmanship and harmonious proportions convey both stability and grace. Today, the Dr. Joseph Halton House remains a well-preserved landmark鈥攁 quiet reminder of Sarasota鈥檚 early ambitions and the individuals whose vision and dedication helped transform the city into the thriving cultural centre it is today.

The Chidsey Library, also known as the Chidsey Building, is a treasured historic landmark in Sarasota and the site of the city鈥檚 first public library. Designed by the Martin Studio of Architecture鈥攍ed by Thomas Reed Martin and Frank C. Martin鈥攖he building opened in May 1941 and was officially dedicated later that year to John and Ida Chidsey, whose generous financial support made the project possible. At its peak in 1946, the library鈥檚 collection had grown to about 18,000 volumes, serving as the intellectual heart of a growing coastal community.

Architecturally, the Chidsey Library is a fine example of the Mediterranean Revival style that shaped much of Sarasota鈥檚 early civic architecture. Its stucco walls, red barrel-tile roof, and graceful arched openings give the building a refined yet inviting presence. The design reflects both function and beauty鈥攁n enduring reminder of a period when public buildings were created to inspire learning as well as civic pride.

The library remained in operation until 1976, when services were transferred to the Selby Library, then located in the former GWIZ building on Boulevard of the Arts. Sarasota County Historical Resources began occupying the Chidsey Building soon after, eventually taking full residence in 1998. Today, it continues to serve the community as a centre for preserving and interpreting local history.

Added to the National Register of Historic Places on May 4, 2011, the Chidsey Library stands as a symbol of Sarasota鈥檚 dedication to culture, education, and architectural heritage鈥攚elcoming visitors to reflect on the city鈥檚 evolution from a small coastal town to a vibrant cultural hub.

Located in the heart of downtown Sarasota's cultural district, the Municipal Auditorium is a historic and iconic event space that has been a beloved community gathering place since it was built in 1938.

With 10,000 square feet of unobstructed floor space, excellent acoustics, and a beautiful Art Deco-style stage, the auditorium is a popular venue for a wide range of events, from elegant galas and business meetings to private parties, seminars, and tradeshows.

The auditorium's solid hardwood maple floor adds to the atmosphere, acoustics, and comfort for all attending events, dances, and concerts, making it a favorite among locals and visitors alike.

Each year, more than 100,000 visitors come to the Sarasota Municipal Auditorium to attend a variety of events, including banquets, concerts, political forums, training seminars, and weddings.

In addition, the venue hosts educational programs, exhibits, and shows, including antique sales, art exhibits, auctions, coin shows, conventions, flea markets, flower and gardening shows, gem and jewelry shows, seminars, and stamp collection and sales exhibits. With its rich history and vibrant energy, the Sarasota Municipal Auditorium is a true gem of the Sarasota community.