The historic homes of Old Naples showcase a blend of “Old Florida” architectural styles developed before modern air conditioning. Many early houses are simple Florida vernacular or “cracker” cottages, built with local Dade County pine and cypress wood, raised foundations, broad porches, and steep hip or gable roofs. These features, such as deep eaves, 12-foot ceilings, and aligned windows for cross-ventilation, reflect a climate-responsive design that kept interiors cool in the subtropical heat. Some homes even used historic construction techniques like tabby mortar, a concrete made of lime, sand, and shell, for thick walls, which proved incredibly durable against hurricanes.
By the 1920s and ’30s, as Naples grew into a winter resort, a few grand homes embraced Mediterranean Revival influences. Spanish Colonial-style villas with stucco walls, red barrel-tile roofs, and archways appeared in Old Naples during the Florida Land Boom. Notably, legendary architect Addison Mizner, famed for Palm Beach, designed at least one Naples residence in 1935, making Naples one of the rare West Coast spots with Mizner homes. Another example is the 1925 “Tile House” (Timken House), a two-story Spanish-Mediterranean home designed by Phineas Paist, an architect of Coral Gables. Still, most pre-1950 Naples houses are modest bungalow and cottage designs rather than grand estates, giving the historic district a quaint, unpretentious charm distinct from newer mansions.
Historical Significance and Development
These historic homes are physical reminders of Naples’ early history as a remote resort village. Naples remained a sleepy “last frontier” on the Gulf until 1885, when Kentucky investors like General John S. Williams and Walter N. Haldeman led the development of a hotel and pier to attract visitors. The Old Naples area, west of Third Street South between 9th and 14th Avenues, became the town’s first neighborhood, with simple cottages built for founding families and winter guests. Many structures date to the late 19th and early 20th centuries, conveying the lifestyle of that era. Early guest registers show prominent visitors like former First Lady Rose Cleveland signing in at local homes. The survival of these houses is especially significant given Naples’ rapid post-war growth; the 1950s–60s boom and ongoing development have made authentic historic buildings relatively scarce. As one local architect observed, “It’s one of the few places in Naples where you can step back in time.” Each historic home embodies a chapter of Naples’ heritage, from the city’s founding by Northern entrepreneurs to the rustic pioneer days and the Jazz Age land boom, making them treasured links to the past.
Notable Historic Homes in Old Naples
Old Naples has a small but remarkable collection of historic residences, each with its own story. Some of the most notable include:
Historic Palm Cottage (1895) – The oldest house in Naples, built in 1895 by town founder Walter Haldeman, using hand-made tabby mortar (seashell concrete) for its walls. Palm Cottage’s design typifies traditional Florida cracker architecture, with a raised wood-frame foundation, broad screened porch, high-pitched roof, and deep overhangs for cooling. Originally constructed as a guest annex for the early Naples Hotel, it later served as a family residence and today operates as a museum run by the Naples Historical Society. Inside, it retains original Dade County pine floors and cypress paneling and is listed on the National Register of Historic Places.
The Addison Mizner Estate (c.1935) – A two-story Spanish-Mediterranean revival home on Gulf Shore Boulevard designed by Addison Mizner, famed architect of Boca Raton and Palm Beach. This white stucco villa with a red tile roof and open arcade is a rare example of Mizner’s work on Florida’s west coast. Its presence highlights the allure Naples held for wealthy 1920s–30s socialites. Naples’ other Mediterranean Revival gems include the 1925 Timken “Tile” House on 8th Avenue, designed by Phineas Paist, which boasts colorful tiles and a courtyard reminiscent of Coral Gables. These elegant homes contrast with Naples’s simpler cottages, showcasing the diverse architectural tastes during the city’s early resort era.
“Westhaven” Bungalow (1920) – A massive Craftsman-style bungalow built by Colonel Robert West, spanning four lots on 11th Avenue South. Westhaven features a low-pitched roof and expansive porch, exemplifying the comfortable bungalow aesthetic popular in the 1910s. Its oversized scale and fine woodworking details reflect the ambitions of one of Naples’ early prominent residents. Nearby on 11th Avenue are other charming survivors like the Periwinkle Cottage (1930) and Martha’s Cottage (1922), which together create a streetscape of picturesque Old Florida cottages.
The Haldeman/“Mandalay” House (1908) – An early beachfront cottage at 1144 Gulf Shore Blvd, built just after 1900. Tucked behind tropical foliage and reachable by an alley, this house, nicknamed “Mandalay,” is a one-story, wood-frame beach retreat with tall shutters and a generous porch. It represents the simple beach houses that Naples’ first permanent residents built by the Gulf long before modern coastal development. Along with the Old Hewitt House (1913), another shuttered, weathered beach cottage on Gulf Shore, it speaks to the rugged yet idyllic lifestyle of Naples’ pioneers.
Many other structures enrich Old Naples’ historic character, from the Naples Mercantile Building (1919) on Third Street, the city’s first general store, to the 1920s Naples Pier, rebuilt multiple times, which anchored the young community. However, the private homes listed above are among the most celebrated in the historic district.
Historic Palm Cottage (1895) – The oldest house in Naples, built in 1895 by town founder Walter Haldeman, using hand-made tabby mortar (seashell concrete) for its walls. Palm Cottage’s design typifies traditional Florida cracker architecture, with a raised wood-frame foundation, broad screened porch, high-pitched roof, and deep overhangs for cooling. Originally constructed as a guest annex for the early Naples Hotel, it later served as a family residence and today operates as a museum run by the Naples Historical Society. Inside, it retains original Dade County pine floors and cypress paneling and is listed on the National Register of Historic Places.
The Addison Mizner Estate (c.1935) – A two-story Spanish-Mediterranean revival home on Gulf Shore Boulevard designed by Addison Mizner, famed architect of Boca Raton and Palm Beach. This white stucco villa with a red tile roof and open arcade is a rare example of Mizner’s work on Florida’s west coast. Its presence highlights the allure Naples held for wealthy 1920s–30s socialites. Naples’ other Mediterranean Revival gems include the 1925 Timken “Tile” House on 8th Avenue, designed by Phineas Paist, which boasts colorful tiles and a courtyard reminiscent of Coral Gables. These elegant homes contrast with Naples’s simpler cottages, showcasing the diverse architectural tastes during the city’s early resort era.
“Westhaven” Bungalow (1920) – A massive Craftsman-style bungalow built by Colonel Robert West, spanning four lots on 11th Avenue South. Westhaven features a low-pitched roof and expansive porch, exemplifying the comfortable bungalow aesthetic popular in the 1910s. Its oversized scale and fine woodworking details reflect the ambitions of one of Naples’ early prominent residents. Nearby on 11th Avenue are other charming survivors like the Periwinkle Cottage (1930) and Martha’s Cottage (1922), which together create a streetscape of picturesque Old Florida cottages.
The Haldeman/“Mandalay” House (1908) – An early beachfront cottage at 1144 Gulf Shore Blvd, built just after 1900. Tucked behind tropical foliage and reachable by an alley, this house, nicknamed “Mandalay,” is a one-story, wood-frame beach retreat with tall shutters and a generous porch. It represents the simple beach houses that Naples’ first permanent residents built by the Gulf long before modern coastal development. Along with the Old Hewitt House (1913), another shuttered, weathered beach cottage on Gulf Shore, it speaks to the rugged yet idyllic lifestyle of Naples’ pioneers.
Many other structures enrich Old Naples’ historic character, from the Naples Mercantile Building (1919) on Third Street, the city’s first general store, to the 1920s Naples Pier, rebuilt multiple times, which anchored the young community. However, the private homes listed above are among the most celebrated in the historic district.
Preservation Efforts and Challenges
Preserving Old Naples’ historic homes has been an ongoing challenge due to intense redevelopment pressure. In recent decades, skyrocketing land values in downtown Naples have made tear-downs lucrative. Many historic cottages sit on prime lots where modern buyers often opt to build larger luxury homes. Because of this, Naples has lost some heritage structures; today, fewer than 60 homes older than 1950 remain in the Naples Historic District. Local advocates have therefore become fiercely dedicated to saving what’s left.
The Naples Historical Society plays a central role in preservation. It purchased Palm Cottage in 1978 to save it from demolition and, after restoring the cottage, got it listed on the National Register in 1982. The Society conducts house tours and walking tours to educate the community and foster appreciation for these landmarks. It also maintains an updated inventory of 60+ historic structures in the Old Naples area and works with city officials on protective measures. In 2017, the Society’s president proposed a comprehensive historic preservation program for Naples, including formal recognition of historic homes, outreach to owners, and city review of any alterations. This led to new local preservation ordinances that incentivize rehabilitation over replacement.
Despite these efforts, challenges remain. Only one house, Palm Cottage, has full legal protection as a landmark, and the concept of preservation is relatively new in a city whose history is so short and compressed. The Naples Historic District itself is listed on the National Register, which recognizes its significance but does not prevent private demolitions. To encourage voluntary preservation, the city has begun offering incentives like allowing minor code variances for historic properties and exploring tax breaks. The community has also rallied after events like Hurricane Ian, when historic homes were damaged, to restore rather than remove them. For example, one 85-year-old cottage on 11th Avenue was painstakingly repaired after Ian and put on the market in hopes a buyer will appreciate its history instead of tearing it down.
The Naples Historical Society plays a central role in preservation. It purchased Palm Cottage in 1978 to save it from demolition and, after restoring the cottage, got it listed on the National Register in 1982. The Society conducts house tours and walking tours to educate the community and foster appreciation for these landmarks. It also maintains an updated inventory of 60+ historic structures in the Old Naples area and works with city officials on protective measures. In 2017, the Society’s president proposed a comprehensive historic preservation program for Naples, including formal recognition of historic homes, outreach to owners, and city review of any alterations. This led to new local preservation ordinances that incentivize rehabilitation over replacement.
Despite these efforts, challenges remain. Only one house, Palm Cottage, has full legal protection as a landmark, and the concept of preservation is relatively new in a city whose history is so short and compressed. The Naples Historic District itself is listed on the National Register, which recognizes its significance but does not prevent private demolitions. To encourage voluntary preservation, the city has begun offering incentives like allowing minor code variances for historic properties and exploring tax breaks. The community has also rallied after events like Hurricane Ian, when historic homes were damaged, to restore rather than remove them. For example, one 85-year-old cottage on 11th Avenue was painstakingly repaired after Ian and put on the market in hopes a buyer will appreciate its history instead of tearing it down.
Discover the Charm of Old Naples
Exploring the historic neighborhoods of Old Naples is like stepping into a vibrant tapestry of history and culture, where every street tells a story. From the quaint cottages to the grand mansions, the area offers a unique blend of old-world charm and modern beach living. Whether you're drawn to the picturesque streets, the rich cultural scene, or the stunning natural beauty, Old Naples has something for everyone. If you're considering making this charming enclave your home, a knowledgeable local expert like Andrew Christopher can guide you through the process with expertise and insight. Reach out to Andrew Christopher today to discover how you can become a part of this extraordinary community.
