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10 Iconic Homes In Metro Orlando

Casa Feliz Orlando
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World-famous Orlando has more to offer than just sunshine and idyll. Beyond the gigantic theme parks and legendary golf courses are some of America’s most charming iconic homes, which all but capture folk tales and fascinating Floridian architecture. While these house styles range from eclectic to traditional, they never fall into McMansion kitsch. 

Here are some of Orlando’s most iconic houses and the stories that built them.

1. Martin Hall

1000 Genius Drive

Martin Hall
Photo Courtesy of Rollins College

Built in the early 1920s as the headquarters of Winter Park’s Businessmen’s Club, this beautiful Mediterranean-inspired mansion was recently sold for $10.6 million. Its previous owner hired local artist Sam Stoltz in the 1930s for a major redesign of the property, leading to the creation of the “Florida Spanish” style prevalent in its time, which features textures that embellish the natural splendor of the marshlands. 

After the death of its owner in 1956, the house was purchased by the nearby Rollins College and renamed Martin Hall, where the Conservatory of Music was housed until 1976. Today, it is a luxurious piece of Winter Park real estate, boasting marbled interiors, a beautifully manicured lawn, and yacht docks that open to the lake’s horizon.

2. Eastbank

724 Bonita Drive

Comstock Harris Eastbank
Photo by Ebyabe

The Comstock-Harris house is a residence that has been with the Harris family since 1928 and has been called Eastbank since its construction in the 18th century. This 60-acre sprawl extends as far as Lake Osceola’s eastern shore, and its historic road was once a camphor tree-lined avenue that opened up to the lavish estate. The house features six fireplaces and a library bedecked with built-in bookshelves. 

3. The Jack Kerouac House

1418 Clouser Avenue

Jack Kerouac House Orlando
Photo Courtesy of Kerouac House

The simple wooden house on Clouser can be easily missed if not for its storied residence. Jack Kerouac, who wrote the great American classic On The Road, lived in this house with his wife and his mother back in the 1950s. The story goes that Kerouac could not afford air-conditioning and would instead write in the evening or under the oak tree behind the house to cool himself. 

Today, the house is listed on the National Register of Historic Places and has been managed by a local literary organization since 2000. The Friends of Jack Kerouac hosts the Writer In Residence Project of Orlando here, giving free board and lodging at the house to aspiring artists who need a space to write.

4. The Poyntz – O’Neal House

614 Lake Avenue

The Poyntz O'Neal House
Photo Courtesy of Orange County Regional History Center

This lakeside residence was built in the late 18th century, inspired by elements of Queen Anne-style architecture. It is one of six houses constructed around Lake Cherokee for newlyweds, thus earning the area’s moniker of “Honeymoon Row”. The outer frame of this lavish love nest was constructed with locally sourced materials, and its interiors offer a glimpse into vintage Americana. 

5. The Palms

240 Trismen Terrace

The Palms Brewer House
Photo by Ebyabe

The historic home sits on what was once a vast tract of land bought by Edward H. Brewer in 1897 from the Rollins College. Intended as a winter retreat for his family, the house underwent numerous renovations and remodeling fashioned in the Georgian revival style. It was sold again in 1937 to Fredrick Detmar Tisman, who sold all but five acres of the property and hired James Gamble Rogers II for another remodeling of the interior. 

With its lakeside location, the house’s lavish facade and impressive columns are turned outwards to Lake Osceola, meaning it is best viewed through an approach from the water. However, the house is not all glitz and glam: most locals know The Palms for a previous owner’s drug bust back in the 1980s, which made local and national headlines for a while. Despite its darker episodes, the property is listed on the National Registry of Historic Places for its beautiful architecture.

6. The Leu House/Mizell Cemetery

1730 N. Forest Avenue

Harry P Leu Gardens
Photo Courtesy of Harry P Leu Gardens

The Leu residence is something of a touchstone for the Orlando community. It was built in the late 18th century and was home to the town’s first sheriff David Mizell – the only sheriff in the history of the locale to die in the line of duty after an ambush in 1870. David was buried here in the town’s first masonic ceremony. It was then bought by Henry P. Leu, a businessman and humanitarian whose supply business helped in building modern-day Orlando. 

This charming farmhouse faces Lake Rowena, and its Colonial Revival facade has been embellished with porches, kitchens, and outbuildings that have been converted to offices today. 

7. Merrywood

1020 Palmer Avenue

Merrywood Orlando
Photo Courtesy of Winter Park Magazine

We return to Winter Park for this iconic house designed by James Gamble Rogers II. With an area of over 7,000 square feet, it is the largest house designed by the renowned architect and was constructed in 1938 for Caroline Plant, a New England native. 

This Spanish-style house acclimates to the Florida weather. Its red tile roof and stucco exterior hearken back to an aesthetic of tropical idyll, which was very much in style for the period.

8. The Rogers Building

37-39 South Magnolia Avenue

Rogers Building Orlando
Photo by Ebyabe

Originally an English men’s club built in the 1880s, this Orlando landmark features Queen Anne architecture right in the heart of the city. Note the metal sidings of the building, which were imported for its construction all the way from England. 

Once a site for shows, dances, and other social events, the building was donated to the city for the patronage of the arts. The Rogers Building contains a lot of history – it even has a ghost story or two!

9. H. Carl Dann House

3206 Greens Avenue

Historic Dann Ranch Orlando
Photo Courtesy of Circa Old Houses

Another home that features frame vernacular architecture, the Dann House was designed by famed artist Sam Stoltz for Howard Carl Dann, who was once president of the Orange County Investment Company. 

With its coquina stone foundation and chimneys, its rustic charms speak to the leisurely lifestyle of the city. The infamously difficult Dubsdread Golf Course is right around the corner of this charming abode. 

10. Casa Feliz

656 North Park Avenue

Casa Feliz Orlando
Photo Courtesy of Casa Feliz Historic Home Museum

Another house designed by James Gamble Rogers II, Casa Feliz (or “Happy House” as its original owner named it) is a true-to-form replica of an Andalusian Cortijo, with an enclosed courtyard and a red brick exterior. This wonderful abode has been home not only to some of Orlando’s most prominent figures. Within its walls, you’ll also find a community’s story of love for culture and identity. 

In 2000, its owners announced they were demolishing Casa Feliz. When the news broke out, the local history community was shocked into action – within a year, they raised over $1.2 million to move the house for preservation. Today, the Casa Feliz Historic Home Museum hosts weddings, social events, and even concerts.

Conclusion

Aside from theme parks and nature preserves, Orlando is also known for its beautiful and storied architecture. Make sure to check out these iconic houses on your next trip!

Looking for an iconic home of your own? Then contact Spouses with Houses Realty to begin your home search today.


**Disclaimer: There is a good chance that this post contains affiliate or sponsor links. If you make a purchase through them, we may receive a small commission at no extra cost to you (for which we are extremely grateful).

Also, while we do our best to highlight LGBTQ-friendly destinations and businesses, info provided is based solely on personal experience and recommendations by community partners. We hope that nobody experiences discrimination or homophobia while visiting Florida, but we make no guarantees. Please inform us if you experience discrimination or homophobia while visiting any destination so we can make updates to our recommendations.

Written by Rachel Covello

Rachel Covello is an award-winning speaker, writer, diversity consultant, and LGBT advocate. She is the Founder of LGBT Equality Alliance, a Chester County, PA nonprofit organization, and CEO of OUTCOAST, an online marketing and concierge platform marketing the Gulf Coast as an LGBTQ-inclusive place to VISIT, CELEBRATE, and LIVE.

Rachel is also an avid event photographer and has captured photos for LGBT organizations around the world, including the IGLTA, NGLCC, NLGJA, and Out & Equal.


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