Reviving an Old Naples Treasure
A Mid-Century Guesthouse Gets a Second Chance
There’s something special about Old Naples. The coastal charm, quiet streets, and a sense of history are just part of what makes it one of my favorite places to be. So, when I had the opportunity to take on this guesthouse project, I couldn’t wait to get started.
Holding Onto History
Let me share a little history about this place. Originally built in the 1950s, this guesthouse came to life during a time when Naples was starting to attract people from northern states seeking sunny, slower-paced living. Over the decades, it has faced its share of challenges—from housing some colorful characters to surviving hurricanes that have battered the coast. The original main house was demolished and rebuilt in the late 1990s, but the guesthouse remained, standing as a quiet reminder of the past.
Thanks to its "grandfathered" status, the guesthouse has remained intact despite modern building restrictions that no longer allow new guesthouses in this area. Preserving it is more than just honoring history; it’s about protecting a piece of Naples that can’t be replaced.
Updating a Historic Property
When a property is "grandfathered," renovations must follow a different set of rules. Here’s what that meant for this guesthouse:
Various aspects of the house are legally non-conforming but are allowed due to their age, including size, setbacks, and use.
Additional regulations apply for properties in flood zones, especially when raising structures or making major renovations.
The property is considered historically significant, requiring special permits and adherence to strict standards.
At the time of earlier renovations, improvements were capped at 50% of the guesthouse’s value.
Under these constraints, the 2000 updates focused on preserving the exterior structure—keeping the layout, foundation, and window placements intact. Hardy wood planks and shutters were added to match the new main house, a new roof was installed, and the screened porch was converted into a bedroom. However, the kitchen and bathroom remained untouched due to budget limitations imposed by the 50% rule.
Hurricane Ian Changes Everything
Being located in a flood zone has always presented challenges, but Hurricane Ian in 2022 was a turning point. The storm brought 43 inches of water into the guesthouse, causing extensive damage. Electrical systems failed, pests moved in, and the structure was left in desperate need of attention.
The homeowners decided it was time for a new approach. This wasn’t just about making repairs; it was a chance to reimagine the space and address long-standing issues, including:
Frequent flooding
Structural damage
Meeting updated building codes
A Collaborative Effort
To bring this vision to life, we assembled an incredible team—architects, structural and mechanical engineers, contractors, surveyors, land-use lawyers, and mold remediation specialists. The first step was navigating the complex permitting and approval process, which included:
Gaining permission to bring the house up to FEMA standards by raising it 5.5 feet.
Addressing zoning and setback requirements tied to its grandfathered status.
Securing an exception to the 50% rule, allowing for more extensive renovations.

Breathing New Life Into the Guesthouse
With approvals in hand, we’re now focused on transforming this guesthouse into a modern, functional retreat while respecting its historical character. Key updates include:
Raising the House: Lifting the structure five and half feet to prevent future flooding and create opportunities for reconfiguring the interior.
Reworking the Layout: Relocating the kitchen and bathroom and lifting the roof another two feet, adding a second full bathroom by utilizing previously unused attic space.
Preserving the Exterior: Keeping the original footprint and design while upgrading to hurricane-resistant windows and durable materials that can withstand Naples’ coastal environment.
The Unexpected Finds
As with any historic renovation, there have been a few surprises along the way:
Mold Remediation: Extensive water damage required a thorough cleanup to ensure the space was safe and healthy.
Structural Opportunities: Discovering that some ceiling beams weren’t structural allowed us to raise the kitchen ceiling, making the space feel brighter and more open.
Pest Challenges: Colonies of termites and bees reminded us of the importance of pest-resistant materials.



Looking Ahead
As we lift the house and finalize design details, the vision for this guesthouse is coming together beautifully. Every decision—from salt-resistant hardware to energy-efficient materials—is about creating a space that’s as functional as it is beautiful. This project is more than a renovation; it’s about creating a home that’s ready to welcome the next chapter of its story.
A Bright Future for a Naples Treasure
This guesthouse has endured so much, but its story is far from over. It’s a privilege to play a role in bringing it back to life, transforming it into a space that honors its history while embracing the future. I can’t wait to see it fully realized and ready to serve as a welcoming retreat for years to come.
If you’ve ever dreamed of reimagining a space with as much heart and history, I’d love to help you bring your vision to life.