1440 Caxambas Court, Marco Island
Year built: 2004
Details: 14,000 square feet, eight bedrooms, eight baths
Developer: Everett Van Hoesen
Why we chose it: We love a house with a name—and Villa Venezia is a moniker that’s been thrown about quite a bit since its creation on Marco Island’s “Millionaires’ Row.” It is a multiple building industry award winner, has hosted charitable fundraisers and turned more than a few heads. It created the most buzz in 2007 by scoring Marco’s record highest sales price at $9 million. But we’ll just daydream about strolling through the lush grounds and gazing out onto Roberts Bay from a well-upholstered window seat.

1141 Paper Fig Court, Sanibel
Year built: 1989
Details: 6,533 square feet, three bedrooms, three baths
Why we chose it: Keeping in mind that this is a driving tour, many of the homes on Sanibel and Captiva are well hidden away behind acres of natural foliage, securing the owners’ privacy. But this darling home on a large corner lot elicited such an “ahhh!” response from us that we just had to include it. Its well-manicured landscaping, sassy blue roof and Key West flavor have us picturing long, hot summer nights of drinking iced tea on the front porch while the world drives by on Periwinkle Way.

3830 Fort Charles Drive, Naples
Year built: 1998
Details: 7,500 square feet
Architect: Richard Meier
Why we chose it: Just when you think you might drown in the sea of red-tiled roofs, you come across this modern masterpiece by the famed architect. From the street, you get a glimpse of the exceptionally groomed lawn, a circular building (which is actually a two-car garage) and the front of the home, which is lined with 2-by-3-foot limestone slabs and no windows. If you want to see the view of the windowed walls and inverted roof that seems to open its arms to the sun, you’ll have to take a boat ride on the bay in Port Royal.

3330 Rum Row, Naples
Year built: 1999
Details: One-and-a-half lots, approximately 10,000 square feet combined
Why we chose it: This sprawling French Colonial charmer stood out for its sunny yellow exterior paired with white and bright pink impatiens that line the length of the home’s façade. While driving the windy roads of Port Royal, we were overwhelmed by all of the Mediterranean manses and appreciated the breath of fresh air this delightful home offered.

1141 Wales Drive, Fort Myers
Year built: Building 1, 1926; building 2, 1944
Details: 10,507 square feet, six bedrooms, six baths
Why we chose it: This amazing home in Fort Myers’ historic district is listed as “Early Floridian” in style, but we’re leaning more toward Spanish Colonial. Known by locals as the “pink castle” (no longer pink), it wraps around its corner lot, just a half a block from the Caloosahatchee River shore. The grounds include a huge playground, a tennis court, gazebo and pool. We cannot find a better place for early—or modern-day—Floridians to spend their days.