The 10 Most Prestigious Homes in Key West

When you think of Key West, you probably picture turquoise waters, swaying palms, and historic cottages. But tucked into this island paradise are some of the most prestigious single-family homes in the Florida Keys. These properties aren’t just houses—they’re retreats, status symbols, and income-generating investments rolled into one.

If you’ve ever wondered what the top tier of Key West real estate looks like, here’s your guide to the ten most exclusive homes currently on the market. 👉 View the full list here.

Spotlight: 1014 Southard Street, Old Town

Among the island’s most impressive properties, 1014 Southard Street is a rare jewel that combines rich history with modern upgrades.

✨ Highlights

• 4 bedrooms, 3.5 bathrooms

• Over 3,000 sq. ft. of living space

• Separate guest cottage with private entry

• Saltwater pool + tropical gardens

• Smart home features throughout

• Tesla charging station + 2023 generator

Built in 1899 by William Cash, this estate exudes historic charm while offering all the comforts of modern living. Its classic design includes dark green shutters, French doors, and cranberry cut-glass transoms, while inside, reclaimed hardwood floors and Blue Castle Limestone bring warmth and sophistication.

The master suite is a sanctuary on the ground level, with a private den, library, and spa-like ensuite. French doors open directly to the pool and lush gardens. Upstairs, two bedrooms share a bath and veranda, while the detached guest cottage offers cathedral ceilings, a built-in bar, and its own poolside deck—perfect for entertaining or hosting guests.

Modern features include Zigbee smart lighting, Ecobee thermostats, an Eero mesh Wi-Fi system, Nest sensors, and advanced security. Off-street parking, a Tesla charging station, and a brand-new generator add convenience to this already exceptional home.

Why It Stands Out

While Key West’s top homes all boast luxury, 1014 Southard Street is special because it blends historic elegance with today’s cutting-edge comforts. It’s rare to find a home in Old Town that has been so thoughtfully restored and updated while preserving its timeless character.

Final Thoughts

The most prestigious homes in Key West aren’t just real estate—they’re a way of life. From waterfront estates with private docks to lovingly restored Victorians, each property offers something unique.

But if you’re looking for a residence that captures the best of both past and present, 1014 Southard Street stands as a shining example of Key West living at its finest.

👉 Curious about the rest? Explore all ten of Key West’s most exclusive homes here.

Spotlight listing provided courtesy of Suzanne Moore, of Suzanne Moore Real Estate