Photo: Rick Lively and Jeanette Silvestri

Everyone wants a slice of the Conch Republic. Here, seven homes that’ll make you want to head south for the winter—or all year-round.

By Lauren Phillips and Marisa Spyker

Once the stomping grounds of Ernest Hemingway, Key West has a wide-ranging list of attractions, from the cheerful debauchery of Duval Street to the natural wonders of Dry Tortugas National Park. The Key Lime Pie is widely acclaimed; the temperature is always warm. Plenty have fallen in love with the pleasures of Key West, but its charming size also means there’s not room for everyone to own a piece of the island.

The real estate here is notoriously pricy, with a median home value of $627,000, more than three times the national median ($205,100). But such is the cost of paradise, and for those who call Key West home, it's entirely worth it. Here, seven homes at various price points that can make your Key West dreams come true.

Related: 10 Best Hotels in Key West

Photo: Nick Doll
Photo: Nick Doll

High Style, $1,349,000
There aren’t many homes in Key West that come with their very own three-story lookout tower. But why be ordinary when in Key West? Architect Kevin Melloncamp incorporated the ‘40s-built tower into this 1,800-square-foot home, which draws the eyes of passersby at the top of the island and comes surrounded by tropical foliage. The tower is attached to a modern addition, so while your kitchen and guest bedrooms might have rounded edges, the entire home does not. Listed by Roger Emmons (305-294-5996).

Photo: Tamara Alverez
Photo: Tamara Alverez

Outdoor Oasis, $995,000
Live indoors and out in this charming 1920s cottage, which recently underwent a complete rebuild to update the interiors and expand its footprint. While the front exterior oozes charming tiny home curb appeal, the inside is spacious, with 12-foot-high ceilings in the great room and a wall of foldaway doors that open onto a party-ready deck complete with a pool and plush tropical landscaping. Listed by Suzanne Moore (305-797-0699).

Photo: Barry Fitzgerald
Photo: Barry Fitzgerald

Waterfront Wonder, $1,288,000
Located on a speck of land just north of Key West, this Lowcountry-inspired home is filled with elegant details, from the coffered ceilings and crown molding to the pine-clad walls. The powdery pink cottage also has a stainless roof and trellis-topped deck for savoring the property’s dreamy bay views. Listed by Leigh Ann Roach (305-587-4535 and leighann@keysrealestate.com).

Photo: Freas Photography
Photo: Freas Photography

Country Charmer, $430,000
If you crave the crystal clear Key West water and balmy weather but don’t necessarily need to be within the bustle of town, here’s your perfect match. Located in the Key West Golf Community—just outside Key West proper on Stock Island—this quiet, charming neighborhood boasts picket fences and mature trees with amenities like a clubhouse, pool, and golf course nearby. This updated townhouse comes fully furnished with two bedrooms, an open floor plan, and serene views of a butterfly garden. Listed by Tommy Mack (855-376-8986).  

Photo: Rob O'Neal
Photo: Rob O'Neal

Tiny Treasure, $600,000
Standing at a mere 720 square feet, this two-bedroom 1920s-built cottage boasts updated bamboo flooring, concrete countertops, and an open-plan living area. But the five-star draw is its central location, just steps from the Southernmost Point and a block from Duval Street. In other words, it’s time to get your party shoes on. Listed by Leigh Ann Roach (305-587-4535).

Photo: Rick Lively and Jeanette Silvestri
Photo: Rick Lively and Jeanette Silvestri

Historic Hideaway, $2,200,000
Surrounded by lush tropical foliage, this ‘40s-built three-bedroom cottage in the heart of Old Town will give the lure of Duval Street a run for its money. Set on a nearly 12,000-square-foot lot, the home features a gourmet kitchen (with an enormous island!) that opens out onto an expansive patio with plenty to offer in alfresco play (think: pool, hot tub, bar, and outdoor dining area). There’s also a separate guest cottage, should you want to share your personal paradise with friends. Listed by Rick Lively (305-797-7233) and Jeanette Silvestri (305-619-0112).

Photo: Freas Photography
Photo: Freas Photography

Midcentury Gem, $699,000
We’re smitten with the tropical welcome of this 1,086-square-foot home, complete with palm trees and citrusy hues on the shutters and front door. Inside, the newly renovated spaces feature a bright and airy floor plan with modern lines, porcelain tile, quartz countertops, and recessed lighting. It’s also centrally located in midtown Key West, making jaunts to pretty much anywhere on the island a breeze. Listed by Tommy Mack (855-376-8986).