FOR SALE | 1006-1008 Fleming Street, Key West, FL
This is the one everyone waits for. An extraordinary Old Town Key West estate tucked behind a privacy wall and gate — offering a main house, 2 guest houses, tropical gardens, and a resort-style pool in the heart of it all. And yes… the sellers are motivated.
Blending timeless island architecture with modern upgrades, this impeccable compound spans three beautifully appointed structures with a total of 4 bedrooms and 4.5 baths — creating the ultimate private retreat just steps from everything Old Town has to offer.
✨ What Makes This Property Exceptional:
• Grand main residence with soaring ceilings & open-concept living
• 40-foot impact-rated Nana glass wall opening to the gardens
• Heated, chilled, saltwater PebbleTec pool with waterfall
• Remote-controlled waterproof outdoor TV for movie nights under the stars
• Gourmet kitchen with top-tier appliances, Italian cabinetry & Silestone counters
• Espresso bar with wine cooler & beverage center
• Two private guest houses — each with kitchenettes
• Whole-house generator, upgraded lighting & irrigation, state-of-the-art sound system
• Two off-street parking spaces
The primary suite offers French doors and a spa-inspired bath designed for relaxation. The front guest house currently serves as a stylish den retreat with a bedroom and bath wrapped in rare iridescent
Czechoslovakian green glass from the 1950s — a true conversation piece.
The rear cottage feels like its own hidden sanctuary with vaulted ceilings, wet bar, outdoor shower, and a private porch overlooking the pool and lush gardens.
From waterfall pool days to al fresco dinners beneath the palms, this property delivers the ultimate Key West indoor-outdoor lifestyle — all in one of Old Town’s most coveted locations.
🌴 A rare opportunity. A private compound. An unforgettable island retreat.
4BD/4.5BA | 3,336 SF | 9,180 SF Lot
#KeyWestHomes #OldTownKeyWest #KeyWestRealEstate #IslandLiving #LuxuryHomes#KeyWestHomes #KeyWestRealEstate #FloridaKeysLiving