$5,595,000

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1008 Fleming Street Key West, FL, United States 33040

Exceptional Old Town compound with pool, gardens, and two guest houses in the heart of Key West. This impeccable property blends timeless architecture with modern updates across three beautifully appointed structures. Behind a privacy wall and gate, the estate includes a grand main residence and two fully equipped guest houses, offering four bedrooms and four-and-a-half baths. The main house welcomes you with an open floor plan, soaring ceilings, and a light-filled living and dining area. A dramatic wall of glass featuring new 40-foot impact-rated Nana doors and skylights opens to reveal lush tropical gardens and a resurfaced PebbleTec pool with a cascading waterfall. The heated, chilled, and saltwater-converted pool includes new tiled coping and a remote-controlled waterproof outdoor TV for movies or game nights under the stars.The gourmet kitchen features top-of-the-line appliances, Italian cabinetry, Silestone countertops, and a new espresso bar with wine cooler and beverage center. Real stone and hardwood floors run throughout, including two spacious bedrooms, each with an en suite bath. The primary suite offers French doors and a spa-like bathroom with premium fixtures. The front guest house provides flexible living space currently a den or ''man cave'' with a bedroom, pantry kitchen, and a stunning bath clad in rare iridescent Czechoslovakian green glass from the 1950s. The rear guest cottage, tucked at the back of the property, includes its own sitting and dining areas, vaulted ceilings, a unique bath with outdoor shower, and a private porch overlooking the pool and garden.Additional upgrades include a whole-house generator, new exterior lighting and irrigation by Blue Island, a state-of-the-art sound system, hurricane and plantation shutters, fresh exterior paint, and lush landscaping. Two off-street parking spaces on Fleming Street complete this remarkable Old Town retreat.

Amenities

  • Bedrooms: 4
  • Full Bathrooms: 4
  • Partial Bathrooms: 1
  • Property Type: Residential
  • Architectural Style: Other
  • Year Built: 1938
  • Built in 1938
  • Home size: 3,336 ft2 / 309.92 m2
  • MLS: 617020
  • Status: Active
Copyright © 2025 Key West Association of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Property brokered by

Truman & Co., Inc.

(305) 292-2244

Presented by Terri Spottswood

  • (305) 292-2244
  • (305) 292-2244 (Office Phone)

Contact Terri Spottswood

Contact Agent


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