MOTIVATED SELLERS! Exceptional Old Town estate with pool

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Home For Sale

1006-1008 Fleming Street

Key West, Florida 33040

Monroe County Water View: Yes

Community: Old Town - Unlisted (1)

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$4,998,000 4 br, 5.0 bath 3336 sq. ft. 0.210 acres

MOTIVATED SELLERS! Exceptional Old Town estate with pool, gardens, and 2 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 & gate, the estate includes a grand main residence and two guest houses (both with kitchenettes), offering a total of 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 & dining areas, wet-bar, vaulted ceilings, a unique bath with outdoor shower & a private porch overlooking the pool & 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. 2 off-street parking spaces complete this remarkable Old Town retreat.

Interior:
  • Bedrooms: 4
  • Baths: 5.0
  • Sq Ft: 3336
  • Year Built: 1938
  • Utilities: 
  • Fireplaces: 
  • Stories: 1
  • Heat/AC: 
  • Garage: 
Exterior:
  • Lot Size: 0.210 acre
  • Lot Dimensions: 
  • View Types: Water
  • Yard: 
  • Siding: Frame
  • Roof: Metal
  • Property Taxes: $24,447
  • MLS #: 617020
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Contact Information:
Beach Home For Sale in Key West, Florida
Listing Agent: Terri Spottswood, Truman & Co. Real Estate Services, 305-587-3407, 305-292-2244 Listing Site, Listing 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.
Ad Number: 6758365
Viewed 88 times.
Updated: Feb 01, 2026

This property is a Home located at 1006-1008 Fleming Street, Key West, Florida 33040, and is currently For Sale at $4,998,000. This Home has 4 bedrooms, 5.0 baths, 3336 sq ft.