1006-1008 Fleming St, Key West, FL 33040

$4,425,000
4
BD
5
BA
3,336
SqFt

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Sold Price
$4,425,000
List Price
$4,795,000
Closing Date
May 26, 2026
MLS#
617020
Status
CLOSED
Island
Key West
County
Monroe
City
Key West
Area
Key West
Subdivision
Old Town - Unlisted (1.0)
Neighborhood
Old Town-N of Truman
Bedrooms
4
Bathrooms
5
Half Baths
1
Living Area
3,336
Acres
0.21
Year Built
1938
Days on Market
214

Property Description

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.

Additional Information

Taxes
$24,447
Interior Features
Custom Cabinets, Wired Audio
Appliances
Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Wine Cooler
Exterior Features
Fence, Guest Quarters, Lighting, Outdoor Shower, Water Feature
Roof
Metal
Pool
Yes
Property Condition
Updated/Remodeled
Zoning
HMDR - Historic Medium Density Residential
Terms
Cash, Conventional

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Listing Courtesy Of Truman & Co. (KW), Contact: 305-292-2244

Selling Office: .