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1008 Fleming Street, Key West, FL 33040

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For Sale

$5,595,000

4 beds • 4 baths • 1 half baths • 3,336 sqft

Estimated Payment

$      /mo. †

APR for 30 years

Change Loan Terms

  • Single Family Detached
    Property type

  • $1,677.16
    Price per square foot

  • Over 50 Years Old
    Age

Explore this Property

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.
MLS# 617020

Courtesy Of Truman & Co. Real Estate Services

(305) 292-2244

Property Features

  • Age
    Over 50 Years Old
  • Amenities
    Wet Bar, Ceiling Fan
  • Appliances
    Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Architecture Style
    Other
  • Cooling System
    Ceiling Fan(s)
  • Floor Covering
    Tile, Wood
  • Lot Size
    0.21 Acres
  • Roof Type
    Metal
  • View Type
    Water

Map and Directions

Directions to 1008 Fleming Street, Key West, FL 33040

Home seller CENTURY 21 All Keys, Inc.

Get to know the neighborhood. A local affiliated CENTURY 21 office will help you set up tours, give advice, and negotiate with sellers.

CENTURY 21 All Keys, Inc.

(305) 294-4200
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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. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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This information is provided for general informational purposes only and should not be relied on in making any home-buying decisions. School information does not guarantee enrollment. Contact a local real estate professional or the school district(s) for current information on schools. This information is not intended for use in determining a person's eligibility to attend a school or to use or benefit from other city, town or local services.

† Based on a 30-year fixed rate of 3.38% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Interest rates are also subject to credit and property approval based on secondary market guidelines. The rates shown are based on average rates for our best qualified customers. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.