855.375.4001
Listing Courtesy of: Brenda Donnelly - Brenda Donnelly Real Estate LLC 305-304-1116
$5,895,000 affordable loan icon Calculate Payment

1109 Fleming Street Key West, FL 33040

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Single Family Residence
6 Beds
7 Baths
... Bed/Bath
3,443 Sq. Ft.

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Last updated on 12/22/2025 3:38 PM
All I want for Christmas is 1109 Fleming Street! Located in the heart of Old Town, this truly magical estate presents an opportunity to own a private compound of remarkable scale and architectural distinction. Set on an oversized lot with off-street parking for two, the property features two fully ...independent residences--each appointed with impact-rated windows and doors. Situated along iconic Millionaire's Row, the main residence is a masterfully restored historic home that pays homage to its original character while embracing today's highest standards of luxury and comfort. Offering four spacious ensuite bedrooms, the main home includes a versatile first-floor suite that can easily function as a first floor primary bedroom or den. Additional features include original Dade County pine walls, reclaimed river wood flooring, soaring ceilings, and generous windows that bathe the interiors in natural light. At the heart of the home lies a chef-caliber gourmet kitchen with custom cabinetry, Sub-Zero and Wolf appliances, sculpted marble countertops, a built-in wine cooler and dedicated coffee center. French doors open to the wraparound porches- offering an idyllic setting for morning coffee, sunset cocktails, or alfresco dining. The estate's newly constructed guest house features two additional ensuite bedrooms, dramatic vaulted ceilings, and a charming loft ideal for additional living. The fully equipped kitchen features high-end Miele appliances and striking artisan tile. Anchoring the property is an extraordinary outdoor living environment conceived by renowned landscape architect Craig Reynolds. This lush, resort-style sanctuary showcases a sparkling saline swimming pool, cascading waterfall, outdoor shower, and a discreet poolside half bath. 1109 Fleming is more than a residence--it is a landmark Old Town estate equally suited for full-time living, a refined second home, or a legacy property to be enjoyed for generations on one of Key West's most prestigious streets. Continue reading
MLS#
617783
Property Type
Single Family
Bedrooms
6
Bathrooms
6 Full/1 Half
Year Built
1925
Square Feet
3,443 sq. ft
Lot Size
0.2
Stories
2.0
Sewer
Sewer Connected

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Walk Score measures the walkability of any address, Transit Score measures access to public transit on a scale of 1-100.

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Listing Courtesy of: Brenda Donnelly - Brenda Donnelly Real Estate LLC 305-304-1116
Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Florida Keys Board of Realtors® Florida Keys MLS, Inc. Real Estate listings held by brokerage firms other than the owner of this site are marked with the MLS logo and detailed information about them includes the name of the listing broker's office. Information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate.

This content last refreshed on 12/22/2025 3:38 PM. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Information is deemed reliable but is not guaranteed.
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