1109 Fleming St, Key West, FL 33040

$5,745,000
6
BD
7
BA
3,443
SqFt

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Sold Price
$5,745,000
List Price
$5,895,000
Closing Date
Mar 26, 2026
MLS#
617783
Status
CLOSED
Island
Key West
County
Monroe
City
Key West
Area
Key West
Subdivision
Old Town - Unrecord (1.0)
Neighborhood
Old Town-N of Truman
Bedrooms
6
Bathrooms
7
Half Baths
1
Living Area
3,443
Acres
0.20
Year Built
1925
Days on Market
95

Property Description

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.

Additional Information

Taxes
$30,859
Interior Features
Custom Cabinets, Granite Counters, Sprinkler System, Walk-In Closet(s), Quartz/Quartzite Counters, Loft
Furnished
Unfurnished
Appliances
Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Some Gas Appliances, Ice Maker, Wine Cooler, Stainless Steel Appliance(s)
Exterior Features
Fence, Guest Quarters, Rain Gutters, Lighting, Outdoor Shower, Privacy Wall, Sprinkler System, Water Feature
Roof
Metal
Pool
Yes
Zoning
HMDR - Historic Medium Density Residential
Terms
Cash, Conventional

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Listing Courtesy Of Brenda Donnelly Real Estate LLC, Contact:

Selling Office: .