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923 Fleming Street, Key West, FL 33040

New Listing
$5,300,000
Property Type: Residential Bedrooms: 7 Baths: 6 Square Footage: 3,121 Lot Size (sq. ft.): 4,525 Status: Active
Current Price: $5,300,000 List Date: 10/31/2026 Last Modified: 10/31/2026

Description

A rare opportunity to own a beautifully renovated historic property on coveted Fleming Street in the heart of Old Town Key West. Thoughtfully designed and renovated with exceptional craftsmanship, this unique property offers 7 bedrooms and 6 baths, creating an extraordinary combination of flexibility, privacy, and Old Town charm. The property is comprised of a 5-bedroom, 4-bath main residence, a separate one-bedroom guest apartment, and a one-bedroom pool cottage, each offering its own living space and kitchen. The guest apartment provides the perfect private quarters for visiting family and friends, or could easily be incorporated into the main residence to create additional living space or an expansive primary suite. The detached pool cottage offers yet another private retreat or rental opportunity. Outdoor living is at the heart of this exceptional property. A secluded, lushly landscaped entertaining area features a lagoon-style heated saltwater pool, tiki bar, and outdoor shower - an ideal setting for relaxing afternoons, sunset cocktails, and entertaining guests. Front and rear balconies provide additional opportunities to enjoy the quintessential Key West lifestyle, from morning coffee to evening cocktails. A private off-street parking space adds an especially valuable convenience in Old Town. Inside, the renovation reflects an exceptional level of craftsmanship and attention to detail, with beautiful finishes and crown molding throughout. Just a few blocks from the energy of Duval Street, the Historic Seaport and all that Old Town Key West has to offer, yet designed to provide a private oasis when you return home. A truly special property with endless possibilities for living, entertaining, and enjoying the Key West lifestyle. Owner is a licensed Florida Real Estate agent.

More Information MLS# 621882

Contract Information

Current Price: $5,300,000 Listing Date: 2026-10-30 Listing Board: Key West Association List Price: $5,300,000 As is Rght to Inspct: Yes Species List: No

Location Tax Legal

Street #: 923 Street Name: Fleming Street Suffix: Street Key/Island: Key West State/Province: FL Zip Code: 33040 County: Monroe Subdivision: Old Town - Unlisted (1.0) Area: 02 - Key West

General Property Description

Realtor.COM Type: Residential - Single Family Style: Single Family Waterfront: No Pool: Yes Year Built: 1889 Lot Size: 45 X 100 Lot SqFt: 4525 Lot Sqft Source: Survey Acres: 0.1 Living Apx SqFt: 3121 SqFt Source: Seller Total Bedrooms: 7 Full Baths: 6 Total Baths: 6 Rentals Allowed: With Restrictions

Status Change Info

Status: Active

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No

Building Style

Above Flood: Unknown

Pool Info

Heated: Yes

Property Features

Fee Includes: None Tax Exemptions: Homestead Waterfront: None Waterview: No Waterview Dockage: None Property Condition: Updated/Remodeled Vehicle Storage: Off Street Parking Furnished: Negotiable Cooling: Ductless; Wall/Window Unit(s) Heating: Ductless Utilities: Elect Separate Meter; FKAA; Municipal Sewer; Water Separate Meter Interior Features: Built-in Cabinets; Dade County Pine; Smoke Alarms; Walk-in Closet(s); Window Treatments Pre-Wired: Satellite Appliances: Dishwasher; Disposal; Dryer; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer Exterior Features: Bar; Detached Guest Qtrs; Fencing; Outdoor Shower Pool Info: In Ground; Salt Water Construction: Frame Floor: Wood Roof: Metal Roof Pets: Pets Allowed Land Size: Less Than 1/4 Acre Terms: Cash; Conventional
Listing Office: Realty ONE Group Destination
Last Updated: October - 31 - 2026
Broker Attribution: rogdestination@gmail.com

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

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