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Home > 923 Fleming Street, Key West, FL 33040 (MLS# 621882)
$5,300,000
923 Fleming Street
Key West, FL 33040
MLS# 621882
7 beds  |  6 baths  |  3121 sqft
923 Fleming Front
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923 Fleming Front 923 Fleming Front 923 Fleming Front Heated salt water pool Pool Backyard at Twilight Tiki Bar Pool Outdoor Shower Outdoor Shower Art Back Deck Back Deck Main Living Room Main Living Room Doors Open Main Living Room Hallway Main Living Room Opening to Kitchen/Dining area Main Dining/Kitchen Main Dining Main Kitchen Main Kitchen Main Kitchen - Custom Cabinets Main Kitchen - Marble Countertops Main First Floor Laundry Bathroom Main First Floor Bathroom Main Hallway Front Entrance Main First Floor Bedroom #1 Main First Floor Bathroom #2 Main Second Floor Bedroom #2 Main Second Floor Bedroom #2 Main Second Floor Bedroom #2 Main Second Floor Bathroom #3 Main Second Floor Bathroom #3 Main Second Floor Walk In Closet Main Second Floor Front Balcony Main Second Floor Bedroom #3 Main Second Floor Bedroom #3 Main Second Floor Bedroom #3 Doors Open Main Second Floor Rear Balcony Main Second Floor Bedroom #4 Main Second Floor Bedroom #4 Main Second Floor Bathroom #4 Main Second Floor Bathroom #4 Main Front Side Balcony Main Front Side Balcony Main Second Floor Stairway Main Second Floor Hallway Stairs Main Third Floor Bedroom #5 Off Street Parking Front Porch Front Porch Entrance Front Entrance Pool at Twilight Outdoor Dining Back of House Twilight 923Fleming Backyard Twilight Backyard Twilight Back Yard Twilight Backyard Twilight Tiki Bar Twilight Guest Apartment Bedroom Guest Apartment Living Room Guest Apartment Living Kitchen Area Guest Apartment Kitchen Guest Apartment Kitchen Dining Guest Apartment Bathroom Pool Cottage Outside Pool Cottage Outside Entrance Pool Cottage Living Room Pool Cottage Living Room Pool Cottage Kitchen Dining Pool Cottage Bedroom Pool Cottage Bathroom

Property 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.

Details
Maps
Contract Information
Listing Board: Key West Association
As is Rght to Inspct: Yes
Species List: No
Current Price: $5,300,000
Listing Date: 2026-10-30
List Price: $5,300,000
Location, Tax & Legal
KW Neighborhood: Old Town-N of Truman
City: KEY WEST
Off Shore Island: No
Mile Marker: 1
Marathon Neighborhood: N/A
Senior Community YN: No
Side: Median
Flood Zone: AE
Alternate Key #: 1005614
Parcel #: 00005430-000000
Zoning: HMDR - Historic Medium Density Residential
Deed Restrictions: No
Legal: KW PT LOT 1 SQR 33 PP-714 OR732-496 OR764-978 OR890-158 OR1174-1565 OR1190-1715 OR1337-948 OR1547-1478 OR1725-1967 OR172
Taxes: 15782.98
Tax Year: 2025
Pub Sewer HkUp: Yes
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
Waterfront: No
Control Depth: 0
Lot Size: 45 X 100
Lot SqFt: 4525
Pool: Yes
Lot Sqft Source: Survey
Total Units: 0
Acres: 0.1
SqFt Source: Seller
Rentals Allowed: With Restrictions
Style: Single Family
Year Built: 1889
Living Apx SqFt: 3121
Total Bedrooms: 7
Full Baths: 6
Total Baths: 6
Remarks & Misc
Remarks – Consumer: 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.
Directions: Between Margarat and Grinnell streets. House is mid block on the left.
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
Fee Includes
None: 1
Dockage
None: 1
Tax Exemptions
Homestead: 1
Appliances
Dishwasher: 1
Disposal: 1
Dryer: 1
Microwave: 1
Oven: 1
Range: 1
Refrigerator: 1
Stainless Steel Appliance(s): 1
Washer: 1
Pets
Pets Allowed: 1
Cooling
Ductless: 1
Wall/Window Unit(s): 1
Heating
Ductless: 1
Waterfront
None: 1
Waterview
No Waterview: 1
Floor
Wood: 1
Interior Features
Built-in Cabinets: 1
Dade County Pine: 1
Smoke Alarms: 1
Walk-in Closet(s): 1
Window Treatments: 1
Property Condition
Updated/Remodeled: 1
Building Style
Above Flood: Unknown
Windows/Doors
Double Hung Windows: 1
French Doors: 1
Glass Doors: 1
Vehicle Storage
Off Street Parking: 1
Construction
Frame: 1
Land Size
Less Than 1/4 Acre: 1
Furnished
Negotiable: 1
Terms
Cash: 1
Conventional: 1
Utilities
Elect Separate Meter: 1
FKAA: 1
Municipal Sewer: 1
Water Separate Meter: 1
Porch/Balcony
Deck: 1
Open Porch/Balcony: 1
Exterior Features
Bar: 1
Detached Guest Qtrs: 1
Fencing: 1
Outdoor Shower: 1
Pool Info
In Ground: 1
Salt Water: 1
Heated: Yes
Pre-Wired
Satellite: 1
Roof
Metal Roof: 1
Status Change Info
Status: Active
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

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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