1109 Fleming Street, Key West, FL 33040
$5,745,000
Property Type:
Residential
Bedrooms:
6
Baths:
7
Square Footage:
3,443
Lot Size (sq. ft.):
8,722
Status:
Closed
Current Price:
$5,745,000
List Date:
12/21/2025
Last Modified:
3/26/2026
Overview
Description
...
(Read more)
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.
Listing Details MLS# 617783
Location, Tax & Legal
- Street #
- 1109
- Street Name
- Fleming
- Street Suffix
- Street
- Key/Island
- Key West
- State/Province
- FL
- Zip Code
- 33040
- County
- Monroe
- Subdivision
- Old Town - Unrecord (1.0)
- Area
- 01 - Key West
- KW Neighborhood
- Old Town-N of Truman
- City
- KEY WEST
- Mile Marker
- 1
- Marathon Neighborhood
- N/A
- Side
- Median
- Flood Zone
- AE,AE
- Alternate Key #
- 1005207
- Parcel #
- 00005020-000000
- Zoning
- HMDR - Historic Medium Density Residential
- Deed Restrictions
- Unknown
- Legal
- KW PT LOT 4 SQR 31 V-191 CO JUDGES DOCKET 79-113 AND 79-114 AND 79-115 OR788-1216 OR788-1241 OR791-1432 OR815-1846 OR115
- Taxes
- 30859.43
- Tax Year
- 2025
- Pub Sewer HkUp
- Yes
Contract Information
- Listing Board
- Key West Association
General Property Description
- Realtor.COM Type
- Residential - Single Family
- Style
- Single Family
- Waterfront
- No
- Pool
- Yes
- Year Built
- 1925
- Lot SqFt
- 8722
- Acres
- 0.2
- Living Apx SqFt
- 3443
- SqFt Source
- Property Data Card
- Total Bedrooms
- 6
- Full Baths
- 6
- Half Baths
- Yes
- Total Baths
- 7
- Rentals Allowed
- With Restrictions
- Control Depth
- 0
- Total Units
- 0
Status Change Info
- Sold Date
- 2026-03-26
Association Info
- Mandatory Home Owners Asc
- No
- 1st Right of Refusal
- No
- Association Fee $
- 0
Building Style
- Above Flood
- Unknown
- Stories
- 2 Stories
- Eyebrow
- Yes
More Information
Vehicle Storage
- Car(s)
- 2
- Off Street Parking
- Yes
Specialty Rooms
- Guest/Servant Qtrs
- Legal
- Loft
- Yes
Appliances
- Other
- Coffee Station
- Dishwasher
- Yes
- Dryer
- Yes
- Gas Appliances
- Yes
- Ice Machine
- Yes
- Microwave
- Yes
- Oven
- Yes
- Range
- Yes
- Refrigerator
- Yes
- Stainless Steel Appliance(s)
- Yes
- Washer
- Yes
- Wine Cooler
- Yes
Pool Info
- Heated
- Yes
- In Ground
- Yes
- Salt Water
- Yes
- Concrete
- Yes
Financial Status
- Standard Sale
- Yes
Remarks & Misc
- Remarks – Consumer
- 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.
Fee Includes
- None
- Yes
Dockage
- None
- Yes
Tax Exemptions
- None
- Yes
Pets
- Pets Allowed
- Yes
Cooling
- Ceiling Fans(s)
- Yes
- Central Air
- Yes
Heating
- Propane
- Yes
- Propane Stove
- Yes
Waterfront
- None
- Yes
Waterview
- No Waterview
- Yes
Floor
- Tile
- Yes
- Wood
- Yes
Interior Features
- Built-in Cabinets
- Yes
- Cathedral Ceilings
- Yes
- Dade County Pine
- Yes
- Drapes/Blinds Incl
- Yes
- Fire Sprinkler
- Yes
- Granite Counter Top
- Yes
- Pantry
- Yes
- Quartz Countertops
- Yes
- Smoke Alarms
- Yes
- Walk-in Closet(s)
- Yes
- Wet Bar
- Yes
- Window Treatments
- Yes
Windows/Doors
- Impact Rstnce Doors
- Yes
- Impact Rstnce Window
- Yes
Security
- Electric Gate
- Yes
Construction
- Frame
- Yes
- Hardi Board Siding
- Yes
Land Size
- Less Than 1/4 Acre
- Yes
Furnished
- Negotiable
- Yes
Terms
- Cash
- Yes
- Conventional
- Yes
Utilities
- FKAA
- Yes
- Municipal Sewer
- Yes
Porch/Balcony
- Open Porch/Balcony
- Yes
Title
- Negotiable
- Yes
Exterior Features
- Detached Guest Qtrs
- Yes
- Fencing
- Yes
- Lighting
- Yes
- Outdoor Shower
- Yes
- Privacy Wall/Fence
- Yes
- Rain Gutters
- Yes
- Sprinkler System
- Yes
- Water Display
- Yes
Pre-Wired
- Cable
- Yes
Roof
- Metal Roof
- Yes
Accessibility Feat
- None
- Yes
GF-Interior Features
- Tankless Hot Wtr Htr
- Yes
Property Features
Fee Includes:
None
Tax Exemptions:
None
Waterfront:
None
Waterview:
No Waterview
Dockage:
None
Building Style:
Eyebrow
Vehicle Storage:
Off Street Parking
Furnished:
Negotiable
Cooling:
Ceiling Fans(s); Central Air
Heating:
Propane; Propane Stove
Utilities:
FKAA; Municipal Sewer
Interior Features:
Built-in Cabinets; Cathedral Ceilings; Dade County Pine; Drapes/Blinds Incl; Fire Sprinkler; Granite Counter Top; Pantry; Quartz Countertops; Smoke Alarms; Walk-in Closet(s); Wet Bar; Window Treatments
Pre-Wired:
Cable
Specialty Rooms:
Loft
Appliances:
Dishwasher; Dryer; Gas Appliances; Ice Machine; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer; Wine Cooler
Exterior Features:
Detached Guest Qtrs; Fencing; Lighting; Outdoor Shower; Privacy Wall/Fence; Rain Gutters; Sprinkler System; Water Display
Accessibility Feat:
None
Pool Info:
In Ground; Salt Water; Concrete
Construction:
Frame; Hardi Board Siding
Floor:
Tile; Wood
Roof:
Metal Roof
Pets:
Pets Allowed
Security:
Electric Gate
Land Size:
Less Than 1/4 Acre
Terms:
Cash; Conventional
Title:
Negotiable
GF-Interior Features:
Tankless Hot Wtr Htr
Listing Office:
Brenda Donnelly Real Estate LLC
Last Updated: March - 26 - 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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