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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

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 co ...

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
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