1006-1008 Fleming Street, Key West, FL 33040
$5,495,000
Property Type:
Residential
Bedrooms:
4
Baths:
5
Square Footage:
3,336
Lot Size (sq. ft.):
9,180
Status:
Active
Current Price:
$5,495,000
List Date:
10/24/2025
Last Modified:
12/09/2025
Description
Exceptional Old Town compound with pool, gardens, and two guest houses in the heart of Key West. This impeccable property blends timeless architecture with modern updates across three beautifully appointed structures. Behind a privacy wall & gate, the estate includes a grand main residence and two guest houses (both with kitchenettes), offering a total of four bedrooms and four-and-a-half baths. The main house welcomes you with an open floor plan, soaring ceilings, and a light-filled living and dining area. A dramatic wall of glass featuring new 40-foot impact-rated Nana doors and skylights opens to reveal lush tropical gardens and a resurfaced PebbleTec pool with a cascading waterfall. The heated, chilled, and saltwater-converted pool includes new tiled coping and a remote-controlled waterproof outdoor TV for movies or game nights under the stars.
The gourmet kitchen features top-of-the-line appliances, Italian cabinetry, Silestone countertops, and a new espresso bar with wine cooler and beverage center. Real stone and hardwood floors run throughout, including two spacious bedrooms, each with an en suite bath. The primary suite offers French doors and a spa-like bathroom with premium fixtures. The front guest house provides flexible living space currently a den or ''man cave'' with a bedroom, pantry kitchen, and a stunning bath clad in rare iridescent Czechoslovakian green glass from the 1950s. The rear guest cottage, tucked at the back of the property, includes its own sitting and dining areas, wet-bar, vaulted ceilings, a unique bath with outdoor shower, and a private porch overlooking the pool and garden.
Additional upgrades include a whole-house generator, new exterior lighting and irrigation by Blue Island, a state-of-the-art sound system, hurricane and plantation shutters, fresh exterior paint, and lush landscaping. Two off-street parking spaces on Fleming Street complete this remarkable Old Town retreat.
More Information MLS# 617020
Contract Information
Listing Board: Key West Association
Bank Owned: No
Current Price: $5,495,000
Listing Date: 2025-10-24
List Price: $5,495,000
Location, Tax & Legal
KW Neighborhood: Old Town-N of Truman
City: KEY WEST
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: AE
Alternate Key #: 1007731
Parcel #: 00007460-000000
Zoning: HMDR - Historic Medium Density Residential
Deed Restrictions: Unknown
Legal: KW PT LOT 3 SQR 45 G36-487 OR80-390 OR459-595 OR1479-1601 OR1740-1862 OR2406-1715 OR2547-1508 OR2692-262 OR2724-2495 OR
Taxes: 24447.08
Tax Year: 2024
Pub Sewer HkUp: Yes
Street #: 1006-1008
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 SqFt: 9180
Pool: Yes
Lot Sqft Source: Property Data Card
Total Units: 0
Acres: 0.21
SqFt Source: Property Data Card
Rentals Allowed: With Restrictions
Min Rental Days: 28
Style: Single Family
Year Built: 1938
Living Apx SqFt: 3336
Total Bedrooms: 4
Full Baths: 4
Half Baths: 1
Total Baths: 5
Remarks & Misc
Remarks – Consumer: Exceptional Old Town compound with pool, gardens, and two guest houses in the heart of Key West. This impeccable property blends timeless architecture with modern updates across three beautifully appointed structures. Behind a privacy wall & gate, the estate includes a grand main residence and two guest houses (both with kitchenettes), offering a total of four bedrooms and four-and-a-half baths. The main house welcomes you with an open floor plan, soaring ceilings, and a light-filled living and dining area. A dramatic wall of glass featuring new 40-foot impact-rated Nana doors and skylights opens to reveal lush tropical gardens and a resurfaced PebbleTec pool with a cascading waterfall. The heated, chilled, and saltwater-converted pool includes new tiled coping and a remote-controlled waterproof outdoor TV for movies or game nights under the stars.
The gourmet kitchen features top-of-the-line appliances, Italian cabinetry, Silestone countertops, and a new espresso bar with wine cooler and beverage center. Real stone and hardwood floors run throughout, including two spacious bedrooms, each with an en suite bath. The primary suite offers French doors and a spa-like bathroom with premium fixtures. The front guest house provides flexible living space currently a den or ''man cave'' with a bedroom, pantry kitchen, and a stunning bath clad in rare iridescent Czechoslovakian green glass from the 1950s. The rear guest cottage, tucked at the back of the property, includes its own sitting and dining areas, wet-bar, vaulted ceilings, a unique bath with outdoor shower, and a private porch overlooking the pool and garden.
Additional upgrades include a whole-house generator, new exterior lighting and irrigation by Blue Island, a state-of-the-art sound system, hurricane and plantation shutters, fresh exterior paint, and lush landscaping. Two off-street parking spaces on Fleming Street complete this remarkable Old Town retreat.
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
Fee Includes
None: 1
Dockage
None: 1
Tax Exemptions
None: 1
Appliances
Dishwasher: 1
Dryer: 1
Microwave: 1
Oven: 1
Range: 1
Refrigerator: 1
Washer: 1
Wine Cooler: 1
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Central Air: 1
Heating
Central: 1
Waterfront
None: 1
Waterview
No Waterview: 1
Floor
Tile: 1
Wood: 1
Interior Features
Built-in Cabinets: 1
Cathedral Ceilings: 1
Drapes/Blinds Incl: 1
Entrance Foyer: 1
Wet Bar: 1
Whirlpool Bath Tub: 1
Window Treatments: 1
Property Condition
Updated/Remodeled: 1
Specialty Rooms
Guest/Servant Qtrs: Legal
Building Style
Above Flood: Unknown
Stories: 1 Story
Windows/Doors
Glass Doors: 1
Impact Rstnce Doors: 1
Other Windows/Doors: 1
Vehicle Storage
Car(s): 2
Off Street Parking: 1
Construction
Frame: 1
Land Size
Less Than 1/4 Acre: 1
Terms
Cash: 1
Conventional: 1
Utilities
Buyer to Verify: 1
FKAA: 1
Municipal Sewer: 1
Whole House Generatr: 1
Porch/Balcony
Deck: 1
Patio: 1
Exterior Features
Detached Guest Qtrs: 1
Fencing: 1
Lanai: 1
Lighting: 1
Outdoor Shower: 1
Water Display: 1
Pool Info
In Ground: 1
Salt Water: 1
Other: Chilled
Heated: Yes
Concrete: 1
Pre-Wired
Surround Sound: 1
Roof
Metal Roof: 1
Financial Status
Bank Owned: No
Shutters
Bahama: 1
Status Change Info
Status: Active
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: None
Waterview: No Waterview
Dockage: None
Property Condition: Updated/Remodeled
Vehicle Storage: Off Street Parking
Cooling: Ceiling Fans(s); Central Air
Heating: Central
Utilities: Buyer to Verify; FKAA; Municipal Sewer; Whole House Generatr
Interior Features: Built-in Cabinets; Cathedral Ceilings; Drapes/Blinds Incl; Entrance Foyer; Wet Bar; Whirlpool Bath Tub; Window Treatments
Pre-Wired: Surround Sound
Appliances: Dishwasher; Dryer; Microwave; Oven; Range; Refrigerator; Washer; Wine Cooler
Exterior Features: Detached Guest Qtrs; Fencing; Lanai; Lighting; Outdoor Shower; Water Display
Pool Info: In Ground; Salt Water; Concrete
Construction: Frame
Shutters: Bahama
Floor: Tile; Wood
Roof: Metal Roof
Pets: Pets Allowed
Land Size: Less Than 1/4 Acre
Terms: Cash; Conventional
Documents
Listing Office:
Truman & Co. (KW)
Last Updated: December - 09 - 2025
Broker Attribution:
305-587-3407
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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