1006-1008 Fleming Street, Key West, FL 33040
$4,795,000
Property Type:
Residential
Bedrooms:
4
Baths:
5
Square Footage:
3,336
Lot Size (sq. ft.):
9,180
Status:
Contingent/Show
Current Price:
$4,795,000
List Date:
10/24/2025
Last Modified:
4/21/2026
Overview
Description
...
(Read more)
MOTIVATED SELLERS! Exceptional Old Town estate with pool, gardens, and 2 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 & dining areas, wet-bar, vaulted ceilings, a unique bath with outdoor shower & a private porch overlooking the pool & 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. 2 off-street parking spaces complete this remarkable Old Town retreat.
Listing Details MLS# 617020
Location, Tax & Legal
- 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
- 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
Contract Information
- Listing Board
- Key West Association
- Bank Owned
- No
General Property Description
- Realtor.COM Type
- Residential - Single Family
- Style
- Single Family
- Waterfront
- No
- Pool
- Yes
- Year Built
- 1938
- Lot SqFt
- 9180
- Lot Sqft Source
- Property Data Card
- Acres
- 0.21
- Living Apx SqFt
- 3336
- SqFt Source
- Property Data Card
- Total Bedrooms
- 4
- Full Baths
- 4
- Half Baths
- Yes
- Total Baths
- 5
- Rentals Allowed
- With Restrictions
- Min Rental Days
- 28
- Control Depth
- 0
- Total Units
- 0
Status Change Info
- Contingent
- Contingent/Show
Association Info
- Mandatory Home Owners Asc
- No
- 1st Right of Refusal
- No
- Association Fee $
- 0
Building Style
- Above Flood
- Unknown
- Stories
- 1 Story
More Information
Vehicle Storage
- Car(s)
- 2
- Off Street Parking
- Yes
Specialty Rooms
- Guest/Servant Qtrs
- Legal
Pool Info
- Other
- Chilled
- Heated
- Yes
- In Ground
- Yes
- Salt Water
- Yes
- Concrete
- Yes
Financial Status
- Bank Owned
- No
Remarks & Misc
- Remarks – Consumer
- MOTIVATED SELLERS! Exceptional Old Town estate with pool, gardens, and 2 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 & dining areas, wet-bar, vaulted ceilings, a unique bath with outdoor shower & a private porch overlooking the pool & 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. 2 off-street parking spaces complete this remarkable Old Town retreat.
Fee Includes
- None
- Yes
Dockage
- None
- Yes
Tax Exemptions
- None
- Yes
Appliances
- Dishwasher
- Yes
- Dryer
- Yes
- Microwave
- Yes
- Oven
- Yes
- Range
- Yes
- Refrigerator
- Yes
- Washer
- Yes
- Wine Cooler
- Yes
Pets
- Pets Allowed
- Yes
Cooling
- Ceiling Fans(s)
- Yes
- Central Air
- Yes
Heating
- Central
- Yes
Waterfront
- None
- Yes
Waterview
- No Waterview
- Yes
Floor
- Tile
- Yes
- Wood
- Yes
Interior Features
- Built-in Cabinets
- Yes
- Cathedral Ceilings
- Yes
- Drapes/Blinds Incl
- Yes
- Entrance Foyer
- Yes
- Wet Bar
- Yes
- Whirlpool Bath Tub
- Yes
- Window Treatments
- Yes
Property Condition
- Updated/Remodeled
- Yes
Windows/Doors
- Glass Doors
- Yes
- Impact Rstnce Doors
- Yes
- Other Windows/Doors
- Yes
Construction
- Frame
- Yes
Land Size
- Less Than 1/4 Acre
- Yes
Terms
- Cash
- Yes
- Conventional
- Yes
Utilities
- Buyer to Verify
- Yes
- FKAA
- Yes
- Municipal Sewer
- Yes
- Whole House Generatr
- Yes
Porch/Balcony
- Deck
- Yes
- Patio
- Yes
Exterior Features
- Detached Guest Qtrs
- Yes
- Fencing
- Yes
- Lanai
- Yes
- Lighting
- Yes
- Outdoor Shower
- Yes
- Water Display
- Yes
Pre-Wired
- Surround Sound
- Yes
Roof
- Metal Roof
- Yes
Shutters
- Bahama
- Yes
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: April - 21 - 2026
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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