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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

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 wi ...

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
Listing Office: Truman & Co. (KW)
Last Updated: April - 21 - 2026
Broker Attribution: 305-587-3407

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