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1006-1008 Fleming Street, Key West, FL 33040

$4,425,000
Property Type: Residential Bedrooms: 4 Baths: 5 Square Footage: 3,336 Lot Size (sq. ft.): 9,180 Status: Closed
Current Price: $4,425,000 List Date: 10/24/2025 Last Modified: 5/26/2026

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

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

Status Change Info

Under Contract Date
2026-04-26
Leased Date
2026-05-26

Association Info

Mandatory Home Owners Asc
No
1st Right of Refusal
No

Building Style

Above Flood
Unknown
# Stories
1 Story

More Information

Vehicle Storage

Car(s)
2

Specialty Rooms

Guest/Servant Qtrs
Legal

Pool Info

Other
Chilled
Heated
Yes

Financial Status

Bank Owned
No

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: May - 26 - 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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