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Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

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$4,425,000
1006-1008 Fleming Street
Key West, FL 33040
MLS# 617020
Status: Closed
4 beds  |  5 baths  |  3336 sqft

 | 

4BD/4.5BA | 3,336sf | 9,180sf Lot
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4BD/4.5BA | 3,336sf | 9,180sf Lot 3 Structures on 9,180sf lot Main House Living Room Entrance Main House Entrance Main House Foyer Main House Kitchen Main House Kitchen Main House Kitchen Espresso Bar Living Room/Breakfast Bar Breakfast Bar Living Room/Breakfast Bar Living Room Dining Room Primary Bedroom, Main House Primary Bedroom, Main House Primary Bathroom Primary Bathroom Primary Bathroom 2nd Bedroom, Main House 2nd Bedroom, Main House En-Suite Bathroom En-Suite Bathroom Dining Room, Main House Backyard to Guest Cottage Guest Cottage Guest Cottage Wet-Bar Guest Cottage Guest Cottage Bathroom Waterfall with Built-In TV Lanai Lanai Lanai with Game Table Guest House Kitchen Guest House Guest House Guest House Bedroom Guest House Bathroom Guest House Guest House Front Porch Guest House Street View Off Street Parking (2 Cars) 1008 Fleming Floor Plan 3 Structures on 9,180sf lot 3 Structures on 9,180sf lot

Property 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 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.

Details
Maps
Documents
Contract Information
Current Price: $4,425,000
Listing Date: 2025-10-24
Listing Board: Key West Association
Leased Price Monthly: $4,425,000
Bank Owned: No
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
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: 1
Total Baths: 5
Rentals Allowed: With Restrictions
Min Rental Days: 28
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Specialty Rooms
Guest/Servant Qtrs: Legal
Building Style
Above Flood: Unknown
# Stories: 1 Story
Vehicle Storage
Car(s): 2
Pool Info
Other: Chilled
Heated: Yes
Financial Status
Bank Owned: No
Status Change Info
Under Contract Date: 2026-04-26
Leased Date: 2026-05-26
Leased Price Monthly: $4,425,000
Status: Closed
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 Documents
View Document Survey
View Document Property Map

Listing Office: Truman & Co. (KW)

Last Updated: May - 26 - 2026

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.


Broker Attribution: 305-587-3407

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David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)