1006-1008 Fleming Street
Key West, FL 33040
MLS# 617020
4 beds | 5 baths | 3336 sqft
Open House (02/08/2026 - 1:00 pm - 3:00 pm)
Property DescriptionMOTIVATED 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 Board: Key West Association
Bank Owned: No
Current Price: $4,998,000
Listing Date: 2025-10-24
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)
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 – 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.
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Ceiling Fans(s): 1
Central Air: 1
Built-in Cabinets: 1
Cathedral Ceilings: 1
Drapes/Blinds Incl: 1
Entrance Foyer: 1
Wet Bar: 1
Whirlpool Bath Tub: 1
Guest/Servant Qtrs: Legal
Above Flood: Unknown
Stories: 1 Story
Glass Doors: 1
Impact Rstnce Doors: 1
Car(s): 2
Off Street Parking: 1
Buyer to Verify: 1
FKAA: 1
Municipal Sewer: 1
Whole House Generatr: 1
Detached Guest Qtrs: 1
Fencing: 1
Outdoor Shower: 1
Water Display: 1
In Ground: 1
Salt Water: 1
Other: Chilled
Heated: Yes
Property Condition: Updated/Remodeled
Vehicle Storage: Off Street Parking
Cooling: Ceiling Fans(s); Central Air
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
Land Size: Less Than 1/4 Acre
Terms: Cash; Conventional
Listing Office: Truman & Co. (KW)
Last Updated: January - 30 - 2026
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Broker Attribution:
305-587-3407