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Chad Shultz
REALTOR®, ABR®, SRS, CPRES, C2EX
(928) 242-1990
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1006-1008 Fleming Street, Key West, FL 33040

$4,795,000
  • 1006-1008 Fleming Street, Key West, FL 33040 Main Photo

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Pending
BEDS4 BATHS4 full 1 partial SQUARE FEET3,336 MLS#617020
STATUSPending PROPERTY TYPEResidential - Single Family SUBDIVISIONOld Town - Unlisted (10)

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.

1006-1008 Fleming Street | MLS# 617020

This single family home located at 1006-1008 Fleming Street, Key West, FL 33040 is currently listed for sale with an asking price of $4,795,000. This property was built in 1938 and has 4 bedrooms and 4 full and 1 partial baths with 3336 sq. ft. 1006-1008 Fleming Street is located in the Old Town - Unlisted (10) subdivision. Search Old Town - Unlisted (10) real estate on chadshultz.adamscameron.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air, Ceiling Fans(s)
Heating: Central
Lot Size: 0.21 Acres
Roof Type: Metal Roof
Stories: 1.0
Taxes: $24,447
Year Built: 1938

Feature Descriptions

Appliances: Washer, Wine Cooler, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Building Above Flood: Unknown
Days on Site: 205
Dockage: None
Exterior: Fencing, Water Display, Outdoor Shower, Lanai, Lighting, Detached Guest Qtrs
Exterior: Frame
Flood Zone: AE
Flooring: Tile, Wood
HOA (1st Right of Refusal) Y/N: No
HOA (Mandatory) Y/N: No
Interior: Drapes/Blinds Incl, Window Treatments, Built-in Cabinets, Whirlpool Bath Tub, Entrance Foyer, Cathedral Ceilings, Wet Bar
Key/Island: Key West
Key West Neighborhood: Old Town-N of Truman
Listing Board: Key West Association
Lot Dimensions: 0.21Acre(s)
Parcel #: 00007460-000000
Parking: Off Street Parking
Parking Space(s): 2
Pets: Pets Allowed
Pool: In Ground, Concrete, Salt Water
Porch/Balcony: Deck, Patio
Property Condition: Updated/Remodeled
Sewer Hookup: Yes
Shutters: Bahama
Swimming Pool: Yes
Tax exemptions: None
Utilities: FKAA, Whole House Generatr, Buyer to Verify, Municipal Sewer
Waterfront: None
Waterview: No Waterview
Windows/Doors: Glass Doors, Impact Rstnce Doors, Other Windows/Doors
Zoning: HMDR - Historic Medium Density Residential

Listed By / Shown By

Listed By

Agency Name: Truman & Co. (KW)
Agency Contact: 305-587-3407

Shown By

Agent Name: Chad Shultz
Agent Phone: (928) 242-1990
Agency Title: Adams Cameron & Co. REALTORS

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Estimated Payment

$ 28,956.80 per month $25,521.00 Principal & Interest $2,037.25 Property Tax $1,398.54 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 05/18/2026. The listing information on this page last changed on 05/18/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Mon 05/18/2026 12:01:52 AM EST) or Miami MLS (last updated Sun 05/17/2026 11:58:14 PM EST) or Stellar MLS (last updated Sun 05/17/2026 11:43:59 PM EST) or Daytona MLS (last updated Sun 05/17/2026 11:36:45 PM EST) or Tallahassee MLS (last updated Sun 05/17/2026 10:48:08 PM EST) or Northeast Florida MLS (last updated Sun 05/17/2026 11:58:53 PM EST) or My State MLS (last updated Sun 05/17/2026 11:30:15 PM EST) or Florida Keys MLS (last updated Sun 05/17/2026 8:29:32 PM EST). Real estate listings held by brokerage firms other than Adams Cameron & Co. REALTORS may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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