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For sale
$5,595,000
4beds
3,336sqft

1008 Fleming St, Key West, FL 33040

4beds
3,336sqft
Single family residence
Built in 1938
9,147 sqft
2 Parking spaces
$1,677 price/sqft

What's special

Private porchResurfaced pebbletec poolCascading waterfallLush tropical gardensEn suite bathSpa-like bathroomOpen floor plan

Exceptional Old Town compound with pool, gardens, and two 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 and gate, the estate includes a grand main residence and two fully equipped guest houses, offering ...

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Source: FLKMLS,MLS#: 617020MLS LogoOriginating MLS: Key West Association
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Living Room - Main House

Kitchen - Main House

Dining Room - Main House

Primary Bedroom - Main House

Primary Bathroom - Main House

Bedroom - Main House

Guest House

Kitchen - Guest House

Zillow last checked: 7 hours ago

Listing updated: October 24, 2025 at 09:08am

Listed by:

Terri Spottswood 305-587-3407,

Truman & Co. (KW),

The Spottswood Team 305-432-4848,

Truman & Co. (KW)

Source: FLKMLS,MLS#: 617020MLS LogoOriginating MLS: Key West Association

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 4
  • Bathrooms: 5
  • Full bathrooms: 4
  • 1/2 bathrooms: 1
Heating
  • Central
Cooling
  • Central Air, Ceiling Fans(s)
Appliances
  • Included: Washer, Wine Cooler, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Features
  • Built-in Cabinets, Whirlpool Bath Tub, Entrance Foyer, Cathedral Ceiling(s), Wet Bar, Sound System
  • Flooring: Tile, Wood
  • Doors: Glass Doors, Impact Rstnce Doors
  • Windows: Drapes/Blinds Incl, Window Treatments, Other Windows/Doors, Bahama
Interior area
  • Total interior livable area: 3,336 sqft
Video & virtual tour

Property

Parking
  • Total spaces: 2
  • Parking features: Off Street
Features
  • Levels: One
  • Stories: 1
  • Patio & porch: Lanai, Deck, Patio
  • Exterior features: Water Display, Outdoor Shower, Lighting
  • Has private pool: Yes
  • Pool features: Heated, In Ground, Concrete, Salt Water
  • Fencing: Fenced
  • Water view: None
  • Waterfront features: None, Dockage: None
Lot
  • Size: 9,147.6 Square Feet
  • Features: Less Than 1/4 Acre
Details
  • Additional structures: Guest House, Detached Guest Qtrs
  • Parcel number: 00007460000000
  • Zoning: HMDR
  • Zoning description: Historic Medium Density Residential

Construction

Type & style
  • Home type: SingleFamily
  • Property subtype: Single Family Residence
Materials
  • Frame
  • Roof: Metal
Condition
  • Updated/Remodeled
  • New construction: No
  • Year built: 1938

Utilities & green energy

  • Electric: Generator
  • Sewer: Municipal Sewer, Public Sewer
  • Utilities for property: FKAA, Buyer to Verify

Community & HOA

Community
  • Subdivision: Old Town - Unlisted (1.0)
HOA
  • Has HOA: No
  • Services included: None
Location
  • Region: Key West

Financial & listing details

  • Price per square foot: $1,677/sqft
  • Tax assessed value: $3,799,127
  • Annual tax amount: $24,447
  • Date on market: 10/24/2025
  • Listing terms: Cash,Conventional

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