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For sale
    • Price cut: $50K (3/30)
    $1,650,000

    1022 Fleming St, Key West, FL 33040

    4beds
    2,016sqft
    : 
    Duplex, Single Family Residence
    Built in 1928
    -- sqft lot
    $1,575,800 Zestimate®
    $818/sqft
    $-- HOA

    What's special

    Large wraparound porchLight-filled historic homeAbundant natural lightInterior staircaseSpacious level
    Invest in Key West with this legal Duplex which can be easily converted to a single family home! Step into a piece of Key West history with this light-filled historic home in the heart of Old Town. Blending old-world charm with modern updates, this property offers easy living and generates income. Whether you're looking for a smart investment, a vacation getaway, or a new primary residence, this property is ready for you. Live in one unit and rent the other, or enjoy the entire home for yourself! There is an interior staircase to enter the upstairs unit.Each spacious level features 2 bedrooms, 1 bathroom, a full kitchen with stainless steel appliances, laundry, and an open-concept living/kitchen/dining area. The lower unit opens to a deck and pool--perfect for relaxing and entertaining. The upper unit is currently rented. It boasts abundant natural light and a large wraparound porch, ideal for enjoying the tropical surroundings. Located in a prime spot close to the Old Seaport, top restaurants, and bars, but in a quieter neighborhood, this home is your ticket to island living in paradise!
    210 days
    |
    1,404
    |
    35
    |

    Zillow last checked: 7 hours ago

    Listing updated: March 30, 2026 at 09:10am

    Listed by:

    Ellen Gvili 305-304-2933,

    Ocean Sotheby's International Realty,

    Marc Ulanowski 815-861-3559,

    Equestrian Sotheby's International Realty

    Source: FLKMLS,MLS#: 616423MLS LogoOriginating MLS: Key West Association

    Tour with a local agent

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 2
      • Full bathrooms: 2
      Heating
      • Ductless
      Cooling
      • Ceiling Fans(s), Ductless
      Appliances
      • Included: Washer, Stainless Steel Appliance(s), Oven, Range, Refrigerator, Dryer
      Features
      • Built-in Cabinets, Sound System
      • Flooring: Tile, Combination, Wood
      • Doors: French Doors
      • Windows: Drapes/Blinds Incl, Double Hung Windows, Wood Frames, Panel
      Interior area
      • Total interior livable area: 2,016 sqft
      Video & virtual tour

      Property

      Accessibility
      • Accessibility features: No
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Open Porch/Balcony, Deck
      • Has private pool: Yes
      • Pool features: In Ground, Concrete
      • Fencing: Fenced
      • Water view: None
      • Waterfront features: None, Dockage: None
      Lot
      • Size: 2,613.6 Square Feet
      • Features: Less Than 1/4 Acre
      Details
      • Parcel number: 00007340000000
      • Zoning: HMDR
      • Zoning description: Historic Medium Density Residential

      Construction

      Type & style
      • Home type: MultiFamily
      • Property subtype: Duplex, Single Family Residence
      • Attached to another structure: Yes
      Materials
      • Frame
      • Roof: Metal
      Condition
      • Updated/Remodeled
      • New construction: No
      • Year built: 1928

      Utilities & green energy

      • Electric: Elect Separate Meter
      • Sewer: Public Sewer
      • Water: Water Separate Meter
      • Utilities for property: FKAA, Cable Connected

      Community & HOA

      Community
      • Features: Bike Paths
      • Security: Smoke Detector(s), Building Security, On Premises System
      • Subdivision: Old Town - Unlisted (1.0)
      HOA
      • Has HOA: No
      • Services included: None
      Location
      • Region: Key West

      Financial & listing details

      • Price per square foot: $818/sqft
      • Tax assessed value: $1,656,783
      • Annual tax amount: $14,546
      • Date on market: 9/9/2025
      • Listing terms: Cash,Conventional
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        Estimated market value

        $1,575,800

        $1.50M - $1.65M

        $5,515/mo

        Price history

        Price history
        DateEventPrice
        3/30/2026Price change$1,650,000-2.9%$818/sqft
        Source: Key West AOR #616423 Report a problem
        3/19/2026Price change$1,700,000-2.9%$843/sqft
        Source: FLKMLS #616423 Report a problem
        2/24/2026Price change$1,750,000-5.4%$868/sqft
        Source: Key West AOR #616423 Report a problem
        2/17/2026Price change$1,850,000-7.5%$918/sqft
        Source: Key West AOR #616977 Report a problem
        10/31/2025Price change$1,999,990-2.4%$992/sqft
        Source: FLKMLS #616977 Report a problem
        10/21/2025Price change$2,050,000-2.4%$1,017/sqft
        Source: FLKMLS #616423 Report a problem
        9/9/2025Listed for sale$2,100,000$1,042/sqft
        Source: Key West AOR #616423 Report a problem
        9/6/2025Listing removed$2,100,000$1,042/sqft
        Source: FLKMLS #614069 Report a problem
        7/16/2025Price change$2,100,000-2.3%$1,042/sqft
        Source: FLKMLS #611458 Report a problem
        4/18/2025Price change$2,150,000-5.9%$1,066/sqft
        Source: Key West AOR #614069 Report a problem
        2/2/2025Price change$2,285,000-4.8%$1,133/sqft
        Source: Key West AOR #611458 Report a problem
        9/13/2024Listed for sale$2,399,000+59.9%$1,190/sqft
        Source: FLKMLS #611458 Report a problem
        9/13/2024Listing removed$4,700$2/sqft
        Source: Zillow Rentals Report a problem
        8/21/2024Price change$4,700-2.1%$2/sqft
        Source: Zillow Rentals Report a problem
        8/7/2024Price change$4,800-4%$2/sqft
        Source: Zillow Rentals Report a problem
        7/23/2024Price change$5,000-2%$2/sqft
        Source: Zillow Rentals Report a problem
        7/1/2024Price change$5,100-1.9%$3/sqft
        Source: Zillow Rentals Report a problem
        5/18/2024Price change$5,200-1%$3/sqft
        Source: Zillow Rentals Report a problem
        4/30/2024Price change$5,250-4.5%$3/sqft
        Source: Zillow Rentals Report a problem
        4/24/2024Price change$5,500-5.2%$3/sqft
        Source: Zillow Rentals Report a problem
        4/5/2024Listed for rent$5,800+5.5%$3/sqft
        Source: Zillow Rentals Report a problem
        10/3/2023Listing removed--
        Source: Zillow Rentals Report a problem
        8/11/2023Listed for rent$5,500$3/sqft
        Source: Zillow Rentals Report a problem
        7/9/2021Sold$1,500,500+30.5%$744/sqft
        Source: FLKMLS #594244 Report a problem
        8/2/2019Sold$1,150,000+15%$570/sqft
        Source: FLKMLS #583489 Report a problem
        7/24/2015Sold$1,000,000$496/sqft
        Source: Public Record Report a problem

        Public tax history

        Public tax history
        YearProperty taxesTax assessment
        2025$14,756 +1.4%$1,656,783 +0.4%
        2024$14,547 +4%$1,650,209 +5.7%
        2023$13,991 +14%$1,561,596 +13.3%
        2022$12,269 +28.7%$1,378,368 +39%
        2021$9,536 +3.4%$991,277 +3.3%
        2020$9,224 $959,522 +7.3%
        2019$9,224 +5.8%$893,930 -16.9%
        2018$8,717 -17%$1,075,130 -0.7%
        2017$10,508 -2.3%$1,083,212 +6.9%
        2016$10,757 +0.9%$1,012,946 +228.4%
        2015$10,657 $308,447

        Find assessor info on the county website

        Monthly payment

        Est. payment
        $9,355/mo
        Principal & interest
        $8228
        Property taxes
        $1127
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          Climate risks

          Neighborhood: Old Town

          Getting around

          92 / 100
          Walker's Paradise
          28 / 100
          Some Transit
          100 / 100
          Biker's Paradise

          Nearby schools

          GreatSchools rating

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