Skip main navigation
Sold for $1,550,000
  • $1,550,000

    1223 Flagler Ave, Key West, FL 33040

    4beds
    2,260sqft
    Single Family Residence
    Built in 1958
    4,356 Square Feet Lot
    $1,595,500 Zestimate®
    $686/sqft
    $6,512 Estimated rent

    Home value

    $1,595,500

    $1.39M - $1.83M

    $6,512/mo

    Zestimate® history
    Loading
    Loading...

    Owner options

    List your home for rent

    $6,512/mo

    Rent Zestimate®

    Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.

    Learn more

    $6,512/mo

    Rent Zestimate®

    Refinance and save

    $9,814/mo

    Est. payment

    Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.

    See today's rates

    $9,814/mo

    Est. payment

    Explore your selling options

    Work with a Zillow partner agent

    Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.

    Get started

    List with your own agent

    Get your home in front of millions of buyers by listing it on Zillow.

    Learn how to do it

    Sell it yourself

    Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).

    List your home

    What's special

    Private oasisLush tropical landscapingOpen floor planOutdoor shower
    Discover your own private oasis in the heart of Key West! This spacious 4BR/3BA two-story home offers over 2,200 sq ft of living space designed for both relaxation and entertaining. Located in desirable Midtown, just minutes from the Casa Marina, Higgs Beach, and White Street Pier, you'll enjoy the perfect balance of island living and everyday convenience. Step inside to find an open floor plan with multiple living and dining areas, a modern kitchen with stainless steel appliances and wine cooler, and flexible spaces ideal for guests or family. The home's layout includes two bedrooms on each level, providing privacy and options for hosting or working from home. Outside, the resort-style backyard is the true highlight: a heated pool with expansive deck, surrounded by lush tropical landscaping and tall privacy fencing. Enjoy the covered lanai for dining al fresco, rinse off in the outdoor shower after a day at the beach, or simply unwind in the shade of palm trees. This fully fenced property is perfect for both peaceful relaxation and lively gatherings. Additional features include off-street parking for 2-3 vehicles, central air, laundry room, ceiling fans, and negotiable furnishings. With a 30-day minimum rental allowance, this property also offers excellent potential as a vacation rental or investment. Whether you're seeking a year-round residence, second home, or income-producing property, 1223 Flagler Avenue delivers the best of Key West living with comfort, charm, and convenience.

    Zillow last checked:

    Listing updated:

    Listed by:

    Jose Wenzel, PA 305-395-1381,

    Preferred Properties (KW),

    Philip Lawrence Lavoie 317-292-4423,

    Preferred Properties (KW)

    Bought with:

    outside mls - FKBR

    Outside Of MLS - FKBR

    Source: FLKMLS,MLS#: 616436MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 3
    • Full bathrooms: 3
    Cooling
    • Central Air, Ceiling Fans(s)
    Appliances
    • Included: Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave, Wine Cooler, Stainless Steel Appliance(s)
    Features
    • Bar
    • Flooring: Tile, Wood, Carpet
    • Furnished: Yes
    Interior area
    • Total structure area: 2,260
    • Total interior livable area: 2,260 sqft

    Property

    Features
    • Patio & porch: Open Porch/Balcony, Deck
    • Exterior features: Outdoor Shower
    • Has private pool: Yes
    • Pool features: In Ground, Decked
    • Fencing: Privacy
    Lot
    • Size: 4,356 Square Feet
    Details
    • Parcel number: 00040490000000
    • Zoning: SF - Single Family

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence
    Materials
    • CBS
    Condition
    • Year built: 1958

    Community & HOA

    Community
    • Security: No Security
    • Subdivision: Tropical Bldt & Investment Co Sub (2.0)
    HOA
    • Has HOA: No
    • Services included: None
    Location
    • Region: Key West

    Financial & listing details

    • Price per square foot: $686/sqft
    • Tax assessed value: $1,196,235
    • Annual tax amount: $10,607
    • Date on market: 9/10/2025
    • Listing terms: No Seller Finance,Cash,Conventional,FHA

    Price history

    DateEventPrice
    11/4/2025Sold$1,550,000-3.1%$686/sqft
    Source: FLKMLS #616436 Report a problem
    10/31/2025Pending sale$1,600,000$708/sqft
    Source: FLKMLS #616436 Report a problem
    9/30/2025Contingent$1,600,000$708/sqft
    Source: Key West AOR #616436 Report a problem
    9/10/2025Listed for sale$1,600,000-10.6%$708/sqft
    Source: FLKMLS #616436 Report a problem
    4/13/2023Listing removed--
    Source: Key West AOR #602866 Report a problem
    11/14/2022Price change$1,790,000-3.2%$792/sqft
    Source: FLKMLS #602866 Report a problem
    10/25/2022Listed for sale$1,850,000+92.7%$819/sqft
    Source: FLKMLS #602866 Report a problem
    1/21/2021Sold$960,000-8.6%$425/sqft
    Source: FLKMLS #592065 Report a problem
    8/12/2020Listed for sale$1,050,000+89.2%$465/sqft
    Source: Last Key Realty, Inc (KW) #592065 Report a problem
    9/30/2014Sold$555,000-5.1%$246/sqft
    Source: Public Record Report a problem
    9/3/2014Pending sale$585,000$259/sqft
    Source: Prudential Knight & Gardner Realty #120265 Report a problem
    8/25/2014Listed for sale$585,000+48.1%$259/sqft
    Source: Prudential Knight & Gardner Realty Report a problem
    10/25/2009Listing removed$395,000+29.5%$175/sqft
    Source: Coldwell Banker Schmitt #544771 Report a problem
    6/1/2009Sold$305,000-22.8%$135/sqft
    Source: MLKAR #544771 Report a problem
    3/15/2009Listed for sale$395,000-15.8%$175/sqft
    Source: Coldwell Banker Schmitt #544771 Report a problem
    1/17/2009Listing removed$469,000$208/sqft
    Source: NCI #544771 Report a problem
    9/16/2008Listed for sale$469,000-5.8%$208/sqft
    Source: NCI #544771 Report a problem
    8/8/2008Listing removed$498,000$220/sqft
    Source: Coldwell Banker** #544771 Report a problem
    3/16/2008Listed for sale$498,000$220/sqft
    Source: NCI #544771 Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$10,403 -1.9%$1,196,235 -0.4%
    2024$10,608 +7.2%$1,200,464 +10%
    2023$9,891 +14.6%$1,091,331 +10%
    2022$8,634 +42.8%$992,119 +56.8%
    2021$6,047 +7%$632,732 +10%
    2020$5,652 $575,211 +10%
    2019$5,652 +12.4%$522,919 +3.5%
    2018$5,028 +1.3%$505,424 -0.1%
    2017$4,964 -1.7%$505,779 +6.8%
    2016$5,050 +0.8%$473,687 +3.8%
    2015$5,010 $456,508
    Find assessor info on the county website

    Neighborhood: White Street Gallery District

    Nearby schools

    GreatSchools rating
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $1,595,500
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $1,595,500