Skip main navigation
Sold for $4,000,000
  • $4,000,000

    37 Cannon Royal Dr, Key West, FL 33040

    4beds
    3,750sqft
    Single Family Residence
    Built in 1998
    0.35 Acres Lot
    $4,022,600 Zestimate®
    $1,067/sqft
    $6,279 Estimated rent

    Home value

    $4,022,600

    $3.50M - $4.63M

    $6,279/mo

    Zestimate® history
    Loading
    Loading...

    Owner options

    List your home for rent

    $6,279/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

    $6,279/mo

    Rent Zestimate®

    Refinance and save

    $25,468/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

    $25,468/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 dockEn suite bathSerene pool and spaLush tropical landscapeElevated observation deckOpen-concept layoutWaterfront property
    Hidden away in the exclusive enclave of Shark Key, 37 Cannon Royal Drive offers a rare balance of architectural elegance and coastal tranquility. This four-bedroom, four-and-a-half-bath home is perfectly positioned on over third an acre of waterfront property, where walls of glass frame sweeping views of the Gulf and fill the interiors with natural light. Inside, a series of exquisite arches adds a touch of old-world charm and craftsmanship, softening transitions between spaces and lending the home a sense of timeless character. Each bedroom is a private retreat with its own en suite bath, offering comfort and privacy for both residents and guests. The open-concept layout features soaring ceilings and expansive living areas that flow effortlessly to the outdoors. A lush tropical landscape surrounds a serene pool and spa, ideal for relaxing or entertaining. Beyond, an elevated observation deck and private dock extend your living space over the water—perfect for sunset views, paddleboarding, or simply taking in the stillness of the sea. Just minutes from Key West, yet worlds away in atmosphere—this is island living, redefined.

    Zillow last checked:

    Listing updated:

    Listed by:

    Dan R Serban 305-797-2352,

    Key West Luxury Real Estate Inc (KW)

    Bought with:

    Christopher B Santry, 3214474

    Last Key Realty, Inc (KW)

    Source: FLKMLS,MLS#: 614936MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 5
    • Full bathrooms: 4
    • 1/2 bathrooms: 1
    Appliances
    • Included: More Appliances, Dryer, Dishwasher, Refrigerator, Oven, Microwave, Freezer
    Interior area
    • Total structure area: 3,750
    • Total interior livable area: 3,750 sqft

    Property

    Features
    • Has private pool: Yes
    • Pool features: Above Ground, Salt Water, Concrete
    • On waterfront: Yes
    Lot
    • Size: 0.35 Acres
    Details
    • Parcel number: 00159252005600
    • Zoning: SR - Sub Urban Residential District

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence
    Materials
    • CBS, Stucco
    Condition
    • Year built: 1998

    Community & HOA

    Community
    • Subdivision: Shark Key (11.0)
    HOA
    • Has HOA: Yes
    • Services included: Common Area Mnt, Security, Other
    • HOA fee: $1,523 quarterly
    Location
    • Region: Key West

    Financial & listing details

    • Price per square foot: $1,067/sqft
    • Tax assessed value: $3,274,688
    • Annual tax amount: $25,374
    • Date on market: 5/7/2025

    Price history

    DateEventPrice
    10/24/2025Sold$4,000,000-11.1%$1,067/sqft
    Source: FLKMLS #614936 Report a problem
    10/12/2025Contingent$4,500,000$1,200/sqft
    Source: Key West AOR #614936 Report a problem
    9/27/2025Price change$4,500,000-4.2%$1,200/sqft
    Source: FLKMLS #614936 Report a problem
    5/7/2025Listed for sale$4,695,000+73.9%$1,252/sqft
    Source: FLKMLS #614936 Report a problem
    9/11/2019Listing removed$2,700,000$720/sqft
    Source: Keller Williams Key West Compass Realty #586291 Report a problem
    9/11/2019Pending sale$2,700,000+19%$720/sqft
    Source: Keller Williams Key West Compass Realty #586291 Report a problem
    9/10/2019Sold$2,269,635-15.9%$605/sqft
    Source: FLKMLS #586291 Report a problem
    9/4/2019Listed for sale$2,700,000$720/sqft
    Source: Keller Williams Key West Compass Realty #586291 Report a problem
    7/6/2019Pending sale$2,700,000$720/sqft
    Source: Keller Williams Key West Compass Realty #586291 Report a problem
    6/26/2019Listed for sale$2,700,000+1900%$720/sqft
    Source: Keller Williams Key West Compass Realty #586291 Report a problem
    4/26/1996Sold$135,000$36/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$26,121 +2.9%$2,790,692 +10%
    2024$25,374 +11%$2,536,993 +10%
    2023$22,850 +11.7%$2,306,357 +10%
    2022$20,452 +20.2%$2,096,688 +15.2%
    2021$17,017 -4%$1,820,438 -3.1%
    2020$17,721 $1,878,263 +84.9%
    2019$17,721 +82.6%$1,016,015 -26.8%
    2018$9,704 -30.3%$1,388,758 +42.2%
    2017$13,915 +46.3%$976,564 +2.1%
    2016$9,510 -0.8%$956,478 +0.7%
    2015$9,586 $949,829
    Find assessor info on the county website

    Neighborhood: 33040

    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
    $4,022,600
    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
    $4,022,600