Skip main navigation
Sold for $2,025,000
  • $2,025,000

    22440 Jolly Roger Dr, Cudjoe Key, FL 33042

    2beds
    1,292sqft
    Single Family Residence
    Built in 1988
    9,583 Square Feet Lot
    $2,029,500 Zestimate®
    $1,567/sqft
    $5,480 Estimated rent

    Home value

    $2,029,500

    $1.77M - $2.33M

    $5,480/mo

    Zestimate® history
    Loading
    Loading...

    Owner options

    List your home for rent

    $5,480/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

    $5,480/mo

    Rent Zestimate®

    Refinance and save

    $12,034/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

    $12,034/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

    Modern eleganceHeated poolSouth west exposureQuartz countertopsZero-grout tiled walk-around porchCozy lounge areasModern blue cabinets
    Experience the epitome of Florida Keys living in this stunning luxury waterfront home on Cudjoe Key. The back of the home has a South West Exposure, for endless ocean views and spectacular nightly sunsets. Constructed with poured concrete for unmatched durability and featuring a poured concrete floor, this home is a sanctuary of modern design and functionality. The property boasts impact-rated windows and doors installed in 2016, including custom 5-panel EuroWall stacking doors that create a seamless indoor-outdoor flow. Modern elegance is evident throughout, with stainless cable railings and a zero-grout tiled walk-around porch. Offered furnished with Restoration Hardware and Room & Board pieces valued at approximately $45,000 (art excluded), also includes TVs.The outdoor spaces feature a heated pool featuring a Coralina stone deck sourced from the Dominican Republic, designed to stay cool underfoot. New pool equipment, including a heater and pump installed in 2018. Boating enthusiasts will appreciate the 21.5' wood dock with a Slide-Moor Dock system, complete with water access, as well as a floating dock system perfect for kayaking and paddleboarding. The property's tropical landscaping, accented with solar yard lighting & cozy lounge areas create wonderful, private space to enjoy serenity or entertain guests.The gourmet kitchen, updated in 2022, features quartz countertops, modern blue cabinets, and Samsung Bespoke appliances. Don't miss your chance to own this luxury retreat in the heart of Cudjoe Key. Just 22 miles to Key West and 3 hours from Miami. Fantastic bar/ restaurant/ and coffee shop within walking distance!

    Zillow last checked:

    Listing updated:

    Listed by:

    Sandra Tuttle 305-923-9161,

    Island Welcome Real Estate

    Bought with:

    Susan Hawkinson, 3597394

    Bascom Grooms Real Estate (KW)

    Source: FLKMLS,MLS#: 613293MLS LogoOriginating MLS: Marathon/Lower Keys

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 2
    • Bathrooms: 2
    • Full bathrooms: 2
    Heating
    • Electric, Heat Pump
    Cooling
    • Central Air, Ductless, Ceiling Fans(s), Heat Pump
    Appliances
    • Included: Washer, Microwave, Range, Refrigerator, Dishwasher, Dryer
    Features
    • Quartz Countertops, Storage
    • Flooring: Laminate
    • Doors: Impact Rstnce Doors
    • Windows: Window Treatments, Impact Rstnce Window
    • Furnished: Yes
    Interior area
    • Total interior livable area: 1,292 sqft

    Property

    Parking
    • Total spaces: 4
    • Parking features: Open
    • Has uncovered spaces: Yes
    Features
    • Patio & porch: Open Porch/Balcony, Screened Patio
    • Exterior features: Lighting, Storage
    • Has private pool: Yes
    • Pool features: Heated, In Ground, Decked, Concrete
    • Has view: Yes
    • View description: Ocean, Water
    • Has water view: Yes
    • Water view: Ocean,Water
    • Waterfront features: Oceanfront, Open Water, Waterfront, Dock: Wood, Dock Length: 22, Dockage: Other Dockage
    Lot
    • Size: 9,583 Square Feet
    • Dimensions: 80 x 120
    • Features: Less Than 1/4 Acre
    Details
    • Parcel number: 00180560
    • Zoning: IS
    • Zoning description: Improved Subivision District

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence
    Materials
    • CBS, Concrete
    • Roof: Metal
    Condition
    • Updated/Remodeled
    • New construction: No
    • Year built: 1988

    Utilities & green energy

    • Sewer: Municipal Sewer, Public Sewer
    • Utilities for property: FKAA, Cable Available, Cable Connected
    Green energy
    • Water conservation: Dual Flush

    Community & HOA

    Community
    • Security: Smoke Detector(s)
    • Subdivision: Cutthroat Harbor Est (23.0)
    HOA
    • Has HOA: No
    • Services included: None
    Location
    • Region: Cudjoe Key

    Financial & listing details

    • Price per square foot: $1,567/sqft
    • Tax assessed value: $1,700,765
    • Annual tax amount: $13,018
    • Date on market: 1/23/2025
    • Listing terms: Assumable,FHA,VA Loan,Conventional,Cash

    Price history

    DateEventPrice
    5/13/2025Sold$2,025,000-7.7%$1,567/sqft
    Source: FLKMLS #613293 Report a problem
    4/21/2025Contingent$2,195,000$1,699/sqft
    Source: Key West AOR #613293 Report a problem
    2/18/2025Price change$2,195,000-4.4%$1,699/sqft
    Source: FLKMLS #613293 Report a problem
    1/23/2025Listed for sale$2,295,000+206%$1,776/sqft
    Source: Key West AOR #613293 Report a problem
    9/25/2015Sold$750,000-6.1%$580/sqft
    Source: MLKAR #566713 Report a problem
    7/23/2015Pending sale$799,000$618/sqft
    Source: Coldwell Banker Schmitt Real Estate Co. #566713 Report a problem
    6/4/2015Price change$799,000-4.8%$618/sqft
    Source: Coldwell Banker Schmitt Real Estate Co. #566713 Report a problem
    4/16/2015Price change$839,000-2.1%$649/sqft
    Source: Coldwell Banker Schmitt Real Estate Co. #566713 Report a problem
    3/27/2015Price change$857,000-1.4%$663/sqft
    Source: Coldwell Banker Schmitt Real Estate Co. #566713 Report a problem
    2/17/2015Listed for sale$869,000+194.6%$673/sqft
    Source: Coldwell Banker Schmitt Real Estate Co #566713 Report a problem
    11/26/1997Sold$295,000$228/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$13,975 +7.3%$1,557,230 +4.8%
    2024$13,019 +18.9%$1,485,358 +54.3%
    2023$10,949 +18.8%$962,830 +10%
    2022$9,219 +15.6%$875,300 +10%
    2021$7,973 -1%$795,727 -0.2%
    2020$8,057 $797,038 +1.6%
    2019$8,057 +2.4%$784,541 +12.4%
    2018$7,870 +7%$697,841 -1%
    2017$7,354 +1.7%$705,074 +13.5%
    2016$7,228 +7.1%$621,181 +42.2%
    2015$6,747 $436,726
    Find assessor info on the county website

    Neighborhood: 33042

    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
    $2,029,500
    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
    $2,029,500