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$1,725,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 2,440 Sq. Ft.
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Stunning oceanfront home. This 4-bedroom, 3-bathroom home is a testament to coastal architecture. Broad, covered balconies, generous outdoor spaces, and a private boat launch capitalize on Keys waterfront living. Large impact glass doors and windows frame ocean views and invite natural light into every room. Soaring, 26' ceilings enhance the open-concept layout with rich wood beams amplifying the aesthetic. The main floor living space includes a renovated and modern kitchen, dining space, living room, laundry, two bedrooms and two bathrooms. Ascend to the upper floor to find a third bedroom perched at the top of the stairs. A catwalk connects the fourth bedroom with ensuite bath and walkout deck that provides spectacular panoramic open water views. The home itself tells a story through design. Restored to its former glory, with additional modern amenities, and blending rustic accents with open, light-filled spaces to showcase the oceanfront setting. This home needs to be seen to be fully appreciated. Schedule your showing today!

Full Property Details for 22542 Jolly Roger Dr

General

  • Price: $1,725,000
  • Taxes: $12,645 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 619558
  • Updated: 5/23/2026
  • Added to Site: 80 day(s) ago

Interior

  • Interior Features: Entrance Foyer, Walk-in Closet(s), Built-in Cabinets, Cathedral Ceilings, Granite Counter Top, Quartz Countertops
  • Appliances: Stainless Steel Appliance(s), Dishwasher, Dryer, Oven, Refrigerator, Washer, Wine Cooler

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4

Exterior

  • Deck/Patio: Open Porch/Balcony, Deck
  • Porch/Patio/Deck: Open Porch/Balcony, Deck

Parking

  • Parking Features: Open, Off Street, Covered

Location

  • Area: 07 - Cudjoe Key
  • County: Monroe
  • Subdivision: Cutthroat Harbor Est (23.0)

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Central Air

Structural Information

  • Architectural Style: Above Flood
  • Construction Status: Updated/Remodeled
  • Construction: Frame
  • Roof: Metal
  • Windows/Doors: Impact Rstnce Doors, Impact Rstnce Window, Shutters
  • Square Feet: 2,440
  • Sq. Ft. Source: Property Data Card
  • Year Built: 1982
  • Property Condition: Updated/Remodeled

Lot Features

  • Property View: Open Water View, Ocean
  • Lot Size (Acres): 0.15
  • Lot Size (Sq. Ft.): 6,930
  • Lot Size Source: Tax Records
  • Lot Dimensions: x
  • Zoning: IS - Improved Subivision District

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Oceanfront, Open Water

Financial Considerations

  • Tax Amount: $12,645.68
  • Tax Year: 2025

Disclosures and Reports

  • Legal Description: Bk 19 Lt 36 Cutthroat Harbor Estates Cudjoe Key Pb4-165 Or222-580 Or781-1811D/C Or781-1812/14 Or781-1815 Or781-1818/19 O
  • Flood Zone: VE, VE, VE
  • APN: 180480000000

Listed by Coldwell Banker Schmitt Islamorada, Lauren Hoefert Dunn (305) 394-3717 and Coldwell Banker Schmitt Real Estate Co. (KW), Sarah Eckert (772) 501-6576

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Listing agents

— 22542 Jolly Roger Dr —

  • Lauren Hoefert Dunn

    Coldwell Banker Schmitt Islamorada

  • Sarah Eckert

    Coldwell Banker Schmitt Real Estate Co. (KW)

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 22542 Jolly Roger Dr

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Sugarloaf School
255 Crane Boulevard, Summerland Key, FL 33042
PK-83 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-1219.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 22542 Jolly Roger Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/23/2026
Price Reduced
$1,725,000
-9.16%
MLS
4/18/2026
Listed
$1,899,000
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 22542 Jolly Roger Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$12,646
-3%
$1,403,446
-3%
2024
$13,049
67%
$1,447,446
35%
2023
$7,822
12%
$1,075,637
23%
2022
$6,968
7%
$872,378
29%
2021
$6,498
—
$674,986
3%
2021
$6,498
30%
$654,140
24%
2019
$5,014
-4%
$529,526
2%
2018
$5,240
-6%
$517,441
-13%
2017
$5,586
4%
$592,695
8%
2016
$5,387
-7%
$550,241
1%
2015
$5,777
-5%
$542,959
11%
2014
$6,050
4%
$486,997
10%
2013
$5,798
—
$442,725
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 22542 Jolly Roger Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Coldwell Banker Schmitt Islamorada, Lauren Hoefert Dunn (305) 394-3717 and Coldwell Banker Schmitt Real Estate Co. (KW), Sarah Eckert (772) 501-6576

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22542 Jolly Roger Drive, Cudjoe Key, FL 33042 (MLS# 619558) is a Single Family property with 4 bedrooms and 3 full bathrooms. 22542 Jolly Roger Drive is currently listed for $1,725,000 and was received on April 13, 2026. Want to learn more about 22542 Jolly Roger Drive? Do you have questions about finding other Single Family real estate for sale in Cudjoe Key? You can browse all Cudjoe Key real estate or contact a Coldwell Banker agent to request more information.

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