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22542 Jolly Roger Drive, 
Cudjoe, FL 33042

$2,100,000


4

Beds


3

Baths


2,440

Sq Ft


Single Family

Active

Listed by

Lauren Hoefert Dunn

Sarah Eckert

Coldwell Banker Schmitt Islamorada

305-664-4470

Last updated:

March 11, 2026, 02:29 PM

MLS#

618818

Source:

FL FKBOR

About This Home

22542 Jolly Roger Drive

This striking 4-bedroom, 3-bathroom home is a testament to coastal architecture, blending rustic design with open, light-filled living spaces to showcase a breathtaking oceanfront setting. Situated on a double lot, totaling .32 acres, the property offers an impressive 120 feet of frontage overlooking Cudjoe Bay -- a rare and commanding presence along the shoreline. Broad, covered balconies, generous outdoor spaces, and a private boat launch capitalize on Keys waterfront living, while large impact glass doors and windows frame sweeping ocean views and invite natural light into every room. Soaring ceilings enhance the open-concept layout with dark wood beams amplifying the impact. The main floor living space includes a fully renovated kitchen, dining space, capacious living room, laundry, two bedrooms and two bathrooms. Ascend to the top 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 the home's optimal panoramic views. The home itself tells a story through design; masterfully blending opposites in a way to complement each other: masculine and feminine, modern lines and traditional warmth, cozy intimacy within spacious rooms. The thoughtful juxtaposition and melding of these elements transform the residence into a statement of artistic expression. Whimsical, eclectic touches are paired with bold architectural features, creating visual intrigue throughout.

Home Facts

Single Family

3 Baths

4 Bedrooms

Built in 1982

Price Summary

2,100,000

$860 per Sq. Ft.

MLS #:

618818

Last Updated:

March 11, 2026, 02:29 PM


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

3

Interior

Living Area:

2,440 Sq. Ft.


Structure

Structure

Architectural Style:

Single Family

Building Area:

2,440 Sq. Ft.

Year Built:

1982


Lot

Lot Size (Sq. Ft):

13,939


Finances & Disclosures

Finances

Price:

$2,100,000

Price per Sq. Ft:

$860 per Sq. Ft.

Source:FL FKBOR
The information being provided by Florida Keys Board Of REALTORS®, Inc. is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Florida Keys Board Of REALTORS®, Inc. All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.