- MLS® #: A11977423
- 22542 Jolly Roger Dr
- Lower Keys, FL 33042-4238
- $2,100,000
- 4 Beds, 3 Bath, 2,440 SqFt
- Residential
This striking 4-bedroom, 3-bathroom home is a testament to coastal architecture, blending rustic design with open, light-filled living spaces that 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—creating a rare and commanding presence along the shoreline. Broad covered balconies and generous outdoor living spaces capture the essence of Keys waterfront living, while large impact glass doors and windows frame sweeping ocean views and invite natural light throughout. Soaring ceilings with dark wood beams enhance the open-concept layout and add dramatic architectural character. The main living level features a fully renovated kitchen, dining area, expansive living room, laundry, two bedrooms, and two bathrooms. Upstairs, a third bedroom sits at the top of the stairs, while a catwalk leads to the fourth bedroom with an ensuite bath and walkout deck positioned to capture the home’s most spectacular panoramic views. Throughout the residence, thoughtful design blends contrasts—modern lines with traditional warmth, cozy intimacy within spacious rooms. Whimsical and eclectic touches pair with bold architectural elements, creating a home that feels both artistic and inviting while celebrating its extraordinary oceanfront setting.
View Virtual TourEssential Information
- MLS® #A11977423
- Price$2,100,000
- CAD Dollar$2,928,765
- UK Pound£1,590,668
- Euro€1,822,838
- Bedrooms4
- Bathrooms3.00
- Full Baths3
- Square Footage2,440
- Year Built1982
- TypeResidential
- Sub-TypeSingle Family Residence
- StyleDetached, Two Story
- StatusActive
Community Information
- Address22542 Jolly Roger Dr
- Area98 Florida Keys
- SubdivisionCUTTHROAT HARBOR ESTS
- CityLower Keys
- CountyMonroe
- StateFL
- Zip Code33042-4238
Amenities
- Parking Spaces2
- ParkingCovered, Guest
- ViewOcean
- Is WaterfrontYes
- WaterfrontOcean Front
Interior
- InteriorLaminate, Vinyl
- HeatingCentral
- CoolingCentral Air, Ceiling Fan(s)
- # of Stories2
- StoriesTwo
Interior Features
Built-in Features, Entrance Foyer, French Door(s)/Atrium Door(s), Upper Level Primary, Vaulted Ceiling(s), Walk-In Closet(s)
Appliances
Dryer, Dishwasher, Refrigerator, Wine Cooler, Washer
Exterior
- RoofAluminum
- ConstructionFrame
Exterior Features
Balcony, Security/High Impact Doors, Porch, Room For Pool
- Office: Coldwell Banker Schmitt R.e.
22542 Jolly Roger Dr on www.jupiteroceanfronthomes.us
Offered at the current list price of $2,100,000, this home for sale at 22542 Jolly Roger Dr features 4 bedrooms and 3 bathrooms. This real estate listing is located in CUTTHROAT HARBOR ESTS of Lower Keys, FL 33042-4238 and is approximately 2,440 square feet. 22542 Jolly Roger Dr is listed under the MLS ID of A11977423 and has been on the Lower Keys real estate market for 38 days.The data relating to real estate on this web site comes in part from the Internet Data Exchange program of the MLS of the REALTOR® Association of Greater Miami and the Beaches, and is updated as of April 4th, 2026 at 2:48pm CDT (date/time).
All information is deemed reliable but not guaranteed by the MLS and should be independently verified. All properties are subject to prior sale, change, or withdrawal. Neither listing broker(s) nor Waterfront Properties and Club Communities shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless from any damages arising from reliance upon these data. © 2026 MLS of RAMB.
The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing