About 22542 Jolly Roger Drive
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!
Features of 22542 Jolly Roger Drive
| MLS® # | 619558 |
|---|---|
| Price | $1,725,000 |
| Bedrooms | 4 |
| Bathrooms | 3.00 |
| Full Baths | 3 |
| Square Footage | 2,440 |
| Acres | 0.15 |
| Year Built | 1982 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Status | Active |
Community Information
| Address | 22542 Jolly Roger Drive |
|---|---|
| Area | 07 - Cudjoe Key |
| Subdivision | Cutthroat Harbor Est (23.0) |
| City | Cudjoe Key |
| County | Monroe |
| State | FL |
| Zip Code | 33042 |
Amenities
| Utilities | FKAA |
|---|---|
| Parking | Open Parking, Off Street Parking, Covered Parking |
| View | Ocean View, Open Water View |
| Is Waterfront | Yes |
| Waterfront | Oceanfront, Open Water |
| Has Pool | No |
Interior
| Interior Features | Cathedral Ceilings, Entrance Foyer, Built-in Cabinets, Granite Counter Top, Walk-in Closet(s), Quartz Countertops |
|---|---|
| Appliances | Washer, Dryer, Dishwasher, Refrigerator, Oven, Wine Cooler, Stainless Steel Appliance(s) |
| Cooling | Central Air |
| Fireplace | No |
| Has Basement | No |
Exterior
| Lot Description | 1/4 - 1/2 Acre |
|---|---|
| Windows | Impact Rstnce Window, Impact Rstnce Doors |
| Roof | Metal Roof |
| Construction | Frame |
Additional Information
| Date Listed | April 13th, 2026 |
|---|---|
| Days on Market | 40 |
| Zoning | IS - Improved Subivision District |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Agent | Lauren Hoefert Dunn |
|---|---|
| Office | Coldwell Banker Schmitt Islamorada |