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.
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.
Property Details
Price:
$2,100,000
MLS #:
A11977423
Status:
Active
Beds:
4
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
CUTTHROAT HARBOR ESTS
Neighborhood:
cutthroatharborests
Listed Date:
Feb 25, 2026
Finished Sq Ft:
2,440
Total Sq Ft:
13,979
Year Built:
1982
See this Listing
Schools
Interior
Appliances
Dishwasher, Dryer, Refrigerator, Washer
Bathrooms
3 Full Bathrooms
Cooling
Ceiling Fan(s), Central Air
Flooring
Vinyl
Heating
Central
Interior Features
Built-in Features, Entrance Foyer, French Doors, Vaulted Ceiling(s), Walk-In Closet(s), No Additional Rooms
Exterior
Architectural Style
Detached, Two Story
Community Features
None
Construction Materials
Frame
Covered Spaces
2
Direction Faces
South
Exterior Features
Open Balcony, Room For Pool
Lot Features
1/4 To Less Than 1/2 Acre Lot
Parking Features
Covered, Guest
Patio And Porch Features
Open Balcony, Open Porch
Roof
Aluminum
View
Direct Ocean
Waterfront Features
WF/Ocean Access, Ocean Front
Financial
Tax Year
2025
Taxes
$12,646
Map
Community
- Address22542 Jolly Roger Dr Lower Keys FL
- SubdivisionCUTTHROAT HARBOR ESTS
- CityLower Keys
- CountyMonroe County
- Zip Code33042
Subdivisions in Lower Keys
Market Summary
Current real estate data for Single Family in Lower Keys as of May 01, 2026
6
Single Family Listed
130
Avg DOM
710
Avg $ / SqFt
$1,063,333
Avg List Price
Property Summary
- Located in the CUTTHROAT HARBOR ESTS subdivision, 22542 Jolly Roger Dr Lower Keys FL is a Single Family for sale in Lower Keys, FL, 33042. It is listed for $2,100,000 and features 4 beds, 3 baths, and has approximately 2,440 square feet of living space, and was originally constructed in 1982. The current price per square foot is $861. The average price per square foot for Single Family listings in Lower Keys is $710. The average listing price for Single Family in Lower Keys is $1,063,333. To schedule a showing of MLS#a11977423 at 22542 Jolly Roger Dr in Lower Keys, FL, contact your CENTURY 21 Carioti agent at 2392986550.
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