Home in 22542 Jolly Roger Dr Lower Keys for sale with MLS# A11977423

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.

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22542 Jolly Roger Dr, Lower Keys, FL 33042

Price
Price:
$2,100,000.00
Original List Price:
$2,100,000.00
Property Status and Type
Listing Type:
For Sale
Status:
Active
Special Sale Conditions:
Listed As Is
Listing Category:
Residential
Property Type:
Single Family House
MLS Number:
A11977423
Description of Last Important Update:
New Listing
Last Major Update on:
March 5, 2026 3:19 pm
Rooms Distribution
Bedrooms:
4
Bathrooms Total:
3
Full Bath:
3
Measures
Living Area:
2,440 Sqft
Built-Up Area:
13,979 Sqft
Lot Area:
6,930 Sqft
Lot Size Unit:
Square Feet
Lot Features:
Quarter To Half Acre Lot
Property Features
View from the Property:
Ocean
Waterfront:
Yes
Waterfront Features:
Ocean Front
Frontage Length:
120
Appliances:
Dryer, Dishwasher, Refrigerator, Washer, Wine Cooler
Interior:
Walk-In Closet(s), Vaulted Ceiling(s), Entrance Foyer, Built-in Features, French Doors Atrium Doors, Upper Level Primary
Exterior:
Balcony, Porch, Room For Pool, Security High Impact Doors
Patio and Porch:
Balcony, Open, Porch
Doors:
French Doors
Air Conditioning
Air Conditioning System:
Central Air, Ceiling Fan(s)
Heating
Heating System:
Central
Property Entrance Faces:
South
Water Access Description:
Restricted Saltwater Access
Construction
Year Built:
1982
Year Built Details:
Unknown
Roof:
Aluminum
Architectural Style:
Two Story, Detached
Levels:
Two
Construction Materials:
Frame
Flooring:
Vinyl, Laminate
Stories:
2
Taxes and Expenses
Tax Annual Amount:
$12,646.00
Tax Year:
2025
Property Tax Status:
Tax Reflects Homestead Exemption
Parking
Garage Spaces:
0
Carport Spaces:
2
Covered Spaces:
2
Parking Features:
Covered, Guest
Carport
Utilities
Sewer:
Public Sewer
Water Source:
Public
Community
Subdivision Name:
CUTTHROAT HARBOR ESTS
Senior Community:
No
Restrictions:
Other Restrictions
Terms
Disclosures:
Flood Plain Disclosure
Listing Terms Considered by Seller:
Cash, Conventional
Occupant Type:
Owner
Buyer Possession:
Close Of Escrow
Zoning and Legal
Tax 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 OR804-659 OR832-479 O
Real Estate Folio Number (Parcel Number):
00180480-000000
Zoning Description:
is
Listing History
Originally published on:
March 5, 2026 3:19 pm
Active on the market since:
February 25, 2026
Price change occurred on:
March 5, 2026 2:49 pm
Listing Status Last Changed On:
March 5, 2026 3:19 pm
Photos updated on:
March 24, 2026 10:28 pm
Last Modified:
March 29, 2026 4:00 pm
Additional Information
Housing Older Persons Act:
No HOPA
Flood Zone:
VE
Type of Association:
None
Rooms Description:
No Additional Rooms
Style:
WF/Ocean Access
Courtesy of:
Coldwell Banker Schmitt R.E.
Attribution:
Not provided
Location
Street Name:
Jolly Roger Dr
Street Number:
22542
City:
Lower Keys
State:
Florida
Zip Code:
33042
County:
Monroe
Latitude:
N24° 39' 40.9''
Longitude:
W82° 31' 1.9''
Property Map

Neighborhood Stats

Source: U.S. Census Bureau, ACS 5-Year Estimates

Median Household Income $101,625
Median Home Value $759,600
Median Rent $2,252/mo
Median Age 52
Population 6,781

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Association of REALTORS®
Disclaimer: IDX listing information is presented by Rebonus Brokerage LLC for consumer informational purposes only. The information 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. Data is deemed reliable but is not guaranteed by the MLS or the real estate broker. This page presents structured listing information sourced directly from the MLS via the RESO Web API feed. Rebonus prioritizes maximum field coverage and data completeness, displaying the most granular MLS-provided attributes available.