22542 Jolly Roger Drive, Cudjoe Key, FL 33042
$2,100,000
Property Type:
Residential
Bedrooms:
4
Baths:
3
Square Footage:
2,440
Lot Size (sq. ft.):
13,979
Status:
Active
Current Price:
$2,100,000
List Date:
2/26/2026
Last Modified:
3/01/2026
Description
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.
More Information MLS# 618818
Contract Information
Listing Board: Florida Keys
As is Rght to Inspct: Yes
Species List: Yes
Current Price: $2,100,000
Listing Date: 2026-02-25
List Price: $2,100,000
Location, Tax & Legal
City: Cudjoe
Off Shore Island: No
Mile Marker: 23
Marathon Neighborhood: N/A
Side: Ocean
Flood Zone: VE,VE,VE
Alternate Key #: 1232491
Parcel #: 00180480-000000
Add'l Parcel #2: 00180470-000000
Zoning: IS - Improved Subivision District
Deed Restrictions: Unknown
Legal: BK 19 LT 36 CUTTHROAT HARBOR ESTATES CUDJOE KEY PB4-165 OR222-580 OR781-1811D/C OR781-1812/14 OR781-1815 OR781-1818/19 O
Taxes: 12645.68
Tax Year: 2025
Pub Sewer HkUp: Yes
Street #: 22542
Street Name: Jolly Roger
Street Suffix: Drive
Key/Island: Cudjoe Key
State/Province: FL
Zip Code: 33042
County: Monroe
Subdivision: Cutthroat Harbor Est (23.0)
Area: 07 - Cudjoe Key
General Property Description
Realtor.COM Type: Residential - Single Family
Waterfront: Yes
Control Depth: 4
Lot SqFt: 13979
Pool: No
Lot Sqft Source: Tax Records
Total Units: 0
Acres: 0.32
SqFt Source: Property Data Card
Rentals Allowed: With Restrictions
Style: Single Family
Year Built: 1982
Living Apx SqFt: 2440
Total Bedrooms: 4
Full Baths: 3
Total Baths: 3
Remarks & Misc
Remarks – Consumer: 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.
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
Fee Includes
None: 1
Dockage
None: 1
Tax Exemptions
Homestead: 1
Appliances
Dishwasher: 1
Dryer: 1
Oven: 1
Refrigerator: 1
Stainless Steel Appliance(s): 1
Washer: 1
Wine Cooler: 1
Pets
Pets Allowed: 1
Cooling
Central Air: 1
Waterfront
Oceanfront: 1
Open Water: 1
Waterview
Ocean View: 1
Open Water View: 1
Interior Features
Built-in Cabinets: 1
Cathedral Ceilings: 1
Entrance Foyer: 1
Granite Counter Top: 1
Quartz Countertops: 1
Walk-in Closet(s): 1
Property Condition
Updated/Remodeled: 1
Building Style
Above Flood: Yes
Windows/Doors
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
Vehicle Storage
Covered Parking: 1
Open Parking: 1
Off Street Parking: 1
Construction
Frame: 1
Land Size
1/4 - 1/2 Acre: 1
Furnished
Unfurnished: 1
Utilities
FKAA: 1
Porch/Balcony
Deck: 1
Open Porch/Balcony: 1
Title
Title Ins - Buyer: 1
Roof
Metal Roof: 1
Shutters
Bahama: 1
Status Change Info
Status: Active
Property Features
Fee Includes: None
Tax Exemptions: Homestead
Waterfront: Oceanfront; Open Water
Waterview: Ocean View; Open Water View
Dockage: None
Property Condition: Updated/Remodeled
Vehicle Storage: Covered Parking; Off Street Parking; Open Parking
Furnished: Unfurnished
Cooling: Central Air
Utilities: FKAA
Interior Features: Built-in Cabinets; Cathedral Ceilings; Entrance Foyer; Granite Counter Top; Quartz Countertops; Walk-in Closet(s)
Appliances: Dishwasher; Dryer; Oven; Refrigerator; Stainless Steel Appliance(s); Washer; Wine Cooler
Construction: Frame
Shutters: Bahama
Roof: Metal Roof
Pets: Pets Allowed
Land Size: 1/4 - 1/2 Acre
Title: Title Ins - Buyer
Listing Office:
Coldwell Banker Schmitt Islamorada
Last Updated: March - 01 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.
