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$2,000,000
22542 Jolly Roger Drive
Cudjoe Key, FL 33042
MLS# 618818
Status: Closed
4 beds  |  3 baths  |  2440 sqft


09 Land and Water
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09 Land and Water 60 Bedroom 4 26 Open Floor Plan 27 Dine with a view 64 Ocean Views 13 Space 23 Foyer 04 Cudjoe 05 Double Lot 07 Ocean 10 Room for a Pool 11 12 16 Home 18 Beach 20-DSC00857 21 Foyer 24 Stairs 25 Interior Staircase 28 Open Floor Plan 30 Living Room 31 Updated Kitchen 32 Updated Kitchen 65 Deck with a View 66 Large Covered Porch 35 36 Bathroom 1 37 Bathroom 1 45 Bedroom 1 46 Bedroom 1 47 Large Closet 1 39 Bathroom 2 40 Bathroom 2 41 Bedroom 2 42 Bedroom 2 43 Laundry 49 Stairs to Top 50 Bedroom 3 52 Bedroom 3 53 54 Catwalk 56 Catwalk 57 Bathroom 3 58 Bathroom 3 59 Bedroom 4 61 Bedroom 4 62 Top Porch 67 Direct Water Access 12 Twilight Floor Plan

Property Description
FULLY RESTORED! This 4-bedroom, 3-bathroom home is a testament to coastal architecture. 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 on the shoreline. 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!

Details
Maps
Contract Information
Current Price: $2,000,000
Listing Date: 2026-02-25
Listing Board: Florida Keys
Leased Price Monthly: $2,000,000
As is Rght to Inspct: Yes
Species List: Yes
Location, Tax & Legal
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
Style: Single Family
Waterfront: Yes
Control Depth: 4
Pool: No
Year Built: 1982
Lot SqFt: 13979
Lot Sqft Source: Tax Records
Acres: 0.32
Living Apx SqFt: 2440
SqFt Source: Property Data Card
Total Bedrooms: 4
Full Baths: 3
Total Baths: 3
Rentals Allowed: With Restrictions
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Building Style
Above Flood: Yes
Status Change Info
Under Contract Date: 2026-09-22
Leased Date: 2026-10-13
Leased Price Monthly: $2,000,000
Status: Closed
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: October - 13 - 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.