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: 3/30/2026

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!

More Information MLS# 618818

Contract Information

Current Price: $2,100,000 Listing Date: 2026-02-25 Listing Board: Florida Keys List Price: $2,100,000 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

Status Change Info

Status: Active

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No

Building Style

Above Flood: Yes

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 - 30 - 2026
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