22542 Jolly Roger Drive, Cudjoe Key, FL 33042

New Listing
$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

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 - 01 - 2026
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