• Home
  • 22542 Jolly Roger Drive, Cudjoe Key, FL 33042 (MLS# 619558)

22542 Jolly Roger Drive, Cudjoe Key, FL 33042

New Listing
$1,899,000
Property Type: Residential Bedrooms: 3 Baths: 4 Square Footage: 2,440 Lot Size (sq. ft.): 6,930 Status: Active
Current Price: $1,899,000 List Date: 4/18/2026 Last Modified: 4/18/2026

Description

Stunning oceanfront home. This 4-bedroom, 3-bathroom home is a testament to coastal architecture. 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# 619558

Contract Information

Listing Board: Florida Keys As is Rght to Inspct: Yes Species List: Yes Current Price: $1,899,000 Listing Date: 2026-04-13 List Price: $1,899,000

Location, Tax & Legal

City: Cudjoe Mile Marker: 23 Marathon Neighborhood: N/A Side: Ocean Flood Zone: VE,VE,VE Alternate Key #: 1232491 Parcel #: 00180480000000 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 Size: X Lot SqFt: 6930 Pool: No Lot Sqft Source: Tax Records Total Units: 0 Acres: 0.15 SqFt Source: Property Data Card Rentals Allowed: With Restrictions Style: Single Family Year Built: 1982 Living Apx SqFt: 2440 Total Bedrooms: 3 Full Baths: 4 Total Baths: 4

Remarks & Misc

Remarks – Consumer: Stunning oceanfront home. This 4-bedroom, 3-bathroom home is a testament to coastal architecture. 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!

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: April - 18 - 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.

Let’s Connect

      Sign Up for Listing Alerts