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

22542 Jolly Roger Drive, Cudjoe Key, FL 33042

$1,899,000

Property Type: Residential Bedrooms: 4 Baths: 3 Square Footage: 2,440 Lot Size (sq. ft.): 6,930 Status: Active

Current Price: $1,899,000 List Date: 4/18/2026 Last Modified: 4/20/2026

Overview

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 ... (Read more)

Listing Details MLS# 619558

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
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

Contract Information

Listing Board: Florida Keys
As is Rght to Inspct: Yes
Species List: Yes

General Property Description

Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 4
Pool: No
Year Built: 1982
Lot SqFt: 6930
Lot Sqft Source: Tax Records
Acres: 0.15
Living Apx SqFt: 2440
SqFt Source: Property Data Card
Total Bedrooms: 4
Full Baths: 3
Total Baths: 3
Rentals Allowed: With Restrictions
Total Units: 0

Association Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0

Building Style

Above Flood: Yes

More Information

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!

Fee Includes

None: Yes

Dockage

None: Yes

Tax Exemptions

Homestead: Yes

Appliances

Dishwasher: Yes
Dryer: Yes
Oven: Yes
Refrigerator: Yes
Stainless Steel Appliance(s): Yes
Washer: Yes
Wine Cooler: Yes

Pets

Pets Allowed: Yes

Cooling

Central Air: Yes

Waterfront

Oceanfront: Yes
Open Water: Yes

Waterview

Ocean View: Yes
Open Water View: Yes

Interior Features

Built-in Cabinets: Yes
Cathedral Ceilings: Yes
Entrance Foyer: Yes
Granite Counter Top: Yes
Quartz Countertops: Yes
Walk-in Closet(s): Yes

Property Condition

Updated/Remodeled: Yes

Windows/Doors

Impact Rstnce Doors: Yes
Impact Rstnce Window: Yes

Vehicle Storage

Covered Parking: Yes
Open Parking: Yes
Off Street Parking: Yes

Construction

Frame: Yes

Land Size

1/4 - 1/2 Acre: Yes

Furnished

Unfurnished: Yes

Utilities

FKAA: Yes

Porch/Balcony

Deck: Yes
Open Porch/Balcony: Yes

Title

Title Ins - Buyer: Yes

Roof

Metal Roof: Yes

Shutters

Bahama: 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: April - 20 - 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.

Search