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

22542 Jolly Roger Drive, Cudjoe Key, FL 33042

$1,725,000
Property Type: Residential Bedrooms: 4 Baths: 3 Square Footage: 2,440 Lot Size (sq. ft.): 6,930 Status: Contingent
Current Price: $1,725,000 List Date: 4/18/2026 Last Modified: 9/22/2026

Overview

Description

Oceanfront living on Cudjoe Key, where broad covered balconies, generous outdoor space, and a private boat launch put Keys waterfront life within reach. This four-bedroom, three-bath home is a study in coastal architecture -- large impact glass doors and windows frame open water views and pull natural light into every room. Soaring 26' ceilings and rich wood beams anchor the open-concept main level, which includes a renovated kitchen, dining space, living room, laundry, and two bedrooms with two full baths. Upstairs, a third bedroom sits at the top of the stairs, and a catwalk leads to the fourth bedroom with ensuite bath and a walkout deck framing panoramic open water views. The home has been restored to its former glory with modern updates layered in -- rustic accents meet open, light-filled spaces that let the oceanfront setting do the talking. Adjacent lot also available for even more ocean enjoyment. Seller financing available: 50% down, 6% for 15 years, no flood or wind in ...

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

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

Status Change Info

Contingent
Contingent

Association Info

Mandatory Home Owners Asc
No
1st Right of Refusal
No

Building Style

Above Flood
Yes

More Information

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: September - 22 - 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.
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