Home in 22777 Jolly Roger Dr. Cudjoe Key for sale with MLS# G5109518

Stop dreaming and start packing. This rare canal-front gem features a 2.75 assumable mortgage for qualified buyers-a game-changer in today's market! Situated on a massive, double-fenced corner lot, this 3-bed, 2-bath home is the ultimate playground. There is enough room to park all your toys, boats, cars, and RV. Your 4-legged family members will love their own large yard. With no HOA, you even have ample space for a chicken coop. A large saltwater pool is perfect for soaking up the sun and enjoying a peaceful afternoon. There is a bonus room for an office or a Zen den. Roof is 2018. In addition, Lot 2, part of the property, includes a potential buildable lot, a rare opportunity to have a second residence, guest house or future income producing home. A significant long term value! This Jolly Roger can be your own slice of paradise, come soak up the sun!

📅 View days on the market

Days on the market

22777 Jolly Roger Dr., Cudjoe Key, FL 33042

Price
Price:
$1,350,000.00
Original List Price:
$1,350,000.00
List Price per Sq Ft (Calculated, Approx.):
$907.26
Property Status and Type
Listing Type:
For Sale
Status:
Active
Listing Category:
Residential
Property Type:
Single Family House
MLS Number:
G5109518
Rooms Distribution
Bedrooms:
3
Bathrooms Total:
2
Full Bath:
2
Additional Rooms:
Bonus Room
Measures
Living Area:
1,488 Sqft
Built-Up Area:
1,488 Sqft
Lot Area:
16,500 Sqft
Building Area Source:
Public Records
Living Area Source:
Owner
Additional Parcels
Lot Features:
Corner Lot, Oversized Lot, Floodzone, Paved, Level, Private, Flood Insurance Required, Landscaped
Lot Size Acres:
0.38
Property Features
View from the Property:
Pool, Water
Waterfront:
Yes
Waterfront Features:
Canal - Saltwater
Private Pool
Swimming Pool Features:
Fiberglass, In Ground, Salt Water, Lighting, Auto Cleaner, Chlorine Free
Furnished:
Unfurnished
Appliances:
Dishwasher, Microwave, Refrigerator, Electric Water Heater, Range
Interior:
Eat-in Kitchen, Ceiling Fans(s), Kitchen/family Room Combo, Living Room/dining Room Combo, Open Floorplan, Thermostat, Primary Bedroom Main Floor, Primarybedroom Upstairs
Exterior:
Balcony, Outdoor Shower, French Doors, Hurricane Shutters, Storage, Private Yard, Private Entrance
Patio and Porch:
Patio, Screened, Covered, Rear Porch
Windows:
Blinds, Shutters, Aluminum Frames
Other Structures:
Shed(s)
Laundry:
Washer Hookup, Electric Dryer Hookup
Air Conditioning System:
Central Air, Wall/window Unit(s), Mini-split Unit(s)
Heating System:
Central, Electric, Heat Pump, Ductless
Fence:
Chain Link
Vegetation and Trees:
Trees/landscaped, Fruit Trees
Property Entrance Faces:
Southwest
Road Responsibility:
Public Maintained Road
Other Equipment:
Private Entrance, Private Yard
Disaster Mitigation:
Hurricane Shutters/windows, Fire/smoke Detection Integration
Water Access
Water Access Features:
Canal - Saltwater
Water Extras
Water Extra Details:
Seawall - Other
Water View
Water View Details:
Gulf/ocean - Partial, Canal
Construction
Year Built:
1974
Roof:
Metal
Architectural Style:
Florida
Levels:
Two
Construction Materials:
Block, Concrete
Flooring:
Tile
Number of stories:
2
Foundation Details:
Block, Concrete Perimeter
Flood Zone Code:
VE
Taxes and Expenses
Tax Annual Amount:
$7,936.76
Tax Year:
2025
Parking
Parking Features:
Guest, Parking Pad, Rv Access/parking, Boat
Utilities
Sewer:
Public Sewer
Utilities Available:
Electricity Connected, Fire Hydrant, Sewer Connected, Water Connected, Public, Propane, Fiber Optics
Water Source:
Public
Community
Minimum Lease Term:
1-7 Days
Pets Allowed?
Number of Pets Allowed:
10
Subdivision Name:
CUTTHROAT HARBOR ESTATES
Community Features:
Street Lights
Senior Community:
No
Terms
Listing Terms Considered by Seller:
Conventional, Assumable (The financing currently in place may be assumed)
Occupant Type:
Vacant
Buyer Possession:
Close Of Escrow
Lease Considered:
Yes
Zoning and Legal
Tax Legal Description:
BK 18 LTS 1 AND 2 CUTTHROAT HARBOR ESTATES PB4-165 CUDJOE KEY OR204-197 OR522-953 OR549-402C OR710-31 OR787-1326 OR1072-1871R/S OR1442-304/05 OR1442-306/07 OR1551-1793/94 OR1789-941 OR1794-1569 OR2162-727 OR2162-728/29TR OR2986-2217COV OR2987-1464 OR 2987-1473
Real Estate Folio Number (Parcel Number):
00179990-000000
Zoning:
IS
Title to the property is held by owner as:
Fee Simple
Listing History
Originally published on:
March 13, 2026 12:14 pm
Active on the market since:
March 13, 2026
Listing Agreement executed on:
March 13, 2026
Listing Status Last Changed On:
March 13, 2026 12:14 pm
Photos updated on:
April 6, 2026 2:39 pm
Last Modified:
April 6, 2026 2:39 pm
Additional Information
Courtesy of:
GARRISON REALTY GROUP LLC
Attribution:
352-805-5550
Road Surface Type:
Asphalt
Location
Street Name:
JOLLY ROGER DR.
Street Number:
22777
City:
CUDJOE KEY
State:
Florida
Zip Code:
33042
County:
Monroe
Latitude:
N24° 39' 37.4''
Longitude:
W82° 31' 14.7''
Property Map

Neighborhood Stats

Source: U.S. Census Bureau, ACS 5-Year Estimates

Median Household Income $101,625
Median Home Value $759,600
Median Rent $2,252/mo
Median Age 52
Population 6,781

Want to schedule an in-person or virtual tour? Have questions?

Want to schedule an in-person or virtual tour? Have questions?
Schedule a Tour or Ask a Question


Mortgage Calculator

Please note: Monthly HOA / Condo Fees Not Included. The calculator shows the listing price as home value. Update all fields at your convenience.

Calculate Your Mortgage Payment

$.00
$.00
6.5
30

Taxes and Insurance

$.00
$.00
%

Financial Analysis

%

%

$

$

$

$

$
Ver la Propiedad Ver la propiedad 22777 Jolly Roger Dr.
Association of REALTORS®
Disclaimer: IDX listing information is presented by Rebonus Brokerage LLC for consumer informational purposes only. Listings courtesy of Stellar MLS, as distributed by MLS GRID. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House information, if any, is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office or agent presenting the information. The data is deemed reliable but is not guaranteed by MLS GRID. Use of MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS and as amended from time to time. Some IDX listings have been excluded from this website. This page presents structured listing information sourced directly from the MLS via the RESO Web API feed. Rebonus prioritizes maximum field coverage and data completeness, displaying the most granular MLS-provided attributes available. Based on information submitted to MLS GRID as of April 6, 2026, 2:39 PM.