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22777 JOLLY ROGER DR. CUDJOE KEY FL 33042

$1,350,000
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22777 JOLLY ROGER DR., CUDJOE KEY, FL 33042 - MLS#MFRG5109518 22777 JOLLY ROGER DR., CUDJOE KEY, FL 33042 - MLS#MFRG5109518 22777 JOLLY ROGER DR., CUDJOE KEY, FL 33042 - MLS#MFRG5109518 22777 JOLLY ROGER DR., CUDJOE KEY, FL 33042 - MLS#MFRG5109518

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
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Overview of 22777 Jolly Roger Dr.

3 Bedrooms
2 Bathrooms
Car Garage
1,488 Square Feet
1,488SF Living Area
Pool:
Yes
Water
Year Built 1974
Listed For 0 Days

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!

This luxury single family home was built in 1974 and features 3 bedrooms, and 2 full bathrooms. This home for sale is 1,488 square feet, with 1,488 sq ft being air conditioned living space. The home has a has a private swimming pool.

Directions to this property are as follows: U.s. 1 Mile Marker 23 Cudjoe Key, Turn Into Cutthroat Dr., First Right Is 22777 Jolly Roger Dr.

Please contact your ZFC agent for more information about MLS# MFRG5109518 or any other homes for sale in Cudjoe Key or elsewhere in the Monroe County area.

Features & Amenities

Appliances

Dishwasher, Electric Water Heater, Microwave, Range, Refrigerator

Other Equipment

Private Entrance, Private Yard

Architecture

Florida

Cooling

Central Air, Mini-Split Unit(s), Wall/Window Unit(s)

Heating

Central, Electric, Heat Pump, Ductless

Flooring

Tile

Parking

Boat, Guest, Parking Pad, R V Access/Parking

Lot Size

16500

View

Pool, Water view

Construction Materials

Block, Concrete

Interior Features

Ceiling Fans(s), Eat-in Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Primary Bedroom Upstairs, Thermostat

Furnished

Unfurnished

Exterior Features

Balcony, French Doors, Hurricane Shutters, Outdoor Shower, Private Entrance, Private Yard, Storage

Lot Features

Corner Lot, Flood Insurance Required, Flood Zone, Landscaped, Level, Oversized Lot, Private, Paved

Patio And Porch Features

Covered, Patio, Rear Porch, Screened

Pool Features

Auto Cleaner, Chlorine Free, Fiberglass, In Ground, Lighting, Salt Water

Roof

Metal

Window Features

Aluminum Frames, Blinds, Shutters

Utilities

Electricity Connected, Fiber Optics, Fire Hydrant, Propane, Public, Sewer Connected, Water Connected

Waterfront Features

Canal-Saltwater

Water Body Name

A T L A N T I C O C E A N F R O M C U D J O E B A Y

Laundry

Electric Dryer Hookup, Washer Hookup

Fencing

Chain Link

Zoning

I S

Year Built

1974

Pets Allowed

Yes

Annual Real Estate Taxes

$7,937 (2025)

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

Property Type

Single Family Home

Other Structures

Shed(s)

Community Features

Street Lights

Direction Faces

Southwest

MLS Number

MFRG5109518

Universal Property Id

U S-12087-N-00179990000000-R-N

Community Name

Cutthroat Harbor Estates

22777 Jolly Roger Dr. Price Calculator

Get Mortgage Quote For This Home

The payment calculator figures for 22777 Jolly Roger Dr. should be used as an estimate only. Loan terms including interest rate, and required downpayment will vary with each lender and/or individual. RE taxes for this home for sale are estimated based on the actual property taxes for this property for the tax year 2025 which are $7,937 but will likely change when this home sells. These estimations are calculated from a list price of $1,350,000 and a 25% down payment and do not include homeowners insurance which will vary greatly depending on the home characteristics and location.

Recent Home Sales near 22777 Jolly Roger Dr.

Address Sale Price Bed Bth Size Location Sale Date
260 Airport Dr S $Log in to view 2 2/0 1,200SF Summerland Key Cove Add # 08/04/2025

MLS# MFRG5109518 Listing History

03/13/2026 Listed for sale by GARRISON REALTY GROUP LLC with MLS# MFRG5109518 with a list price of $1,350,000.

Public Transportation

Key West Transit:

Lower Keys Shuttle

Key West Transit:

Lower Keys Shuttle

This listing of 22777 Jolly Roger Dr. Cudjoe Key FL 33042 was last updated on 2026-03-13 09:12:10. Listing courtesy of GARRISON REALTY GROUP LLC.
MLS

Map of 22777 Jolly Roger Dr. Cudjoe Key FL 33042

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Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Submit Request, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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