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22542 Jolly Roger Dr Lower Keys FL 33042

$2,100,000
USD CAD EUR GBP BTC
22542 Jolly Roger Dr Lower Keys, FL 33042 - MLS#A11977423 22542 Jolly Roger Dr Lower Keys, FL 33042 - MLS#A11977423 22542 Jolly Roger Dr Lower Keys, FL 33042 - MLS#A11977423 22542 Jolly Roger Dr Lower Keys, FL 33042 - MLS#A11977423

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
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Overview of 22542 Jolly Roger Dr

4 Bedrooms
3 Bathrooms
0 Car Garage
13,979 Square Feet
2,440SF Living Area
Pool:
No
Ocean
Year Built 1982
Listed For 30 Days

This striking 4-bedroom, 3-bathroom home is a testament to coastal architecture, blending rustic design with open, light-filled living spaces that showcase a breathtaking oceanfront setting. Situated on a double lot totaling .32 acres, the property offers an impressive 120 feet of frontage overlooking cudjoe bay—creating a rare and commanding presence along the shoreline. broad covered balconies and generous outdoor living spaces capture the essence of keys waterfront living, while large impact glass doors and windows frame sweeping ocean views and invite natural light throughout. Soaring ceilings with dark wood beams enhance the open-concept layout and add dramatic architectural character. the main living level features a fully renovated kitchen, dining area, expansive living room, laundry, two bedrooms, and two bathrooms. Upstairs, a third bedroom sits at the top of the stairs, while a catwalk leads to the fourth bedroom with an ensuite bath and walkout deck positioned to capture the home’s most spectacular panoramic views. throughout the residence, thoughtful design blends contrasts—modern lines with traditional warmth, cozy intimacy within spacious rooms. Whimsical and eclectic touches pair with bold architectural elements, creating a home that feels both artistic and inviting while celebrating its extraordinary oceanfront setting.

This luxury single family home was built in 1982 and features 4 bedrooms, and 3 full bathrooms. This home for sale is 13,979 square feet, with 2,440 sq ft being air conditioned living space. The home has a does not have a private swimming pool.

Striking 4BR oceanfront home on double lot with 120’ on Cudjoe Bay. Soaring ceilings, open living & panoramic views.

Please contact your ZFC agent for more information about MLS# AX-11977423 or any other homes for sale in Lower Keys or elsewhere in the Monroe County area.

Features & Amenities

Appliances

Dryer, Dishwasher, Refrigerator, Wine Cooler, Washer

Architecture

Detached, Two Story

Cooling

Central Air, Ceiling Fans

Heating

Central

Flooring

Laminate, Vinyl

Parking

Covered, Guest

Lot Size

6930 Square Feet

View

Ocean view

Construction Materials

Frame

Interior Features

Built In Features, Entrance Foyer, French Doors Atrium Doors, Upper Level Primary, Vaulted Ceilings, Walk In Closets

Exterior Features

Balcony, Security High Impact Doors, Porch, Room For Pool

Lot Features

Quarter To Half Acre Lot

Patio And Porch Features

Balcony, Open, Porch

Pool Features

None

Door Features

French Doors

Roof

Aluminum

Waterfront Features

Ocean Front

Number Of Stories

2

Year Built

1982

Annual Real Estate Taxes

$12,646 (2025)

Legal Description

Bk 19 Lt 36 Cutthroat Harbor Estates Cudjoe Key Pb4-165 Or222-580 Or781-1811d/c Or781-1812/14 Or781-1815 Or781-1818/19 Or804-659 Or832-479 O

Property Type

Single Family Home

Direction Faces

South

MLS Number

A11977423

Universal Property Id

U S-12087-N-00180480000000-R-N

Days On Market

30

Community Name

Cutthroat Harbor Ests

22542 Jolly Roger Dr Price Calculator

Get Mortgage Quote For This Home

The payment calculator figures for 22542 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 $12,646 but will likely change when this home sells. These estimations are calculated from a list price of $2,100,000 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 22542 Jolly Roger Dr

Address Sale Price Bed Bth Size Location Sale Date
22822 John Silver Ln $Log in to view 3 2/0 3,392SF Cutthroat Harbor Ests 08/21/2025
815 E Shore Dr $Log in to view 7 4/2 12,603SF Summerland Beach Amd 12/01/2025

MLS# AX-11977423 Listing History

12/31/1969 Listed for sale by Coldwell Banker Schmitt R.E. with MLS# AX-11977423 with a list price of $2,100,000.

Open House Schedule for 22542 Jolly Roger Dr

Mar 29
10:00 am - 12:00 pm
This listing of 22542 Jolly Roger Dr Lower Keys FL 33042 was last updated on 2026-03-24 19:00:44. Listing courtesy of Coldwell Banker Schmitt R.E..
MLS

Map of 22542 Jolly Roger Dr Lower Keys 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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