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Irene Medina
REALTOR®, GRI CRS GREEN
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22542 Jolly Roger Dr, Lower Keys, FL 33042

$2,100,000
  • 22542 Jolly Roger Dr, Lower Keys, FL 33042 Main Photo

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Active
BEDS4 BATHS3 full SQUARE FEET2,440 MLS#A11977423
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONCUTTHROAT HARBOR ESTS

Property Description

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 homes 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.

22542 Jolly Roger Dr | MLS# A11977423

This single family home located at 22542 Jolly Roger Dr, Lower Keys, FL 33042 is currently listed for sale with an asking price of $2,100,000. This property was built in 1982 and has 4 bedrooms and 3 full baths with 2440 sq. ft. Jolly Roger Dr is located in the CUTTHROAT HARBOR ESTS subdivision. Search CUTTHROAT HARBOR ESTS real estate on imedina.realty100.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Ceiling Fan(s), Central Air
Heating: Central
Home Style: Detached, Two Story
Lot Size: 0.16 Acres
Roof Type: Aluminum
Taxes: $12,646
Year Built: 1982

Amenities

Built-in Features
Entrance Foyer
French Doors
Vaulted Ceiling(s)
Walk-In Closet(s)
No Additional Rooms
Open Balcony
Room For Pool

Feature Descriptions

Appliances: Dishwasher, Dryer, Refrigerator, Washer
Community Features: None
Crops Included Y/N: No
Days on Site: 63
Door Features: High Impact Doors, French Doors
Exterior: Frame
Flooring: Vinyl
Home Warranty Y/N: No
Lease Considered Y/N: No
Listing Terms: All Cash, Conventional
Lot: 1/4 To Less Than 1/2 Acre Lot
Parcel#: 00180480-000000
Parking: Covered, Guest
Parking Notes: Covered, Guest
Patio/Porch: Open Balcony, Open Porch
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Sewer: Public Sewer
Special View Info: Direct Ocean
Swimming Pool: Yes
Water: Municipal Water
Water Features: WF/Ocean Access, Ocean Front

Listed By / Shown By

Listed By

Agency Name: Coldwell Banker Schmitt R.E.
Agency Phone: 305-451-4422

Shown By

Agent Name: Irene Medina
Agent Phone: Cell: (954) 439-4851
Agency Title: Realty 100

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Estimated Payment

$ 6,340.02 per month $4,673.69 Principal & Interest $1,053.83 Property Tax $612.50 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 05/07/2026. The listing information on this page last changed on 05/07/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 05/07/2026 11:12:48 AM EST) or Miami MLS (last updated Thu 05/07/2026 11:09:15 AM EST) or Stellar MLS (last updated Thu 05/07/2026 11:02:18 AM EST) or Beaches MLS (last updated Thu 05/07/2026 11:00:28 AM EST). Real estate listings held by brokerage firms other than Realty 100 may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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