Date
Details
Price
Change
Source
2/25/2026
Listed
$2,100,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
This striking 4-bedroom, 3-bathroom home is a testament to coastal architecture, blending rustic design with open, light-filled living spaces to 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 -- a rare and commanding presence along the shoreline.Broad, covered balconies, generous outdoor spaces, and a private boat launch capitalize on Keys waterfront living, while large impact glass doors and windows frame sweeping ocean views and invite natural light into every room. Soaring ceilings enhance the open-concept layout with dark wood beams amplifying the impact. The main floor living space includes a fully renovated kitchen, dining space, capacious living room, laundry, two bedrooms and two bathrooms. Ascend to the top floor to find a third bedroom perched at the top of the stairs. A catwalk connects the fourth bedroom with ensuite bath and walkout deck that provides the home's optimal panoramic views.The home itself tells a story through design; masterfully blending opposites in a way to complement each other: masculine and feminine, modern lines and traditional warmth, cozy intimacy within spacious rooms. The thoughtful juxtaposition and melding of these elements transform the residence into a statement of artistic expression. Whimsical, eclectic touches are paired with bold architectural features, creating visual intrigue throughout.
Full Property Details
Full Property Details for 22542 Jolly Roger Dr
General
- Price: $2,100,000
- Taxes: $12,645 (2025)
- Status: Active
- Type: Single Family
- Source: 927
- MLS ID: 618818
- Updated: Today (2/25/2026)
- Added to Site: Today
Interior
- Interior Features: Cathedral Ceilings, Quartz Countertops, Walk-in Closet(s), Granite Counter Top, Built-in Cabinets, Entrance Foyer
- Appliances: Washer, Stainless Steel Appliance(s), Wine Cooler, Oven, Refrigerator, Dishwasher, Dryer
- Furnishings: Unfurnished
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 4
Exterior
- Deck/Patio: Open Porch/Balcony, Deck
Parking
- Parking: Open Parking, Covered Parking, Off Street Parking
Location
- Area: 07 - Cudjoe Key
- County: Monroe
- Subdivision: Cutthroat Harbor Est (23.0)
Community
- Assoc. Fees Include: None
- Pets Allowed: Yes
Heating & Cooling
- Cooling Type: Central Air
Utilities
- Water: Ocean View, Open Water View
- Utility Description: FKAA
Structural Information
- Architectural Style: Single Family
- Construction Status: Updated/Remodeled
- Construction: Frame
- Roof: Metal Roof
- Windows/Doors: Impact Rstnce Window, Impact Rstnce Doors
- Square Feet: 2,440
- Sq. Ft. Source: Property Data Card
- Year Built: 1982
- Property Condition: Updated/Remodeled
Lot Features
- Lot Size (Sq. Ft.): 13,979
- Zoning: IS - Improved Subivision District
Water Features
- Water Front: Yes
- Water View: Yes
- Water Front Type: Oceanfront, Open Water
- Dock Description: None
Financial Considerations
- Tax Amount: $12,645
- Tax Year: 2025
Disclosures and Reports
- 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 O
- Flood Zone: VE, VE, VE
- APN: 00180480-000000
Listed by Coldwell Banker Schmitt Islamorada, Lauren Hoefert Dunn (305) 394-3717 and Coldwell Banker Schmitt Real Estate Co. (KW), Sarah Eckert (772) 501-6576
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Listing agents
— 22542 Jolly Roger Dr —
Lauren Hoefert Dunn
Coldwell Banker Schmitt Islamorada
Sarah Eckert
Coldwell Banker Schmitt Real Estate Co. (KW)
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 22542 Jolly Roger Dr
School District:Monroe County School District, Middle Torch Key, FL
| Name | Grades | Distance |
|---|---|---|
Sugarloaf School 255 Crane Boulevard, Summerland Key, FL 33042 | PK-8 | 3 mi |
Key West High School 2100 Flagler Avenue, Key West, FL 33040 | 9-12 | 19.9 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 22542 Jolly Roger Dr
Tax History
Tax History for 22542 Jolly Roger Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$13,049
—
$1,403,446
-3%
2024
$13,049
67%
$1,447,446
35%
2023
$7,822
12%
$1,075,637
23%
2022
$6,968
7%
$872,378
29%
2021
$6,498
—
$674,986
3%
2021
$6,498
30%
$654,140
24%
2019
$5,014
-4%
$529,526
2%
2018
$5,240
-6%
$517,441
-13%
2017
$5,586
4%
$592,695
8%
2016
$5,387
-7%
$550,241
1%
2015
$5,777
-5%
$542,959
11%
2014
$6,050
4%
$486,997
10%
2013
$5,798
—
$442,725
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 22542 Jolly Roger Dr
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- Single Family
- Active
- Updated 12 days ago
- 3Beds
- 3Total Baths
- 2,486Sq. Ft.
- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 2,134Sq. Ft.
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- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 1,418Sq. Ft.
- Mobile Home
- Active
- Updated 9 hours ago
- 3Beds
- 2Total Baths
- 1,431Sq. Ft.
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- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 2,134Sq. Ft.
- Single Family
- Active
- Updated 17 hours ago
- 3Beds
- 2Total Baths
- 1,714Sq. Ft.
- Condo
- Active
- Updated 4 days ago
- 1Bed
- 1Total Bath
- 754Sq. Ft.
22542 Jolly Roger Drive, Cudjoe Key, FL 33042 (MLS# 618818) is a Single Family property with 4 bedrooms and 3 full bathrooms. 22542 Jolly Roger Drive is currently listed for $2,100,000 and was received on February 25, 2026. Want to learn more about 22542 Jolly Roger Drive? Do you have questions about finding other Single Family real estate for sale in Cudjoe Key? You can browse all Cudjoe Key real estate or contact a Coldwell Banker agent to request more information.