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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1/49
$2,100,000
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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 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.
Full Property Details
Full Property Details for 22542 Jolly Roger Dr
General
- Price: $2,100,000
- Taxes: $12,646 (2025)
- Status: Active
- Type: Single Family
- Source: Greater_Miami
- MLS ID: A11977423
- Updated: 3/24/2026
- Added to Site: 31 day(s) ago
Interior
- Interior Features: Built-in Features, Entrance Foyer, French Doors, Vaulted Ceiling(s), Walk-In Closet(s), No Additional Rooms
- Appliances: Dishwasher, Dryer, Refrigerator, Washer
- Flooring: Vinyl
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 4
- Bedroom Features: Primary Bedroom Upstairs
Other Rooms
- Living Room: No Additional Rooms Sq. Ft.
Exterior
- Exterior Features: Open Balcony, Room for Pool
- Deck/Patio: Open Balcony, Open Porch
Parking
- Carport Spaces: 2
- Covered Spaces: 2
- Parking Features: Covered, Guest
Location
- Area: Cutthroat Harbor Ests
- County: Monroe County
- Subdivision: CUTTHROAT HARBOR ESTS
- Building Name: CUTTHROAT HARBOR ESTS
- Direction Faces: South
Community
- Community Name: Cutthroat Harbor Ests
Heating & Cooling
- Air Conditioning: Yes
- Cooling Type: Ceiling Fan(s), Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Municipal Water
Structural Information
- Architectural Style: Detached, Two Story
- Structure Type: House
- Detached/Attached: Detached
- Construction: Frame
- Roof: Aluminum
- Doors: High Impact Doors, French Doors
- Entry Location: Foyer
- Building Size: 13979
- Square Feet: 2,440
- Living Area: 2,440 Sq. Ft.
- Year Built: 1982
Lot Features
- Property View: Direct Ocean
- Lot Size (Sq. Ft.): 6,930
- Frontage Feet: 120
- Lot Features: 1/4 To Less Than 1/2 Acre Lot
- Zoning: is
Water Features
- Water Front: Yes
- Water Front Desc.: WF/Ocean Access, Ocean Front
Financial Considerations
- Price Per Sq. Ft.: $860.66
- Tax Amount: $12,646
- Tax Year: 2025
- Terms: All Cash, Conventional
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 OR804-659 OR832-479 O
- Restrictions: Other Restrictions
- Inclusions: Restricted Salt Water Access
- Property ID: 00180480-000000
Listed by Coldwell Banker Schmitt R.E.
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Listing agent
— 22542 Jolly Roger Dr —
Coldwell Banker Schmitt R.E.
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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 ATTOM Data Solutions 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 8 days ago
- 4Beds
- 3Total Baths
- 2,440Sq. Ft.
22542 Jolly Roger Dr, Lower Keys, FL 33042 (MLS# A11977423) is a Single Family property with 4 bedrooms and 3 full bathrooms. 22542 Jolly Roger Dr is currently listed for $2,100,000 and was received on February 25, 2026. Want to learn more about 22542 Jolly Roger Dr? Do you have questions about finding other Single Family real estate for sale in Lower Keys? You can browse all Lower Keys real estate or contact a Coldwell Banker agent to request more information.