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Property Description
Welcome to your oceanfront retreat on Cudjoe Key, where panoramic wide open ocean views, exceptional outdoor living, and easy boating access come together to create the quintessential Florida Keys lifestyle. Built on a lot and a half with durable CBS construction, this inviting 2-bedroom, 2-bath, 1,587 sq. ft. home is perfectly positioned to take advantage of its spectacular waterfront setting. The light-filled interior flows effortlessly into the spacious screened porch where you'll enjoy ocean breezes, morning coffee, waterfront dining and unforgettable sunrises and moonlit evenings. Just beyond, an expansive deck provides even more space for entertaining or simply relaxing while overlooking the endless blue waters. Inside, the primary suite serves as a peaceful waterfront sanctuary, featuring a private en-suite bath, walk-in closet, and sliding glass doors that open directly to the deck, allowing you to wake up to breathtaking ocean views each morning. A comfortable guest bedroom offers welcoming accommodations for family and friends. Boaters will appreciate the dock and davits, providing convenient access to the Atlantic for world-class fishing, diving, sandbar adventures and sunset cruises. The lower-level enclosure offers abundant storage for kayaks, paddleboards, fishing gear, and all of your island essentials. Whether you're entertaining guests on the spacious outdoor living areas, heading out for a day on the water, or simply soaking in the tranquil open water views, this Cudjoe Key waterfront home is your opportunity to embrace the relaxed, waterfront lifestyle the Florida Keys are known for.
Full Property Details
Full Property Details for 22410 Jolly Roger Dr
General
- Sold For: $1,500,000
- Taxes: $15,373 (2025)
- Status: Closed
- Type: Single Family
- Source: 927
- MLS ID: 620456
- Added to Site: 53 day(s) ago
Interior
- Interior Features: Walk-in Closet(s), Built-in Cabinets, Drapes/Blinds Incl
- Appliances: Dishwasher, Dryer, Microwave, Oven, Range, Refrigerator, Washer
- Flooring: Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 2
Exterior
- Exterior Features: Storage
- Deck/Patio: Deck, Screened
- Porch/Patio/Deck: Deck, Screened
Parking
- Parking Features: Open, Off Street, Covered, Carport
Location
- Area: 07 - Cudjoe Key
- County: Monroe
- Subdivision: Cutthroat Harbor Est (23.0)
- Driving Directions: From US-1, turn oceanside onto Cutthroat Dr, turn right onto Jolly Roger Dr. Home will be on the left.
Community
- Assoc. Fees Include: None
- Pets Allowed: Yes
Heating & Cooling
- Central air: Yes
- Air Conditioning: Yes
- Cooling Type: Central Air, Ceiling Fans(s)
Structural Information
- Architectural Style: Above Flood
- Construction: CBS
- Roof: Metal
- Windows/Doors: Sliding Glass Doors, Shutters
- Square Feet: 1,587
- Sq. Ft. Source: Property Data Card
- Year Built: 1982
Lot Features
- Property View: Open Water View, Ocean
- Lot Size (Acres): 0.24
- Lot Size (Sq. Ft.): 10,530
- Lot Size Source: Property Data Card
- Zoning: IS - Improved Subivision District
Water Features
- Water Front: Yes
- Water View: Yes
- Water Front Desc.: Oceanfront, Open Water
Financial Considerations
- Tax Amount: $15,373.79
- Tax Year: 2025
- Terms: Cash, Conventional, VA Loan, FHA
Disclosures and Reports
- Legal Description: BK 19 LT 46 & E1/2 LT 47 CUTTHROAT HARBOR ESTATES CUDJOE KEY PB4-165
- Flood Zone: VE, VE, AE
- APN: 00180580-000000
Listed by Coldwell Banker Schmitt Real Estate Co, Lisa H Ferringo (305) 797-1221
Sold by Outside Of MLS, outside of mls
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Schools
Schools serving 22410 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 | 2.8 mi |
Key West High School 2100 Flagler Avenue, Key West, FL 33040 | 9-12 | 19.8 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 22410 Jolly Roger Dr
Date
Details
Price
Change
Source
8/10/2026
Sold
$1,500,000
0.07%
MLS
6/30/2026
Listed
$1,499,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
22410 Jolly Roger Drive, Cudjoe Key, FL 33042 (MLS# 620456) is a Single Family property that was sold at $1,500,000 on August 10, 2026. Want to learn more about 22410 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.

