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$1,350,000
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Property Description
Stop dreaming and start packing. This rare canal-front gem features a 2.75 assumable mortgage for qualified buyers-a game-changer in today's market! Situated on a massive, double-fenced corner lot, this 3-bed, 2-bath home is the ultimate playground. There is enough room to park all your toys, boats, cars, and RV. Your 4-legged family members will love their own large yard. With no HOA, you even have ample space for a chicken coop. A large saltwater pool is perfect for soaking up the sun and enjoying a peaceful afternoon. There is a bonus room for an office or a Zen den. Roof is 2018. In addition, Lot 2, part of the property, includes a potential buildable lot, a rare opportunity to have a second residence, guest house or future income producing home. A significant long term value! This Jolly Roger can be your own slice of paradise, come soak up the sun!
Full Property Details
Full Property Details for 22777 Jolly Roger Dr
General
- Price: $1,350,000
- Taxes: $7,936 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: G5109518
- Updated: 3/13/2026
- Added to Site: 20 day(s) ago
Rental Information
- Min. Lease: 1-7 Days
Interior
- Number of Rooms: 6
- Interior Features: Ceiling Fan(s), Eating Space In Kitchen, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, PrimaryBedroom Upstairs, Thermostat
- Appliances: Dishwasher, Electric Water Heater, Microwave, Range, Refrigerator
- Furnishings: Unfurnished
- Flooring: Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Electric Dryer Hookup, Washer Hookup
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Auto Cleaner, Chlorine Free, Fiberglass, In Ground, Lighting, Salt Water
Exterior
- Exterior Features: Balcony, French Doors, Hurricane Shutters, Outdoor Shower, Private Entrance, Private Yard, Storage
- Deck/Patio: Covered, Patio, Rear Porch, Screened
- Porch/Patio/Deck: Covered, Patio, Rear Porch, Screened
Parking
- Parking Features: Boat, Guest, Parking Pad, RV Parking
Location
- Area: 33042 - Summerland Key
- County: Monroe
- Development Name: 33042 - Summerland Key
- Subdivision: CUTTHROAT HARBOR ESTATES
- Driving Directions: U.S. 1 mile marker 23 Cudjoe Key, turn into Cutthroat Dr., first right is 22777 Jolly Roger Dr.
- Direction Faces: Southwest
Community
- Community Name: 33042 - Summerland Key
- Number of Pets: 10
Heating & Cooling
- Cooling Type: Central Air, Mini-Split Unit(s), Wall/Window Unit(s)
- Heating Type: Central, Electric, Heat Pump, Wall Units / Window Unit
Utilities
- Sewer: Public Sewer
- Water District: ATLANTIC OCEAN FROM CUDJOE BAY
- Water: Public
- Utility Description: Electricity Connected, Fiber Optics, Fire Hydrant, Propane, Public, Sewer Connected, Street Lights, Water Connected
Structural Information
- Architectural Info: Florida
- Architectural Style: Florida
- Exterior Const.: Block, Concrete
- Roof: Metal
- Windows: Aluminum Frames, Blinds, Shutters
- Stories/Levels: Two
- Square Feet: 1,488
- Sq. Ft. Source: Owner
- Year Built: 1974
Additional Structures
- Other Structures: Shed(s)
Lot Features
- Property View: Pool, Water
- Lot Size (Acres): 0.38
- Lot Size (Sq. Ft.): 16,500
- Lot Size: 16500
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
- Fencing (Description): Chain Link
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Canal - Saltwater
- Water Extras: Yes
- Water Front Name: ATLANTIC OCEAN FROM CUDJOE BAY
- Water Front Desc.: Saltwater Canal
Green Features
- Indoor Air Quality: HVAC Filter MERV 8+, Integrated Pest Management, No Smoking-Interior Buildg, Non Toxic Pest Control
Financial Considerations
- Tax Amount: $7,936.76
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: BK 18 LTS 1 AND 2 CUTTHROAT HARBOR ESTATES PB4-165 CUDJOE KEY OR204-197 OR522-953 OR549-402C OR710-31 OR787-1326 OR1072-1871R/S OR1442-304/05 OR1442-306/07 OR1551-1793/94 OR1789-941 OR1794-1569 OR2162-727 OR2162-728/29TR OR2986-2217COV OR2987-1464 OR 2987-1473
- Flood Zone Info: VE
- APN: 179990000000
- Property ID: 179990000000
- Block/Lot/Section: 18
Listed by Garrison Realty Group Llc
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Schools
Schools serving 22777 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 | 3.2 mi |
Key West High School 2100 Flagler Avenue, Key West, FL 33040 | 9-12 | 20.1 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 22777 Jolly Roger Dr
Date
Details
Price
Change
Source
3/13/2026
Listed
$1,350,000
114.29%
MLS
9/30/2019
Sold
$630,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 22777 Jolly Roger Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$7,934
—
$854,875
2%
2024
$7,934
57%
$840,494
53%
2023
$5,066
—
$550,353
6%
2021
$5,073
3%
$518,762
-3%
2022
$4,933
-3%
$534,324
3%
2021
$5,073
102%
$516,342
119%
2019
$2,506
-7%
$235,508
-6%
2018
$2,697
3%
$250,902
2%
2017
$2,625
—
$245,742
2%
2016
$2,635
-3%
$240,688
1%
2015
$2,705
-2%
$239,015
1%
2014
$2,774
-1%
$237,118
1%
2013
$2,802
—
$233,614
—
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 22777 Jolly Roger Dr
22777 Jolly Roger Dr., Cudjoe Key, FL 33042 (MLS# G5109518) is a Single Family property with 3 bedrooms and 2 full bathrooms. 22777 Jolly Roger Dr. is currently listed for $1,350,000 and was received on March 13, 2026. Want to learn more about 22777 Jolly Roger Dr.? 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.

