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$1,289,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,488 Sq. Ft.
  • Updated 5 hours ago
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Stop dreaming and start packing. 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.Buyer to verify. A significant long term value! This Jolly Roger can be your own slice of paradise, come soak up the sun! Seller is licensed Real Estate agent in the state of Florida.

Full Property Details for 22777 Jolly Roger Dr

General

  • Price: $1,289,000
  • Taxes: $8,267 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 619513
  • Updated: 5/13/2026
  • Added to Site: 28 day(s) ago

Interior

  • Number of Rooms: 4
  • Interior Features: Workshop, Utility Room, Built-in Cabinets, Split Bedroom
  • Appliances: Dishwasher, Dryer, Gas Appliances, Microwave, Oven, Range, Refrigerator, Washer
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Pool: Yes
  • Pool Description: Concrete, Salt Water, In Ground

Exterior

  • Exterior Features: Rain Gutters, Fencing, Outdoor Shower, Shed, Storage
  • Deck/Patio: Screened Patio, Open Porch/Balcony, Deck
  • Porch/Patio/Deck: Screened Patio, Open Porch/Balcony, Deck

Parking

  • Parking Features: Off Street

Location

  • Area: 07 - Cudjoe Key
  • County: Monroe
  • Subdivision: Cutthroat Harbor Est (23.0)
  • Driving Directions: US 1 to Cudjoe Key to Cutthroat to Jolly Rodger address.

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Ductless, Central Air, Ceiling Fans(s)
  • Heating Type: Central, Propane Stove

Structural Information

  • Architectural Style: Above Flood
  • Construction: CBS
  • Roof: Metal
  • Windows/Doors: Single Hung Windows, Shutters
  • Square Feet: 1,488
  • Sq. Ft. Source: Property Data Card
  • Year Built: 1974

Lot Features

  • Property View: Canal
  • Lot Size (Acres): 0.37
  • Lot Size (Sq. Ft.): 15,925
  • Lot Size Source: Property Data Card
  • Lot Dimensions: x
  • Zoning: IS - Improved Subivision District

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Canal Front

Financial Considerations

  • Tax Amount: $8,267.46
  • Tax Year: 2025
  • Terms: Cash, Conventional, VA Loan, FHA

Disclosures and Reports

  • 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-
  • Flood Zone: AE, VE
  • APN: 00179990-000000

Listed by Live Local Realty of the Florida Keys, Susan Halligan (305) 906-1100

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Listing agent

— 22777 Jolly Roger Dr —

  • Susan Halligan

    Live Local Realty of the Florida Keys

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 22777 Jolly Roger Dr

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Sugarloaf School
255 Crane Boulevard, Summerland Key, FL 33042
PK-83.2 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-1220.1 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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/16/2026
Listed
$1,289,000
104.6%
MLS
9/30/2019
Sold
$630,000
—
Public Record
Get Price Alerts and Save Property
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 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
—
View All
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 for 22777 Jolly Roger Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Live Local Realty of the Florida Keys, Susan Halligan (305) 906-1100

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22777 Jolly Roger Drive, Cudjoe Key, FL 33042 (MLS# 619513) is a Single Family property with 3 bedrooms and 2 full bathrooms. 22777 Jolly Roger Drive is currently listed for $1,289,000 and was received on April 16, 2026. Want to learn more about 22777 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.

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