Contact One Click Broker
Contacting One Click Broker
  • All fields are required.
Schedule A Showing
Schedule a Showing.
  • All fields are required.
Check this box to Register with us:
Submit an Offer Now!
Submit an Offer Now!
All fields are required.
Print Flyer
22777 Jolly Roger Dr., CUDJOE KEY, FL 33042
Active
  1. Image 1 of 13 For 22777 Jolly Roger Dr.
  2. Image 2 of 13 For 22777 Jolly Roger Dr.
  3. Image 3 of 13 For 22777 Jolly Roger Dr.
  4. Image 4 of 13 For 22777 Jolly Roger Dr.
  5. Image 5 of 13 For 22777 Jolly Roger Dr.
  6. Image 6 of 13 For 22777 Jolly Roger Dr.
  7. Image 7 of 13 For 22777 Jolly Roger Dr.
  8. Image 8 of 13 For 22777 Jolly Roger Dr.
  9. Image 9 of 13 For 22777 Jolly Roger Dr.
  10. Image 10 of 13 For 22777 Jolly Roger Dr.
  11. Image 11 of 13 For 22777 Jolly Roger Dr.
  12. Image 12 of 13 For 22777 Jolly Roger Dr.
  13. Image 13 of 13 For 22777 Jolly Roger Dr.
Property Photos
22777 Jolly Roger Dr.
Image Gallery
Would you like to sell your home before you purchase this one?
Priced at Only: $1,350,000
For more Information Call:
Address: 22777 Jolly Roger Dr., CUDJOE KEY, FL 33042
Property Location and Similar Properties
All
Similar
  1. Image 1 of 13 For 22777 Jolly Roger Dr.
  2. Image 2 of 13 For 22777 Jolly Roger Dr.
  3. Image 3 of 13 For 22777 Jolly Roger Dr.
  4. Image 4 of 13 For 22777 Jolly Roger Dr.
  5. Image 5 of 13 For 22777 Jolly Roger Dr.
  6. Image 6 of 13 For 22777 Jolly Roger Dr.
  7. Image 7 of 13 For 22777 Jolly Roger Dr.
  8. Image 8 of 13 For 22777 Jolly Roger Dr.
  9. Image 9 of 13 For 22777 Jolly Roger Dr.
  10. Image 10 of 13 For 22777 Jolly Roger Dr.
  11. Image 11 of 13 For 22777 Jolly Roger Dr.
  12. Image 12 of 13 For 22777 Jolly Roger Dr.
  13. Image 13 of 13 For 22777 Jolly Roger Dr.
Request More Information
  • All fields are required.
More Like This
  • MLS#: G5109518 ( Residential )
  • Street Address: 22777 Jolly Roger Dr.
  • Viewed: 4
  • Price: $1,350,000
  • Price sqft: $907
  • Waterfront: Yes
  • Wateraccess: Yes
  • Waterfront Type: Canal - Saltwater
  • Year Built: 1974
  • Bldg sqft: 1488
  • Bedrooms: 3
  • Total Baths: 2
  • Full Baths: 2
  • Days On Market: 1
  • Additional Information
  • Geolocation: 24.6604 / -81.4792
  • County: MONROE
  • City: CUDJOE KEY
  • Zipcode: 33042
  • Subdivision: Cutthroat Harbor Estates
  • Provided by: GARRISON REALTY GROUP LLC
  • Contact: Olivia Poto
  • 352-901-3415
  • mfrmls
  • DMCA Notice
  • Description
    Stop dreaming and start packing. This rare canal front gem features a 2.75 assumable mortgage for qualified buyersa game changer in todays 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!
Payment Calculator
  •   Principal & Interest -
  •   Property Tax $
  •   Home Insurance $
  •   HOA Fees $
  •   Mortgage Insurance-
  •   Monthly -
Features
Building and Construction
  • Covered Spaces: 0.00
  • Exterior Features: Balcony, French Doors, Hurricane Shutters, Outdoor Shower, Private Entrance, Private Yard, Storage
  • Fencing: Chain Link
  • Flooring: Tile
  • Living Area: 1488.00
  • Other Structures: Shed(s)
  • Roof: Metal
Land Information
  • Lot Features: Corner Lot, Flood Insurance Required, FloodZone, Landscaped, Level, Oversized Lot, Private, Paved
Garage and Parking
  • Garage Spaces: 0.00
  • Open Parking Spaces: 0.00
  • Parking Features: Boat, Guest, Parking Pad, RV Access/Parking
Eco-Communities
  • Pool Features: Auto Cleaner, Chlorine Free, Fiberglass, In Ground, Lighting, Salt Water
  • Water Source: Public
Utilities
  • Carport Spaces: 0.00
  • Cooling: Central Air, Mini-Split Unit(s), Wall/Window Unit(s)
  • Heating: Central, Electric, Heat Pump, Ductless
  • Pets Allowed: Yes
  • Sewer: Public Sewer
  • Utilities: Electricity Connected, Fiber Optics, Fire Hydrant, Propane, Public, Sewer Connected, Water Connected
Finance and Tax Information
  • Home Owners Association Fee: 0.00
  • Insurance Expense: 0.00
  • Net Operating Income: 0.00
  • Other Expense: 0.00
  • Tax Year: 2025
Other Features
  • Appliances: Dishwasher, Electric Water Heater, Microwave, Range, Refrigerator
  • Country: US
  • Furnished: Unfurnished
  • Interior Features: Ceiling Fans(s), Eat-in Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, PrimaryBedroom Upstairs, Thermostat
  • 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
  • Levels: Two
  • Area Major: 33042 - Summerland Key
  • Occupant Type: Vacant
  • Parcel Number: 00179990-000000
  • Possession: Close Of Escrow
  • Style: Florida
  • View: Pool, Water
  • Zoning Code: IS
Similar Properties

Active
Details for 142 Peg Leg Lane, Cudjoe, FL 33042
$1,529,999.00 ($716.29 / sqft )

142 Peg Leg Lane More Like This

Welcome to your dream coastal retreat! Perched on concrete stilts with sweeping views, this newer 4 bedroom, 3 bath luxury home offers the perfect blend of island elegance and modern comfort. Two spac

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 3
  3. Approx. 2136 sqft
  1. MLSID: 615839
  2. Provided by Amerifirst Realty
  3. Contact Alex Perez
  4. (305) 595-8616
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
59 Pictures and Information
Active
Details for 27433 Antigua Lane, Ramrod, FL 33042
$1,480,000.00 ($698.11 / sqft )

27433 Antigua Lane More Like This

NEW CONSTRUCTION POOL HOME COMPLETED 2025 & MOVE IN READY!Welcome to your brand new coastal retreat on Ramrod Key. This luxury 4 bedroom, 3 bath residence delivers world class construction, refined

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 3
  3. Approx. 2120 sqft
  1. MLSID: 617241
  2. Provided by Bluescape Real Estate
  3. Contact Kelly Dawn Gardner
  4. (305) 394-5981
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
64 Pictures and Information
Active
Details for 16941 Driftwood Lane, Sugarloaf, FL 33042
$1,395,000.00 ($820.59 / sqft )

16941 Driftwood Lane More Like This

There are homes that check boxes, and then there are homes that speak to you the moment you step inside. This custom, meticulously crafted 3BR/3BA, 1,700 sq ft CBS masterpiece in the heart of Sugarloa

  1. Request Information
  1. Bedrooms: 3
  2. Baths: 3
  3. Approx. 1700 sqft
  1. MLSID: 617678
  2. Provided by Taylor & Assoc. RE, Inc.
  3. Contact Colbert A Taylor
  4. (305) 509-9928
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
71 Pictures and Information
Active
Details for 887 Bay Drive, Summerland, FL 33042
$1,595,000.00 ($788.82 / sqft )

887 Bay Drive More Like This

This 3 bedroom, 3 bath concrete fortress on a deep water canal (5' draft) is located in the highly sought after Summerland Cove with quick access to both the Gulf and Atlantic just a 15 minute boat r

  1. Request Information
  1. Bedrooms: 3
  2. Baths: 3
  3. Approx. 2022 sqft
  1. MLSID: 618272
  2. Provided by Realty Executives Florida Keys Summerland Branch
  3. Contact Amy Hanson
  4. (305) 440-3250
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
26 Pictures and Information
Active
Details for 27372 Indies Drive, Ramrod, FL 33042
$1,499,000.00 ($832.78 / sqft )

27372 Indies Drive Virtual Tour More Like This

**OPEN HOUSE* Today, Friday, March 6 from 11:00AM to 1:00 PMOffered for the first time, this custom built 4 bedroom, 3 bathroom waterfront residence on Ramrod Key showcases refined coastal design, exc

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 3
  3. Approx. 1800 sqft
  1. MLSID: 618860
  2. Provided by KeyIsle Realty
  3. Contact Sandra Dolowy
  4. (305) 923-6159
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
50 Pictures and Information
Active
Details for 27374 Guadaloupe Lane, Ramrod, FL 33042
$1,499,000.00 ($999.33 / sqft )

27374 Guadaloupe Lane More Like This

New Construction coming Fall 2026. Step into the laid back charm of the Florida Keys with this spacious 1,500 sqft home, perfectly situated along a peaceful boating canal in the Lower Keys, a short bo

  1. Request Information
  1. Bedrooms: 3
  2. Baths: 3
  3. Approx. 1500 sqft
  1. MLSID: 619016
  2. Provided by Meyer and Boumerhi Realty LLC
  3. Contact Nick Boumerhi
  4. (305) 587-0268
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
18 Pictures and Information
Active
Details for 16823 E Point Drive, Sugarloaf, FL 33042
$1,450,000.00 ($833.33 / sqft )

16823 E Point Drive Virtual Tour More Like This

Nestled in the prestigious South Point neighborhood of Sugarloaf Shores, this waterfront home offers the perfect blend of coastal tranquility and convenient access to Key West just a short 15 minute

  1. Request Information
  1. Bedrooms: 3
  2. Baths: 3
  3. Approx. 1740 sqft
  1. MLSID: 619026
  2. Provided by Coldwell Banker Schmitt Lower Keys (KW)
  3. Contact Diane Corliss
  4. (305) 872-3050
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
47 Pictures and Information
Active
Details for 845 Pirates Road, Little Torch, FL 33042
$1,449,000.00 ($796.15 / sqft )

845 Pirates Road Virtual Tour More Like This

**OPEN HOUSE** Sunday, March 15, from 12:00PM 2:00 PMDiscover waterfront living in Jolly Roger Estates on Little Torch Key. This beautifully maintained 3 bedroom, 3 bathroom canal front home offers

  1. Request Information
  1. Bedrooms: 3
  2. Baths: 3
  3. Approx. 1820 sqft
  1. MLSID: 619055
  2. Provided by KeyIsle Realty
  3. Contact Sandra Dolowy
  4. (305) 923-6159
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
55 Pictures and Information
Nearby Subdivisions
Cutthroat Harbor Estates  
Skip to Main Content
  1. One Click Broker
  2. 800.557.8193
  3. Toll Free: 800.557.8193
  4. billing@brokeridxsites.com