Price Reduced! Motivated Seller...
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.
For sale
Price cut: $94K (5/27)
$1,195,000
22777 Jolly Roger Dr, Cudjoe Key, FL 33042
3beds
1,488sqft
:
Get pre-qualified$7,062/mo
Single Family Residence
Built in 1974
0.37 Acres Lot
$1,149,100 Zestimate®
$803/sqft
$-- HOA
What's special
Large saltwater poolMassive double-fenced corner lot
- 99 days |
- 657 |
- 28 |
Zillow last checked:
Listing updated:
Listed by:
Susan Halligan 305-906-1100,
Live Local Realty of the Florida Keys
Source: FLKMLS,MLS#: 619513
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Bedroom 1
- Level: Main
Bedroom 2
- Level: Second
Bedroom 3
- Level: Second
Family room
- Level: Main
Heating
- Has Heating (Unspecified Type)
Cooling
- Central Air, Ceiling Fans(s), Ductless
Appliances
- Included: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Gas Appliances
- Laundry: Laundry Room
Features
- Built-in Features
- Flooring: Tile
Interior area
- Total structure area: 1,488
- Total interior livable area: 1,488 sqft
Property
Parking
- Parking features: RV Access/Parking, Storage
Features
- Levels: Multi/Split
- Patio & porch: Open Porch/Balcony, Deck, Screened Patio
- Exterior features: Rain Gutters, Outdoor Shower, Storage
- Has private pool: Yes
- Pool features: In Ground, Salt Water, Concrete
- Fencing: Fenced
- On waterfront: Yes
Lot
- Size: 0.37 Acres
Details
- Additional structures: Shed(s)
- Parcel number: 00179990000000
- Zoning: IS - Improved Subivision District
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- CBS
Condition
- Year built: 1974
Community & HOA
Community
- Subdivision: Cutthroat Harbor Est (23.0)
HOA
- Has HOA: No
- Services included: None
Location
- Region: Cudjoe Key
Financial & listing details
- Price per square foot: $803/sqft
- Tax assessed value: $854,875
- Annual tax amount: $8,267
- Date on market: 4/16/2026
- Listing terms: Cash,Conventional,FHA
Estimated market value
$1,149,100
$1.09M - $1.21M
$6,084/mo
Price history
| Date | Event | Price |
|---|---|---|
| 7/16/2026 | Listed for rent | $6,000$4/sqft |
Source: Zillow Rentals Report a problem | ||
| 5/27/2026 | Price change | $1,195,000-7.3%$803/sqft |
Source:  FLKMLS #619513 Report a problem | ||
| 4/16/2026 | Listed for sale | $1,289,000-4.5%$866/sqft |
Source: FLKMLS #619513 Report a problem | ||
| 4/15/2026 | Listing removed | $1,350,000$907/sqft |
Source:  Stellar MLS #G5109518 Report a problem | ||
| 3/21/2026 | Listing removed | $6,000$4/sqft |
Source: Zillow Rentals Report a problem | ||
| 3/19/2026 | Listed for rent | $6,000$4/sqft |
Source: Zillow Rentals Report a problem | ||
| 3/13/2026 | Listed for sale | $1,350,000+114.3%$907/sqft |
Source: Stellar MLS #G5109518 Report a problem | ||
| 5/29/2024 | Listing removed | -- |
Source: Zillow Rentals Report a problem | ||
| 4/14/2024 | Listed for rent | $6,000+9.1%$4/sqft |
Source: Zillow Rentals Report a problem | ||
| 10/5/2023 | Listing removed | -- |
Source: Zillow Rentals Report a problem | ||
| 9/24/2023 | Listed for rent | $5,500$4/sqft |
Source: Zillow Rentals Report a problem | ||
| 6/13/2023 | Listing removed | -- |
Source: Zillow Rentals Report a problem | ||
| 5/22/2023 | Price change | $5,500-15.4%$4/sqft |
Source: Zillow Rentals Report a problem | ||
| 5/13/2023 | Listed for rent | $6,500$4/sqft |
Source: Zillow Rentals Report a problem | ||
| 9/30/2019 | Sold | $630,000-2.9%$423/sqft |
Source: FLKMLS #583360 Report a problem | ||
| 8/5/2019 | Price change | $649,000-5.8%$436/sqft |
Source: Coldwell Banker Schmitt Real Estate Co. #583360 Report a problem | ||
| 4/29/2019 | Price change | $689,000-0.7%$463/sqft |
Source: Coldwell Banker Schmitt Real Estate Co. #583360 Report a problem | ||
| 4/5/2019 | Price change | $694,000-0.7%$466/sqft |
Source: Coldwell Banker Schmitt Real Estate Co. #583360 Report a problem | ||
| 12/21/2018 | Listed for sale | $699,000+342.4%$470/sqft |
Source: Coldwell Banker Schmitt RE Co. Lower Keys Office #583360 Report a problem | ||
| 2/7/1997 | Sold | $158,000$106/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $8,267 +4.2% | $854,875 +1.7% |
| 2024 | $7,934 +56.6% | $840,494 +52.7% |
| 2023 | $5,066 +2.7% | $550,353 +3% |
| 2022 | $4,933 -2.8% | $534,324 +3% |
| 2021 | $5,073 -0.4% | $518,762 +0.5% |
| 2020 | $5,092 | $516,342 +119.2% |
| 2019 | $5,092 +103.2% | $235,508 -6.1% |
| 2018 | $2,506 -7.1% | $250,902 +2.1% |
| 2017 | $2,697 +2.8% | $245,742 +2.1% |
| 2016 | $2,625 -0.4% | $240,688 +0.7% |
| 2015 | $2,635 | $239,015 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 33042
Nearby schools
GreatSchools rating
- 6/10Sugarloaf SchoolGrades: PK-8Distance: 3.1 mi
- 4/10Key West High SchoolGrades: 9-12Distance: 20.1 mi
- $168,405-- bd-- ba-- sqftCutlass Ln, Summerland Key, FL 33042Off Market
- $930,0002 bd2 ba1k sqft221 Cutthroat Dr, Cudjoe Key, FL 33042Sold
- $--6,000 Square FeetPark Lot, Summerland Key, FL 33042Off Market
- $765,0002 bd2 ba1k sqft201 Cutthroat Dr, Cudjoe Key, FL 33042Sold
- $1,433,8002 bd5 ba1k sqft22786 Jolly Roger Dr, Cudjoe Key, FL 33042Off Market
- $1,324,7002 bd2 ba1.2k sqft22776 Jolly Roger Dr, Cudjoe Key, FL 33042Off Market
- $1,032,3001 bd1 ba640 sqft22794 Jolly Roger Dr, Cudjoe Key, FL 33042Off Market
- $757,6002 bd1 ba600 sqft22757 Jolly Roger Dr, Cudjoe Key, FL 33042Off Market
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
Similar homes
- $1,199,0003 bd2 ba1.2k sqft24347 Caribbean Dr W, Summerland Key, FL 33042For Sale
MLS ID #617789, Shirley Carey, Berkshire Hathaway HomeServices Knight & Gardner Realty. FLKMLS - $1,269,0002 bd2 ba1.1k sqft116 Spanish Main Dr, Cudjoe Key, FL 33042For Sale
MLS ID #619922, Lissete Cadwell P.A., Florida Keys Realty Group LLC. FLKMLS - $1,185,0003 bd2 ba1.1k sqft706 Caribbean Dr E, Summerland Key, FL 33042For Sale
MLS ID #620281, Donna Pezzi, Keller Williams Key West Compass Realty. FLKMLS - $949,0003 bd2 ba960 sqft22953 John Silver Ln, Cudjoe Key, FL 33042For Sale
MLS ID #619680, Lisa H Ferringo, Coldwell Banker Schmitt Real Estate Co. FLKMLS - $1,299,0003 bd2 ba1.7k sqft21025 3rd Ave, Cudjoe Key, FL 33042For SaleMLS ID #619427, Diane Corliss, Coldwell Banker Schmitt Real Estate Co. FLKMLS
- $949,0003 bd2 ba1.1k sqft342 Spanish Main Dr, Cudjoe Key, FL 33042For SaleMLS ID #620535, Monika Rydzak, eXp Realty LLC KW Branch. FLKMLS
- $1,200,0002 bd2 ba1k sqft637 Caribbean Dr E, Summerland Key, FL 33042For SaleMLS ID #619455, Donna Pezzi, Keller Williams Key West Compass Realty. FLKMLS
- $895,0003 bd2 ba1.2k sqft135 Tortuga Ln, Cudjoe Key, FL 33042For SaleMLS ID #620163, Kathleen Reed, Bruno Realty Group, Inc. FLKMLS
- $975,0002 bd2 ba1.2k sqft22748 Blackbeard Ln, Cudjoe Key, FL 33042For SaleMLS ID #617545, Lindsay Ryan, EXP Realty LLC. FLKMLS
- $1,300,0002 bd2 ba1.3k sqft466 W Shore Dr, Summerland Key, FL 33042For SaleMLS ID #620321, Donna Pezzi, Keller Williams Key West Compass Realty. FLKMLS
- $1,199,0003 bd2 ba1.4k sqft27414 Guadaloupe Ln, Ramrod Key, FL 33042For SaleMLS ID #618854, Pamela A Stangler, Expert Realty LLC. FLKMLS
- $1,100,0002 bd2 ba1k sqft667 Caribbean Dr E, Summerland Key, FL 33042For SaleMLS ID #619318, Donna Pezzi, Keller Williams Key West Compass Realty. FLKMLS
- $1,499,0003 bd3 ba1.5k sqft21007 4th Ave, Cudjoe Key, FL 33042For SaleMLS ID #620454, Diane Corliss, Coldwell Banker Schmitt Real Estate Co. FLKMLS
- $1,200,0002 bd2 ba1.3k sqft17286 Jamaica Ln, Sugarloaf Key, FL 33042For SaleMLS ID #619901, Lisa H Ferringo, Coldwell Banker Schmitt Real Estate Co. FLKMLS
- $1,399,0003 bd2 ba1.5k sqft21250 Conch Dr, Cudjoe Key, FL 33042For SaleMLS ID #618382, Lisa H Ferringo, Coldwell Banker Schmitt Real Estate Co. FLKMLS
- $1,399,0002 bd2 ba1.3k sqft21012 6th Ave, Cudjoe Key, FL 33042For SaleMLS ID #619865, Lisa H Ferringo, Coldwell Banker Schmitt Real Estate Co. FLKMLS
- $1,349,0003 bd3 ba1.8k sqft845 Pirates Rd, Little Torch Key, FL 33042For SaleMLS ID #619055, Sandra Dolowy, KeyIsle Realty. FLKMLS
- $1,250,0001 bd3 ba1.2k sqft27001 Overseas Hwy, Summerland Key, FL 33042For SaleMLS ID #618610, Bobby W Coe IV, RE/MAX Keys Connection (KW). FLKMLS
- $799,0003 bd2 ba1.5k sqft195 W Shore Dr, Summerland Key, FL 33042For SaleMLS ID #617998, Lisa H Ferringo, Coldwell Banker Schmitt Real Estate Co. FLKMLS
- $1,379,0003 bd3 ba1.7k sqft16941 Driftwood Ln, Sugarloaf Key, FL 33042For SaleMLS ID #617678, Colbert A Taylor, Taylor & Assoc. RE, Inc.. FLKMLS
