Offered in the highly sought-after Jolly Roger Estates, this beautifully maintained, one-owner canal-front home is just 11 years old and truly move-in ready. Elevated and thoughtfully designed, the 1,296 sq. ft. residence offers three bedrooms and two bathrooms, enhanced by refined finishes including crown molding, tray ceilings, tile showers, and a bright, open-concept living space ideal for coastal living. Built for both comfort and peace of mind, the home features a metal roof installed in 2018 along with impact-rated windows and doors throughout. Enjoy added privacy and nightly sunset views over the protected salt marsh directly across the street—an unspoiled natural backdrop that will never be developed. Boaters will appreciate the free-flowing, clear-water canal with excellent access to both the ocean and the bay. The private dock with a 7,000-lb side-lift boat elevator makes heading out for fishing, diving, or sunset cruises effortless. The spacious lot offers a large driveway, double covered parking, and ample room for boat trailers and additional vehicles. Downstairs, a full concrete pad and enclosed angler's room provide the perfect space for storing fishing gear, dive equipment, and all your island toys. Located near mile marker 28.5, Jolly Roger Estates is a peaceful, palm-lined waterfront community on the Atlantic side of Little Torch Key, offering direct access to Pine Channel and world-class boating, fishing, and diving at nearby Looe Key Reef.
Single-familyProperty Type
2015Year Built
6,000 sq ftLot Size
$656Price/Sq.Ft.
2 car garageParking
Listed by Jo Ann Cook, Cook• Ocean Sotheby's International
•305-360-7968 (agent)
•jcook@oceansir.com (agent)
•305-735-4095 (broker)
•jcook@oceansir.com (broker)
Bought with TEMP USER• MIAMI ASSOCIATION OF REALTORS®
Est. $4,276 per month, based on comparable rentals
Sale and tax history for 437 Pirates Rd
Sale History
Tax History
Date
Event
Price
FLKMLS #620124
Sep 15, 2026
Sold
$850,000
$656/sq ft
Jul 15, 2026
Contingent
—
Jun 18, 2026
Price Changed
$894,000
$690/sq ft
Jun 4, 2026
Price Changed
$895,000
$691/sq ft
Jun 1, 2026
Listed
$895,555
$691/sq ft
+33
MOTIVATED SELLER! Offered in the highly sought-after Jolly Roger Estates, this beautifully maintained, one-owner canal-front home is just 11 years old and truly move-in ready. Elevated and thoughtfully designed, the 1,296 sq. ft. residence offers three bedrooms and two bathrooms, enhanced by refined finishes including crown molding, tray ceilings, tile showers, and a bright, open-concept living space ideal for coastal living. Built for both comfort and peace of mind, the home features a metal roof installed in 2018 along with impact-rated windows and doors throughout. Enjoy added privacy and nightly sunset views over the protected salt marsh directly across the street--an unspoiled natural backdrop that will never be developed. Boaters will appreciate the free-flowing, clear-water canal with excellent access to both the ocean and the bay. The private dock with a 7,000-lb side-lift boat elevator makes heading out for fishing, diving, or sunset cruises effortless. The spacious lot offers a large driveway, double covered parking, and ample room for boat trailers and additional vehicles. Downstairs, a full concrete pad and enclosed angler's room provide the perfect space for storing fishing gear, dive equipment, and all your island toys. Located near mile marker 28.5, Jolly Roger Estates is a peaceful, palm-lined waterfront community on the Atlantic side of Little Torch Key, offering direct access to Pine Channel and world-class boating, fishing, and diving at nearby Looe Key Reef. Just 24 miles from Key West, this exceptional property delivers the perfect blend of island tranquility and convenient access to dining, entertainment, and amenities--an ideal full-time residence, second home, or investment in the Florida Keys lifestyle.
MARMLS #A11998100
Sep 15, 2026
Sold
$850,000
$656/sq ft
Sep 4, 2026
Pending
—
Aug 9, 2026
Contingent
—
Jun 2, 2026
Price Changed
$895,000
$691/sq ft
Jun 2, 2026
Relisted
—
May 31, 2026
Listing Removed
—
Jan 1, 2026
Listed
$899,000
$694/sq ft
FLKMLS #617906
Jun 1, 2026
Listing Removed
—
May 5, 2026
Price Changed
$896,000
$691/sq ft
Apr 27, 2026
Price Changed
$897,000
$692/sq ft
Apr 20, 2026
Price Changed
$898,000
$693/sq ft
Mar 7, 2026
Price Changed
$899,000
$694/sq ft
Mar 3, 2026
Price Changed
$939,000
$725/sq ft
Feb 20, 2026
Price Changed
$944,000
$728/sq ft
Jan 2, 2026
Listed
$949,000
$732/sq ft
MARMLS #A11877522
Dec 31, 2025
Listing Removed
—
Oct 13, 2025
Price Changed
$974,000
$752/sq ft
Jun 7, 2025
Listed
$979,000
$755/sq ft
FLKMLS #615353
Dec 30, 2025
Listing Removed
—
Nov 5, 2025
Price Changed
$969,000
$748/sq ft
Oct 13, 2025
Price Changed
$974,000
$752/sq ft
Aug 18, 2025
Price Changed
$979,000
$755/sq ft
Jul 8, 2025
Price Changed
$989,000
$763/sq ft
Jun 25, 2025
Price Changed
$995,000
$768/sq ft
Jun 6, 2025
Listed
$1,050,000
$810/sq ft
FLKMLS #567337
Mar 4, 2016
Sold
$480,000
$370/sq ft
Apr 28, 2015
Listed
$489,000
$377/sq ft
Public Records
Apr 7, 1998
Sold
$20,000
$15/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$7,478 (+8.3%)
2024
$6,907 (+6.8%)
2023
$6,469 (+15.0%)
2022
$5,623 (+8.8%)
2021
$5,169 (+4.0%)
$253,575 + $233,914
$487,489
2020
$4,969 (+0.4%)
$248,850 + $212,372
$461,222
2019
$4,951 (−2.4%)
$248,850 + $212,372
$461,222
2018
$5,073 (+10.3%)
$243,000 + $214,935
$457,935
2017
$4,599 (+279.2%)
$238,500 + $215,080
$453,580
2015
$1,213 (+65.5%)
$222,555 + $186,274
$408,829
2014
$733
Public record
Public record
Zoning
Beds
3
Baths
2
Stories
2
Lot width
—
Lot depth
—
Lot size
6,000 Sq. Ft.
Year renovated
2017
Sq. Ft.
1,296
Year built
2015
Style
Single Family Residential
County
Monroe County
APN
2866 29 00215230000000
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Oct 9, 2026.
IS
III
Improved Subdivision District
The purpose of the IS district is to accommodate the legally vested residential development rights of the owners of lots in subdivisions that were lawfully established and improved prior to the adoption of this LDC. For the purpose of this section, improved lots are those that are served by a dedicated and accepted existing road of porous or nonporous material, that have an approved potable water supply, and that have sufficient uplands to accommodate the proposed use in accordance with the required setbacks. This district is not intended to be used for new land use districts of this classification within the county.
Zone overlays
Tier III Overlay District
Permitted uses
Include but are not limited to:
Housing-Multiple units
Infrastructure
Property details
Parking
Garage/Carport Information
Has Garage
# of Garage Spaces: 2
Parking
Features: Driveway
# of Covered Spaces: 2
Interior
Virtual Tour
Bathroom Information
# of Full Bathrooms: 2
Room Information
Room Types: Workshop
Equipment
Appliances: Built-In Oven, Dryer, Dishwasher, Electric Range, Electric Water Heater, Disposal, Microwave, Refrigerator, Washer
Interior Features
Flooring: Tile
Other Features: Second Floor Entry, Workshop
Exterior
Building Information
Stories: 1
Year Built Details: Effective Year Built
Roof Details: Metal
Construction Details: Modular/Prefab
Exterior Features
Exterior Features: Balcony, Deck
Patio And Porch Features: Balcony, Deck, Open
Lot Information
Lot Size Area: 6,000
Lot Features: Less Than Quarter Acre
Road Frontage Type: City Street
Is Waterfront
Waterfront Features: Canal Front
Frontage Length: 60
Frontage Length Remarks: 60
Zoning Description: is
Property Information
Has View
Direction Faces: West
Financial
Tax Information
Annual Tax Amount: $7,478
Tax Year: 2025
Utilities
Utility Information
Sewer: Public Sewer
Water Source: Public
Heating & Cooling
Has Cooling
Cooling: Central Air, Ceiling Fan(s)
Has Heating
Heating: Central
Public facts
Beds: 3
Baths: 2.0
Sq. Ft.: 1,296
Stories: 2.0
Lot Size: 6,000 square feet
Style: Single Family Residential
Year Built: 2015
Year Renovated: 2017
County: Monroe County
APN: 2866 29 00215230000000
Home facts updated by county records on Oct 9, 2026
Around this home
Schools
Sugarloaf School
Public PreK-8 • Assigned • 8.9mi
6/10
Key West High School
Public 9-12 • Assigned • 25.5mi
4/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
Heat Factor
We're working on getting current and accurate heat risk information for this home.
10/10 Wind Factor
99% chance of strong winds in next 30 years
1/10 Air Factor
0 unhealthy days expected this year, 0 days in 30 years
Provided by First Street
Historical weather
Little Torch Key, FL • 33042
Average low and high temperatures (°F)
74
64
77
67
81
70
83
74
89
80
91
81
92
83
91
81
88
80
85
77
81
72
78
69
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
84/ 100
Very good sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
7.7 hrs
5.3 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$822,000 – $995,000
Sell confidently with a local market expert in Little Torch Key.