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$899,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,296 Sq. Ft.
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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.

Full Property Details for 437 Pirates Rd

General

  • Price: $899,000
  • Taxes: $7,478 (2025)
  • Status: Active
  • Type: Single Family
  • Source: Greater_Miami
  • MLS ID: A11998100
  • Updated: 4/29/2026
  • Added to Site: 146 day(s) ago

Interior

  • Interior Features: Second Floor Entry, Workshop
  • Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Electric Range, Refrigerator, Wall Oven, Washer
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3
  • Bedroom Features: Primary Bath Shower

Other Rooms

  • Living Room: Workshop Sq. Ft.

Additional Information

  • Security/Safety: Fire Alarm

Exterior

  • Exterior Features: Open Balcony
  • Deck/Patio: Deck, Open Balcony

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Additional Spaces Available, Driveway

Location

  • Area: Jolly Roger Estates
  • County: Monroe County
  • Subdivision: JOLLY ROGER ESTATES
  • Building Name: JOLLY ROGER ESTATES
  • Direction Faces: West

Community

  • Community Name: Jolly Roger Estates
  • Association: Yes

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Ceiling Fan(s), Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Municipal Water

Structural Information

  • Architectural Style: Detached, One Story
  • Structure Type: House
  • Detached/Attached: Detached
  • Construction: Modular Construction
  • Roof: Metal Roof
  • Building Size: 2842
  • Square Feet: 1,296
  • Living Area: 1,296 Sq. Ft.
  • Year Built: 2015

Lot Features

  • Property View: Canal, Water
  • Lot Size (Sq. Ft.): 6,000
  • Frontage Feet: 60
  • Lot Features: Less Than 1/4 Acre Lot
  • Zoning: is

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: WF/Ocean Access, Canal Front

Financial Considerations

  • Price Per Sq. Ft.: $693.67
  • Tax Amount: $7,478
  • Tax Year: 2025
  • Terms: Conventional, FHA-Va Approved, VA Loan

Disclosures and Reports

  • Legal Description: BK 1 LT 6 JOLLY ROGER ESTATES LITTLE TORCH KEY PB5-34 OR358-388 OR493-875 OR525-675 OR898-1386 OR911-2401 OR1058-2037 OR1437-803 OR1482-1655
  • Restrictions: No Restrictions
  • Inclusions: Boatlift
  • Property ID: 00215230-000000

Listed by Ocean Sotheby's International

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Listing agent

— 437 Pirates Rd —

  • Ocean Sotheby's International

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 437 Pirates Rd

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Sugarloaf School
255 Crane Boulevard, Summerland Key, FL 33042
PK-88.9 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-1225.5 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 437 Pirates Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/01/2026
Listed
$899,000
87.29%
MLS
3/03/2016
Sold
$480,000
—
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 437 Pirates Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$6,907
—
$837,026
1%
2024
$6,907
7%
$832,835
—
2023
$6,469
25%
$835,215
71%
2021
$5,169
-8%
$487,489
-24%
2022
$5,623
9%
$643,091
39%
2021
$5,169
4%
$461,222
1%
2019
$4,951
-2%
$457,690
—
2018
$5,073
10%
$457,935
1%
2017
$4,599
32%
$453,580
11%
2016
$3,482
187%
$408,829
1354%
2015
$1,214
66%
$28,110
10%
2014
$733
78%
$25,555
10%
2013
$412
—
$23,232
—
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.

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Listed by Ocean Sotheby's International

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437 Pirates Rd, Lower Sugarloaf Key, FL 33042 (MLS# A11998100) is a Single Family property with 3 bedrooms and 2 full bathrooms. 437 Pirates Rd is currently listed for $899,000 and was received on January 01, 2026. Want to learn more about 437 Pirates Rd? Do you have questions about finding other Single Family real estate for sale in Lower Sugarloaf Key? You can browse all Lower Sugarloaf Key real estate or contact a Coldwell Banker agent to request more information.

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