437 Pirates Rd

Summerland Key, FL 33042

$895,000
Price
3
Beds
1,296 Sq. Ft.
$691 / Sq. Ft.
1,296
Sq. Ft.
$691
per Sq. Ft.
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Description

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...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.

Property Details for 437 Pirates Road

Subdivision
JOLLY ROGER ESTATES
Complex Name
JOLLY ROGER ESTATES
Style
WF/Ocean Access
Waterfront
Yes
Waterfront Description
Canal Front
View
Canal, Water View
Unit View
Canal, Water
Area
98 Florida Keys
LISTING UPDATED: 06/02/2026 11:31 AM

Property Details for 437 Pirates Road

StatusActive
MLS #A11998100
Days on Market177
Taxes$7,478 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single
Year Built2015
Lot Size0.14 AC / 6,000 SF
CountyMonroe County
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Location

Listing Courtesy of Ocean Sotheby's International
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Building Information for 437 Pirates Road

Stories1Year Built2015Building Size-Lot Size0.14 AC / 6,000 SF

Payment Calculator

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$5,083 per month

30 year fixed, 6.36% Interest

Principal and Interest

$4,460

Property Taxes

$623

HOA Dues

$0

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Property Information for 437 Pirates Road

Location Information
Schools
  • Elementary School: Sugarloaf
  • Middle School: Sugarloaf
  • Senior High School: Key West
Location Information
  • Parcel Number Free Text: 00215230-000000
  • FolioNum2ndParcel: 00215230000000
  • Parcel Number MLX: 0
  • MLS Area: 98 Florida Keys
  • Township Range: 21, 0021, 2152
  • Section: 28
  • Subdivision Complex Bldg: JOLLY ROGER ESTATES
  • Num Interior Levels: One
  • Zoning Information: is
General Information
Parking
  • Num Garage Spaces: 2
  • Garage Description: Driveway
  • Carport Description: Driveway
  • Parking Description: Additional Spaces Available, Driveway
General Information
  • Style of Property: Single Family Residence
  • Property Type Information: Single Family Residence
  • Prop Type-Type of Building: Single Family Residence
  • County Land Code: Monroe County
  • Front Exposure: West
  • Housing Older Persons Act: No HOPA
  • Balcony Porch/Patio: Yes
  • Total Acreage: 0
  • Property Sq Ft: 6000
  • Num Floors: 1
  • Road Frontage: Public Road
  • Lot Description: Less Than 1/4 Acre Lot
  • Waterfront Frontage: 60
  • Water Access: Boatlift
  • Water View: Canal
  • Waterview Description: Canal
  • Boat Access: Lift
  • Boat Services: Lift
  • Pool: No
  • Design: Detached
  • Design Description: One Story
  • Construction: Modular Construction
  • Construction Type: Modular Construction
  • Roof: Metal
  • Roof Description: Metal Roof
  • Column Description: Modular
  • Flooring: Tile Floors
  • Floor Description: Tile Floors
  • Directions: US #1 to Pirates Road, Little Torch. 1/2 mile down on the left, sign on property.
  • Virtual Tour: https://www.propertypanorama.com/instaview/mia/A11998100
  • Security Information: Fire Alarm
Room Information
Room Information
  • Rooms Description: Workshop
  • Bedroom Description: Primary Bath Shower
  • Master Bath Features: Separate Shower
Additional Property Information
Utilities
  • Heating Description: Central Heat
  • Cooling Description: Ceiling Fans, Central Cooling
  • Water Description: Municipal Water
  • Sewer Description: Municipal Sewer
Additional Property Information
  • Pet Restrictions: No Restrictions
  • Guest Accommodations: No
  • Room Count: 0
  • Num of Baths: 2.0
  • Furnished: Unfurnished
  • Interior Features: Second Floor Entry
  • Equipment Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Fire Alarm, Microwave, Electric Range, Refrigerator, Wall Oven, Washer
  • Windows Treatment: Balcony
  • Exterior Features: Deck, Open Balcony
  • Subdivision Information: Public Road
  • Deed Restrictions: Unknown
  • Amenities: Lift, Balcony, Fire Alarm
Financial Information
Financial Information
  • Total Mortgage: $360,000
  • Type of Association: Voluntary
  • Flood Zone: AE
  • Tax Year: 2025
  • Tax Information: Tax Reflects No Exemptions
  • Special Information: None
Agent / Office Information
Listing Information
  • Transaction Type: Residential, Single Family Residence

Property History for 437 Pirates Road

DateEvent & SourcePriceAppreciation
Jun 2, 2026

Price Change

Beaches MLS #A11998100

$895,000—
Jun 2, 2026

Price Change

MiamiRE #A11998100

$895,000—
Jun 2, 2026

Listed (Active)

MiamiRE #A11998100

—
DateEvent & SourcePrice
06/02/2026

Price Change

Beaches MLS #A11998100

$895,000
06/02/2026

Price Change

MiamiRE #A11998100

$895,000
06/02/2026

Listed (Active)

MiamiRE #A11998100

—

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 437 Pirates Road

Taxable ValueLand$543,000Additions$294,026Total$837,026
Tax Record2024$6,907 ($576 / month)
Home Facts
Beds3Baths2Total Finished SqFt1,296 SqFtAbove Grade Finished SqFt1,296 SqFtStories2Lot Size6,000 SqFtStyleSingle Family ResidenceYear Built2015Year Renovated2017CountyMONROEAPN00215230-000000

Schools near 437 Pirates Road

This home is within Monroe.
Rating
School
Type
Grades
Distance
Sugarloaf School
Public - PK to 8
Key West High School
Public - 9 to 12
Big Pine Academy
Charter - PK to 5
The College Of The Florida Keys Academy
Charter - 9 to 12
Rating
School
Distance
Sugarloaf School
PublicPK to 8

Key West High School
Public9 to 12

Big Pine Academy
CharterPK to 5

The College Of The Florida Keys Academy
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 437 Pirates Road, Summerland Key, FL 33042

437 Pirates Road is a single family home for sale in Summerland Key, FL 33042. This property was listed for sale on January 1, 2026 by Ocean Sotheby's International, it's currently listed at $895,000. It has been on the market for a total of 177 days and was last sold on March 4, 2016. This listing's school district is Monroe. Nearby schools include Sugarloaf School, Key West High School and Big Pine Academy. 437 Pirates Road is a 3-bed, 2-bath, 1,296 sqft single family home built in 2015.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Ocean Sotheby's International

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.