437 Pirates Rd

Summerland Key, FL 33042

$949,000
Price
3
Beds
1,296 Sq. Ft.
$732 / Sq. Ft.
1,296
Sq. Ft.
$732
per Sq. Ft.
an aerial view of multiple house
an aerial view of a house with swimming pool and sitting area
an aerial view of a house with a garden and plants
an aerial view of a swimming pool with outdoor seating
a front view of a house with a yard
a view of balcony with wooden floor and fence
an outdoor space with furniture
a roof deck with table and chairs
a view of a livingroom with furniture and a ceiling fan
a view of backyard with large tree
a house view with a garden space
a living room with furniture and a large window
a living room with furniture a fireplace and a flat screen tv
a living room with furniture a flat screen tv and a large window
a living room with granite countertop furniture and a wooden floor
a kitchen with granite countertop kitchen island stainless steel appliances a stove a sink a dining table and chairs
a kitchen with a refrigerator sink and stove top oven
a kitchen with a table and chairs
a kitchen with a dining table cabinets appliances and a window
a bedroom with a bed and a chandelier
a bedroom with a bed and ceiling fan
a bedroom with a bed dresser and a window
a bathroom with a granite countertop sink a light fixture and a mirror
a bedroom with a bed and a window
a bedroom with a bed and a chandelier
a bathroom with a bath tub a sink and a mirror
a view of room with window and wooden floor
a living room with a window and a table
a utility room with closet dryer and washer
an aerial view of a house with a yard and a sitting area
an aerial view of residential building and ocean
an aerial view of multiple house
an aerial view of a swimming pool with outdoor seating
an aerial view of residential houses with outdoor space
a view of a storage & utility room
a street sign on a wall next to a road
a picture of a park

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. 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.
  1. Listed by Jo Ann Cook • Ocean Sotheby's International
  2. Listed by Ally Kelley • Ocean Sotheby's International

Property Details for 437 Pirates Road

Waterfront
Canal Front, Salt Ponds
Waterfront
Yes
Zoning
IS - Improved Subivision District
Subdivision
Jolly Roger Estates (28.5)
Directions
US #1 to Pirates Road, Little Torch. 1/2 mile down on the left, sign on property.
Vehicle Storage
Guest Parking, Trailer Storage, Covered Parking, RV Parking Open, Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 01/02/2026 10:33 AM

Property Details for 437 Pirates Road

StatusActive
MLS #617906
Days on Market20
Taxes$7,478 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built2015
Lot Size0.14 AC / 6,000 SF
CountyMonroe County

Location

Listing Courtesy of Ocean Sotheby's International
Add your commute

Building Information for 437 Pirates Road

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

Payment Calculator

$5,248 per month

30 year fixed, 6.15% Interest

Principal and Interest

$4,625

Property Taxes

$623

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 437 Pirates Road

Summary
Location and General Information
  • Waterview: Canal View, Salt Ponds
  • Area: 10 - Little, Middle, Big Torch Keys
  • Absolute Longitude: 81.387663
  • Control Depth: 4
  • Off Shore Island: No
  • Listing Board: Marathon/Lower Keys
  • Side: Ocean
  • Mile Marker: 28.5
  • Marathon Neighborhood: N/A
  • Key/Island: Little Torch Key
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Furnished: Unfurnished
  • Tax Year: 2025
  • Tax Exemptions: None
Property
Lot Information
  • Acres: 0.14
  • Parcel #: 00215230-000000
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: BK 1 LT 6 JOLLY ROGER ESTATES LITTLE TORCH KEY PB5-34
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Flood Zone: AE
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 39
  • Document Count: 0
  • Building Style: Above Flood: Yes
  • Building Style: Stilt Column Height: Tall - 10Ft & Over
  • Security: Patrolled Area
Utilities
  • Utilities: FKAA, Cable Available, Elect Separate Meter, Water Separate Meter, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Species List: No
  • Pool: No
  • Porch/Balcony: Open Porch/Balcony, Deck
Interior and Exterior Features
Interior Features
  • Floor: Tile
  • Interior Features: Built-in Cabinets, Tray Ceilings, Window Treatments, Walk-in Closet(s), Smoke Alarms
  • Pre-Wired: Cable
  • Appliances: Washer, Stainless Steel Appliance(s), Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Construction: Modular, Hardi Board Siding
  • Dockage: Boat Lift
  • Windows/Doors: Impact Rstnce Window, Impact Rstnce Doors
Room Information
  • Specialty Rooms: Utility Room, Workshop

Property History for 437 Pirates Road

DateEvent & SourcePriceAppreciation
Jan 2, 2026

Listed (Active)

FKMLS #617906

$949,000—
Dec 31, 2025

Expired

MiamiRE #A11877522

—
Dec 30, 2025

Temp Off Market

FKMLS #615353

—
Oct 13, 2025

Price Change

MiamiRE #A11877522

$974,000—
Jun 7, 2025

Listed (Active)

MiamiRE #A11877522

$979,000—
Jun 6, 2025

Price Change

FKMLS #615353

$1,050,000—
Jun 6, 2025

Price Change

FKMLS #615353

$995,000—
Jun 6, 2025

Price Change

FKMLS #615353

$989,000—
Jun 6, 2025

Price Change

FKMLS #615353

$979,000—
Jun 6, 2025

Price Change

FKMLS #615353

$974,000—
Jun 6, 2025

Listed (Active)

FKMLS #615353

$969,000—
Mar 4, 2016

Sold

FKMLS #567337

$480,000—
Mar 3, 2016

Sold (Public Record)

Public Record #568037041

$480,000

+22.5% / yr

Dec 23, 2015

Pending

FKMLS #567337

—
Apr 28, 2015

Listed (Active)

FKMLS #567337

$489,000—
Dec 17, 2002

Sold (Public Record)

Public Record #107061303

$33,000—
DateEvent & SourcePrice
01/02/2026

Listed (Active)

FKMLS #617906

$949,000
12/31/2025

Expired

MiamiRE #A11877522

—
12/30/2025

Temp Off Market

FKMLS #615353

—
10/13/2025

Price Change

MiamiRE #A11877522

$974,000
06/07/2025

Listed (Active)

MiamiRE #A11877522

$979,000
06/06/2025

Price Change

FKMLS #615353

$1,050,000
06/06/2025

Price Change

FKMLS #615353

$995,000
06/06/2025

Price Change

FKMLS #615353

$989,000
06/06/2025

Price Change

FKMLS #615353

$979,000
06/06/2025

Price Change

FKMLS #615353

$974,000
06/06/2025

Listed (Active)

FKMLS #615353

$969,000
03/04/2016

Sold

FKMLS #567337

$480,000
03/03/2016

Sold (Public Record)

Public Record #568037041

$480,000

+22.5% / yr

12/23/2015

Pending

FKMLS #567337

—
04/28/2015

Listed (Active)

FKMLS #567337

$489,000
12/17/2002

Sold (Public Record)

Public Record #107061303

$33,000

For completeness, Compass 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 2, 2026 by Ocean Sotheby's International, it's currently listed at $949,000. It has been on the market for a total of 20 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 descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes 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.