437 Pirates Rd

Off Market

437 Pirates Rd

Monroe County FL 33042

2842 sq. ft.

0.14 ac.

Single-Family

Last sold for $850,000

Jo Ann Cook, last sold this property on 15 September 2026 after 158 days on market.

Overview

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.

Features

3 bedrooms

2 bathrooms

2 carspaces

2 garage spaces

2842 sq. ft. floor area

0.14 ac. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Monroe County over the last 12 months, the estimated median property value of 437 Pirates Rd is $950k.

Median value

$950k

Estimated value range

$560k - $4.15m

Median days on market

124

Estimated value trend

-13%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Monroe County. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 437 Pirates Rd

2026

Sold

$850,000

15 Sep 2026 by Jo Ann Cook, of Ocean Sotheby's International

2016

Sold

$480,000

04 Mar 2016 by Beata Sharpe

Happy sellers in Monroe County

90%

90% of sellers in Monroe County reported that their sale price either exceeded or met their price expectations.

Monroe County stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 4 reviews in Monroe County over the last 12 months.

Local market activity for 3 bedroom single-family properties in Monroe County

In the last 12 months, 7 three-bedroom single-family properties similar to 437 Pirates Rd, have been sold.

This represents a 75% increase in three-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Monroe County for a market analysis.

Sandra Tuttle

at Island Welcome Real Estate

(74 reviews)

Get a market analysis

Melissa Meier

(1 review)

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TRISH BRUMMER

at Waterfront Keys Realty Inc.

(12 reviews)

Get a market analysis

Lisa Ferringo

at Coldwell Banker Schmitt Lower Keys

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Monroe County

Sandra Tuttle

Sellers who recommend Sandra Tuttle have praised them for being local expert, reliable, responsive, clear communication, great negotiation, well-connected, and detail-oriented