OFF MARKET

Off Market Mar 2022 for $1.2M

$1,294,762

Est. refi paymentEst. refi $7,277/mo

•

1,232

sq ft

375 Pirates Rd, Little Torch Key, FL 33042

About this home

WOW! Is what you'll say when you enter this 3Bd/2BA beauty in desirable Jolly Roger Estates! Bring your suitcase and your fishing pole and start enjoying life in the beautiful Florida Keys. This clear, flow-through canal front home comes with it all! EVERYTHING including the boat and the brand-new trailer, all the furniture (inside and out), one-of-kind accent pieces, and off the hook artwork! The house was completely remodeled in 2018. Tile floors throughout, stainless steel appliances, granite counter tops, impact windows and doors, metal roof and Hardi Board siding. Engineered dock and lift plans FDEP and ACOE approval submitted and pending. Paver driveway and stone added in 2021, the house was also rewired and re-plumbed in 2021 and the whole underneath of the house has been painted. New fishing station with running water and new outdoor shower. Plenty of room for a pool or a tiki bar to entertain your friends and family! Enjoy some of the best boating in the Lower Keys from this oceanside location. Quick access to amazing fishing, the famous Looe Reef, and stunning sand bars. Close to shopping, restaurants, taverns and 1.4 miles to the 4A boat launch. Less than 30 miles to Marathon and Key West. The current owners purchased this as their forever home and have created a turn key, rock solid, meticulously maintained, move in ready, piece of paradise. A business situation required a pivot in their plans hence the reason for the sale. This stunner won't last long, come see for yourself!

Single-familyProperty Type

1990Year Built

6,000 sq ftLot Size

$1,051Est. Price/Sq.Ft.

Listed by Cindy Tafel • EXP Realty LLC

Bought with Caroline Bauer • At Home in Key West, Inc.

Redfin checked: a minute ago

•Source:FLKMLS #599009

Redfin Estimate

$1,294,762

$30K since sold in March 2022$2,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 84.6% higher than the average sale price ($701K) of 6 comparable homes.

SOLD JUN 10, 2026
$540,000
A
3 beds2 baths984 sq ft
27059 Old State Road 4A, Ramrod Key, FL 33042
SOLD MAR 23, 2026
$775,000
B
3 beds2 baths1,152 sq ft
27360 St Croix Ln, Ramrod Key, FL 33042
SOLD JUN 25, 2026
$880,000
C
3 beds2 baths1,408 sq ft
27415 Barbuda Ln, Ramrod Key, FL 33042
SOLD JAN 14, 2026
$725,000
D
3 beds2 baths1,078 sq ft
27394 Saint Lucie Ln, Ramrod Key, FL 33042
SOLD JUN 2, 2026
$595,000
E
3 beds2 baths1,104 sq ft
27147 Dolphin Rd, Ramrod Key, FL 33042
SOLD JUL 16, 2026
$693,800
F
3 beds2 baths1,039 sq ft
29048 Iris Dr, Big Pine Key, FL 33043

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$4,299/mo

Redfin rental estimate

List your home for rent

Market trends in 33042, FL

Last updated July 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-List Price

95.8%

+1.2% MoM

Median sale price

$1.1M

$10K MoM

Avg. days on market

121d

11 days MoM

Recently sold homes

4 MoM

New listings for sale

NEW 11 HRS AGO
$982,600
2 beds2 baths864 sq ft
701 Spanish Main Dr #198, Cudjoe Key, FL 33042
NEW 1 DAY AGO
$950,000
2 beds1 bath902 sq ft
24923 Park Dr, Summerland Key, FL 33042
3D WALKTHROUGH
$1,099,000
3 beds2 baths1,488 sq ft
27334 Guadaloupe Ln, Ramrod Key, FL 33042
$849,000
3 beds3 baths1,800 sq ft
22832 John Silver Ln, Cudjoe Key, FL 33042
See all

Provided by Redfin

Sale history for 375 Pirates Rd

Date

Event

Price

FLKMLS #599009

Mar 21, 2022

Sold

$1,265,000

$1,027/sq ft

Jan 5, 2022

Contingent

—

Jan 3, 2022

Listed

$1,265,000

$1,027/sq ft

FLKMLS #593791

Mar 18, 2021

Sold

$714,000

$580/sq ft

Dec 16, 2020

Listed

$719,000

$584/sq ft

+27

FLKMLS #95273

Jun 28, 2006

Sold

$700,000

$568/sq ft

Dec 8, 2005

Listed

$739,000

$600/sq ft

FLKMLS #529115

Jun 28, 2006

Sold

$700,000

$568/sq ft

Jun 23, 2005

Listed

$739,000

$600/sq ft

Public Records

Oct 28, 1991

Sold

$185,000

$150/sq ft

Public Records

Jul 1, 1988

Sold

$26,000

$21/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$10,084 (+4.9%)

$543,000 + $521,192

$1,064,192

2024

$9,613 (+0.2%)

$543,000 + $495,769

$1,038,769

2023

$9,597 (+47.9%)

$570,000 + $473,596

$1,043,596

2022

$6,488 (+21.7%)

$375,000 + $300,444

$675,444

2021

$5,332 (+5.7%)

$253,575 + $251,690

$505,265

2020

$5,042 (+0.5%)

$248,850 + $220,301

$469,151

2019

$5,015 (+6.3%)

$248,850 + $220,301

$469,151

2018

$4,717 (+0.8%)

$243,000 + $177,606

$420,606

2017

$4,677 (+4.6%)

$238,500 + $182,160

$420,660

2015

$4,473 (+4.8%)

$222,555 + $169,086

$391,641

2014

$4,269

Tax history for 375 Pirates Rd

Year

Property tax

Land + Additions

Assessment*

2025

$10,084 (+4.9%)

$543,000 + $521,192

$1,064,192

2024

$9,613 (+0.2%)

$543,000 + $495,769

$1,038,769

2023

$9,597 (+47.9%)

$570,000 + $473,596

$1,043,596

2022

$6,488 (+21.7%)

$375,000 + $300,444

$675,444

2021

$5,332 (+5.7%)

$253,575 + $251,690

$505,265

2020

$5,042 (+0.5%)

$248,850 + $220,301

$469,151

2019

$5,015 (+6.3%)

$248,850 + $220,301

$469,151

2018

$4,717 (+0.8%)

$243,000 + $177,606

$420,606

2017

$4,677 (+4.6%)

$238,500 + $182,160

$420,660

2015

$4,473 (+4.8%)

$222,555 + $169,086

$391,641

2014

$4,269

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

6,000 Sq. Ft.

Year renovated

2019

Sq. Ft.

1,520

Year built

1990

Style

Single Family Residential

County

Monroe County

APN

2866 29 00215270000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 10, 2026.

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

Parking / Garage Information
Vehicle Storage: Carport, Off Street Parking, Open Parking, Covered Parking

Interior

Virtual Tour

Interior Features
Interior Features: Granite Counter Top, Walk-in Closet, Storage, Smoke Alarms, Sky Light(s)
Flooring: Tile Floor
Windows/Doors: Impact Rstnce Doors, Sliding Glass Doors, Impact Rstnce Window
Cooling/Heating: Ceiling Fans, Window/Wall Unit, Central A/C
Appliances: Dishwasher, Washer, Range, Stainless Steel Appl, Refrigerator, Oven, Microwave, Dryer
Furnished: Furnished

Bathroom Information
# of Full Baths: 2

Specialty Room Information
Specialty Rooms: Laundry Room

Exterior

Boat Slip/Dock Information
Dockage: Dock Length: 600
Dockage: Dock: Wood

Exterior Features
Exterior Features: Fencing, Storage, Privacy Wall/Fence, Outdoor Shower
Porch/Balcony: Deck, Open Porch/Balcony

Property Features
Accessibility Features: None
On Waterfront
Waterfront Type: Canal Front
Waterview: Canal View, Salt Ponds

Property Information
Property Condition: Updated/Remodeled
Deed Restrictions: Unknown
Pets: Pets Allowed
Rentals Allowed: With Restrictions
Min Rental Days: 28

Lot Information
Acres: 0.14
Zoning: IS - Improved Subivision District
Land Size: Less Than 1/4 Acre
Control Depth: 3
Flood Zone: AE 8

Building Information
Year Built: 1,990
Sq. Ft. Source: Property Data Card
Building Style: Above Flood: Yes
Construction: Hardi Board Siding
Roof: Metal Roof

Subdivision/Neighborhood
Subdivision: Jolly Roger Estates (28.5)
Marathon Neighborhood: N/A

Financial

Tax Information
Taxes: $5,331.61
Tax Year: 2,021
Tax Exemptions: Homestead

Financial Information
Terms: Cash, VA, FHA, Conventional

Utilities

Utility Information
Utilities: Buyer to Verify
Pre-Wired: Cable, Satellite, Cat 5
Has Public Sewer Hook-up

Location

Homeowners Association Information
Association Info: 1st Right of Refusal: No
Association Info: Association Fee $: 0.00
Fee Includes: None

Location Information
Side: Ocean
Mile Marker: 28.50
Directions: US 1 to MM 28.5 to Pirates Rd. House is half way down on the left side.

Public facts

Beds: 3
Baths: 2.0
Sq. Ft.: 1,520
Stories: 2.0
Lot Size: 6,000 square feet
Style: Single Family Residential
Year Built: 1990
Year Renovated: 2019
County: Monroe County
APN: 2866 29 00215270000000

Home facts updated by county records on Jul 10, 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

Lifestyle

Provided by Walk Score and Local Logic

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)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 10 hours in June and 7.3 hours in December, placing it above the U.S. average for solar exposure.

10 hrs

7.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.23M – $1.49M

Sell confidently with a local market expert in Little Torch Key. 3 minutes to get started.

Nearby similar homes

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22832 John Silver Ln, Cudjoe Key, FL 33042

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3D WALKTHROUGH

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NEW CONSTRUCTION

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New listings for sale in 33042

NEW 11 HRS AGO

$982,600

2 beds2 baths864 sq ft

701 Spanish Main Dr #198, Cudjoe Key, FL 33042

NEW 1 DAY AGO

$950,000

2 beds1 bath902 sq ft

24923 Park Dr, Summerland Key, FL 33042

3D WALKTHROUGH

$1,099,000

3 beds2 baths1,488 sq ft

27334 Guadaloupe Ln, Ramrod Key, FL 33042

$849,000

3 beds3 baths1,800 sq ft

22832 John Silver Ln, Cudjoe Key, FL 33042

Home values near 375 Pirates Rd

Data from public records.

Address	Redfin Estimate
355 Pirates Rd, Little Torch Key, FL 3 Beds \| 2 Baths \| 1452 Sq. Ft.	$892,556
447 Pirates Rd, Little Torch Key, FL 3 Beds \| 2 Baths \| 984 Sq. Ft.	$994,262

Address	Redfin Estimate
437 Pirates Rd, Little Torch Key, FL 3 Beds \| 2 Baths \| 1296 Sq. Ft.	—
325 Pirates Rd, Little Torch Key, FL 3 Beds \| 2 Baths \| 1320 Sq. Ft.	$1,019,603

Address	Redfin Estimate
345 Pirates Rd, Little Torch Key, FL 2 Beds \| 2 Baths \| 1142 Sq. Ft.	$973,983
427 Pirates Rd, Little Torch Key, FL 3 Beds \| 2.5 Baths \| 2303 Sq. Ft.	$1,430,071

Property information provided by FLKMLS when last listed in 2022. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 33042, FL

Sale history for 375 Pirates Rd

Tax history for 375 Pirates Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 33042

Home values near 375 Pirates Rd

More real estate resources