OFF MARKET

Off market nov 2021 for $3.4M

$4,192,245

Est. refi paymentEst. refi $24,744/mo

•

3,252

sq ft

66 Front St, Key West, FL 33040

About this home

Lushly landscaped oasis with 3 story, detached single family home w/ classic Key West architectural design in the Truman Annex, including the special Truman Annex transient license. Enjoy your own heated pool w/ waterfall. The first level is an open design including kitchen, dining, living area, powder room; and, just off the dining, a den that's easily converted to additional sleeping quarters. The 2nd level has laundry and 2 main suites sharing a spacious deck overlooking the pool. The 3rd floor has 2, dormered bedrooms w/ shared bath. Up just one more set of stairs is a widow walk w/ glorious vistas of Old Town & sunset over the Gulf. Wood floors throughout, impact glass windows & doors, and pool house w/ powder room & outdoor shower abutting a two-car garage with electric gate.

Single-familyProperty Type

1998Year Built

5,022 sq ftLot Size

$1,289Est. Price/Sq.Ft.

1 garage spacesParking

Listed by Roger Cousineau • Keller Williams Key West Compass Realty

Listed by Edward Russell • Keller Williams Key West Compass Realty

Bought with Gary Thomas • Preferred Properties (KW)

Redfin checked: a few seconds ago

•Source:FLKMLS #590493

Redfin Estimate

$4,192,245

$767K since sold in November 2021$169K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 15.4% lower than the average sale price ($4.96M) of 6 comparable homes.

SOLD MAY 7, 2026
$7,200,000
A
4 beds3.5 baths2,650 sq ft
16 Sunset Key Dr, Key West, FL 33040
SOLD JUN 29, 2026
$2,750,000
B
5 beds4.5 baths2,721 sq ft
1114 Packer St, Key West, FL 33040
SOLD JUL 20, 2026
$5,800,000
C
3 beds3 baths1,927 sq ft
293 Sunset Key Dr, Key West, FL 33040
SOLD SEP 16, 2026
$6,600,000
D
3 beds2.5 baths2,528 sq ft
5 Sunset Key Dr, Key West, FL 33040
SOLD JAN 27, 2026
$3,095,000
E
4 beds4 baths1,653 sq ft
512 Emma St, Key West, FL 33040
SOLD APR 9, 2026
$4,300,000
F
4 beds4.5 baths3,624 sq ft
406 United St, Key West, FL 33040

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$9,452/mo

Redfin rental estimate

List your home for rent

Market trends in 33040, FL

Last updated September 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

94.4%

1.2% MoM

Median sale price

$1,000K

$294 MoM

Avg. days on market

135d

5 days MoM

Recently sold homes

111

3 MoM

New listings for sale

NEW 17 HRS AGO
$2,895,000
3 beds3 baths1,600 sq ft
711 Olivia St, Key West, FL 33040
OPEN SAT, 11AM TO 1PM
$1,050,000
3 beds2 baths1,248 sq ft
3315 Donald Ave, Key West, FL 33040
FOR SALE BY OWNER
$1,150,000
3 beds3 baths1,618 sq ft
3344 Pearl Ave, Key West, FL 33040
$2,399,000
4 beds3 baths1,854 sq ft
1320 Eliza St, Key West, FL 33040
VIDEO TOUR
$879,000
3 beds2.5 baths1,821 sq ft
212 Avenue G, Key West, FL 33040
$2,649,000
3 beds3 baths2,002 sq ft
410 Louisa St, Key West, FL 33040
3D WALKTHROUGH
$1,505,000
3 beds3 baths1,680 sq ft
1414 18th St, Key West, FL 33040
$2,229,000
3 beds3 baths1,702 sq ft
3801 Flagler Ave, Key West, FL 33040
$995,000
2 beds2 baths1,008 sq ft
2514 Flagler Ave, Key West, FL 33040
3D WALKTHROUGH
$1,929,000
3 beds3 baths1,672 sq ft
1607 Sunshine Dr, Key West, FL 33040
See all

Provided by Redfin

Sale history for 66 Front St

Date

Event

Price

FLKMLS #590493

Nov 30, 2021

Sold

$3,425,000

$1,053/sq ft

Oct 15, 2021

Contingent

—

Apr 5, 2020

Listed

$3,700,000

$1,138/sq ft

FLKMLS #113446

May 15, 2020

Listing Removed

—

Aug 19, 2010

Listed

$1,995,000

$613/sq ft

FLKMLS #112300

May 15, 2020

Listing Removed

—

Jan 12, 2010

Listed

$2,295,000

$706/sq ft

FLKMLS #111042

May 15, 2020

Listing Removed

—

Jun 16, 2009

Listed

$2,495,000

$767/sq ft

FLKMLS #109681

May 15, 2020

Listing Removed

—

Nov 17, 2008

Listed

$2,495,000

$767/sq ft

FLKMLS #115764

Feb 14, 2012

Sold

$1,862,500

$573/sq ft

Dec 19, 2011

Listed

$1,995,000

$613/sq ft

FLKMLS #108244

Nov 3, 2008

Listing Removed

—

Apr 1, 2008

Listed

$2,850,000

$876/sq ft

FLKMLS #91839

Nov 7, 2003

Sold

$1,950,000

$600/sq ft

Aug 13, 2002

Listed

$2,100,000

$646/sq ft

Public Records

Dec 16, 1998

Sold

$1,079,700

$332/sq ft

Public Records

Jan 21, 1998

Sold

$300,000

$92/sq ft

Public Records

May 17, 1990

Sold

$161,900

$50/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$28,114 (+0.2%)

$2,364,570 + $984,979

$3,349,549

2024

$28,070 (−10.6%)

$2,364,570 + $985,945

$3,350,515

2023

$31,407 (+22.1%)

2022

$25,730 (+21.1%)

$1,967,121 + $1,096,480

$3,063,601

2021

$21,248 (−4.5%)

$1,650,168 + $727,373

$2,377,541

2020

$22,247 (−1.2%)

$1,760,850 + $738,003

$2,498,853

2019

$22,511 (−1.8%)

$1,760,850 + $738,003

$2,498,853

2018

$22,936 (+51.8%)

2017

$15,109 (−5.3%)

2015

$15,949 (−3.4%)

2014

$16,504

Tax history for 66 Front St

Year

Property tax

Land + Additions

Assessment*

2025

$28,114 (+0.2%)

$2,364,570 + $984,979

$3,349,549

2024

$28,070 (−10.6%)

$2,364,570 + $985,945

$3,350,515

2023

$31,407 (+22.1%)

2022

$25,730 (+21.1%)

$1,967,121 + $1,096,480

$3,063,601

2021

$21,248 (−4.5%)

$1,650,168 + $727,373

$2,377,541

2020

$22,247 (−1.2%)

$1,760,850 + $738,003

$2,498,853

2019

$22,511 (−1.8%)

$1,760,850 + $738,003

$2,498,853

2018

$22,936 (+51.8%)

2017

$15,109 (−5.3%)

2015

$15,949 (−3.4%)

2014

$16,504

*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
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

5,022 Sq. Ft.

Year renovated

2005

Sq. Ft.

2,852

Year built

1998

Style

Single Family Residential

County

Monroe County

APN

0668 25 00006700000602

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 9, 2026.

HPRD

Historic Planned Redevelopment And Development District

The historic planned redevelopment and development district HPRD is established to implement comprehensive plan policies for areas designated HPRD on the comprehensive plan future land use map. The HPRD district shall provide a management framework for directing future redevelopment in several redeveloping fringe areas within and outside the review area of the historic architectural review commission.; The HPRD district includes the Truman Annex project, including Sunset Island. The HPRD district shall provide a basis for encouraging additional development and redevelopment activities in other areas. Such new development and redevelopment shall be designed to advance the goals, objectives and policies of the comprehensive plan. For instance, the HPRD district shall promote the following: Historic preservation.; Neighborhood facility improvements.; Architectural and urban design amenities which are consistent with the traditional Old Town historic character and which further subarea design and improvement strategies.; An increased supply of affordable housing which is accessible to targeted income groups over a longterm period.; Off-site parking facilities, including parking structures at strategically located areas through contributions to a special parking fund to be established to assist in financing construction of off-site centrally located parking facilities.

Permitted uses

Include but are not limited to:

Housing-Group
Housing-Single unit
Housing-Multiple units
Office

Property details

Parking

Parking / Garage Information
Vehicle Storage: Auto Door Opener, Off Street Parking, Detached, Garage
Vehicle Storage: Car(s): 2

Interior

Interior Features
Windows/Doors: Double Hung Windows, Impact Rstnce Window, Impact Rstnce Doors, French Doors
Cooling/Heating: Ceiling Fans, Heat, Central A/C
Appliances: Dishwasher, Range, Washer, Refrigerator, Microwave, Dryer
Furnished: Furniture Negotiable

Bathroom Information
# of Full Baths: 3
# of Half Baths: 2

Exterior

Boat Slip/Dock Information
Dockage: None

Exterior Features
Exterior Features: Fencing, Outdoor Shower, Landscape Lighting
Has Pool
Pool Is Heated
Pool Information: Concrete, In Ground
Porch/Balcony: Deck, Widow's Walk, Patio, Open Porch/Balcony

Security
Patrolled Area

Property Features
Waterfront Type: None
Waterview: No Waterview

Property Information
Deed Restrictions: Unknown
Pets: Pets w/Restrictions: YES
Rentals Allowed: With Restrictions

Lot Information
Acres: 0.12
Zoning: HPRD - Hist Planned Redevelopment & Dev Dist
Land Size: Less Than 1/4 Acre
Flood Zone: AE

Building Information
Year Built: 1,998
Sq. Ft. Source: Tax Records
Building Style: Stories: 3
Building Style: Above Flood: Yes
Construction: Frame
Roof: Metal Roof

Subdivision/Neighborhood
Subdivision: Old Town - Unrecord (1.0)
Key West Neighborhood: Truman Annex
Marathon Neighborhood: N/A

Financial

Tax Information
Taxes: $22,247
Tax Year: 2,020
Tax Exemptions: None

Financial Information
Terms: Cash, Conventional

Utilities

Utility Information
Utilities: FKAA, Municipal Sewer
Has Public Sewer Hook-up

Location

Homeowners Association Information
Mandatory Home Owners Association
Association Info: 1st Right of Refusal: Yes
Association Info: Association Fee $: 925.00
Association Info: Association/Maintenance Fee Per: Quarterly
Fee Includes: Common Area Maintenance, Security

Location Information
Side: Median
Mile Marker: 1.00

Public facts

Beds: 5
Baths: 4.0
Sq. Ft.: 2,852
Stories: 3.0
Lot Size: 5,022 square feet
Style: Single Family Residential
Year Built: 1998
Year Renovated: 2005
County: Monroe County
APN: 0668 25 00006700000602

Home facts updated by county records on Oct 9, 2026

Around this home

Schools

Horace O'bryant School

Public PreK-8 • Assigned • 1.3mi

3/10

Key West High School

Public 9-12 • Assigned • 1.9mi

4/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

8/10 Flood Factor

Estimated 74-82% chance 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

Key West, FL • 33040

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 10.1 hours in June and 7.3 hours in December, placing it above the U.S. average for solar exposure.

10.1 hrs

7.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$3.98M – $4.82M

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

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3D WALKTHROUGH

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3D WALKTHROUGH

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New listings for sale in 33040

NEW 17 HRS AGO

$2,895,000

3 beds3 baths1,600 sq ft

711 Olivia St, Key West, FL 33040

OPEN SAT, 11AM TO 1PM

$1,050,000

3 beds2 baths1,248 sq ft

3315 Donald Ave, Key West, FL 33040

FOR SALE BY OWNER

$1,150,000

3 beds3 baths1,618 sq ft

3344 Pearl Ave, Key West, FL 33040

$2,399,000

4 beds3 baths1,854 sq ft

1320 Eliza St, Key West, FL 33040

VIDEO TOUR

$879,000

3 beds2.5 baths1,821 sq ft

212 Avenue G, Key West, FL 33040

$2,649,000

3 beds3 baths2,002 sq ft

410 Louisa St, Key West, FL 33040

3D WALKTHROUGH

$1,505,000

3 beds3 baths1,680 sq ft

1414 18th St, Key West, FL 33040

$2,229,000

3 beds3 baths1,702 sq ft

3801 Flagler Ave, Key West, FL 33040

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Home values near 66 Front St

Data from public records.

Address	Redfin Estimate
101 Front Street #6, Key West, FL 2 Beds \| 2.5 Baths \| 1100 Sq. Ft.	$1,153,054
101 Front Street #4, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,138,526

Address	Redfin Estimate
101 Front Street #16, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,032,258
101 Front Street #24, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,238,865

Address	Redfin Estimate
101 Front Street #26, Key West, FL 2 Beds \| 2.5 Baths \| 1292 Sq. Ft.	$1,494,290
101 Front Street #10, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,206,085

Property information provided by FLKMLS when last listed in 2020. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 33040, FL

Sale history for 66 Front St

Tax history for 66 Front St

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 33040

Home values near 66 Front St

More real estate resources