OFF MARKET

Off Market Jan 2025 for $4.4M

$4,077,575

Est. refi paymentEst. refi $33,399/mo

•

3,213

sq ft

64 Front St, Key West, FL 33040

About this home

Your DREAM home awaits. . Located in Truman Annex, where luxury meets island living. This stunning 5-bedroom, 5-bathroom residence boasts over 3000 sq ft of living space offering unparalleled comfort and elegance. As you step inside you are greeted by an expansive and open floor plan, featuring 11ft high ceilings and abundant natural light that illuminates the interior. The kitchen and dining area are open and spacious perfect for entertaining guests. The lavish master suite is a sanctuary of relaxation. Open and full of natural light streaming in from the glass doors that lead to your covered balcony. The en suite bath is completely updated, open and spacious with dual sinks. Featuring fully enclosed steam shower! Each additional bedroom is generously sized and appointed. Two of the bedrooms are adjoined by a remodeled Jack and Jill bathroom and one with a beautiful en suite bath. Outside, the tropical Oasis awaits, with sparkling resurfaced and new tile pool with brand new waterfall surrounded by beautiful landscaping. Lounge poolside or beat the heat in your pool house. Additional features include tube elevator, covered parking, and balconies on the front and back of the home. Numerous updates from bathrooms to new ac units, resurfaced pool, new waterfall and fresh paint throughout

Single-familyProperty Type

1989Year Built

5,007 sq ftLot Size

$1,269Est. Price/Sq.Ft.

Listed by Matthew Sheehan • Saltwater Real Estate Florida Keys, Inc

Bought with Solaris Gregory • Expert Realty LLC (HQ)

Redfin checked: a few seconds ago

•Source:FLKMLS #611378

Redfin Estimate

$4,077,575

$322K since sold in January 2025$3,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11.7% lower than the average sale price ($4.62M) of 6 comparable homes.

SOLD JUN 29, 2026
$2,750,000
A
5 beds4.5 baths2,721 sq ft
1114 Packer St, Key West, FL 33040
SOLD MAY 7, 2026
$7,200,000
B
4 beds3.5 baths2,650 sq ft
16 Sunset Key Dr, Key West, FL 33040
SOLD MAR 16, 2026
$4,225,000
C
5 beds5.5 baths3,434 sq ft
515 Amelia St, Key West, FL 33040
SOLD JUL 20, 2026
$5,800,000
D
3 beds3 baths1,927 sq ft
293 Sunset Key Dr, Key West, FL 33040
SOLD MAR 12, 2026
$3,422,500
E
5 beds5.5 baths3,006 sq ft
1022 Packer 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

$9,172/mo

Redfin rental estimate

List your home for rent

Market trends in 33040, FL

Last updated August 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-List Price

95.5%

0.0% MoM

Median sale price

$997K

$103K MoM

Avg. days on market

141d

11 days MoM

Recently sold homes

116

18 MoM

New listings for sale

NEW 2 MINS AGO
$1,050,000
3 beds2 baths1,350 sq ft
26 Spoonbill Way, Key West, FL 33040
NEW 6 HRS AGO
$1,375,000
2 beds2 baths948 sq ft
1216 Packer St, Key West, FL 33040
NEW 9 HRS AGO
$869,000
2 beds1 bath680 sq ft
620 Thomas St #149, Key West, FL 33040
NEW 29 HRS AGO
$2,980,000
3 beds2 baths1,782 sq ft
728 Poor House Ln, Key West, FL 33040
NEW 33 HRS AGO
$649,000
1 bed1 bath626 sq ft
806 Florida St Apt 5, Key West, FL 33040
3D WALKTHROUGH
$599,900
3 beds2 baths1,050 sq ft
3314 Northside Dr #55, Key West, FL 33040
$2,919,000
3 beds4 baths3,461 sq ft
3615 Eagle Ave, Key West, FL 33040
$455,000
2 beds1 bath696 sq ft
3312 Northside Dr Apt 407, Key West, FL 33040
OPEN SAT, 11:30AM TO 1:30PM
$950,000
2 beds1 bath610 sq ft
611 Grinnell St #6, Key West, FL 33040
$375,000
— beds— baths— sq ft
5555 College Rd Unit Barracuda 10, Key West, FL 33040
See all

Provided by Redfin

Sale history for 64 Front St

Date

Event

Price

FLKMLS #611378

Jan 2, 2025

Sold

$4,400,000

$1,369/sq ft

Nov 20, 2024

Contingent

—

Sep 7, 2024

Listed

$4,599,000

$1,431/sq ft

FLKMLS #609046

Sep 7, 2024

Listing Removed

—

Sep 6, 2024

Price Changed

$4,599,000

$1,431/sq ft

May 30, 2024

Price Changed

$4,950,000

$1,541/sq ft

May 30, 2024

Relisted

—

May 27, 2024

Listing Removed

—

May 16, 2024

Price Changed

$5,199,000

$1,618/sq ft

Apr 28, 2024

Price Changed

$5,590,000

$1,740/sq ft

Mar 4, 2024

Listed

$5,700,000

$1,774/sq ft

FLKMLS #604823

Aug 18, 2023

Sold

$4,025,000

$1,253/sq ft

Jul 20, 2023

Contingent

—

Jul 14, 2023

Price Changed

$4,500,000

$1,401/sq ft

Apr 21, 2023

Relisted

—

Apr 10, 2023

Contingent

—

Apr 4, 2023

Listed

$4,800,000

$1,494/sq ft

Spectacular home in great location in the award-winning Truman Annex. This beautiful home custom built in 1989, includes five bedrooms and five bathrooms. There are four sets of covered decks, a lovely guest house and off street covered parking. Plenty of room here to enjoy the inside outside lifestyle we so adore here in Key West. Easy walking distance to restaurants, galleries, sunset celebration and Fort Zachary Taylor State Park and Beach. Very easy to show.

FLKMLS #107150

May 15, 2020

Listing Removed

—

Nov 30, 2007

Listed

$2,999,000

$933/sq ft

FLKMLS #512723

May 15, 2020

Listing Removed

—

Aug 23, 2002

Listed

$2,200,000

$685/sq ft

FLKMLS #114305

Jan 25, 2013

Sold

$2,300,000

$716/sq ft

Feb 9, 2011

Listed

$2,350,000

$731/sq ft

FLKMLS #110579

Jun 17, 2009

Listing Removed

—

Mar 24, 2009

Listed

$575,000

$179/sq ft

FLKMLS #108556

Jun 17, 2009

Listing Removed

—

May 13, 2008

Listed

$2,295,000

$714/sq ft

FLKMLS #103725

Jul 27, 2007

Listing Removed

—

Oct 17, 2006

Listed

$3,695,000

$1,150/sq ft

FLKMLS #92623

Mar 12, 2004

Sold

$1,800,000

$560/sq ft

Aug 28, 2003

Listed

$1,950,000

$607/sq ft

FLKMLS #414262

Jun 12, 2000

Sold

$1,425,000

$444/sq ft

Apr 6, 1999

Listed

$1,495,000

$465/sq ft

Public Records

May 16, 1995

Sold

$635,000

$198/sq ft

Public Records

Aug 28, 1992

Sold

$390,000

$121/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$29,885 (+0.2%)

$2,353,290 + $1,211,509

$3,564,799

2024

$29,820 (−4.7%)

$2,353,290 + $1,209,818

$3,563,108

2023

$31,306 (+19.1%)

2022

$26,295 (+5.7%)

2021

$24,875 (−4.3%)

$1,642,296 + $1,149,519

$2,791,815

2020

$25,987 (+1.6%)

$1,752,450 + $1,174,590

$2,927,040

2019

$25,578 (+9.1%)

$1,752,450 + $1,174,590

$2,927,040

2018

$23,435 (+8.6%)

2017

$21,580 (+8.2%)

$1,762,464 + $575,231

$2,337,695

2015

$19,948 (−1.9%)

$1,575,943 + $506,400

$2,082,343

2014

$20,339

Tax history for 64 Front St

Year

Property tax

Land + Additions

Assessment*

2025

$29,885 (+0.2%)

$2,353,290 + $1,211,509

$3,564,799

2024

$29,820 (−4.7%)

$2,353,290 + $1,209,818

$3,563,108

2023

$31,306 (+19.1%)

2022

$26,295 (+5.7%)

2021

$24,875 (−4.3%)

$1,642,296 + $1,149,519

$2,791,815

2020

$25,987 (+1.6%)

$1,752,450 + $1,174,590

$2,927,040

2019

$25,578 (+9.1%)

$1,752,450 + $1,174,590

$2,927,040

2018

$23,435 (+8.6%)

2017

$21,580 (+8.2%)

$1,762,464 + $575,231

$2,337,695

2015

$19,948 (−1.9%)

$1,575,943 + $506,400

$2,082,343

2014

$20,339

*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

6,100 Sq. Ft.

Year renovated

2010

Sq. Ft.

3,213

Year built

1989

Style

Single Family Residential

County

Monroe County

APN

0668 25 00006700000500

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 10, 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: Carport

Interior

Virtual Tour

Interior Features
Interior Features: Smoke Alarms, Window Treatments, Tray Ceilings
Flooring: Tile Floor, Carpet, Wood Floor
Windows/Doors: French Doors, Wood Windows
Cooling/Heating: Central A/C, Ceiling Fans
Appliances: Washer, Microwave, Oven, Refrigerator, Dishwasher, Dryer
Furnished: Furniture Negotiable

Bathroom Information
# of Full Baths: 5

Exterior

Boat Slip/Dock Information
Dockage: None

Exterior Features
Exterior Features: Fencing, Fruit Tree(s)
Has Pool
Pool Information: In Ground, Concrete
Porch/Balcony: Open Porch/Balcony, Patio

Security
Manned Gate, Patrolled Area

Property Features
Waterfront Type: None
Waterview: No Waterview

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

Lot Information
Acres: 0.11
Zoning: HPRD - Hist Planned Redevelopment & Dev Dist
Land Size: Less Than 1/4 Acre
Flood Zone: AE

Building Information
Year Built: 1,989
Sq. Ft. Source: Tax Records
Building Style: Stories: 2
Building Style: Above Flood: Unknown
Construction: Frame
Roof: Metal Roof

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

Financial

Tax Information
Taxes: $31,305.80
Tax Year: 2,023
Tax Exemptions: None

Financial Information
Terms: Cash, Conventional

Utilities

Utility Information
Utilities: FKAA, Buyer to Verify
Pre-Wired: Other: Hotwire
Has Public Sewer Hook-up

Location

Homeowners Association Information
Mandatory Home Owners Association
Association Info: 1st Right of Refusal: Yes
Association Info: Association Fee $: 1324.00
Association Info: Association/Maintenance Fee Per: Quarterly
Fee Includes: Cable, Other, Security, Common Area Maintenance

Location Information
Side: Median
Mile Marker: 1.00

Neighborhood Features
Beach

Public facts

Beds: 5
Baths: 5.0
Sq. Ft.: 3,213
Stories: 2.0
Lot Size: 6,100 square feet
Style: Single Family Residential
Year Built: 1989
Year Renovated: 2010
County: Monroe County
APN: 0668 25 00006700000500

Home facts updated by county records on Jul 10, 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

$3.87M – $4.69M

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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NEW 6 HRS AGO

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New listings for sale in 33040

NEW 2 MINS AGO

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26 Spoonbill Way, Key West, FL 33040

NEW 6 HRS AGO

$1,375,000

2 beds2 baths948 sq ft

1216 Packer St, Key West, FL 33040

NEW 9 HRS AGO

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2 beds1 bath680 sq ft

620 Thomas St #149, Key West, FL 33040

NEW 29 HRS AGO

$2,980,000

3 beds2 baths1,782 sq ft

728 Poor House Ln, Key West, FL 33040

NEW 33 HRS AGO

$649,000

1 bed1 bath626 sq ft

806 Florida St Apt 5, Key West, FL 33040

3D WALKTHROUGH

$599,900

3 beds2 baths1,050 sq ft

3314 Northside Dr #55, Key West, FL 33040

$2,919,000

3 beds4 baths3,461 sq ft

3615 Eagle Ave, Key West, FL 33040

$455,000

2 beds1 bath696 sq ft

3312 Northside Dr Apt 407, Key West, FL 33040

OPEN SAT, 11:30AM TO 1:30PM

$950,000

2 beds1 bath610 sq ft

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Home values near 64 Front St

Data from public records.

Address	Redfin Estimate
58 Front St, Key West, FL 6 Beds \| 7 Baths \| 4636 Sq. Ft.	$4,055,079
56 Front St, Key West, FL 2 Beds \| 2.5 Baths \| 2295 Sq. Ft.	$3,789,338

Address	Redfin Estimate
62 Front St, Key West, FL 4 Beds \| 3 Baths \| 2486 Sq. Ft.	$4,103,560
412 Porter Ln Apt 8, Key West, FL 2 Beds \| 2 Baths \| 1036 Sq. Ft.	$1,483,646

Address	Redfin Estimate
66 Front St, Key West, FL 5 Beds \| 4 Baths \| 3252 Sq. Ft.	$4,008,181
402 Porter Ln Apt 18, Key West, FL 2 Beds \| 2 Baths \| 1023 Sq. Ft.	$1,365,132

Property information provided by FLKMLS when last listed in 2024. 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 64 Front St

Tax history for 64 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 64 Front St

More real estate resources