OFF MARKET

Off market oct 2021 for $3.4M

$4,345,110

Est. refi paymentEst. refi $19,909/mo

•

4,636

sq ft

58 Front St, Key West, FL 33040

About this home

Conch Casa Grande is the largest home in Truman Annex, with 4636 sq ft of living space. With 11 foot ceilings and detailed woodwork, this grand home captures the essence of another era. Just off the front hall is the first of six bedrooms. There are four bedrooms on the 2nd floor, and a 6th bedroom on the 3rd floor. All six bedrooms have en suite bathrooms. This home has a TRUMAN ANNEX SPECIAL TRANSIENT LICENSE, which has already generated $300,000 this year in gross annual income. This is a potential short sale. It is a condition of entering into a sales contract that the Buyer separately purchase from Seller the furniture and art work presently on the premises. There are several exclusions of artwork and the Grandfather clock.

Single-familyProperty Type

1999Year Built

5,001 sq ftLot Size

$937Est. Price/Sq.Ft.

2 spacesParking

Listed by Christopher Santry • Last Key Realty, Inc (KW)

Listed by Alexis O'Donnell • Last Key Realty, Inc (KW)

Bought with Leigh Ann Roach • Berkshire Hathaway HomeServices Knight & Gardner Realty

Bought with Christopher Santry • Last Key Realty, Inc (KW)

Redfin checked: a few seconds ago

•Source:FLKMLS #589735

Redfin Estimate

$4,345,110

$945K since sold in October 2021$258K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.2% higher than the average sale price ($4.09M) 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 MAY 12, 2026
$1,275,000
B
8 beds10 baths2,432 sq ft
720-726 Emma St, 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 JUN 29, 2026
$2,750,000
D
5 beds4.5 baths2,721 sq ft
1114 Packer St, Key West, FL 33040
SOLD JUL 20, 2026
$5,800,000
E
3 beds3 baths1,927 sq ft
293 Sunset Key Dr, Key West, FL 33040
SOLD MAY 21, 2026
$3,300,000
F
5 beds6 baths3,667 sq ft
400 Aronovitz Ln, 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

$9,019/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

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 4 HRS AGO
$5,200,000
4 beds3 baths2,058 sq ft
1100 Johnson St, Key West, FL 33040
NEW 5 HRS AGO
$749,000
4 beds2 baths1,304 sq ft
6415 2nd Ter, Stock Island, FL 33040
NEW 7 HRS AGO
$1,399,000
3 beds3 baths1,374 sq ft
1221 Ashby St, Key West, FL 33040
NEW 8 HRS AGO
$1,895,000
4 beds3.5 baths2,282 sq ft
1423 Rose St, Key West, FL 33040
OPEN SAT, 10AM TO 1PM
$1,699,000
2 beds2.5 baths1,463 sq ft
615 Amelia St, Key West, FL 33040
NEW 32 HRS AGO
$1,999,999
4 beds3 baths2,342 sq ft
220 Angela St Unit A&B, Key West, FL 33040
NEW 32 HRS AGO
$3,850,000
5 beds3.5 baths2,280 sq ft
415 & 417 Truman Ave, Key West, FL 33040
3D WALKTHROUGH
$1,195,000
3 beds2 baths1,052 sq ft
2911 Seidenberg Ave, Key West, FL 33040
$1,695,000
4 beds4.5 baths2,027 sq ft
5 Hilton Haven Dr, Key West, FL 33040
$1,169,000
2 beds2.5 baths1,124 sq ft
927 Thomas St #1, Key West, FL 33040
See all

Provided by Redfin

Sale history for 58 Front St

Date

Event

Price

Public Records

Oct 27, 2021

Sold

$3,400,000

$733/sq ft

FLKMLS #589735

Oct 26, 2021

Listing Removed

—

Oct 26, 2021

Sold

$3,400,000

$733/sq ft

Aug 29, 2021

Contingent

—

Feb 4, 2020

Listed

$3,900,000

$841/sq ft

FLKMLS #583770

May 15, 2020

Listing Removed

—

Jan 17, 2019

Listed

$4,399,000

$949/sq ft

FLKMLS #576410

May 15, 2020

Listing Removed

—

Jul 26, 2017

Listed

$4,950,000

$1,068/sq ft

FLKMLS #122484

May 31, 2016

Listing Removed

—

Nov 30, 2015

Listed

$4,850,000

$1,046/sq ft

FLKMLS #121690

Oct 7, 2015

Listing Removed

—

Jun 17, 2015

Listed

$4,850,000

$1,046/sq ft

Beaches MLS #R2929209

Nov 30, 2008

Listing Removed

—

May 30, 2008

Listed

$3,995,000

$862/sq ft

FLKMLS #104548

May 19, 2008

Listing Removed

—

Jan 10, 2007

Listed

$4,460,000

$962/sq ft

FLKMLS #102230

Jul 20, 2006

Listing Removed

—

Apr 14, 2006

Listed

$6,000,000

$1,294/sq ft

FLKMLS #514144

May 30, 2003

Listing Removed

—

Dec 7, 2002

Listed

$4,200,000

$906/sq ft

Public Records

Jul 8, 1997

Sold

$212,000

$46/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$35,294 (+1.5%)

$2,350,000 + $1,872,458

$4,222,458

2024

$34,789 (−0.4%)

2023

$34,911 (+21.8%)

2022

$28,653 (+2.7%)

$1,955,000 + $1,462,798

$3,417,798

2021

$27,890 (−3.5%)

$1,640,000 + $1,496,055

$3,136,055

2020

$28,909 (+4.7%)

2019

$27,612 (+4.3%)

2018

$26,474 (+13.9%)

2017

$23,244 (+8.8%)

$1,760,239 + $812,204

$2,572,443

2015

$21,365 (+2.5%)

$1,575,214 + $644,062

$2,219,276

2014

$20,848

Tax history for 58 Front St

Year

Property tax

Land + Additions

Assessment*

2025

$35,294 (+1.5%)

$2,350,000 + $1,872,458

$4,222,458

2024

$34,789 (−0.4%)

2023

$34,911 (+21.8%)

2022

$28,653 (+2.7%)

$1,955,000 + $1,462,798

$3,417,798

2021

$27,890 (−3.5%)

$1,640,000 + $1,496,055

$3,136,055

2020

$28,909 (+4.7%)

2019

$27,612 (+4.3%)

2018

$26,474 (+13.9%)

2017

$23,244 (+8.8%)

$1,760,239 + $812,204

$2,572,443

2015

$21,365 (+2.5%)

$1,575,214 + $644,062

$2,219,276

2014

$20,848

*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

5.5

Stories

Lot width

—

Lot depth

—

Lot size

5,001 Sq. Ft.

Year renovated

2018

Sq. Ft.

4,912

Year built

1999

Style

Single Family Residential

County

Monroe County

APN

0668 25 00006700000401

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, Off Street Parking
Vehicle Storage: Car(s): 2

Interior

Interior Features
Interior Features: Built-in Cabinets, Other, Window Treatments, Walk-in Closet, Smoke Alarms, Foyer, Drapes/Blinds Incl
Flooring: Wood Floor
Windows/Doors: Double Hung Windows, French Doors
Cooling/Heating: Central A/C
Appliances: Dishwasher, Range, Washer, Refrigerator, Freezer, Oven, Microwave, Dryer, Disposal
Furnished: Furniture Negotiable

Bathroom Information
# of Full Baths: 7

Specialty Room Information
Specialty Rooms: Laundry Room

Exterior

Boat Slip/Dock Information
Dockage: None

Exterior Features
Exterior Features: Fencing, Privacy Wall/Fence
Has Pool
Pool Is Heated
Pool Information: Concrete, In Ground
Pool Information: Dimensions: 0.00 x 0.00
Pool Info: Other: Eq Incld;
Porch/Balcony: Deck, Open Porch/Balcony

Security
Manned Gate, Patrolled Area

Property Features
Waterfront Type: None
Waterview: No Waterview

Property Information
Deed Restrictions: Unknown
Pets: Pets Allowed
Rentals Allowed: Yes
Min Rental Days: 7

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: 1,999
Sq. Ft. Source: Seller
Building Style: Stories: 3
Building Style: Above Flood: Yes
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: $27,612.28
Tax Year: 2,019
Tax Exemptions: None

Financial Information
Terms: Cash, Not Assumable, No Seller Finance, Conventional

Utilities

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

Location

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

Location Information
Side: Ocean
Mile Marker: 1.00

Public facts

Beds: 6
Baths: 5.5
Sq. Ft.: 4,912
Stories: 2.0
Lot Size: 5,001 square feet
Style: Single Family Residential
Year Built: 1999
Year Renovated: 2018
County: Monroe County
APN: 0668 25 00006700000401

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

7/10 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

$4.13M – $5.00M

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 listings for sale in 33040

NEW 4 HRS AGO3D WALKTHROUGH

$5,200,000

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1100 Johnson St, Key West, FL 33040

NEW 5 HRS AGO

$749,000

4 beds2 baths1,304 sq ft

6415 2nd Ter, Stock Island, FL 33040

NEW 7 HRS AGO

$1,399,000

3 beds3 baths1,374 sq ft

1221 Ashby St, Key West, FL 33040

NEW 8 HRS AGO

$1,895,000

4 beds3.5 baths2,282 sq ft

1423 Rose St, Key West, FL 33040

OPEN SAT, 10AM TO 1PM3D WALKTHROUGH

$1,699,000

2 beds2.5 baths1,463 sq ft

615 Amelia St, Key West, FL 33040

NEW 32 HRS AGO

$1,999,999

4 beds3 baths2,342 sq ft

220 Angela St Unit A&B, Key West, FL 33040

NEW 32 HRS AGO

$3,850,000

5 beds3.5 baths2,280 sq ft

415 & 417 Truman Ave, Key West, FL 33040

3D WALKTHROUGH

$1,195,000

3 beds2 baths1,052 sq ft

2911 Seidenberg Ave, Key West, FL 33040

$1,695,000

4 beds4.5 baths2,027 sq ft

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Home values near 58 Front St

Data from public records.

Address	Redfin Estimate
51 Front Street, Key West, FL 4 Beds \| 4 Baths \| 3991 Sq. Ft.	$7,984,703
62 Front Street, Key West, FL 4 Beds \| 3 Baths \| 2486 Sq. Ft.	$4,071,711

Address	Redfin Estimate
52 Front Street, Key West, FL 5 Beds \| 6 Baths \| 3353 Sq. Ft.	$4,247,233
54 Front Street, Key West, FL 3 Beds \| 3.5 Baths \| 3024 Sq. Ft.	$3,929,474

Address	Redfin Estimate
64 Front Street, Key West, FL 5 Beds \| 5 Baths \| 3213 Sq. Ft.	$4,066,259
66 Front Street, Key West, FL 5 Beds \| 4 Baths \| 3252 Sq. Ft.	$4,022,795

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 58 Front St

Tax history for 58 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 58 Front St

More real estate resources