OFF MARKET

Off market may 2021 for $999K

$1,214,891

Est. refi paymentEst. refi $7,634/mo

•

1,140

sq ft

101 Front St #5, Key West, FL 33040

About this home

Unique opportunity to own a successful vacation rental in sought after Truman Annex. Upon entering the home you will observe soaring 11 ft ceilings and an open floor plan. Kitchen, living room and half bath located on the 1st floor. Take the stairs to the 2nd floor and you will find the master bedroom which features a private balcony and en-suite bath. Guest bedroom is located on the 3rd floor with en-suite bath. Property features private deck and courtyard accompanied by grill and patio set, the prefect spot to enjoy a happy hour cocktail. One reserved parking space included with purchase. Shared pool exclusive to Foundry residents. Special Truman Annex transient license with restrictions included.

TownhomeProperty Type

1995Year Built

855 sq ftLot Size

$1,066Est. Price/Sq.Ft.

1 spaceParking

Listed by Teodora Masters • Bascom Grooms Real Estate (KW)

Listed by Paige Bethel • Bascom Grooms Real Estate (KW)

Bought with Miriam Novotny • Vacasa Florida, LLC

Redfin checked: a few seconds ago

•Source:FLKMLS #595190

Redfin Estimate

$1,214,891

$216K since sold in May 2021$27K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.8% lower than the average sale price ($1.29M) of 6 comparable homes.

SOLD MAY 20, 2026
$1,345,000
A
2 beds2.5 baths1,216 sq ft
101 Front St #8, Key West, FL 33040
SOLD OCT 13, 2026
$1,375,000
B
2 beds2 baths960 sq ft
568 Porter Ln, Key West, FL 33040
SOLD MAY 1, 2026
$1,050,000
C
2 beds2.5 baths960 sq ft
212 Southard St, Key West, FL 33040
SOLD APR 1, 2026
$1,245,000
D
2 beds2.5 baths960 sq ft
528 Porter Ln, Key West, FL 33040
SOLD MAR 2, 2026
$1,070,000
E
2 beds2.5 baths960 sq ft
208 Fleming St, Key West, FL 33040
SOLD APR 15, 2026
$1,650,000
F
2 beds2.5 baths1,420 sq ft
212 Fleming 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

$4,380/mo

Redfin rental estimate

List your home for rent

Market trends in 33040, FL

Last updated October 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

94.0%

0.4% MoM

Median sale price

$1.0M

$33K MoM

Avg. days on market

136d

1 days MoM

Recently sold homes

13 MoM

New listings for sale

NEW 30 MINS AGO
$1,150,000
2 beds2.5 baths1,237 sq ft
12 Mccoy Cir #12, Key West, FL 33040
NEW 4 HRS AGO
$995,000
2 beds2 baths980 sq ft
2601 S Roosevelt Blvd Unit 602A, Key West, FL 33040
NEW 24 HRS AGO
$750,000
3 beds2 baths1,130 sq ft
210 4th St, Key West, FL 33040
NEW 29 HRS AGO
$557,000
3 beds2 baths1,070 sq ft
3930 S Roosevelt Blvd Unit 105W, Key West, FL 33040
OPEN SUN, 12PM TO 2PM
$1,898,000
3 beds2.5 baths2,205 sq ft
421 United St, Key West, FL 33040
NEW 32 HRS AGO
$1,850,000
5 beds3 baths2,146 sq ft
530 White St, Key West, FL 33040
$40,000
2 beds2 baths1,100 sq ft
617 Front St Unit 1st Q Float, Key West, FL 33040
$2,895,000
2 beds2 baths1,472 sq ft
726 Simonton St, Key West, FL 33040
$1,290,000
2 beds2 baths1,458 sq ft
702 Florida St, Key West, FL 33040
$1,700,000
2 beds2 baths1,311 sq ft
1800 Atlantic Blvd Unit 327C, Key West, FL 33040
See all

Provided by Redfin

Sale history for 101 Front St #5

Year

Property tax

Land + Additions

Assessment*

2026

$9,241 (−8.5%)

$630,000 + $450,754

$1,080,754

2025

$10,097 (+5.2%)

$698,250 + $460,774

$1,159,024

2024

$9,595 (+5.3%)

2023

$9,116 (+14.4%)

2022

$7,966 (+15.9%)

$546,000 + $365,165

$911,165

2021

$6,873 (−6.4%)

$514,599 + $221,389

$735,988

2020

$7,345 (−1.5%)

$559,927 + $232,726

$792,653

2019

$7,456 (+0.3%)

$559,927 + $232,726

$792,653

2018

$7,432 (+4.7%)

$540,818 + $238,440

$779,258

2017

$7,095 (+11.2%)

$521,413 + $207,382

$728,795

2015

$6,378 (−3.2%)

$549,402 + $169,270

$718,672

2014

$6,588

Tax history for 101 Front St #5

Year

Property tax

Land + Additions

Assessment*

2026

$9,241 (−8.5%)

$630,000 + $450,754

$1,080,754

2025

$10,097 (+5.2%)

$698,250 + $460,774

$1,159,024

2024

$9,595 (+5.3%)

2023

$9,116 (+14.4%)

2022

$7,966 (+15.9%)

$546,000 + $365,165

$911,165

2021

$6,873 (−6.4%)

$514,599 + $221,389

$735,988

2020

$7,345 (−1.5%)

$559,927 + $232,726

$792,653

2019

$7,456 (+0.3%)

$559,927 + $232,726

$792,653

2018

$7,432 (+4.7%)

$540,818 + $238,440

$779,258

2017

$7,095 (+11.2%)

$521,413 + $207,382

$728,795

2015

$6,378 (−3.2%)

$549,402 + $169,270

$718,672

2014

$6,588

*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

2.5

Stories

Lot width

—

Lot depth

—

Lot size

855 Sq. Ft.

Year renovated

2015

Sq. Ft.

1,140

Year built

1995

Style

Single Family Residential

County

Monroe County

APN

0668 25 00004590002205

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Nov 12, 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: Assigned Parking
Vehicle Storage: Car(s): 1

Interior

Virtual Tour

Interior Features
Interior Features: Granite Counter Top, Smoke Alarms
Flooring: Carpet, Wood Floor, Marble
Windows/Doors: French Doors
Cooling/Heating: Ceiling Fans, Central A/C
Appliances: Dishwasher, Washer, Refrigerator, Range, Microwave, Dryer
Furnished: Furnished

Bathroom Information
# of Full Baths: 2
# of Half Baths: 1

Exterior

Boat Slip/Dock Information
Dockage: None

Exterior Features
Has Pool
Pool Is Heated
Pool Information: In Ground
Porch/Balcony: Deck, Open Porch/Balcony

Security
Manned Gate, Patrolled Area, Other Security

Property Features
Waterfront Type: None
Waterview: No Waterview

Property Information
Deed Restrictions: Yes
Pets: Pets w/Restrictions: YES
Rentals Allowed: With Restrictions
Min Rental Days: 7

Lot Information
Acres: 0.02
Zoning: HPRD - Hist Planned Redevelopment & Dev Dist
Land Size: Less Than 1/4 Acre
Flood Zone: AE

Building Information
Year Built: 1,995
Sq. Ft. Source: Property Data Card
Building Style: Townhouse
Building Style: Stories: 3
Building Style: Above Flood: Unknown
Construction: CBS, Combo Construction
Roof: Metal Roof

Subdivision/Neighborhood
Subdivision: The Foundry (1.0)
Key West Neighborhood: Truman Annex
Marathon Neighborhood: N/A

Financial

Tax Information
Taxes: $7,050.94
Tax Year: 2,020
Tax Exemptions: None

Financial Information
Terms: Cash, Conventional

Utilities

Utility Information
Utilities: Cable Available, Municipal Sewer, FKAA
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: Maintenance Fee $: 1475.00
Association Info: Association/Maintenance Fee Per: Quarterly
Fee Includes: Building Insurance, Security, Common Area Maintenance

Location Information
Side: Ocean
Mile Marker: 0.00
Directions: The Foundry is located in Truman Annex. Take Southard Street to Emma Street. Emma turns into Front Street. Property is located on left hand side.

Neighborhood Features
Community Pool

Public facts

Beds: 2
Baths: 2.5
Sq. Ft.: 1,140
Stories: 3.0
Lot Size: 855 square feet
Style: Single Family Residential
Year Built: 1995
Year Renovated: 2015
County: Monroe County
APN: 0668 25 00004590002205

Home facts updated by county records on Nov 12, 2026

Around this home

Schools

K - 12
Preschool & daycare

Horace O'bryant School

Public PreK-8 • Assigned • 1.3mi

3/10

Key West High School

Public 9-12 • Assigned • 1.9mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

7/10 Flood Factor

Estimated 72-80% 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)

73°

65°

76°

67°

79°

71°

81°

75°

86°

81°

88°

82°

89°

83°

90°

81°

87°

80°

85°

78°

80°

73°

77°

69°

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

$1.16M – $1.40M

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

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Home values near 101 Front St #5

Data from public records.

Address	Redfin Estimate
101 Front Street Unit 6, Key West, FL 2 Beds \| 2.5 Baths \| 1100 Sq. Ft.	$1,176,589
101 Front Street Unit 4, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,076,669
101 Front Street Unit 10, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,454,847
101 Front Street Unit 9, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,252,847
101 Front Street Unit 18, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,283,272
101 Front Street Unit 12, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,293,223
101 Front Street Unit 13, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,318,142

Address	Redfin Estimate
101 Front Street Unit 16, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,072,859
101 Front Street Unit 14, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,317,972
101 Front Street Unit 7, Key West, FL 2 Beds \| 2.5 Baths \| 1100 Sq. Ft.	$1,334,085
101 Front Street Unit 20, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,313,997
101 Front Street Unit 19, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,296,062
101 Front Street Unit 22, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,234,840
101 Front Street Unit 23, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,612,763

Address	Redfin Estimate
101 Front Street Unit 26, Key West, FL 2 Beds \| 2.5 Baths \| 1292 Sq. Ft.	$1,390,688
101 Front Street Unit 24, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,314,183
101 Front Street Unit 17, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,259,236
101 Front Street Unit 8, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,325,221
101 Front Street Unit 2, Key West, FL 2 Beds \| 2.5 Baths \| 1292 Sq. Ft.	$1,543,890
101 Front Street Unit 3, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,224,298
101 Front Street Unit 15, Key West, FL 2 Beds \| 2.5 Baths \| 1216 Sq. Ft.	$1,171,465

Property information provided by FLKMLS when last listed in 2021. 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 101 Front St #5

Tax history for 101 Front St #5

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 101 Front St #5

More real estate resources