106 Front St, Key West, FL 33040
OFF MARKET

106 Front St
Key West, FL 33040

Truman Annex
  • 4 Beds
  • 4 Baths
  • 4,222 sqft

$4,853,100

Trulia Estimate
as of Jul 20, 2026
Est. Refi. Payment $27,752/mo*
Refinance Your Home

$4,853,100

Trulia Estimate
as of Jul 20, 2026
Est. Refi. Payment $27,752/mo*
Refinance Your Home
4 Beds
4 Baths
4,222 sqft

Local Information

  • Map ViewExplore the area around 106 Front St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 106 Front St, Key West, FL. 106 Front St is in the Truman Annex neighborhood in Key West, FL and in ZIP code 33040. This property has 4 bedrooms, 4 bathrooms and approximately 4,222 sqft of floor space. This property has a lot size of 7500 sqft and was built in 1999.
106 Front St, Key West, FL 33040 is a 4 bedroom, 4 bathroom, 4,222 sqft single-family home in Truman Annex, built in 1999. It last sold for $170,000 on Jan 20, 1994. It is currently off market. The Trulia Estimate is $4,853,100, with a rent estimate of $7,865/month.

Home Highlights

Parking
Garage
Outdoor
Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 106 Front St

Interior Features

Heating & Cooling
Heating: Forced AirHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Softwood, Hardwood

Exterior Features

Exterior Home Features
Roof: MetalExterior: OtherFoundation Type: Concrete
Pool
Pool
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 7500 sqft

Price History for 106 Front St

DatePriceEventSource
01/20/1994$170,000Sold
N/A

Market trends in Key West

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.23M
$20.83KMoM
Sale-to-List Price
94.6%
0.3%MoM
Price per sq ft
$958
$15MoM
Available listings
288
17MoM
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Property Tax and Assessment

Year2025
Tax$36,672
Assessment$4,390,013
Home facts updated by county records

Comparable Sales for 106 Front St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
101 Admirals Ln, Key West, FL
0.03
Single-Family Home
$6,300,000
10/10/25
5
4
3,173
326 Caroline St, Key West, FL
0.05
Single-Family Home
$6,350,000
01/15/26
5
5.5
4,279
316 Southard St, Key West, FL
0.24
Single-Family Home
$3,500,000
10/20/25
3
3.5
2,532
400 Aronovitz Ln, Key West, FL
0.29
Single-Family Home
$3,300,000
05/21/26
5
6
3,667
512 Emma St, Key West, FL
0.16
Single-Family Home
$3,095,000
01/27/26
4
4
1,653
517 Elizabeth St, Key West, FL
0.41
Single-Family Home
$3,750,000
10/20/25
4
3
2,173
322 Southard St, Key West, FL
0.23
Single-Family Home
$1,695,000
04/10/26
3
3
1,553
215 Whitehead St, Key West, FL
0.15
Single-Family Home
$2,300,000
02/25/26
3
3
1,514
407-415 Olivia St, Key West, FL
0.46
Single-Family Home
$3,500,000
08/08/25
6
5
3,171
314 Southard St, Key West, FL
0.23
Single-Family Home
$900,000
12/01/25
3
2
1,451

Nearby homes

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Assigned Schools

These are the assigned schools for 106 Front St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Truman Annex
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Truman Annex

At least 1 Trulia users voted on each feature.

  • 100 % Say it's walkable to grocery stores

  • 100 % Say it's quiet

  • 100 % Say there's wildlife

  • 100 % Say neighbors are friendly

  • 100 % Say it's walkable to restaurants

  • 100 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "It’s a great neighborhood, we absolutely love having the opportunity to be able to live here!! We don’t have young kids so can’t really express things that are impt for them to know!!"
    1
    Flag
  • Langanlady
    "I have a 2 minute commute to the county courthouse. I could walk or bike but I am lazy and drive a car. "
    0
    Flag
  • Maya T.
    "This is the heart of historic Old Town Key West!"
    1
    Flag

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Homes for sale near 106 Front St

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Off Market Homes Near 106 Front St

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