106 Front St, Key West, FL 33040
OFF MARKET

$4,758,400

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 4,222 sqft

106 Front St, Key West, FL 33040

Truman Annex
Est. Refi. Payment $28,628/mo*
Refinance Your Home
Currently Off Market - Sold Jan 20, 1994 for $170,000

Home Value

Trulia Estimate
$4.76M
Since last month
Decreased$235K (-4.7%)
Since last year
Increased$68K (+1.4%)
Since last sale
Increased$5M (+2,703.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +22% in the last 10 years
MonthEstimated value
2026
September 2026$4.77M
August 2026$5M
July 2026$4.96M
June 2026$4.95M
May 2026$4.95M
April 2026$4.78M
March 2026$4.84M
February 2026$4.68M
January 2026$4.54M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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
0.23
Single-Family Home
$3,500,000
10/20/25
3
3.5
2,532
512 Emma St, Key West, FL
0.16
Single-Family Home
$3,095,000
01/27/26
4
4
1,653
400 Aronovitz Ln, Key West, FL
0.30
Single-Family Home
$3,300,000
05/21/26
5
6
3,667
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
1006 & 1008 Fleming St, Key West, FL
0.54
Single-Family Home
$4,425,000
05/26/26
4
4.5
3,336
215 Whitehead St, Key West, FL
0.15
Single-Family Home
$2,300,000
02/25/26
3
3
1,514
616 Eaton St, Key West, FL
0.33
Single-Family Home
$7,250,000
08/13/26
5
6
4,000

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
101 Admirals Ln, Key West, FL 33040
0.03
$6,487,800
5
4
3,173
Off Market
326 Caroline St, Key West, FL 33040
0.05
$6,350,000
5
5.5
4,279
Recently Sold
328 Whitehead St #0, Key West, FL 33040
0.07
$1,929,700
3
2
2,192
Off Market
103 Front St, Key West, FL 33040
0.03
$6,850,000
3
3
3,000
For Sale
159 Front St #11, Key West, FL 33040
0.03
$1,072,000
2
2.5
1,225
Off Market
101 Front St #1, Key West, FL 33040
0.04
$1,541,300
2
2.5
1,292
Off Market
101 Front St #2, Key West, FL 33040
0.04
$1,752,700
2
2.5
1,292
Off Market
101 Front St #8, Key West, FL 33040
0.04
$1,345,000
2
2.5
1,216
Recently Sold
101 Front St #15, Key West, FL 33040
0.04
$1,256,600
2
2.5
1,216
Off Market
101 Front St #18, Key West, FL 33040
0.04
$1,376,100
2
2.5
1,216
Off Market
101 Front St #20, Key West, FL 33040
0.04
$1,350,500
2
2.5
1,216
Off Market
101 Front St #23, Key West, FL 33040
0.04
$1,663,500
2
2.5
1,216
Off Market

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

Home Highlights

Single-Family Home
Built in 1999
4,222 sqft
$1,127/sqft
Garage

About this House

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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,758,400.

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 and Tax history

DateEventPrice
Jan 20, 1994
Source: N/A
Sold
$170,000

Market trends in Key West

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.14M
$143KMoM
Sale-to-List Price
—
Price per sq ft
$865
$67MoM
Available listings
255
17MoM

Around this home

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

LGBTQ Local Legal Protections

Frequently asked questions about 106 Front St

  • What is 106 Front St estimated to be worth?
    Trulia's estimated value for 106 Front St in Key West, FL is $4,758,400.
  • What is the price history for 106 Front St?
    106 Front St in Key West, FL last sold for $170,000 in January 1994.
  • Is Key West a buyer's or seller's market?
    Key West is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Key West?
    The median sale price in Key West is $1.14M. That is down $143K from the prior month.
  • Does 106 Front St have a pool?
    Yes, 106 Front St in Key West, FL has a pool.
  • How big is the lot at 106 Front St?
    The lot at 106 Front St in Key West, FL is about 0.17 acres (7,500 sq ft).

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Apartments for Rent

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Off Market Homes Near 106 Front St

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