108 Front St, Key West, FL 33040
OFF MARKET

108 Front St
Key West, FL 33040

Truman Annex
  • 4 Beds
  • 5 Baths
  • 1,788 sqft

$3,627,400

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $20,973/mo*
Refinance Your Home

$3,627,400

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $20,973/mo*
Refinance Your Home
4 Beds
5 Baths
1,788 sqft

Local Information

  • Map ViewExplore the area around 108 Front St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1995
Living Area
1,788 sqft
Price/Sqft
$2,029

About this House

This single-family home is located at 108 Front St, Key West, FL. 108 Front St is in the Truman Annex neighborhood in Key West, FL and in ZIP code 33040. This property has 4 bedrooms, 5 bathrooms and approximately 1,788 sqft of floor space. This property has a lot size of 5000 sqft and was built in 1995.
108 Front St, Key West, FL 33040 is a 4 bedroom, 5 bathroom, 1,788 sqft single-family home in Truman Annex, built in 1995. It last sold for $139,000 on Jan 24, 1994. It is currently off market. The Trulia Estimate is $3,627,400, with a rent estimate of $7,226/month.

Home Details for 108 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: PilingPatio
Pool
Pool
Parking & Garage
Parking: Carport

Property Information

Year Built
Year Built: 1995Year Updated: 1997
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 5000 sqft

Price History for 108 Front St

DatePriceEventSource
01/24/1994$139,000Sold
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$10,140
Assessment$3,190,761
Home facts updated by county records

Comparable Sales for 108 Front St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
512 Emma St, Key West, FL
0.17
Single-Family Home
$3,095,000
01/27/26
4
4
1,653
215 Whitehead St, Key West, FL
0.14
Single-Family Home
$2,300,000
02/25/26
3
3
1,514
322 Southard St, Key West, FL
0.24
Single-Family Home
$1,695,000
04/10/26
3
3
1,553
517 Elizabeth St, Key West, FL
0.41
Single-Family Home
$3,750,000
10/20/25
4
3
2,173
314 Southard St, Key West, FL
0.24
Single-Family Home
$900,000
12/01/25
3
2
1,451
316 Southard St, Key West, FL
0.24
Single-Family Home
$3,500,000
10/20/25
3
3.5
2,532
807 Thomas St, Key West, FL
0.40
Single-Family Home
$1,500,000
04/08/26
4
4
1,536
529 Simonton St, Key West, FL
0.35
Single-Family Home
$2,700,000
08/03/26
4
3
1,800
418 William St, Key West, FL
0.45
Single-Family Home
$3,285,000
03/18/26
4
3
1,852
101 Admirals Ln, Key West, FL
0.04
Single-Family Home
$6,300,000
10/10/25
5
4
3,173

Nearby homes

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Assigned Schools

These are the assigned schools for 108 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

LGBTQ Local Legal Protections

Apartments for Rent

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Explore by feature - Pet Friendly

23 pet-friendly rentals in Key West, FL

Explore by feature - Garage

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Explore by feature - Air Conditioning

101 rentals with air conditioning in Key West, FL

Explore by feature - Pool

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

9 rentals with an outdoor space in Key West, FL

Homes for sale near 108 Front St

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Off Market Homes Near 108 Front St

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Frequently asked questions about 108 Front St

  • What is 108 Front St estimated to be worth?
    Trulia's estimated value for 108 Front St in Key West, FL is $3,627,400.
  • What is the price history for 108 Front St?
    108 Front St in Key West, FL last sold for $139,000 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 $1.23M. That is up $20.83K from the prior month.
  • Does 108 Front St have a pool?
    Yes, 108 Front St in Key West, FL has a pool.
  • How big is the lot at 108 Front St?
    The lot at 108 Front St in Key West, FL is about 0.11 acres (5,000 sq ft).