66 Front St, Key West, FL 33040
Property image
Property image
OFF MARKET

$3,907,600

Trulia Estimate
  • 5 Beds
  • 4 Baths
  • 3,252 sqft

66 Front St, Key West, FL 33040

Truman Annex
Est. Refi. Payment $23,522/mo*
Refinance Your Home
Currently Off Market - Sold Nov 30, 2021 for $3,425,000

Home Value

Trulia Estimate
$3.91M
Since last month
Increased$18K (+0.5%)
Since last year
Decreased$119K (-3%)
Since last sale
Increased$474K (+13.8%)
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 +12% in the last 10 years
MonthEstimated value
2026
September 2026$3.9M
August 2026$3.88M
July 2026$3.96M
June 2026$4.01M
May 2026$3.94M
April 2026$3.98M
March 2026$3.92M
February 2026$3.87M
January 2026$3.86M
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
512 Emma St, Key West, FL
0.10
Single-Family Home
$3,095,000
01/27/26
4
4
1,653
400 Aronovitz Ln, Key West, FL
0.27
Single-Family Home
$3,300,000
05/21/26
5
6
3,667
316 Southard St, Key West, FL
0.20
Single-Family Home
$3,500,000
10/20/25
3
3.5
2,532
101 Admirals Ln, Key West, FL
0.04
Single-Family Home
$6,300,000
10/10/25
5
4
3,173
517 Elizabeth St, Key West, FL
0.43
Single-Family Home
$3,750,000
10/20/25
4
3
2,173
326 Caroline St, Key West, FL
0.12
Single-Family Home
$6,350,000
01/15/26
5
5.5
4,279
215 Whitehead St, Key West, FL
0.21
Single-Family Home
$2,300,000
02/25/26
3
3
1,514
515 Amelia St, Key West, FL
0.63
Single-Family Home
$4,225,000
03/16/26
5
5.5
3,434
418 William St, Key West, FL
0.48
Single-Family Home
$3,285,000
03/18/26
4
3
1,852
529 Simonton St, Key West, FL
0.36
Single-Family Home
$2,700,000
08/03/26
4
3
1,800

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
64 Front St, Key West, FL 33040
0.01
$4,465,300
5
5
3,213
Off Market
410 Porter Ln #10, Key West, FL 33040
0.04
$1,458,000
2
2.5
1,100
Off Market
406 Porter Ln, Key West, FL 33040
0.04
$1,406,600
2
2.5
1,036
Off Market
415 Porter Ln #415, Key West, FL 33040
0.04
$754,000
2
1.5
936
Off Market
416 Porter Ln #4, Key West, FL 33040
0.04
$860,500
2
2
1,025
Off Market
418 Porter Ln #18, Key West, FL 33040
0.04
$829,500
2
2
1,035
Off Market
407 Porter Ln #13, Key West, FL 33040
0.04
$809,800
2
2.5
1,025
Off Market
404 Porter Ln #16, Key West, FL 33040
0.04
$1,565,000
2
2
1,002
Recently Sold
417 Porter Ln, Key West, FL 33040
0.04
$1,435,000
2
2.5
1,023
Off Market
101 Admirals Ln, Key West, FL 33040
0.04
$6,487,800
5
4
3,173
Off Market
208 Fleming St, Key West, FL 33040
0.07
$1,070,000
2
2.5
960
Recently Sold
208 Fleming St #0, Key West, FL 33040
0.07
$830,300
2
2.5
-
Off Market

Local Information

  • Map ViewExplore the area around 66 Front St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1998
3,252 sqft
$1,202/sqft
Garage

About this House

What's unique:Old townTruman annexHeated pool
This single-family home is located at 66 Front St, Key West, FL. 66 Front St is in the Truman Annex neighborhood in Key West, FL and in ZIP code 33040. This property has 5 bedrooms, 5 bathrooms and approximately 3,252 sqft of floor space. This property has a lot size of 5227 sqft and was built in 1998.
66 Front St, Key West, FL 33040 is a 5 bedroom, 5 bathroom, 3,252 sqft single-family home in Truman Annex, built in 1998. It last sold for $3,425,000 on Nov 30, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,907,600.

Home Details for 66 Front St

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
AtticCeiling Fan
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Softwood, Hardwood

Exterior Features

Exterior Home Features
Roof: MetalDeckExterior: OtherFoundation Type: PilingPatioPorch
Pool
Pool
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1998Year Updated: 2000
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Furnished

Community

Units in Building: 1

Lot Information

Lot Area: 5022 sqft

Price and Tax history

DateEventPrice
Nov 30, 2021
Source: FLKMLS #590493
Sold
$3,425,000
Oct 15, 2021
Source: Key West AOR #590493
Contingent
$3,700,000
Mar 9, 2021
Source: FLKMLS #590493
Listed For Sale
$3,700,000
Jul 22, 2020
Source: Agent Provided
ListingRemoved
$3,700,000
May 25, 2020
Source: Agent Provided
Listed For Sale
$3,700,000

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 66 Front St

  • What is 66 Front St estimated to be worth?
    Trulia's estimated value for 66 Front St in Key West, FL is $3,907,600.
  • What is the price history for 66 Front St?
    66 Front St in Key West, FL last sold for $3,425,000 in November 2021.
  • 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 66 Front St have air conditioning?
    Yes, 66 Front St in Key West, FL has air conditioning.
  • Does 66 Front St have a pool?
    Yes, 66 Front St in Key West, FL has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

85 rentals with a pool in Key West, FL

Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

8 rentals with an outdoor space in Key West, FL

Apartments for Rent

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Off Market Homes Near 66 Front St

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