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

66 Front St
Key West, FL 33040

Truman Annex
  • 5 Beds
  • 4 Baths
  • 3,252 sqft

$4,006,000

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $23,069/mo*
Refinance Your Home

$4,006,000

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $23,069/mo*
Refinance Your Home
5 Beds
4 Baths
3,252 sqft

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

Property Type
Single-Family Home
Year Built
1998
Living Area
3,252 sqft
Price/Sqft
$1,232
Parking
Garage

About this House

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. It is currently off market. The Trulia Estimate is $4,006,000, with a rent estimate of $7,878/month.

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 History for 66 Front St

DatePriceEventSource
11/30/2021$3,425,000Sold
FLKMLS #590493
10/15/2021$3,700,000ContingentKey West AOR #590493
03/09/2021$3,700,000Listed For SaleFLKMLS #590493
07/22/2020$3,700,000ListingRemovedAgent Provided
05/25/2020$3,700,000Listed For SaleAgent Provided
04/24/2020$3,700,000ListingRemovedAgent Provided
04/05/2020$3,700,000Listed For SaleAgent Provided
02/14/2012$1,862,500Sold
FLKMLS #115764
11/21/2003$1,950,000Sold
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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$28,114
Assessment$3,349,549
Home facts updated by county records

Comparable Sales for 66 Front St

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 homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 66 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

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

22 pet-friendly rentals in Key West, FL

Explore by feature - Garage

9 rentals with a garage in Key West, FL

Explore by feature - Air Conditioning

100 rentals with air conditioning in Key West, FL

Explore by feature - Pool

72 rentals with a pool in Key West, FL

Explore by feature - Washer/dryer

71 rentals with a washer/dryer in Key West, FL

Explore by feature - Outdoor Space

10 rentals with an outdoor space in Key West, FL

Homes for sale near 66 Front St

Skip to last item
Skip to first item

Off Market Homes Near 66 Front St

Skip to last item
Skip to first item

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 $4,006,000.
  • 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 $1.23M. That is up $20.83K 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.