66 Front St, Key West, FL 33040
OFF MARKET

66 Front St
Key West, FL 33040

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

$4,016,800

Trulia Estimate
as of Jun 21, 2026
Est. Refi. Payment $22,627/mo*
Refinance Your Home

$4,016,800

Trulia Estimate
as of Jun 21, 2026
Est. Refi. Payment $22,627/mo*
Refinance Your Home
5 Beds
4 Baths
3,252 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

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

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 May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.2M
$61.67KMoM
Sale-to-List Price
94.9%
0.4%MoM
Price per sq ft
$940
$14MoM
Available listings
304
28MoM
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Property Tax and Assessment

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

Homeowner tools

Estimated monthly rent$7,878/mo
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Homes for rent near 66 Front St

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Comparable Sales for 66 Front St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
400 Aronovitz Ln, Key West, FL
0.26
Single-Family Home
$3,300,000
05/21/26
5
6
3,667
512 Emma St, Key West, FL
0.10
Single-Family Home
$3,095,000
01/27/26
4
4
1,653
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
407-415 Olivia St, Key West, FL
0.42
Single-Family Home
$3,500,000
08/08/25
6
5
3,171
326 Caroline St, Key West, FL
0.12
Single-Family Home
$6,350,000
01/15/26
5
5.5
4,279
58 Sunset Key Dr, Key West, FL
0.64
Single-Family Home
$3,600,000
07/21/25
4
4
2,288
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

Nearby homes

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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

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Apartments for Rent

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Homes for sale near 66 Front St

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Off Market Homes Near 66 Front St

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66 Front St, Key West, FL 33040 is a 5 bedroom, 5 bathroom, 3,252 sqft single-family home built in 1998. 66 Front St is located in Truman Annex, Key West. This property is not currently available for sale. 66 Front St was last sold on Nov 30, 2021 for $3,425,000. The current Trulia Estimate for 66 Front St is $4,016,800.