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

$1,416,500

Trulia Estimate
as of Sep 22, 2026
  • 2 Beds
  • 3 Baths
  • 1,292 sqft

101 Front St, Key West, FL 33040

Truman Annex

Home Highlights

Single-Family Home
1,292 sqft
$1,096/sqft

Local Information

  • Map ViewExplore the area around 101 Front St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

About this House

Key West Found by AvantStay Close to Shops w Patio Shared Pool Week Long Stays Only offers a spacious holiday home in Key West city centre. The property features two bedrooms and a comfortable living room, ensuring ample space for relaxation and entertainment.

Modern Amenities: Guests enjoy free WiFi throughout the property, air-conditioning, and a fully equipped kitchen with a refrigerator, dishwasher, oven, and stovetop. Additional amenities include a washing machine, private bathroom, patio, and a TV.

Prime Location: Located less than 1 km from Simonton Street Beach and Duval Street, the property is close to attractions such as Key West Aquarium and Ernest Hemingway Home and Museum. Key West International Airport is 4 km away, providing convenient travel options.

Explore the Surroundings: The area offers water sports, including snorkelling and diving, and various points of interest within walking distance. Highly rated by guests, the property ensures a pleasant and memorable stay.
101 Front St, Key West, FL 33040 is a 2 bedroom, 3 bathroom, 1,292 sqft single-family home in Truman Annex. It last sold for $1,040,000 on Feb 15, 2018 (20,700% above the $5,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,416,500, with a rent estimate of $5,175/month.

Home Details for 101 Front St

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Tile

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Pool
Pool
Parking & Garage
Parking: Off Street Parking, On Site

Comparable Sales for 101 Front St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
212 Fleming St, Key West, FL
0.14
Single-Family Home
$1,650,000
04/15/26
2
2.5
1,420 sqft
216 Fleming St, Key West, FL
0.14
Single-Family Home
$1,850,000
01/07/26
2
2.5
1,312 sqft
618 Mickens Ln, Key West, FL
0.27
Single-Family Home
$800,000
12/09/25
2
2.5
1,056 sqft
612 Mickens Ln, Key West, FL
0.26
Single-Family Home
$979,000
04/09/26
2
1.5
823 sqft
314 Southard St, Key West, FL
0.24
Single-Family Home
$900,000
12/01/25
3
2
1,451 sqft
322 Southard St, Key West, FL
0.25
Single-Family Home
$1,695,000
04/10/26
3
3
1,553 sqft
215 Whitehead St, Key West, FL
0.17
Single-Family Home
$2,300,000
02/25/26
3
3
1,514 sqft
4 Aronovitz Ln, Key West, FL
0.31
Single-Family Home
$1,275,000
07/24/26
3
3
1,748 sqft
718 Chapman Ln, Key West, FL
0.35
Single-Family Home
$970,000
09/25/25
4
3
1,026 sqft
515 Petronia St, Key West, FL
0.46
Single-Family Home
$1,400,000
03/31/26
2
2
1,200 sqft

Nearby homes

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

Rental Market Trends in Truman Annex

Last updated Sep 2026
Trulia Rent Estimate$5,175/mo
Average rent
$5K
$120MoM
Available listings
2
View rental market trends in Key West, FL

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

Price and Tax history

DateEventPrice
Apr 4, 2021
Source: FLKMLS #592502
ListingRemoved
Mar 8, 2021
Source: FLKMLS #592502
ListingRemoved
Oct 9, 2020
Source: FLKMLS #592502
Listed For Sale
$1,039,000
Feb 15, 2018
Source: FLKMLS #574858
Sold
$1,040,000
Jan 12, 2018
Source: Agent Provided
PriceChange
$1,149,000
Price increased by 15%

Frequently asked questions about 101 Front St

  • What is 101 Front St estimated to be worth?
    Trulia's estimated value for 101 Front St in Key West, FL is $1,416,500.
  • What is the price history for 101 Front St?
    101 Front St in Key West, FL last sold for $1,040,000 in February 2018.
  • 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 101 Front St have air conditioning?
    Yes, 101 Front St in Key West, FL has air conditioning.
  • Does 101 Front St have a pool?
    Yes, 101 Front St in Key West, FL has a pool.

Homes for rent near 101 Front St

Skip to last item
Skip to first item

Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
Skip to last item
  • Results are loading
Skip to first item