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

101 Front St
Key West, FL 33040

Truman Annex
  • 2 Beds
  • 3 Baths
  • 1,292 sqft

$1,450,000

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $8,398/mo*
Refinance Your Home

$1,450,000

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $8,398/mo*
Refinance Your Home
2 Beds
3 Baths
1,292 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

Home Highlights

Property Type
Single-Family Home
Living Area
1,292 sqft
Price/Sqft
$1,122

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). It is currently off market. The Trulia Estimate is $1,450,000, with a rent estimate of $5,207/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
Room & Shared Space
Shared space is furnished

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

Price History for 101 Front St

DatePriceEventSource
04/04/2021ListingRemovedFLKMLS #592502
03/08/2021ListingRemovedFLKMLS #592502
10/09/2020$1,039,000Listed For SaleFLKMLS #592502
02/15/2018$1,040,000Sold
FLKMLS #574858
01/12/2018$1,149,000PriceChange
Agent Provided
12/27/2017$995,000PriceChange
Agent Provided
03/22/2017$1,149,000Listed For SaleAgent Provided
03/31/2016$950,000Sold
FLKMLS #122617
02/17/2016$999,000PendingAgent Provided
01/05/2016$999,000Listed For SaleAgent Provided
10/22/2014$809,100Sold
N/A
09/19/2014$689,800PriceChange
Agent Provided
08/22/2014$390,000PriceChange
Agent Provided
08/16/2014$689,800Listed For SaleAgent Provided
03/24/2011$725,000ListingRemovedN/A
12/05/2009$725,000PriceChange
N/A
11/04/2009$830,000PriceChange
N/A
04/10/2009$1,050,000PriceChange
N/A
02/27/2009$1,100,000PriceChange
N/A
09/12/2008$1,150,000PriceChange
N/A
07/18/2008$1,060,000PriceChange
N/A
07/04/2008$1,050,000PriceChange
N/A
06/20/2008$1,150,000PriceChange
N/A
05/11/2008$1,250,000Listed For SaleN/A
04/27/2006$1,222,400Sold
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$10,118
Assessment$1,161,516
Home facts updated by county records

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

Nearby homes

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Assigned Schools

These are the assigned schools for 101 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

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

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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 101 Front St

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Off Market Homes Near 101 Front St

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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 $1,450,000.
  • 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 $1.23M. That is up $20.83K 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.