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

157 Front St
Key West, FL 33040

Truman Annex
  • 2 Beds
  • 2 Baths
  • 1,100 sqft

$735,900

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $4,299/mo*
Refinance Your Home

$735,900

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $4,299/mo*
Refinance Your Home
2 Beds
2 Baths
1,100 sqft

Local Information

  • Map ViewExplore the area around 157 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
1,100 sqft
Price/Sqft
$669

About this House

ANCHOR HOUSE est. 1904 is a stylish townhome with a rich history and a modern facelift. The building was originally occupied by the Navy over a hundred years ago as the original foundry where anchors were forged. It's come a long way from its industrial roots; this beautiful restoration has kept the charm of the original forge as evidenced by the gorgeous brick walls! while adding modern finishes and contemporary touches at every turn, all while being located within the Truman Annex, Key West's most exclusive gated community. You'll be within walking distance of everything Key West has to offer: restaurants, shopping, attractions, and nightlife. In addition to its excellent location, ANCHOR HOUSE est. 1904 features an oversized outdoor courtyard and a covered parking space. Combined with Last Key Realty's unrivaled Guest Services, a stay here will be un-forge-ttable.

This property is adults-only: all guests need to be 25 years of age or older (or above the age of 18 if they are traveling with a parent/guardian).

THE LOCATION...

Truman Annex is a private, gated community right in Old Town, Key West. You'll be just a few blocks from Mallory Square, Duval Street and all the restaurants, shopping, and attractions of Old Town, yet you'll benefit from the peace and quiet that Truman Annex is known for. Although you won't need a car to get around from this excellent location, there is a reserved off-street parking space.

Compliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes "Quiet Time" in all outdoor areas, public and private, after 10PM.

THE COMMUNITY POOL & FORT ZACHARY TAYLOR STATE PARK...

The landscaped community pool is located just across the street, with chaises and a cabana with restrooms. Or you can walk to Fort Zachary Taylor State Park, with the prettiest beach in Key West, just a half mile away from your front door.

THE LIVING AREA...

ANCHOR HOUSE est. 1904 has a bright and airy first floor living area, with soaring ceilings and a pair of French double doors that allow plenty of natural light to flood in. This unit features lots of modern touches while still embracing the buildings original beauty. The living room features a large flat-screen TV and a large sofa. There's also a convenient powder room located on the first floor. The kitchen is fully equipped with all the appliances and tools you'll need to prepare a home cooked meal. The indoor dining table seats four comfortably. The private courtyard out front is the perfect place to relax with a book or cold drink in hand. The courtyard is complete with a propane BBQ grill and patio furniture.

THE ACCOMMODATIONS...

** Master Suite: Located on the Second Floor with a King bed, a large flat screen TV, closet space, and an en-suite bathroom with a walk-in shower.

** Second Bedroom: Located on the Second Floor with a Queen bed, a large flat screen TV, closet space, and an en-suite bathroom with a walk-in shower.

ALL LAST KEY VACATION HOMES INCLUDE:

** Washer and Dryer
** Central Heat and A/C
** Ceiling Fans
** Flat Screen TVs in Living Room & All Bedrooms
** Fully Equipped Kitchen
** Basic stock of spices
** Starter supply of paper products
** Starter set of cleaning products
** Linens and Towels provided
** Wireless high-speed Internet access & full cable included

In addition, this fully stocked home also includes, but is not limited to the amenities on this list:

** Community Pool Access
** Propane BBQ Grill
** Assigned Off-street Covered Parking for 1 Car (vehicle size restrictions - no vehicle over 18' long or 80'' wide)

Other notes:

** Interim housekeeping provided upon request
** This property will accommodate up to 4 adults
** No Pets Allowed
** Smoking is not permitted in any Last Key Realty home. In addition, the Foundry does not permit smoking in the front garden patio areas or balconies. Therefore, this home is not a good fit for vacationers needing smoking accommodations.
** Adults Only - all guests need to be 25 years of age or older (or above the age of 18 if they are traveling with a parent/guardian).
** No bleach is permitted on property

Please handle the property with care, cause you will be responsible for any damages caused during your stay on the property.
157 Front St, Key West, FL 33040 is a 2 bedroom, 2 bathroom, 1,100 sqft single-family home in Truman Annex. It is currently off market. The Trulia Estimate is $735,900, with a rent estimate of $4,222/month.

Home Details for 157 Front St

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: Central Air, Wall UnitHeating Fuel: Heat Pump
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood, 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

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$0
Assessment$50
Home facts updated by county records

Comparable Sales for 157 Front St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
200 Greene St, Key West, FL
0.17
Single-Family Home
$20,000
03/27/26
2
2
1,000
216 Fleming St, Key West, FL
0.14
Single-Family Home
$1,850,000
01/07/26
2
2.5
1,312
212 Fleming St, Key West, FL
0.14
Single-Family Home
$1,650,000
04/15/26
2
2.5
1,420
612 Mickens Ln, Key West, FL
0.27
Single-Family Home
$979,000
04/09/26
2
1.5
823
618 Mickens Ln, Key West, FL
0.27
Single-Family Home
$800,000
12/09/25
2
2.5
1,056
314 Southard St, Key West, FL
0.25
Single-Family Home
$900,000
12/01/25
3
2
1,451
617 Front St, Key West, FL
0.46
Single-Family Home
$117,000
04/28/26
2
2
1,100
515 Petronia St, Key West, FL
0.46
Single-Family Home
$1,400,000
03/31/26
2
2
1,200
215 Whitehead St, Key West, FL
0.17
Single-Family Home
$2,300,000
02/25/26
3
3
1,514
621 Elizabeth St #2, Key West, FL
0.50
Single-Family Home
$1,625,000
04/21/26
2
2
1,256

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 157 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 157 Front St

Skip to last item
Skip to first item

Off Market Homes Near 157 Front St

Skip to last item
Skip to first item

Frequently asked questions about 157 Front St

  • What is 157 Front St estimated to be worth?
    Trulia's estimated value for 157 Front St in Key West, FL is $735,900.
  • 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.
  • What are the closest schools to 157 Front St?
    The closest schools to 157 Front St in Key West, FL are Gerald Adams Elementary School (Pre-K, rated 4/10), Key West High School (rated 4/10), Monroe Virtual Instruction Program (Elementary/Middle/High).
  • Does 157 Front St have air conditioning?
    Yes, 157 Front St in Key West, FL has air conditioning.
  • Does 157 Front St have a pool?
    Yes, 157 Front St in Key West, FL has a pool.