Home Highlights
Single-Family Home
1,100 sqft
$626/sqft
Local Information
- Map ViewExplore the area around 157 Front St.
- Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
- Shop & Eat
-- mins to
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.
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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $688,400, with a rent estimate of $4,332/month.
Home Details for 157 Front St
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Heating & Cooling Heating: Heat PumpAir ConditioningCooling System: Central Air, Wall UnitHeating Fuel: Heat Pump |
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher |
Levels, Entrance, & Accessibility Floors: Hardwood, Tile |
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Property Type / Style Property Type: Single Family Home |
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Lease Term: 1 YearAvailable: now |
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Pool Pool |
Parking & Garage Parking: Off Street Parking, On Site |
Comparable Sales for 157 Front St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.17 | Single-Family Home | $20,000 | 03/27/26 | 2 | 2 | 1,000 sqft | |
0.14 | Single-Family Home | $1,850,000 | 01/07/26 | 2 | 2.5 | 1,312 sqft | |
0.14 | Single-Family Home | $1,650,000 | 04/15/26 | 2 | 2.5 | 1,420 sqft | |
0.27 | Single-Family Home | $979,000 | 04/09/26 | 2 | 1.5 | 823 sqft | |
0.27 | Single-Family Home | $800,000 | 12/09/25 | 2 | 2.5 | 1,056 sqft | |
0.25 | Single-Family Home | $900,000 | 12/01/25 | 3 | 2 | 1,451 sqft | |
0.46 | Single-Family Home | $138,000 | 07/21/26 | 2 | 2 | 1,200 sqft | |
0.46 | Single-Family Home | $1,400,000 | 03/31/26 | 2 | 2 | 1,200 sqft | |
0.17 | Single-Family Home | $2,300,000 | 02/25/26 | 3 | 3 | 1,514 sqft | |
0.50 | Single-Family Home | $1,625,000 | 04/21/26 | 2 | 2 | 1,256 sqft |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
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OFF MARKETPreferred Properties (KW)
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SOLDJAN 15, 2026Keller Williams Key West Compass Realty
SOLDMAR 17, 2026Keller Williams Key West Compass Realty
OFF MARKETKeller Williams Key West Compass Realty
Rental Market Trends in Truman Annex
Last updated Sep 2026
Trulia Rent Estimate$4,332/mo
Average rent
$5K
$120MoM
Available listings
2
Around this home
Neighborhood Overview
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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Price and Tax history
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $0 | $50 |
Home facts updated by county records
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 $688,400.
- 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.
- 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.
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Affordability
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