103 Front St
Key West, FL 33040
Truman Annex
3 Beds
3 Baths
3,000 sqft
3 Beds
3 Baths
3,000 sqft
Home Highlights
Outdoor
Patio, Pool
HOA
$3,405/Monthly
Price/Sqft
$2,283
Listed
180+ days ago
Climate Control
Central Air, Ceiling Fans
Local Information
- Map ViewExplore the area around 103 Front St.
- Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
- Shop & Eat
-- mins to
About this House
103 Front Street is a one of a kind masterpiece of architectural design and modern aesthetic. Built in the early 1900s, this imposing structure has been thouroughly restored and updated into a stunning home. The interior features a large great room with soaring ceilings, custom beams and woodwork. This home is perfect for entertaining on a large scale or enjoying a quiet evening. A dramatic staircase leads to a second floor walkway which is open to the main level. The floor plan provides privacy for each bedroom with the primary suite at one end of the hallway and a guest bedroom suite at the other end. Another guest bedroom and bath are on the first floor creating an option for a first floor primary bedroom. Custom features throughout are evidence of the artistic ingenuity used in the design of this impressive home. The kitchen features custom wood cabinets and granite countertops and is open to the dining area. Tall windows and french doors flood the home with sunlight.
This home is perfect for indoor/outdoor entertaining. A wet bar features custom built ins plus an icemaker and refrigerator.
Fronted by a white picket fence, the home sits back from the street and is adorned by tropical foliage. This unique structure with thick brick walls and impressivly tall windows offers passers by a glimpse of the historic origins of the Truman Annex. Its location in the heart of old town Key West provides easy walkability to the waterfront promenade, Ft. Taylor beach, cultural venues, shops and restaurants. The property comprises two lots with a large swimming pool and spa plus an outdoor shower between the covered and open air loggia and parking. There's plenty of space for entertaining outdoors under the palm trees. This estate home is one of a kind was restored to the highest standards. One must see this home to appreciate the incredible design and attention to detail that went into this historic treasure.
This home is perfect for indoor/outdoor entertaining. A wet bar features custom built ins plus an icemaker and refrigerator.
Fronted by a white picket fence, the home sits back from the street and is adorned by tropical foliage. This unique structure with thick brick walls and impressivly tall windows offers passers by a glimpse of the historic origins of the Truman Annex. Its location in the heart of old town Key West provides easy walkability to the waterfront promenade, Ft. Taylor beach, cultural venues, shops and restaurants. The property comprises two lots with a large swimming pool and spa plus an outdoor shower between the covered and open air loggia and parking. There's plenty of space for entertaining outdoors under the palm trees. This estate home is one of a kind was restored to the highest standards. One must see this home to appreciate the incredible design and attention to detail that went into this historic treasure.
Last check for updates: about 20 hours ago
Listing courtesy of Laura A McChesney, (305) 923-6639
Preferred Properties (KW)
Key West Sisters, (305) 747-0369
Preferred Properties (KW)
Source: FLKMLS, MLS#617136
Also Listed on FLKMLS.
Home Details for 103 Front St
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Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3 |
Dimensions and Layout Living Area: 3000 Square Feet |
Appliances & Utilities Appliances: Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave, Ice MakerDishwasherDryerMicrowaveRefrigeratorWasher |
Heating & Cooling Has CoolingAir Conditioning: Central Air,Ceiling Fans(s) |
Windows, Doors, Floors & Walls Flooring: Wood, Marble |
Levels, Entrance, & Accessibility Floors: Wood, Marble |
View No View |
Security Security: Security Guard, Other, Security System |
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Exterior Home Features Patio / Porch: PatioFencing: FencedExterior: Lighting, Outdoor Shower, Storage, Water DisplayHas a Private Pool |
Parking & Garage No Attached Garage |
Pool Pool: In Ground, ConcretePool |
Frontage Not on Waterfront |
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Days on Market: 180+ |
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Year Built Year Built: 1918 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence |
Building Construction Materials: Combo Construction, Other |
Property Information Parcel Number: 00004590002157 |
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Price List Price: $6,850,000Price Per Sqft: $2,283 |
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MLS Status: Active |
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Direction & Address City: Key WestCommunity: The Foundry (1.0) |
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Listing Agent Listing ID: 617136 |
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Building Area Building Area: 3000 Square Feet |
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HOA Fee Includes: Maintenance Structure, Insurance, Common Area Mnt, SecurityHas an HOAHOA Fee: $10,214/Quarterly |
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Lot Area: 8712 sqft |
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Mls Number: 617136 |
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.
Market trends in Key West
Last updated July 2026
Avg. sale price
$1.28M
$50KMoM
Sale-to-List Price
95.1%
0.5%MoM
Price per sq ft
$933
$26MoM
Available listings
271
17MoM
Home Value
Trulia Estimate
$6.25MSince last month
Increased$28K (+0.5%)Since last year
Increased$275K (+4.7%)Since last sale
Increased$6M (+1,753.4%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +38% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| August 2026 | $6.12M |
| July 2026 | $6.09M |
| June 2026 | $6.1M |
| May 2026 | $6.13M |
| April 2026 | $6.12M |
| March 2026 | $6.01M |
| February 2026 | $6.05M |
| January 2026 | $6.09M |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.26 | Single-Family Home | $1,695,000 | 04/10/26 | 3 | 3 | 1,553 | |
0.04 | Single-Family Home | $6,300,000 | 10/10/25 | 5 | 4 | 3,173 | |
0.26 | Single-Family Home | $3,500,000 | 10/20/25 | 3 | 3.5 | 2,532 | |
0.15 | Single-Family Home | $2,300,000 | 02/25/26 | 3 | 3 | 1,514 | |
0.25 | Single-Family Home | $900,000 | 12/01/25 | 3 | 2 | 1,451 | |
0.31 | Single-Family Home | $1,275,000 | 07/24/26 | 3 | 3 | 1,748 | |
0.06 | Single-Family Home | $6,350,000 | 01/15/26 | 5 | 5.5 | 4,279 | |
0.17 | Single-Family Home | $3,095,000 | 01/27/26 | 4 | 4 | 1,653 | |
0.46 | Single-Family Home | $3,150,000 | 09/19/25 | 3 | 3 | 2,100 | |
0.15 | Single-Family Home | $1,650,000 | 04/15/26 | 2 | 2.5 | 1,420 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.01 | $1,146,000 | 2 | 2.5 | 1,225 | Off Market | |
0.03 | $2,886,000 | 2 | 2.5 | 1,500 | Off Market | |
0.03 | $2,226,700 | 2 | 2.5 | 1,296 | Off Market | |
0.03 | $3,340,100 | 2 | 2.5 | 1,850 | Off Market | |
0.04 | $1,922,800 | 2 | 2.5 | 1,350 | Off Market | |
0.04 | $1,977,100 | 2 | 2 | 1,550 | Off Market | |
0.04 | $2,156,400 | 3 | 2.5 | 1,800 | Off Market | |
0.04 | $2,249,999 | 3 | 3 | 1,325 | For Sale | |
0.04 | $3,474,100 | 3 | 2.5 | 1,850 | Off Market | |
0.04 | $2,200,000 | 2 | 2.5 | 1,350 | Recently Sold | |
0.04 | $3,400,000 | 3 | 2 | 2,088 | Recently Sold |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Nov 1, 2025 Source: FLKMLS #617136 | Listed For Sale | $6,850,000 |
Apr 1, 2025 Source: Engel & Volkers #NS1080891 | ListingRemoved | $6,500,000 |
Sep 12, 2024 Source: Stellar MLS #NS1080891 | Listed For Sale | $6,500,000 |
Sep 6, 2024 Source: Key West AOR #609252 | ListingRemoved | $6,500,000 |
Mar 18, 2024 Source: FLKMLS #609252 | Listed For Sale | $6,500,000 |
May 21, 2022 Source: FLKMLS #598752 | ListingRemoved | |
Dec 8, 2021 Source: FLKMLS #598752 | Listed For Sale | $6,300,000 |
Jun 1, 2018 Source: Agent Provided | ListingRemoved | $5,950,000 |
Nov 3, 2017 Source: Agent Provided | Listed For Sale | $5,950,000 |
Jun 1, 2017 Source: Agent Provided | ListingRemoved | $5,950,000 |
Nov 10, 2016 Source: Agent Provided | Listed For Sale | $5,950,000 |
Apr 28, 1997 Source: N/A | Sold | $330,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $35,716 | $4,273,714 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Laura A McChesney, Preferred Properties (KW)
Agent Phone: (305) 923-6639
MLS Internet Data Exchange (IDX) information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys MLS.
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Frequently asked questions about 103 Front St
- What is the estimated monthly payment for 103 Front St?Based on a $6,850,000 list price with 20% down at today's rates, the estimated monthly payment for 103 Front St in Key West, FL is approximately $40,456 (about $35,700 principal & interest, $4,681 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- How does the list price for 103 Front St compare to homes in Key West?103 Front St in Key West, FL is listed at $6,850,000, about 436% above the $1.28M median sale price in Key West.
- What are the closest schools to 103 Front St?The closest schools to 103 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).
- What is 103 Front St estimated to be worth?Trulia's estimated value for 103 Front St in Key West, FL is $6,252,600.
- Does 103 Front St have air conditioning?Yes, 103 Front St in Key West, FL has air conditioning.
- Does 103 Front St have a pool?Yes, 103 Front St in Key West, FL has a pool.
103 Front St, Key West, FL 33040 is a 3 bedroom, 3 bathroom, 3,000 sqft single-family home built in 1918. 103 Front St is located in Truman Annex, Key West. This property is currently available for sale and was listed by FLKMLS on Nov 1, 2025. The MLS # for this home is MLS# 617136.