103 Front St
Key West, FL 33040
Truman Annex
3 Beds
3 Baths
3,000 sqft
3 Beds
3 Baths
3,000 sqft
Local Information
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Description
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. 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 between the covered and open air loggia and parking. There's a poolside outdoor shower and space for entertaining on a grand or intimate scale. 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.
Home Highlights
Parking
Carport
Outdoor
Patio, Pool
View
No Info
HOA
$3,405/Monthly
Price/Sqft
$2,283
Listed
180+ days ago
Home Details for 103 Front St
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Interior Details Wet Bar |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3 |
Dimensions and Layout Living Area: 3000 Square Feet |
Appliances & Utilities Utilities: FKAA, PropaneAppliances: Washer, Ice Machine, Microwave, Oven, Refrigerator, Dishwasher, DryerDishwasherDryerMicrowaveRefrigeratorWasher |
Heating & Cooling Has CoolingAir Conditioning: Central Air,Ceiling Fans(s) |
Windows, Doors, Floors & Walls Window: Double Hung Windows, Wood Frames, OtherDoor: Impact Rstnce Doors, French DoorsFlooring: Wood, Marble |
Levels, Entrance, & Accessibility Stories: 2Levels: TwoFloors: Wood, Marble |
Security Security: Security System, Patrolled Area, Other |
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Exterior Home Features Roof: MetalPatio / Porch: PatioFencing: FencedExterior: Water Display, Storage, Sprinkler System, Outdoor Shower, LightingHas a Private PoolSprinkler System |
Parking & Garage Has a CarportNo GarageNo Attached GarageNo Open ParkingParking Spaces: 2Parking: Carport,Off Street |
Pool Pool: In Ground, ConcretePool |
Frontage Waterfront: None, Dockage: NoneNot on Waterfront |
Water & Sewer Sewer: Municipal Sewer, Public Sewer |
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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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HOA Fee Includes: Maintenance Structure, Security, Maintenance Grounds, Building InsuranceAssociation for this Listing: Key West AssociationHas an HOAHOA Fee: $10,214/Quarterly |
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Lot Area: 8712 sqft |
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Mls Number: 617136Water View: None |
Last check for updates: about 14 hours ago
Listing courtesy of Laura A McChesney, (305) 923-6639
Preferred Properties (KW)
Key West Sisters, (305) 747-0369
Preferred Properties (KW)
Originating MLS: Key West Association
Source: FLKMLS, MLS#617136
Price History for 103 Front St
| Date | Price | Event | Source |
|---|---|---|---|
| 11/01/2025 | $6,850,000 | Listed For Sale | FLKMLS #617136 |
| 04/01/2025 | $6,500,000 | ListingRemoved | Engel & Volkers #NS1080891 |
| 09/12/2024 | $6,500,000 | Listed For Sale | Stellar MLS #NS1080891 |
| 09/06/2024 | $6,500,000 | ListingRemoved | Key West AOR #609252 |
| 03/18/2024 | $6,500,000 | Listed For Sale | FLKMLS #609252 |
| 05/21/2022 | ListingRemoved | FLKMLS #598752 | |
| 12/08/2021 | $6,300,000 | Listed For Sale | FLKMLS #598752 |
| 06/01/2018 | $5,950,000 | ListingRemoved | Agent Provided |
| 11/03/2017 | $5,950,000 | Listed For Sale | Agent Provided |
| 06/01/2017 | $5,950,000 | ListingRemoved | Agent Provided |
| 11/10/2016 | $5,950,000 | Listed For Sale | Agent Provided |
| 04/28/1997 | $330,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $35,716 |
| Assessment | $4,273,714 |
Home facts updated by county records
Comparable Sales for 103 Front St
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 | |
0.25 | Single-Family Home | $900,000 | 12/01/25 | 3 | 2 | 1,451 | |
0.16 | Single-Family Home | $2,300,000 | 02/25/26 | 3 | 3 | 1,514 | |
0.07 | Single-Family Home | $6,350,000 | 01/15/26 | 5 | 5.5 | 4,279 | |
0.16 | Single-Family Home | $3,095,000 | 01/27/26 | 4 | 4 | 1,653 | |
0.47 | 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 |
Assigned Schools
These are the assigned schools for 103 Front St.
- Key West High School
- 9-12
- Public
- 1288 Students
3/10GreatSchools RatingParent Rating AverageSmall town, small mentality, the teachers are amazing but the overall quality is poor. Lots of bullying and old bubba mentality of your not from key West, you'll never truly fit inParent Review5mo ago - Gerald Adams Elementary School
- PK-5
- Public
- 631 Students
4/10GreatSchools RatingParent Rating AverageIt's a great school with diversity. I recommend this school over Poinciana. The staff is amazing.Parent Review8y ago - Monroe Virtual Franchise
- K-12
- Public
- 19 Students
NAGreatSchools RatingParent Rating Average
No reviews available for this school. 
Check out schools near 103 Front St.
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
Learn more about our methodology.
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 Board of Realtors.
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.