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.
For sale
$6,850,000
103 Front St, Key West, FL 33040
3beds
3,000sqft
Single Family Residence
Built in 1918
8,712 Square Feet Lot
$-- Zestimate®
$2,283/sqft
$3,405/mo HOA
What's special
Adorned by tropical foliageDramatic staircaseCustom beams and woodworkImposing structureCustom features throughout
- 332 days
- 1,725
- 86
Zillow last checked:
Listing updated:
Listed by:
Laura A McChesney 305-923-6639,
Preferred Properties (KW),
Key West Sisters 305-747-0369,
Preferred Properties (KW)
Source: FLKMLS,MLS#: 617136
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 3
Cooling
- Central Air, Ceiling Fans(s)
Appliances
- Included: Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave, Ice Maker
Features
- Built-in Features, Granite Counters
- Flooring: Wood, Marble
Interior area
- Total structure area: 3,000
- Total interior livable area: 3,000 sqft
Property
Features
- Patio & porch: Patio
- Exterior features: Lighting, Outdoor Shower, Storage, Water Display
- Has private pool: Yes
- Pool features: In Ground, Concrete
- Fencing: Fenced
Lot
- Size: 8,712 Square Feet
Details
- Parcel number: 00004590002157
- Zoning: HPRD - Hist Planned Redevelopment & Dev Dist
- Other equipment: Irrigation Equipment
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Combo Construction, Other
Condition
- Year built: 1918
Community & HOA
Community
- Security: Security Guard, Other, Security System
- Subdivision: The Foundry (1.0)
HOA
- Has HOA: Yes
- Services included: Maintenance Structure, Insurance, Common Area Mnt, Security
- HOA fee: $10,214 quarterly
Location
- Region: Key West
Financial & listing details
- Price per square foot: $2,283/sqft
- Tax assessed value: $4,273,714
- Annual tax amount: $34,272
- Date on market: 11/1/2025
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 11/1/2025 | Listed for sale | $6,850,000+5.4%$2,283/sqft |
Source: | ||
| 4/1/2025 | Listing removed | $6,500,000$2,167/sqft |
Source: | ||
| 9/12/2024 | Listed for sale | $6,500,000$2,167/sqft |
Source: | ||
| 9/6/2024 | Listing removed | $6,500,000$2,167/sqft |
Source: | ||
| 3/18/2024 | Listed for sale | $6,500,000+3.2%$2,167/sqft |
Source: | ||
| 5/21/2022 | Listing removed | -- |
Source: | ||
| 12/8/2021 | Listed for sale | $6,300,000+5.9%$2,100/sqft |
Source: | ||
| 6/1/2018 | Listing removed | $5,950,000$1,983/sqft |
Source: Keller Williams Key West Compass Realty #577304 Report a problem | ||
| 11/3/2017 | Listed for sale | $5,950,000$1,983/sqft |
Source: Keller Williams Key West Compass Realty #577304 Report a problem | ||
| 6/1/2017 | Listing removed | $5,950,000$1,983/sqft |
Source: Compass Realty (KW) #572689 Report a problem | ||
| 11/10/2016 | Listed for sale | $5,950,000+1703%$1,983/sqft |
Source: Compass Realty (KW) #572689 Report a problem | ||
| 4/28/1997 | Sold | $330,000$110/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $35,716 +4.2% | $4,273,714 +4.2% |
| 2024 | $34,273 +5.1% | $4,099,838 +10% |
| 2023 | $32,620 +14.8% | $3,727,125 +10% |
| 2022 | $28,409 -0.3% | $3,388,295 +5.7% |
| 2021 | $28,504 -5.7% | $3,206,196 -6.1% |
| 2020 | $30,236 | $3,413,546 -0.2% |
| 2019 | $30,236 -1% | $3,418,720 +1.8% |
| 2018 | $30,554 -0.4% | $3,357,602 +0.6% |
| 2017 | $30,663 +0.6% | $3,336,822 +10.9% |
| 2016 | $30,467 +4.1% | $3,009,375 +12.3% |
| 2015 | $29,267 | $2,679,948 |
Find assessor info on the county website
Monthly payment
Est. payment






