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.
For sale
$6,850,000
103 Front St, Key West, FL 33040
3beds
3,000sqft
Est.:
Single Family Residence
Built in 1918
8,712 Square Feet Lot
$-- Zestimate®
$2,283/sqft
$3,405/mo HOA
What's special
Poolside outdoor showerAdorned by tropical foliageProperty comprises two lotsCustom beams and woodwork
- 163 days |
- 2,239 |
- 71 |
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
Originating MLS: Key West Association
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 3
Cooling
- Central Air, Ceiling Fans(s)
Appliances
- Included: Washer, Ice Machine, Microwave, Oven, Refrigerator, Dishwasher, Dryer
Features
- Wet Bar, Built-in Cabinets, Granite Counters, Cathedral Ceiling(s)
- Flooring: Wood, Marble
- Doors: Impact Rstnce Doors, French Doors
- Windows: Double Hung Windows, Wood Frames, Other
Interior area
- Total interior livable area: 3,000 sqft
Property
Parking
- Total spaces: 2
- Parking features: Carport, Off Street
- Has carport: Yes
Features
- Levels: Two
- Stories: 2
- Patio & porch: Patio
- Exterior features: Water Display, Storage, Sprinkler System, Outdoor Shower, Lighting
- Has private pool: Yes
- Pool features: In Ground, Concrete
- Fencing: Fenced
- Water view: None
- Waterfront features: None, Dockage: None
Lot
- Size: 8,712 Square Feet
- Features: Less Than 1/4 Acre
Details
- Parcel number: 00004590002157
- Zoning: HPRD
- Zoning description: Hist Planned Redevelopment & Dev Dist
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Combo Construction, Other
- Roof: Metal
Condition
- Year built: 1918
Utilities & green energy
- Sewer: Municipal Sewer, Public Sewer
- Utilities for property: FKAA, Propane
Community & HOA
Community
- Security: Security System, Patrolled Area, Other
- Subdivision: The Foundry (1.0)
HOA
- Has HOA: Yes
- Services included: Maintenance Structure, Security, Maintenance Grounds, Building Insurance
- 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
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
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
$41,995/mo
Principal & interest
$33909
Property taxes
$4681
HOA Fees
$3405
More affordability tools
Climate risks
Neighborhood: Truman Annex
Nearby schools
GreatSchools rating
- 4/10Gerald Adams Elementary SchoolGrades: PK-5Distance: 4.2 mi
- NAMonroe Virtual FranchiseGrades: K,2-3,5-12Distance: 0.8 mi
- 3/10Key West High SchoolGrades: 9-12Distance: 1.9 mi
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Florida
- Monroe County
- Key West
- 33040
- Truman Annex
- 103 Front St




