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. On one end is the primary bedroom with a large en suite. At the other end is an en suite guest bedroom. The custom features throughout are evidence of the ingenuity used in the design of this impressive home. A third bedroom and full bath on the main floor features doors that open to a separate private patio. The kitchen features custom wood cabinets and granite countertops and is open to the dining area. Extra tall windows and french doors flood the home with sunlight. Entertaining indoors or out is easy in this spacious home. 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 is set on two lots with a large swimming pool and spa between the covered open air loggia and parking. There's a poolside outdoor shower and lots of 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
4,200sqft
Est.:
Single Family Residence
Built in 1918
8,712 Square Feet Lot
$-- Zestimate®
$1,631/sqft
$3,405/mo HOA
What's special
Large swimming poolPrivate patioTropical foliageGranite countertopsExtra tall windowsFrench doorsWhite picket fence
- 110 days |
- 2,644 |
- 71 |
Zillow last checked: 8 hours ago
Listing updated: November 01, 2025 at 06:16am
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: 4,200 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: $1,631/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%$1,631/sqft |
Source: | ||
| 4/1/2025 | Listing removed | $6,500,000$1,548/sqft |
Source: | ||
| 9/12/2024 | Listed for sale | $6,500,000$1,548/sqft |
Source: | ||
| 9/6/2024 | Listing removed | $6,500,000$1,548/sqft |
Source: | ||
| 3/18/2024 | Listed for sale | $6,500,000+3.2%$1,548/sqft |
Source: | ||
| 5/21/2022 | Listing removed | -- |
Source: | ||
| 12/8/2021 | Listed for sale | $6,300,000+5.9%$1,500/sqft |
Source: | ||
| 6/1/2018 | Listing removed | $5,950,000$1,417/sqft |
Source: Keller Williams Key West Compass Realty #577304 Report a problem | ||
| 11/3/2017 | Listed for sale | $5,950,000$1,417/sqft |
Source: Keller Williams Key West Compass Realty #577304 Report a problem | ||
| 6/1/2017 | Listing removed | $5,950,000$1,417/sqft |
Source: Compass Realty (KW) #572689 Report a problem | ||
| 11/10/2016 | Listed for sale | $5,950,000+1703%$1,417/sqft |
Source: Compass Realty (KW) #572689 Report a problem | ||
| 4/28/1997 | Sold | $330,000$79/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
BuyAbility℠ payment
Est. payment
$41,899/mo
Principal & interest
$33813
Property taxes
$4681
HOA Fees
$3405
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
- 4/10Key West High SchoolGrades: 9-12Distance: 1.9 mi




