103 Front Street, Key West, FL 33040

$6,850,000
Property Type: Residential Bedrooms: 3 Baths: 3 Square Footage: 4,200 Lot Size (sq. ft.): 8,814 Status: Active
Current Price: $6,850,000 List Date: 11/01/2025 Last Modified: 11/01/2025

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. 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.

More Information MLS# 617136

Contract Information

Listing Board: Key West Association Current Price: $6,850,000 Listing Date: 2025-11-01 List Price: $6,850,000

Location, Tax & Legal

KW Neighborhood: Truman Annex City: KEY WEST Mile Marker: 1 Marathon Neighborhood: N/A Side: Median Flood Zone: AE,AE Alternate Key #: 8849389 Parcel #: 00004590-002157 Zoning: HPRD - Hist Planned Redevelopment & Dev Dist Deed Restrictions: Yes Legal: KW PT LOTS 2 & 3 SQR 28 (.2023 AC) OR1307-1729 OR1307-1732/35 OR1307-1736/39 OR1329-1340/44 OR1331-518/21 OR1332-323/76 Taxes: 34272.76 Tax Year: 2024 Pub Sewer HkUp: Yes Street #: 103 Street Name: Front Street Suffix: Street Key/Island: Key West State/Province: FL Zip Code: 33040 County: Monroe Subdivision: The Foundry (1.0) Area: 01 - Key West

General Property Description

Realtor.COM Type: Residential - Single Family Waterfront: No Control Depth: 0 Lot Size: Double lot with two parcels Lot SqFt: 8814 Pool: Yes Lot Sqft Source: Property Data Card Total Units: 0 Acres: 0.2 SqFt Source: Property Data Card Rentals Allowed: With Restrictions Min Rental Days: 28 Style: Single Family Year Built: 1918 Living Apx SqFt: 4200 Total Bedrooms: 3 Full Baths: 3 Total Baths: 3

Remarks & Misc

Remarks – Consumer: 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. Directions: Southard into the Truman Annex. Right on Front St to 103.

Association Info

Mandatory Home Owners Asc: Yes 1st Right of Refusal: Yes Assoc Approval Req: Yes Association Fee $: 10214 Assoc/Mnt Fee Per: Quarterly

Fee Includes

Bldg Exterior Mnt: 1 Building Insurance: 1 Common Area Mnt: 1 Security: 1

Dockage

None: 1

Tax Exemptions

None: 1

Appliances

Dishwasher: 1 Dryer: 1 Ice Machine: 1 Microwave: 1 Oven: 1 Refrigerator: 1 Washer: 1

Cooling

Ceiling Fans(s): 1 Central Air: 1

Waterfront

None: 1

Waterview

No Waterview: 1

Floor

Marble: 1 Wood: 1

Interior Features

Built-in Cabinets: 1 Cathedral Ceilings: 1 Granite Counter Top: 1 Security System: 1 Wet Bar: 1

Building Style

Above Flood: Unknown Stories: 2 Stories

Windows/Doors

Double Hung Windows: 1 French Doors: 1 Impact Rstnce Doors: 1 Wood Windows: 1

Vehicle Storage

Car(s): 2 Carport: 1 Off Street Parking: 1

Security

Patrolled Area: 1 Other: 1

Construction

Combo Construction: 1 Other: 1

Land Size

Less Than 1/4 Acre: 1

Furnished

Unfurnished: 1

Utilities

FKAA: 1 Municipal Sewer: 1 Propane: 1

Porch/Balcony

Patio: 1

Exterior Features

Fencing: 1 Lighting: 1 Outdoor Shower: 1 Sprinkler System: 1 Storage: 1 Water Display: 1

Pool Info

In Ground: 1 Concrete: 1

Roof

Metal Roof: 1

Shutters

Other: 1

Status Change Info

Status: Active

Property Features

Fee Includes: Bldg Exterior Mnt; Building Insurance; Common Area Mnt; Security Tax Exemptions: None Waterfront: None Waterview: No Waterview Dockage: None Vehicle Storage: Carport; Off Street Parking Furnished: Unfurnished Cooling: Ceiling Fans(s); Central Air Utilities: FKAA; Municipal Sewer; Propane Interior Features: Built-in Cabinets; Cathedral Ceilings; Granite Counter Top; Security System; Wet Bar Appliances: Dishwasher; Dryer; Ice Machine; Microwave; Oven; Refrigerator; Washer Exterior Features: Fencing; Lighting; Outdoor Shower; Sprinkler System; Storage; Water Display Pool Info: In Ground; Concrete Construction: Combo Construction; Other Shutters: Other Floor: Marble; Wood Roof: Metal Roof Security: Patrolled Area; Other Land Size: Less Than 1/4 Acre
Listing Office: Preferred Properties (KW)
Last Updated: November - 01 - 2025
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