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103 Front Street, Key West, FL 33040

$6,850,000
Property Type: Residential Bedrooms: 3 Baths: 3 Square Footage: 3,000 Lot Size (sq. ft.): 8,814 Status: Active
Current Price: $6,850,000 List Date: 11/01/2025 Last Modified: 5/29/2026

Overview

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. 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 i ...

Listing Details MLS# 617136

Location, Tax & Legal

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
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

Contract Information

Listing Board
Key West Association

General Property Description

Realtor.COM Type
Residential - Single Family
Style
Single Family
Waterfront
No
Pool
Yes
Year Built
1918
Lot SqFt
8814
Lot Sqft Source
Property Data Card
Acres
0.2
Living Apx SqFt
3000
SqFt Source
Property Data Card
Total Bedrooms
3
Full Baths
3
Total Baths
3
Rentals Allowed
With Restrictions
Min Rental Days
28
Control Depth
0
Total Units
0

Association Info

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

Building Style

Above Flood
Unknown
Stories
2 Stories

More Information

Vehicle Storage

Car(s)
2
Carport
Yes
Off Street Parking
Yes

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. 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.
Directions
Southard into the Truman Annex. Right on Front St to 103.

Fee Includes

Bldg Exterior Mnt
Yes
Building Insurance
Yes
Common Area Mnt
Yes
Security
Yes

Dockage

None
Yes

Tax Exemptions

None
Yes

Appliances

Dishwasher
Yes
Dryer
Yes
Ice Machine
Yes
Microwave
Yes
Oven
Yes
Refrigerator
Yes
Washer
Yes

Cooling

Ceiling Fans(s)
Yes
Central Air
Yes

Waterfront

None
Yes

Waterview

No Waterview
Yes

Floor

Marble
Yes
Wood
Yes

Interior Features

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

Windows/Doors

Double Hung Windows
Yes
French Doors
Yes
Impact Rstnce Doors
Yes
Wood Windows
Yes

Security

Patrolled Area
Yes
Other
Yes

Construction

Combo Construction
Yes
Other
Yes

Land Size

Less Than 1/4 Acre
Yes

Furnished

Unfurnished
Yes

Utilities

FKAA
Yes
Municipal Sewer
Yes
Propane
Yes

Porch/Balcony

Patio
Yes

Exterior Features

Fencing
Yes
Lighting
Yes
Outdoor Shower
Yes
Sprinkler System
Yes
Storage
Yes
Water Display
Yes

Pool Info

In Ground
Yes
Concrete
Yes

Roof

Metal Roof
Yes

Shutters

Other
Yes

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: May - 29 - 2026
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