103 Front St

Key West, FL 33040

$6,850,000
Price
3
Beds
3,000 Sq. Ft.
$2,283 / Sq. Ft.
3,000
Sq. Ft.
$2,283
per Sq. Ft.
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02-DJI_20240219103941_0143_D_CH1-HIGH-HI
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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...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.

Property Details for 103 Front Street

Waterfront
None
Waterfront
No
Zoning
HPRD - Hist Planned Redevelopment & Dev Dist
Subdivision
The Foundry (1.0)
Directions
Southard into the Truman Annex. Right on Front St to 103.
Vehicle Storage
Carport, Off Street Parking
LISTING UPDATED: 05/29/2026 11:51 AM

Property Details for 103 Front Street

StatusActive
MLS #617136
Days on Market245
Taxes$34,273 / year
HOA Fees$10,214 / quarter
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1918
Lot Size0.20 AC / 8,814 SF
CountyMonroe County
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Location

Listing Courtesy of Preferred Properties (KW)
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Building Information for 103 Front Street

Stories2Year Built1918Building Size-Lot Size0.20 AC / 8,814 SF

Payment Calculator

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$40,395 per month

30 year fixed, 6.36% Interest

Principal and Interest

$34,134

Property Taxes

$2,856

HOA Dues

$3,405

The Payment Calculator is for illustrative purposes only.

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Property Information for 103 Front Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 01 - Key West
  • Absolute Longitude: 81.80686
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Median
  • KW Neighborhood: Truman Annex
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: Yes
  • Association Info: 1st Right of Refusal: Yes
  • Association Info: Assoc Approval Req: Yes
  • Fee Includes: Bldg Exterior Mnt, Security, Common Area Mnt, Building Insurance
  • Furnished: Unfurnished
  • Tax Year: 2024
  • Tax Exemptions: None
Property
Lot Information
  • Lot Size: Double lot with two parcels
  • Acres: 0.2
  • SqFt Remarks: Buyer to verify.
  • Parcel #: 00004590-002157
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • 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
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Flood Zone: AE,AE
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Yes
  • Picture Count: 44
  • Document Count: 1
  • Building Style: Above Flood: Unknown
  • Security: Patrolled Area, Other
Utilities
  • Utilities: FKAA, Propane, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: In Ground, Concrete
  • Porch/Balcony: Patio
Interior and Exterior Features
Interior Features
  • Floor: Wood, Marble
  • Interior Features: Wet Bar, Built-in Cabinets, Security System, Granite Counter Top, Cathedral Ceilings
  • Appliances: Washer, Ice Machine, Microwave, Oven, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Shutters: Other
  • Construction: Combo Construction, Other
  • Dockage: None
  • Exterior Features: Fencing, Water Display, Storage, Sprinkler System, Outdoor Shower, Lighting
  • Windows/Doors: Double Hung Windows, Impact Rstnce Doors, Wood Windows, French Doors

Property History for 103 Front Street

DateEvent & SourcePriceAppreciation
Nov 1, 2025

Listed (Active)

FKMLS #617136

$6,850,000—
Mar 31, 2025

Temp Off Market

FKMLS #609252

—
Mar 31, 2025

Cancelled

MFRMLS #NS1080891

$6,500,000—
DateEvent & SourcePrice
11/01/2025

Listed (Active)

FKMLS #617136

$6,850,000
03/31/2025

Temp Off Market

FKMLS #609252

—
03/31/2025

Cancelled

MFRMLS #NS1080891

$6,500,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 103 Front Street

Taxable ValueLand$3,072,300Additions$1,201,414Total$4,273,714
Tax Record2024$34,273 ($2,856 / month)
Home Facts
Beds3Baths2.5Total Finished SqFt4,200 SqFtAbove Grade Finished SqFt4,200 SqFtStories2Lot Size8,880 SqFtStyleSingle Family ResidenceYear Built1918Year Renovated2016CountyMONROEAPN00004590-002157

Schools near 103 Front Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Gerald Adams Elementary School
Public - PK to 5
Monroe Virtual Instruction Program
Public - K to 12
Key West High School
Public - 9 to 12
Monroe Virtual Instruction Program (District Provided)
Public - K to 5
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Monroe Virtual Instruction Program
PublicK to 12

Key West High School
Public9 to 12

Monroe Virtual Instruction Program (District Provided)
PublicK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 103 Front Street, Key West, FL 33040

103 Front Street is a single family home for sale in Key West, FL 33040. This property was listed for sale on November 1, 2025 by Preferred Properties (KW), it's currently listed at $6,850,000. This listing's school district is Monroe. Nearby schools include Gerald Adams Elementary School, Monroe Virtual Instruction Program and Key West High School. 103 Front Street is a 3-bed, 3-bath, 3,000 sqft single family home built in 1918.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Preferred Properties (KW)

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.