103 Front St

Key West, FL 33040

$6,850,000
Price
3
Beds
4,200 Sq. Ft.
$1,631 / Sq. Ft.
4,200
Sq. Ft.
$1,631
per Sq. Ft.
a view of house with outdoor space and trees
a view of a house with a small yard and plants
a view of a back yard of the house
a view of a house with a window
a view of an chairs and tables in the patio
a view of a chairs in a room
a view of a patio with dining table and chairs
a kitchen with stainless steel appliances granite countertop a stove and a sink
a kitchen with stainless steel appliances granite countertop a sink a stove and a refrigerator
a kitchen that has a stove and a table
a view of an outdoor space
a living room with furniture a fireplace and windows
a view of entryway and hall with wooden floor
a view of a patio with dining table and chairs
a outdoor space with furniture
a living room with furniture a flat screen tv and a large window
a building outdoor space with patio lots of furniture
a outdoor living space with patio furniture and a grill
a outdoor living space with patio furniture and a chandelier
a view of a chairs and tables in the patio
a living room with furniture
a view of an entryway
a view of an entryway with wooden floor
a outdoor space with chairs
a bathroom with a tub sink and mirror
a bathroom with a sink toilet and shower
a view of a balcony with furniture and wooden floor
a view of outdoor space with wooden floor and staircase
a bedroom with bed and wooden floor
a bathroom with a sink toilet and shower
a view of a patio with table and chairs potted plants with wooden floor
a bathroom with a sink a mirror and shower
a front view of a house with a porch
a view of a house with a swimming pool
a view of a house with backyard porch and sitting area
a swimming pool with outdoor seating
a view of a house with a yard
a view of a building with a large windows
a front view of a house with a yard
a view of a porch
a picture of city view
a view of lake and city
a view of a city

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...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.
  1. Listed by Laura A McChesney • Preferred Properties (KW)
  2. Listed by Key West Sisters • Preferred Properties (KW)

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: 11/01/2025 01:16 PM

Property Details for 103 Front Street

StatusActive
MLS #617136
Days on Market93
Taxes$34,273 / year
HOA Fees$10,214 / quarter
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1918
Lot Size0.20 AC / 8,814 SF
CountyMonroe County

Location

Listing Courtesy of Preferred Properties (KW)
Add your commute

Building Information for 103 Front Street

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

Payment Calculator

$39,646 per month

30 year fixed, 6.15% Interest

Principal and Interest

$33,386

Property Taxes

$2,856

HOA Dues

$3,405

The Payment Calculator is for illustrative purposes only.

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
  • 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: 0
  • 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—
Oct 28, 2024

Listed (Active)

FKMLS #609252

—
Sep 11, 2024

Expired

FKMLS #609252

—
Sep 9, 2024

Temp Off Market

FKMLS #609252

—
Mar 19, 2024

Listed (Active)

MFRMLS #NS1080891

$6,500,000—
Mar 11, 2024

Listed (Active)

FKMLS #609252

$6,500,000—
May 20, 2022

Expired

FKMLS #598752

—
Dec 8, 2021

Listed (Active)

FKMLS #598752

$6,300,000—
May 31, 2018

Expired

FKMLS #577304

—
Nov 2, 2017

Listed (Active)

FKMLS #577304

$5,950,000—
May 31, 2017

Expired

FKMLS #572689

—
Nov 8, 2016

Listed (Active)

FKMLS #572689

$5,950,000—
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
10/28/2024

Listed (Active)

FKMLS #609252

—
09/11/2024

Expired

FKMLS #609252

—
09/09/2024

Temp Off Market

FKMLS #609252

—
03/19/2024

Listed (Active)

MFRMLS #NS1080891

$6,500,000
03/11/2024

Listed (Active)

FKMLS #609252

$6,500,000
05/20/2022

Expired

FKMLS #598752

—
12/08/2021

Listed (Active)

FKMLS #598752

$6,300,000
05/31/2018

Expired

FKMLS #577304

—
11/02/2017

Listed (Active)

FKMLS #577304

$5,950,000
05/31/2017

Expired

FKMLS #572689

—
11/08/2016

Listed (Active)

FKMLS #572689

$5,950,000

For completeness, Compass 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, 4,200 sqft single family home built in 1918.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. 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.