$6,850,000

Estimated payment $38,573/month

Total Views 529
3 Beds
3 Baths
4,200 Sq Ft
$1,631 Price per Sq Ft

About This Home

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.

Listing Agent

Laura McChesney

Preferred Properties (KW) License #494597 Listed on: 11/01/2025

Co-Listing Agent

Jenny Perry

Preferred Properties (KW)

Map

Home Details

Home Type

Single Family

Est. Annual Taxes

$32,620

Year Built

1918

Lot Details

0

Listing Details

  • Property Type: Residential
  • Style: Single Family
  • First Right of Refusal: Yes
  • Association Approval Required: Yes
  • Association Fee: 10214.00
  • Mandatory HOA: Yes
  • Fee Includes: Bldg Exterior Mnt, Security, Common Area Mnt, Building Insurance
  • Key Island: Key West
  • K W Neighborhood: Truman Annex
  • Limited Representation: No
  • Marathon Neighborhood: N/A
  • Mile Marker: 1.00
  • Min Rental Days: 28.00
  • M L S Identifier: 20060123165453488875000000
  • Pets W Restrictions: YES
  • Property Group I D: 19990816212109142258000000
  • Side: Median
  • State Province: FL
  • Taxes: 34272.76
  • Vehicle Storage: Carport, Off Street Parking
  • Vehicle Storage Cars: 2
  • Year Built: 1918
  • Alternate Key Number: 8849389
  • Cooling Heating: Central Air, Ceiling Fans(s)
  • Lot Sq Ft: 8814.00
  • Pool Info: In Ground, Concrete
  • Porch Balcony: Patio
  • Association Maintenance Fee Per: Quarterly
  • Shutters: Other
  • Tax Exemptions: None
  • Building Style Above Flood: Unknown
  • Building Style Stories: 2 Stories
  • Estimated Living Sq Ft: 4200.00
  • Sewer Hook Up: Yes
  • Statistical Purposes Only: No
  • Special Features: None
  • Property Sub Type: Detached
  • Stories: 2

Interior Features

  • Interior Amenities: Wet Bar, Built-in Cabinets, Security System, Granite Counter Top, Cathedral Ceilings
  • Total Bathrooms: 3.00
  • Full Bathrooms: 3
  • Appliances: Washer, Ice Machine, Microwave, Oven, Refrigerator, Dishwasher, Dryer
  • Floor: Wood, Marble
  • Windows/Doors: Double Hung Windows, Impact Rstnce Doors, Wood Windows, French Doors
  • Total Bedrooms: 3

Exterior Features

  • Dockage: None
  • Waterfront: None
  • Waterfront: No
  • Construction: Combo Construction, Other
  • Exterior Features: Fencing, Water Display, Storage, Sprinkler System, Outdoor Shower, Lighting
  • Roof: Metal Roof
  • Waterview: No Waterview
  • Pool: Yes

Utilities

  • Security: Patrolled Area, Other
  • Utilities: FKAA, Propane, Municipal Sewer

Lot Info

  • Deed Restrictions: Yes
  • Flood Zone: AE,AE
  • Parcel Number: 00004590-002157
  • Lot Size: Double lot with two parcels
  • Land Size: Less Than 1/4 Acre
  • Acres: 0.20

Rental Info

  • Rentals Allowed: With Restrictions
  • Furnished: Unfurnished

Tax Info

  • Tax Year: 2024

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2024 $32,620 $4,111,198 $2,910,600 $1,200,598
2023 $32,620 $4,068,145 $2,910,600 $1,157,545
2022 $28,409 $3,388,295 $2,402,400 $985,895
2021 $28,504 $3,206,196 $2,213,424 $992,772
2020 $30,236 $3,413,546 $2,408,389 $1,005,157
2019 $30,554 $3,418,720 $2,390,489 $1,028,231
2018 $30,663 $3,357,602 $2,308,909 $1,048,693
2017 $30,467 $3,336,822 $0 $0
2016 $29,267 $3,009,375 $0 $0
2015 $27,148 $2,679,948 $0 $0
2014 $26,465 $2,594,703 $0 $0
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
11/01/2025 11/01/25 For Sale $6,850,000 -- $1,631 / Sq Ft
Source: Key West Association of REALTORS®

Purchase History

Date Type Sale Price Title Company
Warranty Deed $330,000 --
Warranty Deed $229,900 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Open $1,500,000 Credit Line Revolving
Source: Public Records

Source: Key West Association of REALTORS®

MLS Number: 617136

Key West Association of REALTORS®

APN: 00004590-002157