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103 Front Street, Key West, FL - photo 1

$6,850,000

103 Front Street

Key West, FL 33040

Estimated payment $35,212/month

HOA not listed, not included · estimated tax · estimated insurance · 20% down, 6.5%, 30 yr

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3Beds
3Baths
3,000Sq Ft
$2283Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

Built in 1918
8,712 sqft Lot

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. 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.

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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:3
  • •Bathrooms:3
  • •Full bathrooms:3
  • •Half bathrooms:0

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:3,000 sqft
  • •Total interior livable area:3,000 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:8,712 sqft

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Single Family Residence
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:1918

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Price history

DateEventPrice
11/1/2026Listed for sale$6,850,000$2283/sqft

Listing Agent

Laura A McChesney

Preferred Properties (KW)

Brokerage Phone: 305-294-3040

Source: Florida Keys MLS · MLS #617136

Data Powered by Home Junction, Inc.

Nearby

Schools

MONROE VIRTUAL INSTRUCTION PROGRAM

Elementary · 0.8 mi

MONROE VIRTUAL FRANCHISE

High · 0.8 mi

MONROE VIRTUAL ACADEMY (COURSE OFFERINGS)

High · 0.8 mi

Supermarkets

Beef Jerky Experience

0.2 mi

Faustos

0.3 mi

Johnson's Grocery

0.4 mi

Dining

Paris Dining Room - Carnival Triumph

0.1 mi

Scarlet Restaurant

0.2 mi

La Luna

0.4 mi

Parks

Truman Waterfront Park

0.2 mi

Memorial Sculpture Garden

0.3 mi

Nancy Forrester's Secret Garden

0.4 mi

Beaches

Truman Beach

0.8 mi

South Beach

0.9 mi

Dog Beach

1.1 mi

Nearby amenity locations include data © OpenStreetMap contributors.