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1022 Fleming Street
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Property Description

Invest in Key West with this legal Duplex which can be easily converted to a single family home! Step into a piece of Key West history with this light-filled historic home in the heart of Old Town. Blending old-world charm with modern updates, this property offers easy living and generates income. Whether you're looking for a smart investment, a vacation getaway, or a new primary residence, this property is ready for you. Live in one unit and rent the other, or enjoy the entire home for yourself! There is an interior staircase to enter the upstairs unit.

Each spacious level features 2 bedrooms, 1 bathroom, a full kitchen with stainless steel appliances, laundry, and an open-concept living/kitchen/dining area. The lower unit opens to a deck and pool--perfect for relaxing and entertaining. The upper unit is currently rented. It boasts abundant natural light and a large wraparound porch, ideal for enjoying the tropical surroundings.

Located in a prime spot close to the Old Seaport, top restaurants, and bars, but in a quieter neighborhood, this home is your ticket to island living in paradise!

Overview

Property Status
Sold
Date Sold
July 31, 2026
Lot Size
2,724 Sq.Ft.
MLS ID
616423
Property Type
Multi-Family
Year Built
1928

Features & Amenities

Total Area
2,016 Sq.Ft.
Neighborhood
Old Town
Architecture Styles
Above Flood
Water Frontage
None
View Description
No Waterview
Pool
Concrete, In Ground
Roof
Metal
Heat Type
Ductless
Air Conditioning
Ductless, Ceiling Fans(s)
Appliances
Stainless Steel Appliance(s), Dryer, Oven, Range, Refrigerator, Washer
Other Interior Features
Built-in Cabinets, Drapes/Blinds Incl, Smoke Alarms, Wired for Sound
Security Features
On Premises System, Secured Building
Other Exterior Features
Fencing
Sales Price
$1,600,000
Real Estate Tax
$14,547/yr
Zoning
HMDR - Historic Medium Density Residential

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1022 Fleming Street

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for your interest in 1022 Fleming Street, Key West, FL 33040

1022 Fleming Street
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Carries its own unique character yet shares the same laid-back rhythm of life that defines the Keys.

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1022 Fleming Street

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