1022 Fleming Street, Key West, FL 33040 (MLS# 616423)

1022 Fleming Street, Key West, FL 33040

$1,650,000

Virtual Tour

http://tours.keyspropertyvisuals.com/vtnb/361696

Dining area downstairs & French doors leading to backyard

French doors leading to back porch upstairs

Property Type: Residential Bedrooms: 4 Baths: 2 Square Footage: 2,016 Lot Size (sq. ft.): 2,724 Status: Active

Current Price: $1,650,000 List Date: 4/21/2026 Last Modified: 4/27/2026

Overview

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, ... (Read more)

Listing Details MLS# 616423

Location, Tax & Legal

Street #: 1022
Street Name: Fleming
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Old Town - Unlisted (1.0)
Area: 02 - Key West
KW Neighborhood: Old Town-N of Truman
City: KEY WEST
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: AE
Alternate Key #: 1007617
Handicap Access: No
Zoning: HMDR - Historic Medium Density Residential
Deed Restrictions: Unknown
Taxes: 14546.9
Tax Year: 2024
Pub Sewer HkUp: Yes

Contract Information

Listing Board: Key West Association
As is Rght to Inspct: Yes
Potential Short Sale: No
Bank Owned: No
Species List: No

General Property Description

Realtor.COM Type: Residential - Single Family
Style: Duplex
Waterfront: No
Pool: Yes
Year Built: 1928
Total Units: 2
Lot SqFt: 2724
Acres: 0.06
Living Apx SqFt: 2016
SqFt Source: Tax Records
Total Bedrooms: 4
Full Baths: 2
Total Baths: 2
Floor Number: 2
Rentals Allowed: With Restrictions
Min Rental Days: 29
Control Depth: 0

Status Change Info

Contingent: None

Association Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0

Building Style

Above Flood: Yes
Stories: 2 Stories

More Information

Financial Status

Bank Owned: No
Potential Short Sale: No

Remarks & Misc

Remarks – Consumer: 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!

Fee Includes

None: Yes

Dockage

None: Yes

Tax Exemptions

None: Yes

Appliances

Dryer: Yes
Oven: Yes
Range: Yes
Refrigerator: Yes
Stainless Steel Appliance(s): Yes
Washer: Yes

Pets

Pets Allowed: Yes

Cooling

Ceiling Fans(s): Yes
Ductless: Yes

Heating

Ductless: Yes

Waterfront

None: Yes

Waterview

No Waterview: Yes

Floor

Combo: Yes
Tile: Yes
Wood: Yes

Neighborhood Feature

Bike Paths: Yes

Interior Features

Built-in Cabinets: Yes
Drapes/Blinds Incl: Yes
Smoke Alarms: Yes

Property Condition

Updated/Remodeled: Yes

Windows/Doors

Double Hung Windows: Yes
French Doors: Yes
Wood Windows: Yes

Security

On Premises System: Yes
Secured Building: Yes

Construction

Frame: Yes

Land Size

Less Than 1/4 Acre: Yes

Furnished

Negotiable: Yes

Terms

Cash: Yes
Conventional: Yes

Utilities

Elect Separate Meter: Yes
FKAA: Yes
Water Separate Meter: Yes

Porch/Balcony

Deck: Yes
Open Porch/Balcony: Yes

Title

Negotiable: Yes

Exterior Features

Fencing: Yes

Pool Info

In Ground: Yes
Concrete: Yes

Pre-Wired

Cable: Yes
Surround Sound: Yes

Roof

Metal Roof: Yes

Shutters

Panel: Yes

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: None Waterview: No Waterview Dockage: None Property Condition: Updated/Remodeled Furnished: Negotiable Cooling: Ceiling Fans(s); Ductless Heating: Ductless Utilities: Elect Separate Meter; FKAA; Water Separate Meter Interior Features: Built-in Cabinets; Drapes/Blinds Incl; Smoke Alarms Pre-Wired: Cable; Surround Sound Appliances: Dryer; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer Exterior Features: Fencing Pool Info: In Ground; Concrete Construction: Frame Shutters: Panel Floor: Combo; Tile; Wood Roof: Metal Roof Pets: Pets Allowed Neighborhood Feature: Bike Paths Security: On Premises System; Secured Building Land Size: Less Than 1/4 Acre Terms: Cash; Conventional Title: Negotiable

Listing Office: Ocean Sotheby's International Realty

Last Updated: April - 27 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.