1022 Fleming St Key West, FL 33040
Old Town NeighborhoodEstimated payment $10,160/month
About This Home
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!
Listing Agent
Ocean Sotheby's International Realty License #3043680 Listed on: 04/21/2026
Open House Schedule
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Sunday, May 24, 202611:00 am to 1:00 pm5/24/2026 11:00:00 AM +00:005/24/2026 1:00:00 PM +00:00Invest 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. 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. Whether you're looking for a smart investment, a vacation getaway, or a new primary residence, this property is ready for you.Add to Calendar
Map
Property Details
Home Type
Multi-Family
Year Built
1928
Lot Details
2,614 Sq Ft Lot
Listing Details
- Property Type: Residential
- Year Built: 1928
- Building Style Above Flood: Yes
- Property Condition: Updated/Remodeled
- Property Sub Type: Duplex
- Co List Office Mls Id: kwa.276530584
- Co List Office Phone: 561-771-2626
- Co List Office Mls Id: kwa.office20314
- Co List Office Phone: 305-294-1117
- Subdivision Name: Old Town - Unlisted (1.0)
- Special Features: 4097
Interior Features
- Interior Amenities: Built-in Cabinets, Wired for Sound
- Appliances: Washer, Dryer, Refrigerator, Range, Oven, Stainless Steel Appliance(s)
- Full Bathrooms: 2
- Total Bedrooms: 4
Exterior Features
- Waterfront: No
- Exterior Features: Fencing
- Construction Type: Frame
- Waterfront: None
- Roof: Metal Roof
Utilities
- Utilities: Water Separate Meter, Elect Separate Meter
- Cooling: Ceiling Fans(s), Ductless
- Utilities: FKAA, Water Separate Meter, Elect Separate Meter
Condo/Co-op/Association
- Pets Allowed: Yes
Lot Info
- Lot Size Sq Ft: 2724.0
Rental Info
- Furnished: Unfurnished
Tax Info
- Tax Year: 2024
- Tax Annual Amount: 14546.9
Multi Family
- Number Of Units Total: 2
Home Values in the Area
Average Home Value in this Area
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 |
|---|---|---|---|---|
| 2025 | $14,756 | $1,656,783 | $858,550 | $798,233 |
| 2024 | $13,991 | $1,650,209 | $858,550 | $791,659 |
| 2023 | $13,991 | $1,561,596 | $789,109 | $772,487 |
| 2022 | $12,269 | $1,378,368 | $597,618 | $780,750 |
| 2021 | $9,536 | $991,277 | $453,124 | $538,153 |
| 2020 | $9,224 | $959,522 | $415,247 | $544,275 |
| 2019 | $8,717 | $893,930 | $405,427 | $488,503 |
| 2018 | $10,508 | $1,075,130 | $506,432 | $568,698 |
| 2017 | $10,757 | $1,083,212 | $0 | $0 |
| 2016 | $10,657 | $1,012,946 | $0 | $0 |
| 2015 | $3,507 | $308,447 | $0 | $0 |
| 2014 | $3,657 | $305,999 | $0 | $0 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 03/30/2026 03/30/26 | Price Changed | $1,650,000 | -2.9% | $818 / Sq Ft | |
| 03/19/2026 03/19/26 | Price Changed | $1,700,000 | -2.9% | $843 / Sq Ft | |
| 02/24/2026 02/24/26 | Price Changed | $1,750,000 | -5.4% | $868 / Sq Ft | |
| 02/16/2026 02/16/26 | Price Changed | $1,850,000 | -7.5% | $918 / Sq Ft | |
| 10/31/2025 10/31/25 | Price Changed | $1,999,990 | -2.4% | $992 / Sq Ft | |
| 10/21/2025 10/21/25 | Price Changed | $2,050,000 | -2.4% | $1,017 / Sq Ft | |
| 09/07/2025 09/07/25 | For Sale | $2,100,000 | +40.0% | $1,042 / Sq Ft | |
| 07/09/2021 07/09/21 | Sold | $1,500,500 | +1.0% | $744 / Sq Ft | View Prior Sale |
| 04/18/2021 04/18/21 | Price Changed | $1,485,000 | -6.6% | $737 / Sq Ft | |
| 01/18/2021 01/18/21 | For Sale | $1,590,000 | +38.3% | $789 / Sq Ft | |
| 08/02/2019 08/02/19 | Sold | $1,150,000 | -16.6% | $570 / Sq Ft | View Prior Sale |
| 06/02/2019 06/02/19 | Pending | -- | -- | -- | |
| 01/03/2019 01/03/19 | For Sale | $1,379,000 | +37.9% | $684 / Sq Ft | |
| 07/24/2015 07/24/15 | Sold | $1,000,000 | -8.7% | $496 / Sq Ft | View Prior Sale |
| 07/03/2015 07/03/15 | Pending | -- | -- | -- | |
| 06/09/2015 06/09/15 | For Sale | $1,095,000 | -- | $543 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | -- | None Listed On Document | |
| Warranty Deed | $1,500,500 | Florida Title Professional | |
| Warranty Deed | $1,150,000 | Attorney | |
| Warranty Deed | $1,000,000 | Attorney | |
| Warranty Deed | $142,000 | -- | |
| Warranty Deed | $94,500 | -- |
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $862,500 | Commercial |
Source: Key West Association of REALTORS®
MLS Number: 616423
APN: 00007340-000000
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