1022 Fleming St, Key West, FL 33040
FOR SALE

1022 Fleming St
Key West, FL 33040

Old Town
  • 4 Beds
  • 2 Baths
  • 2,016 sqft

$1,650,000

Original price: $1,700,000
Est. Mortgage $9,202/mo*
Get Pre-Qualified

$1,650,000

Original price: $1,700,000
Est. Mortgage $9,202/mo*
Get Pre-Qualified
4 Beds
2 Baths
2,016 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

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!

Home Highlights

Parking
No Info
Outdoor
Porch, Deck, Pool
View
No Info
HOA
None
Price/Sqft
$818
Listed
180+ days ago

Home Details for 1022 Fleming St

Interior Features

Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2016 Square Feet
Appliances & Utilities
Utilities: FKAA, Cable ConnectedAppliances: Washer, Stainless Steel Appliance(s), Oven, Range, Refrigerator, DryerDryerRefrigeratorWasher
Heating & Cooling
Heating: DuctlessHas CoolingAir Conditioning: Ceiling Fans(s),DuctlessHas HeatingHeating Fuel: Ductless
Gas & Electric
Electric: Elect Separate Meter
Windows, Doors, Floors & Walls
Window: Drapes/Blinds Incl, Double Hung Windows, Wood Frames, PanelDoor: French DoorsFlooring: Tile, Combination, Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: NoFloors: Tile, Combination, Wood
Security
Security: Smoke Detector(s), Building Security, On Premises System

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Open Porch/Balcony, DeckFencing: FencedHas a Private Pool
Pool
Pool: In Ground, ConcretePool
Frontage
Waterfront: None, Dockage: NoneNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Days on Market: 180+

Property Information

Year Built
Year Built: 1928
Property Type / Style
Property Type: ResidentialProperty Subtype: Duplex, Single Family Residence
Building
Construction Materials: FrameNot a New ConstructionAttached To Another Structure
Property Information
Condition: Updated/Remodeled

Price & Status

Price
List Price: $1,650,000Price Per Sqft: $818

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: Key WestCommunity: Old Town - Unlisted (1.0)

Agent Information

Listing Agent
Listing ID: 616423

Community

Community Features: Bike Paths

HOA

HOA Fee Includes: NoneAssociation for this Listing: Key West AssociationNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 2613.6 sqft

Offer

Contingencies: NoneListing Terms: Cash, Conventional

Miscellaneous

Mls Number: 616423Water View: None

Additional Information

Bike Paths
Last check for updates: about 15 hours ago
Listing courtesy of Ellen Gvili, (305) 304-2933
Ocean Sotheby's International Realty
Marc Ulanowski, (815) 861-3559
Equestrian Sotheby's International Realty
Originating MLS: Key West Association
Source: FLKMLS, MLS#616423
Also Listed on FLKMLS, FLKMLS, Key West AOR, Key West AOR, Key West AOR, Key West AOR, FLKMLS.

Price History for 1022 Fleming St

DatePriceEventSource
04/21/2026$1,650,000PendingToActiveFLKMLS #616423
04/13/2026$1,650,000ContingentFLKMLS #616977
03/30/2026$1,650,000PriceChange
Key West AOR #616423
03/19/2026$1,700,000PriceChange
FLKMLS #616423
02/24/2026$1,750,000PriceChange
Key West AOR #616423
02/17/2026$1,850,000PriceChange
Key West AOR #616977
10/31/2025$1,999,990PriceChange
FLKMLS #616977
10/21/2025$2,050,000PriceChange
FLKMLS #616423
09/09/2025$2,100,000Listed For SaleKey West AOR #616423
09/06/2025$2,100,000ListingRemovedFLKMLS #614069
07/16/2025$2,100,000PriceChange
FLKMLS #611458
04/18/2025$2,150,000PriceChange
Key West AOR #614069
02/02/2025$2,285,000PriceChange
Key West AOR #611458
09/13/2024$2,399,000Listed For SaleFLKMLS #611458
09/13/2024$4,700ListingRemovedZillow Rentals
08/21/2024$4,700PriceChange
Zillow Rentals
08/07/2024$4,800PriceChange
Zillow Rentals
07/23/2024$5,000PriceChange
Zillow Rentals
07/01/2024$5,100PriceChange
Zillow Rentals
05/18/2024$5,200PriceChange
Zillow Rentals
04/30/2024$5,250PriceChange
Zillow Rentals
04/24/2024$5,500PriceChange
Zillow Rentals
04/05/2024$5,800Listed For RentZillow Rentals
07/09/2021$1,500,500Sold
FLKMLS #594244
08/02/2019$1,150,000Sold
FLKMLS #583489
07/24/2015$1,000,000Sold
N/A

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Property Tax and Assessment

Year2025
Tax$14,756
Assessment$1,656,783
Home facts updated by county records

Comparable Sales for 1022 Fleming St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
621 Elizabeth St, Key West, FL
0.34
Multi-Family Home
$1,625,000
04/20/26
3
2
1,594
620 White St, Key West, FL
0.16
Multi-Family Home
$800,000
02/24/26
3
2
1,421
830 Fleming St, Key West, FL
0.17
Multi-Family Home
$1,350,000
10/20/25
3
4
1,989
514 Margaret St, Key West, FL
0.17
Multi-Family Home
$1,400,000
01/14/26
5
3.5
2,068
737 Olivia St, Key West, FL
0.39
Multi-Family Home
$1,525,000
07/08/25
3
3
1,860
704 Caroline St, Key West, FL
0.35
Multi-Family Home
$1,750,000
08/05/25
4
5
2,080
708 William St, Key West, FL
0.36
Multi-Family Home
$1,752,000
11/17/25
4
3.5
1,967
1113 Watson St, Key West, FL
0.51
Multi-Family Home
$1,300,000
03/20/26
5
3
1,819
1210 Virginia St, Key West, FL
0.51
Multi-Family Home
$900,000
02/20/26
3
2.5
1,740

Assigned Schools

These are the assigned schools for 1022 Fleming St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Old Town
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Old Town

At least 1 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 100 % Say people would walk alone at night

  • 100 % Say there are sidewalks

  • 100 % Say streets are well-lit

  • 100 % Say neighbors are friendly

  • 100 % Say it's quiet

  • 100 % Say it's walkable to grocery stores

  • 100 % Say it's walkable to restaurants

  • 100 % Say parking is easy

  • 100 % Say car is needed

  • 67 % Say there's holiday spirit

  • 50 % Say there are community events

  • 50 % Say they plan to stay for at least 5 years

  • 50 % Say kids play outside

Learn more about our methodology.
  • David Atkinson
    "I so look forward to getting to Key West. I volunteer at the Tropic and love it. It feels like home."
    0
    Flag
  • Trulia User
    "Dogs are welcomed at 90% of the restaurants. Everyone will remember your dogs name but not yours! I love living here with my dog Jack."
    0
    Flag
  • Trulia User
    "Key West is a huge dog community. They even are allowed in some restaurants . When I walk my dog on the main tourist street (Duval St) I get stopped many times from people wanting to pet my dog. A group of dog owners meet up at the park in the morning every day."
    0
    Flag
  • Sgarvin3281
    " Bikes are all you need small island. Safe and secure. No commute I do t work here it is a vacation community."
    0
    Flag
  • Trulia User
    "Everywhere dogs are welcome here in key west, Florida. Come joining us here in key west. Most food and service places, boats, and entertainment venues are good with dogs."
    0
    Flag
  • Trulia User
    "Feels very safe, super clean, super walkable in old town, and Catholic school looks very vibrant. "
    0
    Flag
  • Trulia User
    "Great people, great neighborhood, great police, family friendly events. Lots of things to do within a decent drive. Very family friendly generally "
    0
    Flag
  • Key W. B. F.
    "Gatherings on the local Mangia Mangia bench at 900 Southard street, safe & friendly town. Feel connected & welcomed in Key West. Enjoy the peaceful neighborhood & the tropical weather! You can walk or bike to everything you need & want!"
    0
    Flag
  • Kfowler
    "I am not currently aware of any neighborhood events that would bring the neighbors closer. However, both my husband and I would be open to any such event that would do so and would improve the neighborhood. The area is beautiful and well maintained, with a few exceptions. "
    2
    Flag
  • Hannah B.
    "Vintage Cottage houses, small island feel, Duval Street in a few minutes with hundreds of worldly trendy restaurants "
    6
    Flag
  • Drlynmar
    "Neighborhood newsletter. Proximity to OldTown events, festivals and parades. Walk to everything. Parks, beaches, dog park. Grocery and restaurant delivery. "
    2
    Flag
  • Venomousink1970
    "the neighborhood is great I myself do not like living in Key West anymore and looking to relocate and Asheville North Carolina or the surrounding areas people are very friendly here except for the homeless vagrants that beg for money and yell at you when you don't give them any"
    0
    Flag
  • Lorettamdt
    "Old Town is historic. Our neighbors are friendly. We walk everywhere. No need for a car. Restaurants are within walking distance. Beaches are a bicycle ride away. "
    0
    Flag
  • mangiamangia
    "Lived in this neighborhood for 25 years. Walk and anywhere. Far enough of Duval to escape the noise and drunks."
    0
    Flag
  • Sajsk
    "vacationed in that area -- charming and great location and amenities, yet quiet."
    0
    Flag
  • Rjones
    "This is a great street and great neighborhood. Qiet, yet close enough to Duval and White streets to enjoy all Key West has to offer. "
    0
    Flag

LGBTQ Local Legal Protections

Ellen Gvili, Ocean Sotheby's International Realty
Agent Phone: (305) 304-2933
MLS Internet Data Exchange (IDX) information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys Board of Realtors.
1022 Fleming St, Key West, FL 33040 is a 4 bedroom, 2 bathroom, 2,016 sqft multi-family built in 1928. 1022 Fleming St is located in Old Town, Key West. This property is currently available for sale and was listed by FLKMLS on Sep 9, 2025. The MLS # for this home is MLS# 616423.