1022 Fleming St, Key West, FL 33040
Property image
Property image
SOLD
JUL 31, 2026

1022 Fleming St
Key West, FL 33040

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

$1,600,000

Last Sold: Jul 31, 2026
3% below list $1.65M
$794/sqft
Est. Refi. Payment $9,174/mo*
Refinance Your Home

$1,600,000

Last Sold: Jul 31, 2026
3% below list $1.65M
$794/sqft
Est. Refi. Payment $9,174/mo*
Refinance Your Home
4 Beds
2 Baths
2,016 sqft

Local Information

  • Map ViewExplore the area around 1022 Fleming St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1928
Living Area
2,016 sqft
Price/Sqft
$794/sqft
HOA
None

About this House

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!
1022 Fleming St, Key West, FL 33040 is a 4 bedroom, 2 bathroom, 2,016 sqft multi-family in Old Town, built in 1928. It last sold for $1,600,000 on Jul 31, 2026 (3% below the $1,650,000 asking price). More recently, it was listed as a rental in May 2024 with an asking price of $5,200 per month. That rental listing was removed on September 13, 2024. It is currently off market. The Trulia Estimate is $1,562,300, with a rent estimate of $5,678/month.

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: Water Separate Meter, Elect Separate MeterAppliances: Washer, Dryer, Refrigerator, Range, Oven, Stainless Steel Appliance(s)DryerRefrigeratorWasher
Heating & Cooling
Heating: Has Heating Unspecified TypeHas CoolingAir Conditioning: Ceiling Fans(s),DuctlessHas HeatingHeating Fuel: Has Heating Unspecified Type
Windows, Doors, Floors & Walls
Flooring: Tile, Wood, Combination
Levels, Entrance, & Accessibility
Floors: Tile, Wood, Combination
View
No View
Security
Security: Building Security, On Premises System

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/Balcony, DeckFencing: FencedHas a Private Pool
Pool
Pool: In Ground, ConcretePool
Frontage
Not on Waterfront

Property Information

Year Built
Year Built: 1928
Property Type / Style
Property Type: ResidentialProperty Subtype: Duplex
Building
Construction Materials: FrameNot a New Construction
Property Information
Condition: Updated/Remodeled

Price & Status

Price
List Price: $1,650,000Price Per Sqft: $794/sqft

Active Status

MLS Status: Closed

Media

Location

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

Building

Building Area
Building Area: 2016 Square Feet

Community

Community Features: Bike Paths

HOA

HOA Fee Includes: NoneNo HOA

Lot Information

Lot Area: 2613.6 sqft

Offer

Listing Terms: Cash, Conventional

Miscellaneous

Mls Number: 616423

Additional Information

Bike Paths
Last check for updates: about 3 hours ago
Listed by Ellen Gvili, (305) 304-2933
Ocean Sotheby's International Realty
Bought with: The Spottswood Team, (305) 432-4848, Truman & Co. (KW)
Co-Buyer's Agent: Terri Spottswood, (305) 587-3407, Truman & Co. (KW)
Source: FLKMLS, MLS#616423

Price History for 1022 Fleming St

DatePriceEventSource
07/31/2026$1,600,000Sold
FLKMLS #616423
07/20/2026$1,650,000ContingentFLKMLS #616423
06/16/2026$1,650,000PendingFLKMLS #616423
05/27/2026$1,650,000ContingentFLKMLS #616977
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$5,200Listed For RentZillow Rentals
07/13/2021$1,500,500Sold
N/A
08/05/2019$1,150,000Sold
N/A
07/24/2015$1,000,000Sold
N/A

Market trends in Key West

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.23M
$20.83KMoM
Sale-to-List Price
94.6%
0.3%MoM
Price per sq ft
$958
$15MoM
Available listings
288
17MoM
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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
1030 James St, Key West, FL
0.12
Multi-Family Home
$1,800,000
05/26/26
3
3
1,700
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
0.16
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
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

Nearby homes

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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

  • 60 % Say they plan to stay for at least 5 years

  • 50 % Say there are community events

  • 50 % Say kids play outside

Sourced by Trulia users. 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

Apartments for Rent

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Explore by feature - Pet Friendly

19 pet-friendly rentals in Key West, FL

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Explore by feature - Outdoor Space

12 rentals with an outdoor space in Key West, FL

Homes for sale near 1022 Fleming St

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Off Market Homes Near 1022 Fleming St

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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 MLS.