Fleming Street, Key West, FL

Everything we know about Fleming Street in Key West: what is for sale, what has sold, what the homes are like and which communities the street runs through — from the MLS record and county parcel data, refreshed nightly.

54 homes sit on Fleming Street in Key West, FL (ZIP 33040), built 1884–2008, a typical 2,016 sq ft with 4 bedrooms. 4 are for sale right now from $1,775,000 to $3,500,000. Homes that sold since 2023 went for a median $2,050,000.

For sale on Fleming Street now

416 Fleming Street, home for sale on Fleming Street
$3,500,000
5 bd · 4.5 ba · built 1938
416 Fleming Street
Listing courtesy of Keller Williams Key West Compass Realty
800 Fleming Street #Unit C1, home for sale on Fleming Street
$2,399,000
2 bd · 2.5 ba · built 1910
800 Fleming Street #Unit C1
Listing courtesy of Truman & Co. (KW)
809 Fleming Street, home for sale on Fleming Street
$1,795,000
4 bd · 3 ba · built 1906
809 Fleming Street
Listing courtesy of Century 21 Circle- Islamorada

The homes on Fleming Street

43 single-family, 11 condo/townhome/other. Built by decade: 1880s 3, 1890s 2, 1900s 2, 1910s 4, 1920s 9, 1930s 21, 1940s 3, 1970s 1, 1990s 7, 2000s 1.

Last recorded sales (parcel record)

AddressSoldDateBuiltSq ft
1022 Fleming Street$1,600,0002026-07-3119282,016
1006-1008 Fleming Street$4,425,0002026-05-2619383,336
212 Fleming Street$1,650,0002026-04-1519951,420
1109 Fleming Street$5,745,0002026-03-2619253,443
208 Fleming Street$1,070,0002026-03-021995960
216 Fleming Street$1,850,0002026-01-0719951,312
830 Fleming Street$1,350,0002025-10-2019131,989
214 Fleming Street$1,800,0002025-07-0819951,312
808 Fleming Street$1,800,0002025-02-1419282,003
908 Fleming Street$8,600,0002024-08-0619904,250
1108 Fleming Street$2,254,0002023-08-1719331,688
925 Fleming Street$3,500,0002023-06-2919332,508
1113 Fleming Street$2,200,0002023-04-0519251,623
1114 Fleming Street$2,050,0002023-03-2919182,023
717 Fleming Street$2,400,0002023-01-0418991,567
1002 Fleming Street$2,915,0002022-08-0519382,400
810 Fleming Street$1,225,0002021-07-3019332,016
723 Fleming Street$3,725,0002021-06-2119332,832
918 Fleming Street$1,860,0002021-06-1619082,860
1030 Fleming Street$2,300,0002021-05-1019382,787

How to read this

Home counts, build years, sizes and last sales come from the county parcel record joined to MLS history; listings and 12-month closings from the live MLS feeds as of October 15, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 233 homes for sale in Key West, homes for sale in 33040.

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Common questions

How many homes are on Fleming Street in Key West?

54 homes in the parcel and MLS record, built between 1884 and 2008.

Are there homes for sale on Fleming Street?

4 listed right now, from $1,775,000.

What do homes on Fleming Street sell for?

Homes that sold since 2023 went for a median $2,050,000.