1008 Fleming St, Key West, FL 33040
SOLD
MAY 29, 2026

1008 Fleming St
Key West, FL 33040

Old Town
  • 3 Beds
  • 4 Baths
  • 760 sqft

$4,425,000

Last Sold: May 29, 2026
$5,822/sqft
Est. Refi. Payment $25,196/mo*
Refinance Your Home

$4,425,000

Last Sold: May 29, 2026
$5,822/sqft
Est. Refi. Payment $25,196/mo*
Refinance Your Home
3 Beds
4 Baths
760 sqft

Local Information

  • Map ViewExplore the area around 1008 Fleming St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 1008 Fleming St, Key West, FL. 1008 Fleming St is in the Old Town neighborhood in Key West, FL and in ZIP code 33040. This property has 3 bedrooms, 4 bathrooms and approximately 760 sqft of floor space. The last sold price per dimension was $5,822/sqft. This property has a lot size of 9180 sqft and was built in 1938.
1008 Fleming St, Key West, FL 33040 is a 3 bedroom, 4 bathroom, 760 sqft single-family home in Old Town, built in 1938. It last sold for $4,425,000 on May 29, 2026. It is currently off market. The Trulia Estimate is $4,430,300, with a rent estimate of $5,136/month.

Home Highlights

Parking
No Info
Outdoor
No Info
View
No Info
HOA
None
Price/Sqft
$5,822/sqft
Listed
Less than a day ago

Home Details for 1008 Fleming St

Interior Features

Heating & Cooling
Heating: Forced AirHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Softwood, Concrete, Hardwood

Exterior Features

Exterior Home Features
Roof: MetalExterior: OtherFoundation Type: Concrete Block

Property Information

Year Built
Year Built: 1938
Property Type / Style
Property Type: Single Family Home

Price & Status

Price
Price Per Sqft: $5,822/sqft

Community

Units in Building: 1

Lot Information

Lot Area: 9180 sqft

Price History for 1008 Fleming St

DatePriceEventSource
05/29/2026$4,425,000Sold
N/A
02/27/2024$5,000,000Sold
N/A
03/02/2018$3,100,000Sold
N/A
02/17/2015$2,750,000Sold
N/A
12/21/2011$2,600,000Sold
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$37,407
Assessment$4,410,748
Home facts updated by county records

Comparable Sales for 1008 Fleming St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1006 & 1008 Fleming St, Key West, FL
0.00
Single-Family Home
$4,425,000
05/26/26
4
4.5
3,336
1014 Southard St, Key West, FL
0.10
Single-Family Home
$4,700,000
04/30/26
4
3.5
3,026
1020 Southard St, Key West, FL
0.09
Single-Family Home
$3,350,000
12/03/25
3
3.5
2,438
715 Frances St, Key West, FL
0.21
Single-Family Home
$3,400,000
11/07/25
3
3.5
1,890
626 Canfield Ln, Key West, FL
0.15
Single-Family Home
$2,600,000
09/26/25
3
2
1,223
1108 Curry Ln, Key West, FL
0.09
Single-Family Home
$2,620,000
06/02/26
3
3
1,292
906 Southard St, Key West, FL
0.13
Single-Family Home
$3,250,000
05/27/26
3
3
2,188
517 Elizabeth St, Key West, FL
0.27
Single-Family Home
$3,750,000
10/20/25
4
3
2,173
510 Margaret St, Key West, FL
0.12
Single-Family Home
$2,850,000
04/17/26
4
4
1,968

Nearby homes

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Assigned Schools

These are the assigned schools for 1008 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

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