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

$4,442,500

Trulia Estimate
  • 3 Beds
  • 4 Baths
  • 760 sqft

1008 Fleming St, Key West, FL 33040

Old Town
Est. Refi. Payment $25,832/mo*
Refinance Your Home
Currently Off Market - Sold May 29, 2026 for $4,425,000

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1014 Southard St, Key West, FL
0.09
Single-Family Home
$4,700,000
04/30/26
4
3.5
3,026
1006 & 1008 Fleming St, Key West, FL
0.12
Single-Family Home
$4,425,000
05/26/26
4
4.5
3,336
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
1110 Elgin Ln, Key West, FL
0.11
Single-Family Home
$1,850,000
06/29/26
3
3
1,256
517 Elizabeth St, Key West, FL
0.27
Single-Family Home
$3,750,000
10/20/25
4
3
2,173

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
419 Grinnell St, Key West, FL 33040
0.05
-
-
-
-
Off Market
409 Grinnell St, Key West, FL 33040
0.07
$2,350,000
4
2
1,628
Recently Sold
1006 Fleming St, Key West, FL 33040
0.00
-
4
4.5
3,304
Off Market
408 Grinnell St, Key West, FL 33040
0.08
-
4
4
2,475
Off Market
506 Grinnell St, Key West, FL 33040
0.04
$999,000
3
1.5
1,416
For Sale
1025 Elgin Ln, Key West, FL 33040
0.09
$1,150,000
2
2
885
For Sale
1022 Fleming St, Key West, FL 33040
0.04
$1,600,000
4
2
2,016
Recently Sold
1016 Eaton St, Key West, FL 33040
0.09
$800,000
2
1.5
752
Recently Sold
508 Grinnell St, Key West, FL 33040
0.04
$2,595,000
3
3
2,049
For Sale
4 Fletcher Ln, Key West, FL 33040
0.09
$1,803,100
4
3
1,596
Off Market
3 Fletcher Ln, Key West, FL 33040
0.09
-
2
2
1,216
Off Market
1015 Eaton St, Key West, FL 33040
0.11
$1,900,000
4
3
1,738
Recently Sold

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

Home Highlights

Property Type
Single-Family Home
Year Built
1938
Living Area
760 sqft
Price/Sqft
$5,822/sqft

About this House

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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,442,500, with a rent estimate of $4,066/month.

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 and Tax history

DateEventPrice
May 29, 2026
Source: N/A
Sold
$4,425,000
Feb 27, 2024
Source: N/A
Sold
$5,000,000
Mar 2, 2018
Source: N/A
Sold
$3,100,000
Feb 17, 2015
Source: N/A
Sold
$2,750,000
Dec 21, 2011
Source: N/A
Sold
$2,600,000

Market trends in Key West

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.28M
$50KMoM
Sale-to-List Price
95.1%
0.5%MoM
Price per sq ft
$933
$26MoM
Available listings
271
17MoM

Around this home

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

Frequently asked questions about 1008 Fleming St

  • What is 1008 Fleming St estimated to be worth?
    Trulia's estimated value for 1008 Fleming St in Key West, FL is $4,442,500.
  • What is the price history for 1008 Fleming St?
    1008 Fleming St in Key West, FL last sold for $4,425,000 in May 2026.
  • Is Key West a buyer's or seller's market?
    Key West is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Key West?
    The median sale price in Key West is $1.28M. That is up $50K from the prior month.
  • How big is the lot at 1008 Fleming St?
    The lot at 1008 Fleming St in Key West, FL is about 0.21 acres (9,180 sq ft).

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