1029 Fleming St, Key West, FL 33040
Property image
Property image
OFF MARKET

$5,654,400

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 3,706 sqft

1029 Fleming St, Key West, FL 33040

Historic Seaport
Est. Refi. Payment $32,650/mo*
Refinance Your Home
Currently Off Market - Sold Jun 25, 2013 for $3,650,000

Home Value

Trulia Estimate
$5.65M
Since last month
Increased$89K (+1.6%)
Since last year
Increased$223K (+4.1%)
Since last sale
Increased$2M (+55.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +86% in the last 10 years
MonthEstimated value
2026
August 2026$5.68M
July 2026$5.6M
June 2026$5.68M
May 2026$5.69M
April 2026$5.52M
March 2026$5.42M
February 2026$5.38M
January 2026$5.22M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
0.13
Single-Family Home
$4,700,000
04/30/26
4
3.5
3,026
1006 & 1008 Fleming St, Key West, FL
0.17
Single-Family Home
$4,425,000
05/26/26
4
4.5
3,336
1020 Southard St, Key West, FL
0.13
Single-Family Home
$3,350,000
12/03/25
3
3.5
2,438
906 Southard St, Key West, FL
0.19
Single-Family Home
$3,250,000
05/27/26
3
3
2,188
1109 Fleming St, Key West, FL
0.04
Single-Family Home
$5,745,000
03/26/26
6
6.5
3,443
418 William St, Key West, FL
0.26
Single-Family Home
$3,285,000
03/18/26
4
3
1,852
517 Elizabeth St, Key West, FL
0.32
Single-Family Home
$3,750,000
10/20/25
4
3
2,173
715 Frances St, Key West, FL
0.24
Single-Family Home
$3,400,000
11/07/25
3
3.5
1,890
1008 Fleming St, Key West, FL
0.07
Single-Family Home
$4,425,000
05/29/26
3
4
760
728 Love Ln, Key West, FL
0.31
Single-Family Home
$3,150,000
09/19/25
3
3
2,100

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
1022 Fleming St, Key West, FL 33040
0.03
$1,600,000
4
2
2,016
Recently Sold
511 Frances St, Key West, FL 33040
0.06
$3,249,200
4
3.5
1,903
Off Market
524 Frances St, Key West, FL 33040
0.08
$4,532,900
4
3.5
3,015
Off Market
1006 Fleming St, Key West, FL 33040
0.06
-
4
4.5
3,304
Off Market
11 Lowes Ln, Key West, FL 33040
0.08
$2,421,300
3
3
1,635
Off Market
1113 Curry Ln #2, Key West, FL 33040
0.06
$1,281,300
4
3
1,528
Off Market
1109 Stump Ln, Key West, FL 33040
0.08
$2,249,000
3
3
1,724
For Sale
1109 Fleming St, Key West, FL 33040
0.04
$5,745,000
6
6.5
3,443
Recently Sold
10 Lowe Ln, Key West, FL 33040
0.10
$2,320,500
3
3.5
1,511
Off Market
531 Frances St, Key West, FL 33040
0.10
$1,825,000
3
2.5
1,681
Recently Sold
413 Frances St, Key West, FL 33040
0.03
$2,145,600
3
3
1,536
Off Market
1113 Stump Ln, Key West, FL 33040
0.09
$4,450,000
4
4.5
2,985
For Sale

Local Information

  • Map ViewExplore the area around 1029 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
3,706 sqft
Price/Sqft
$1,526

About this House

This single-family home is located at 1029 Fleming St, Key West, FL. 1029 Fleming St is in the Historic Seaport neighborhood in Key West, FL and in ZIP code 33040. This property has 4 bedrooms, 3 bathrooms and approximately 3,706 sqft of floor space. This property has a lot size of 7181 sqft and was built in 1938.
1029 Fleming St, Key West, FL 33040 is a 4 bedroom, 3 bathroom, 3,706 sqft single-family home in Historic Seaport, built in 1938. It last sold for $3,650,000 on Jun 25, 2013. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $5,654,400, with a rent estimate of $7,692/month.

Home Details for 1029 Fleming St

Interior Features

Heating & Cooling
Heating: Forced AirHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Softwood, Hardwood

Exterior Features

Exterior Home Features
Roof: MetalExterior: OtherFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
Parking: Carport

Property Information

Year Built
Year Built: 1938Year Updated: 2000
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 7181 sqft

Price and Tax history

DateEventPrice
Jun 25, 2013
Source: N/A
Sold
$3,650,000
Jan 30, 2003
Source: FLKMLS #92121
Sold
$1,350,000

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

Historic Seaport
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Historic Seaport

At least 38 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 90 % Say people would walk alone at night

  • 88 % Say it's walkable to restaurants

  • 84 % Say it's walkable to grocery stores

  • 83 % Say there are sidewalks

  • 79 % Say streets are well-lit

  • 67 % Say yards are well-kept

  • 64 % Say they plan to stay for at least 5 years

  • 62 % Say there's holiday spirit

  • 60 % Say there's wildlife

  • 59 % Say there are community events

  • 57 % Say it's quiet

  • 43 % Say parking is easy

  • 42 % Say neighbors are friendly

  • 35 % Say kids play outside

  • 30 % Say car is needed

Sourced by Trulia users. Learn more about our methodology.
  • Mari.lindsley
    "I've lived here for 2 years and enjoy the walkability to local theatres and restaurants. There's a strong homeless contingency that detracts from the seaport. But you can't blame them for wanting to be in paradise."
    11
    Flag
  • Tom
    "There are many festivals and events that include the Key West Historic Harbor. Venues include Schooner Wharf, Waterfront Brewery, The Marker, etc.."
    2
    Flag
  • Bwruble
    "Tourist don’t clean up after their dogs, but locals do. This is a wonderful neighborhood. Gecko lane is especially beautiful and very private. "
    1
    Flag
  • Ctmortman
    "Perfect place for dogs. There are several dog pearls on the island and some restaurants are pet friendly. I own a dog watching business on Marco Island...a service much needed there"
    2
    Flag
  • Sue S.
    "We vacationed here for the month of February 2014. We did not rent a car but had bikes for a week. We are walkers and walked an average of 1-2 miles for dinner and many miles during the day touring, hiking, etc. This area is accessible to most anything."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 1029 Fleming St

  • What is 1029 Fleming St estimated to be worth?
    Trulia's estimated value for 1029 Fleming St in Key West, FL is $5,654,400.
  • What is the price history for 1029 Fleming St?
    1029 Fleming St in Key West, FL last sold for $3,650,000 in June 2013.
  • 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.
  • Does 1029 Fleming St have a pool?
    Yes, 1029 Fleming St in Key West, FL has a pool.
  • How big is the lot at 1029 Fleming St?
    The lot at 1029 Fleming St in Key West, FL is about 0.16 acres (7,181 sq ft).

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Apartments for Rent

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Off Market Homes Near 1029 Fleming St

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