414 Simonton St, Key West, FL 33040
OFF MARKET

414 Simonton St
Key West, FL 33040

Historic Seaport
  • 4 Beds
  • 2 Baths
  • 308 sqft (on 0.36 acres)

$3,681,900

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $21,383/mo*
Refinance Your Home

$3,681,900

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $21,383/mo*
Refinance Your Home
4 Beds
2 Baths
308 sqft
(on 0.36 acres)

Local Information

  • Map ViewExplore the area around 414 Simonton 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
1933
Lot Size
0.36 acres
Living Area
308 sqft
Price/Sqft
$11,954

About this House

This single-family home is located at 414 Simonton St, Key West, FL. 414 Simonton St is in the Historic Seaport neighborhood in Key West, FL and in ZIP code 33040. This property has 4 bedrooms, 2 bathrooms and approximately 308 sqft of floor space. This property has a lot size of 0.36 acres and was built in 1933.
414 Simonton St, Key West, FL 33040 is a 4 bedroom, 2 bathroom, 308 sqft single-family home in Historic Seaport, built in 1933. It last sold for $820,000 on Dec 3, 2012. It is currently off market. The Trulia Estimate is $3,681,900, with a rent estimate of $2,731/month.

Home Details for 414 Simonton St

Interior Features

Heating & Cooling
Heating: Forced AirHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2ElevatorFloors: Other, Concrete
Interior Details
Attic
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: MetalExterior: Other, WoodFoundation Type: Concrete

Property Information

Year Built
Year Built: 1933
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 2

Lot Information

Lot Area: 0.36 acres

Price History for 414 Simonton St

DatePriceEventSource
12/03/2012$820,000Sold
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$63,751
Assessment$7,542,560
Home facts updated by county records

Comparable Sales for 414 Simonton St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
314 Southard St, Key West, FL
0.26
Single-Family Home
$900,000
12/01/25
3
2
1,451
716 Elizabeth St, Key West, FL
0.28
Single-Family Home
$875,000
09/30/25
3
2
1,049
626 Canfield Ln, Key West, FL
0.37
Single-Family Home
$2,600,000
09/26/25
3
2
1,223
612 Mickens Ln, Key West, FL
0.28
Single-Family Home
$979,000
04/09/26
2
1.5
823
320 Margaret St, Key West, FL
0.27
Single-Family Home
$1,325,000
02/26/26
3
1.5
1,368
318 Margaret St, Key West, FL
0.27
Single-Family Home
$900,000
08/25/25
2
2
1,463
1016 Eaton St, Key West, FL
0.41
Single-Family Home
$800,000
06/10/26
2
1.5
752
718 Chapman Ln, Key West, FL
0.41
Single-Family Home
$970,000
09/25/25
4
3
1,026
322 Southard St, Key West, FL
0.25
Single-Family Home
$1,695,000
04/10/26
3
3
1,553
729 Windsor Ln, Key West, FL
0.31
Single-Family Home
$865,000
03/23/26
2
1
723

Nearby homes

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Assigned Schools

These are the assigned schools for 414 Simonton 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

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

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Homes for sale near 414 Simonton St

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Off Market Homes Near 414 Simonton St

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