421 Simonton St, Key West, FL 33040
OFF MARKET

421 Simonton St
Key West, FL 33040

Historic Seaport
  • 3 Beds
  • 4 Baths
  • 1,488 sqft

$2,665,400

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $15,374/mo*
Refinance Your Home

$2,665,400

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $15,374/mo*
Refinance Your Home
3 Beds
4 Baths
1,488 sqft

Local Information

  • Map ViewExplore the area around 421 Simonton St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1933
Living Area
1,488 sqft
Price/Sqft
$1,791

About this House

This multi-family home is located at 421 Simonton St, Key West, FL. 421 Simonton St is in the Historic Seaport neighborhood in Key West, FL and in ZIP code 33040. This property has 3 bedrooms, 4 bathrooms and approximately 1,488 sqft of floor space. This property has a lot size of 3536 sqft and was built in 1933.
421 Simonton St, Key West, FL 33040 is a 3 bedroom, 4 bathroom, 1,488 sqft multi-family in Historic Seaport, built in 1933. It last sold for $1,200,000 on Jun 2, 2016. It is currently off market. The Trulia Estimate is $2,665,400, with a rent estimate of $5,041/month.

Home Details for 421 Simonton St

Interior Features

Heating & Cooling
Heating: Forced AirHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Softwood, Hardwood

Exterior Features

Exterior Home Features
Roof: MetalExterior: OtherFoundation Type: Concrete

Property Information

Year Built
Year Built: 1933
Property Type / Style
Property Type: Multi Family

Community

Units in Building: 1

Lot Information

Lot Area: 3536 sqft

Price History for 421 Simonton St

DatePriceEventSource
06/02/2016$1,200,000Sold
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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2024
Tax$26,523
Assessment$3,726,336
Home facts updated by county records

Comparable Sales for 421 Simonton St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
419 Simonton St, Key West, FL
0.04
Multi-Family Home
$1,325,000
06/02/26
4
4
2,469
308 Peacon Ln, Key West, FL
0.15
Multi-Family Home
$850,000
10/31/25
3
2.5
1,296
830 Fleming St, Key West, FL
0.25
Multi-Family Home
$1,350,000
10/20/25
3
4
1,989
514 Margaret St, Key West, FL
0.26
Multi-Family Home
$1,400,000
01/14/26
5
3.5
2,068
621 Elizabeth St, Key West, FL
0.23
Multi-Family Home
$1,625,000
04/20/26
3
2
1,594
708 William St, Key West, FL
0.33
Multi-Family Home
$1,752,000
11/17/25
4
3.5
1,967
415 Julia St, Key West, FL
0.52
Multi-Family Home
$1,250,000
01/22/26
3
4
1,464
1030 James St, Key West, FL
0.42
Multi-Family Home
$1,800,000
05/26/26
3
3
1,700
716 Elizabeth St, Key West, FL
0.29
Multi-Family Home
$875,000
10/01/25
3
2
1,049
1022 Fleming St, Key West, FL
0.41
Multi-Family Home
$1,600,000
07/31/26
4
2
2,016

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 421 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

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

22 pet-friendly rentals in Key West, FL

Explore by feature - Garage

9 rentals with a garage in Key West, FL

Explore by feature - Air Conditioning

100 rentals with air conditioning in Key West, FL

Explore by feature - Pool

72 rentals with a pool in Key West, FL

Explore by feature - Washer/dryer

71 rentals with a washer/dryer in Key West, FL

Explore by feature - Outdoor Space

10 rentals with an outdoor space in Key West, FL

Homes for sale near 421 Simonton St

Skip to last item
Skip to first item

Off Market Homes Near 421 Simonton St

Skip to last item
Skip to first item

Frequently asked questions about 421 Simonton St

  • What is 421 Simonton St estimated to be worth?
    Trulia's estimated value for 421 Simonton St in Key West, FL is $2,665,400.
  • What is the price history for 421 Simonton St?
    421 Simonton St in Key West, FL last sold for $1,200,000 in June 2016.
  • 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 $1.23M. That is up $20.83K from the prior month.