421-423 Simonton St

Key West, FL 33040

$5,850,000
Price
6
Beds
3,010 Sq. Ft.
$1,944 / Sq. Ft.
3,010
Sq. Ft.
$1,944
per Sq. Ft.
a front view of a house with a yard
a living room with furniture and wooden floor
a living room with furniture and a flat screen tv with wooden floor
a kitchen with stainless steel appliances granite countertop a refrigerator and a stove top oven
a view of a dining room with furniture window and wooden floor
a kitchen with stainless steel appliances wooden cabinets a stove a sink and a microwave
a bedroom with a bed and a chandelier
a bathroom with a granite countertop sink toilet a mirror and shower
a view of a backyard with a table and chairs
a view of a patio with couches and potted plants
a bedroom with a bed and a flat screen tv on dresser
a bathroom with a granite countertop sink a toilet and shower
a bedroom with a bed and a flat screen tv
a bedroom with a bed and a flat screen tv
a bathroom with a granite countertop sink a mirror and shower
a living room with furniture a flat screen tv and a large window
a living room with furniture and a flat screen tv
a kitchen with stainless steel appliances granite countertop a refrigerator stove microwave and sink
a large kitchen with stainless steel appliances granite countertop a stove a sink dishwasher and a refrigerator
workspace with wooden floor and windows
a view of deck with patio
a view of patio with a table and chairs
a view of a backyard with a patio
a view of backyard with outdoor and trees
a bedroom with a bed and a lamp on dresser
a bedroom with a bed and a lamp on dresser
a bathroom with a sink and shower
a bedroom with a bed and flat screen tv
a bedroom with a bed and a flat screen tv
a bedroom with a bed and flat screen tv
a bathroom with a sink vanity mirror and toilet
a bedroom with a bed and a flat tv screen on dresser
a bedroom with a large bed and a chandelier
a bathroom with a granite countertop sink a mirror and shower
a bedroom with a bed and a flat screen tv
a bedroom with bed and window
a bathroom with a sink vanity and a mirror

Description

Two Transient Homes Now Available For Sale. Just one block off world-famous Duval Street, this rare property offers two homes - each 3 bedrooms, 3.5 baths and private pools. These have strong rental histories. These well-appointed residences blend island charm with modern comfort, featuring open-concept living areas, updated kitchens and private ensuite bedrooms. Thoughtfully designed for guest privacy and relaxation, each home includes its own outdoor lounging space and pool--perfect for cooling...Two Transient Homes Now Available For Sale. Just one block off world-famous Duval Street, this rare property offers two homes - each 3 bedrooms, 3.5 baths and private pools. These have strong rental histories. These well-appointed residences blend island charm with modern comfort, featuring open-concept living areas, updated kitchens and private ensuite bedrooms. Thoughtfully designed for guest privacy and relaxation, each home includes its own outdoor lounging space and pool--perfect for cooling off after a day in the sun or enjoying a quiet evening under the palms. Whether you're looking for a investment opportunity, a vacation retreat with rental flexibility, or a mix of both, this unique setup delivers unmatched versatility just steps from the vibrant restaurants, galleries, and nightlife of Duval Street.
  1. Listed by Will Langley • Berkshire Hathaway HomeServices Knight & Gardner Realty
  2. Listed by Logan Guevremont • Berkshire Hathaway HomeServices Knight & Gardner Realty

Property Details for 421-423 Simonton Street

Waterfront
None
Waterfront
No
Zoning
HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Subdivision
Old Town - Unlisted (1.0)
Pets
Pets Allowed
LISTING UPDATED: 12/09/2025 01:04 PM

Property Details for 421-423 Simonton Street

StatusActive
MLS #614546
Days on Market283
Taxes$26,523 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeMulti Family
MLS TypeResidential / Duplex
Year Built2020
Lot Size0.08 AC / 3,520 SF
CountyMonroe County

Location

Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
Add your commute

Building Information for 421-423 Simonton Street

Stories2Residences2Year Built2020Building Size-Lot Size0.08 AC / 3,520 SF

Payment Calculator

$30,722 per month

30 year fixed, 6.15% Interest

Principal and Interest

$28,512

Property Taxes

$2,210

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 421-423 Simonton Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 02 - Key West
  • Absolute Longitude: 81.801587
  • Control Depth: 0
  • Off Shore Island: No
  • Listing Board: Key West Association
  • Side: Median
  • KW Neighborhood: Old Town-N of Truman
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • License Info: # of City License: 2
  • License Info: Transient Rntl Licns: Yes
  • Fee Includes: None
  • Furnished: Negotiable
  • Tax Year: 2024
  • Tax Exemptions: None
Property
Lot Information
  • Lot Size: 44 x 80
  • Acres: 0.08
  • Parcel #: 00006360-000000
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: KW PT LOT 4 SQR 36 G12-444/45 OR564-150 OR1176-1632/33 OR2799-1921/22 OR2799-1925/26
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Flood Zone: X
  • Rentals Allowed: Yes
  • Deed Restrictions: Unknown
  • Picture Count: 38
  • Document Count: 0
  • Building Style: Above Flood: Yes
Utilities
  • Utilities: FKAA, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Species List: No
  • Pool: Yes
  • Pool Info: In Ground
  • Porch/Balcony: Open Porch/Balcony, Deck
Interior and Exterior Features
Interior Features
  • Interior Features: Built-in Cabinets, Smoke Alarms
  • Pre-Wired: Cable
  • Appliances: Washer, Stainless Steel Appliance(s), Microwave, Oven, Range, Refrigerator, Dryer
Exterior Features
  • Roof: Metal Roof
  • Construction: Combo Construction
  • Dockage: None
  • Exterior Features: Privacy Wall/Fence

Property History for 421-423 Simonton Street

DateEvent & SourcePriceAppreciation
Apr 8, 2025

Price Change

FKMLS #614546

$6,500,000—
Apr 8, 2025

Listed (Active)

FKMLS #614546

$5,850,000—
DateEvent & SourcePrice
04/08/2025

Price Change

FKMLS #614546

$6,500,000
04/08/2025

Listed (Active)

FKMLS #614546

$5,850,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 421-423 Simonton Street

Taxable ValueLand$478,122Additions$1,567,839Total$2,045,961
Tax Record2019$18,871 ($1,573 / month)
Home Facts
Baths6.5Total Finished SqFt3,010 SqFtAbove Grade Finished SqFt3,010 SqFtStories2Lot Size3,520 SqFtStyleMulti-Family Dwelling (2-4)Year Built1933Year Renovated2017CountyMONROEAPN00006360000000

Schools near 421-423 Simonton Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Gerald Adams Elementary School
Public - PK to 5
Monroe Virtual Franchise
Public - 2 to 12
Key West High School
Public - 9 to 12
Monroe Virtual Instruction Program (District Provided)
Public - K to 5
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Monroe Virtual Franchise
Public2 to 12

Key West High School
Public9 to 12

Monroe Virtual Instruction Program (District Provided)
PublicK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 421-423 Simonton Street, Key West, FL 33040

421-423 Simonton Street is a multi-family home for sale in Key West, FL 33040. This property was listed for sale on April 8, 2025 by Berkshire Hathaway HomeServices Knight & Gardner Realty, it's currently listed at $5,850,000. This listing's school district is Monroe. Nearby schools include Gerald Adams Elementary School, Monroe Virtual Franchise and Key West High School. 421-423 Simonton Street is a 6-bed, 8-bath, 3,010 sqft multi-family home built in 2020.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.