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$5,850,000

  • For Sale
  • Active
  • Duplex
  • 6 Beds
  • 6 Full Baths
  • 2 Partial Baths
  • 3,010 Sq. Ft.
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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.

Full Property Details for 421 - 423 Simonton St

General

  • Price: $5,850,000
  • Taxes: $26,522 (2024)
  • Status: Active
  • Type: Duplex
  • Source: 927
  • MLS ID: 614546
  • Updated: 5/13/2026
  • Added to Site: 414 day(s) ago

Interior

  • Interior Features: Built-in Cabinets, Smoke Alarms
  • Appliances: Stainless Steel Appliance(s), Dryer, Microwave, Oven, Range, Refrigerator, Washer

Rooms

Bathrooms

  • Total Bathrooms: 8
  • Full Bathrooms: 6
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 6

Additional Information

  • Pool: Yes
  • Pool Description: In Ground

Exterior

  • Exterior Features: Privacy Wall/Fence
  • Deck/Patio: Open Porch/Balcony, Deck
  • Porch/Patio/Deck: Open Porch/Balcony, Deck

Location

  • Area: 02 - Key West
  • County: Monroe
  • Subdivision: Old Town - Unlisted (1.0)

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Central Air, Ceiling Fans(s)

Structural Information

  • Architectural Style: Above Flood
  • Construction: Combo Construction
  • Roof: Metal
  • Square Feet: 3,010
  • Sq. Ft. Source: Property Data Card
  • Year Built: 2020

Unit Information

  • Units in Building: 2

Lot Features

  • Property View: No Waterview
  • Lot Size (Acres): 0.08
  • Lot Size (Sq. Ft.): 3,520
  • Lot Dimensions: 44 x 80
  • Zoning: HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med

Water Features

  • Water View: Yes

Financial Considerations

  • Tax Amount: $26,522.53
  • Tax Year: 2024

Disclosures and Reports

  • Legal Description: KW PT LOT 4 SQR 36 G12-444/45 OR564-150 OR1176-1632/33 OR2799-1921/22 OR2799-1925/26
  • Flood Zone: X
  • APN: 00006360-000000

Listed by Berkshire Hathaway HomeServices Knight & Gardner Realty, Will Langley (305) 394-9020 and Berkshire Hathaway HomeServices Knight & Gardner Realty, Logan Guevremont (305) 394-1244

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Listing agents

— 421 - 423 Simonton St —

  • Will Langley

    Berkshire Hathaway HomeServices Knight & Gardner Realty

  • Logan Guevremont

    Berkshire Hathaway HomeServices Knight & Gardner Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 421 - 423 Simonton St

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Horace O'bryant School
1105 Leon Street, Key West, FL 33040
6-81 mi
Gerald Adams Elementary School
5855 College Road, Key West, FL 33040
PK-53.9 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-121.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 421 - 423 Simonton St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/08/2025
Listed
$5,850,000
387.5%
MLS
6/01/2016
Sold
$1,200,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 421 - 423 Simonton St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$26,523
—
$3,732,234
—
2024
$26,523
7%
$3,726,336
8%
2023
$24,710
29%
$3,452,692
66%
2021
$19,099
-5%
$2,083,295
-14%
2022
$20,207
6%
$2,427,088
18%
2021
$19,099
1%
$2,055,784
—
2019
$18,872
77%
$2,045,961
106%
2018
$10,687
-2%
$992,373
-1%
2017
$10,940
7%
$1,002,267
9%
2016
$10,264
-3%
$919,265
—
2015
$10,534
-3%
$918,849
1%
2014
$10,816
1%
$911,779
2%
2013
$10,761
—
$896,633
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 421 - 423 Simonton St

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Berkshire Hathaway HomeServices Knight & Gardner Realty, Will Langley (305) 394-9020 and Berkshire Hathaway HomeServices Knight & Gardner Realty, Logan Guevremont (305) 394-1244

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421 - 423 Simonton Street, Key West, FL 33040 (MLS# 614546) is a Duplex property with 6 bedrooms, 6 full bathrooms and 2 partial bathrooms. 421 - 423 Simonton Street is currently listed for $5,850,000 and was received on April 08, 2025. Want to learn more about 421 - 423 Simonton Street? Do you have questions about finding other Duplex real estate for sale in Key West? You can browse all Key West real estate or contact a Coldwell Banker agent to request more information.

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