$6,500,000

421-423 Simonton St Key West, FL 33040

Old Town Neighborhood

Estimated payment $36,521/month

Total Views 17,873
6 Beds
8 Baths
3,010 Sq Ft
$2,159 Price per Sq Ft

About This Home

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.

Listing Agent

Will Langley

Berkshire Hathaway HomeServices Knight & Gardner Realty License #3242135 Listed on: 04/08/2025

Berkshire Hathaway HomeServices Knight & Gardner Realty

Co-Listing Agent

Logan Guevremont

Berkshire Hathaway HomeServices Knight & Gardner Realty License #3451909

Map

Property Details

Home Type

Multi-Family

Est. Annual Taxes

$24,710

Year Built

2020

Lot Details

0

Listing Details

  • Property Type: Residential
  • Style: Duplex
  • As Is Right To Inspect: Yes
  • First Right of Refusal: No
  • Mandatory HOA: No
  • Fee Includes: None
  • Key Island: Key West
  • K W Neighborhood: Old Town-N of Truman
  • Limited Representation: No
  • Marathon Neighborhood: N/A
  • Mile Marker: 1.00
  • Min Rental Days: 3.00
  • M L S Identifier: 20060123165453488875000000
  • Off Shore Island: No
  • Pets: Pets Allowed
  • Property Group I D: 19990816212109142258000000
  • Side: Median
  • State Province: FL
  • Taxes: 26522.53
  • Year Built: 2020
  • Alternate Key Number: 1006581
  • Cooling Heating: Central Air, Ceiling Fans(s)
  • Lot Sq Ft: 3520.00
  • Pool Info: In Ground
  • Porch Balcony: Open Porch/Balcony, Deck
  • License Info Number Of City License: 2
  • Species List: No
  • Tax Exemptions: None
  • Building Style Above Flood: Yes
  • Building Style Stories: 2 Stories
  • License Info Transient Rntl Licns: Yes
  • Estimated Living Sq Ft: 3010.00
  • Pre Wired: Cable
  • Sewer Hook Up: Yes
  • Statistical Purposes Only: No
  • Special Features: None
  • Property Sub Type: MultiFamily
  • Stories: 2

Interior Features

  • Interior Amenities: Built-in Cabinets, Smoke Alarms
  • Total Bathrooms: 8.00
  • Full Bathrooms: 6
  • Appliances: Washer, Stainless Steel Appliance(s), Microwave, Oven, Range, Refrigerator, Dryer
  • Half Bathrooms: 2
  • Total Bedrooms: 6

Exterior Features

  • Dockage: None
  • Waterfront: None
  • Waterfront: No
  • Construction: Combo Construction
  • Exterior Features: Privacy Wall/Fence
  • Roof: Metal Roof
  • Waterview: No Waterview
  • Pool: Yes

Utilities

  • Utilities: FKAA, Municipal Sewer

Lot Info

  • Deed Restrictions: Unknown
  • Flood Zone: X
  • Parcel Number: 00006360-000000
  • Lot Size: 44 x 80
  • Land Size: Less Than 1/4 Acre
  • Acres: 0.08

Rental Info

  • Rentals Allowed: Yes
  • Furnished: Negotiable

Tax Info

  • Tax Year: 2024

Multi Family

  • Total Units: 2.00

Range of Values:

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Average Value
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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2024 $24,710 $3,726,336 $1,349,990 $2,376,346
2023 $24,710 $3,452,692 $1,157,253 $2,295,439
2022 $20,207 $2,427,088 $704,774 $1,722,314
2021 $19,099 $2,083,295 $534,371 $1,548,924
2020 $18,799 $2,055,784 $489,702 $1,566,082
2019 $18,872 $2,045,961 $478,122 $1,567,839
2018 $10,687 $992,373 $695,552 $296,821
2017 $10,940 $1,002,267 $0 $0
2016 $10,264 $919,265 $0 $0
2015 -- $918,850 $0 $0
2014 -- $911,780 $0 $0
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
04/08/2025 04/08/25 For Sale $6,500,000 -- $2,159 / Sq Ft
Source: Key West Association of REALTORS®

Purchase History

Date Type Sale Price Title Company
Quit Claim Deed -- None Available
Warranty Deed $1,200,000 None Available
Deed $45,500 --
Source: Public Records

Source: Key West Association of REALTORS®

MLS Number: 614546

Key West Association of REALTORS®

APN: 00006360-000000

Florida Monroe County Key West 33040 Old Town

421-423 Simonton St, Key West, FL

This home is located at 421-423 Simonton St, Key West, FL 33040 and is currently priced at $6,500,000, approximately $2,159 per square foot. This property was built in 2020. 421-423 Simonton St is a home located in Monroe County with nearby schools including Gerald Adams Elementary School, Key West High School, and The Basilica School of Saint Mary Star of the Sea.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Key West Association of REALTORS® IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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Will Langley
Listing Agent
Will Langley
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Berkshire Hathaway HomeServices Knight & Gardner Realty
(786) 481-1293