#610558, Damian Vantriglia, Listing Office: Berkshire Hathaway Knight & Gardner
421-423 Simonton St Key West, FL 33040
Property details
About 421-423 Simonton St
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.
Highlights
Summary
- MLS Number: 614546
- MLS Name: KeyWest
- Office Name: Berkshire Hathaway Knight & Gardner
- Office Phone: (305) 294-5155
- Listing Agent: Will Langley
The data relating to real estate for sale on this web site comes in part from the IDX Program of Key West Association of REALTORS®, Inc. Information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Listing(s) information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright 2025 Key West Association of REALTORS®, Inc. All rights reserved.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 4/18/2025, 12:45:57 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Get an agent. Get a mortgage. Save big.¹

$6,500,000
421-423 Simonton St
Sell your home with Rocket and save even more!
Seller rebate
0.5% sale price²
Price information
Property sales
We're sorry, we currently don't have property sales data for this listing.
Tax history
We're sorry, we currently don't have tax history data for this listing.
Nearby schools
6
Poinciana Elementary School
Public District PK-5
2.1 mi
•1407 Kennedy Dr
2
Gerald Adams Elementary School
Public District PK-5
3.9 mi
•5855 College Rd
9
Big Pine Academy
Public Charter PK-5
28.5 mi
•30220 Overseas Hwy
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $34,714. Typical income of Key West, FL residents is less than $<35k annually. The most common type of family is single, no kids. The majority of residents in this area have high school diploma education.
Similar homes for sale
This home is located at 421-423 Simonton St in Key West, FL and zip code 33040. This 3,010 square foot home, which was built in 2020, sits on a 0.08 acre lot. Features: 6 bedrooms, 8 bathrooms. It has been listed on Rocket Homes since April 8, 2025 and is currently priced at $6,500,000.
Key West, FL housing market in March 2025 saw over 5 listings sold above listed price, more than 6 sold at listed price and over 41 sold below. The number of listings in Key West, FL increased by 9.3% between February and March 2025. In March 2025 median list price was $1,050,000 and the average listing age was 96 days.