529 Simonton St

$2,975,000
Price
4
Beds
1,800 Sq. Ft.
$1,653 / Sq. Ft.
1,800
Sq. Ft.
$1,653
per Sq. Ft.

Description

X Flood Zone 13ft above sea-level! Gorgeous CONCH home in the ultimate Old Town location - only one block from Duval, in a neighborhood lined with historic homes! Live in the heart of Old Town where charming architecture, iconic streetscapes, and Key West's finest restaurants and shops are right outside your door. This beautifully restored 1889 Conch home has been completely renovated in 2022 to the studs, blending historic character with sophisticated modern upgrades. Currently configured as a single...X Flood Zone 13ft above sea-level! Gorgeous CONCH home in the ultimate Old Town location - only one block from Duval, in a neighborhood lined with historic homes! Live in the heart of Old Town where charming architecture, iconic streetscapes, and Key West's finest restaurants and shops are right outside your door. This beautifully restored 1889 Conch home has been completely renovated in 2022 to the studs, blending historic character with sophisticated modern upgrades. Currently configured as a single family home, open-concept living area, 10 ft ceilings and restored Dade County Pine throughout. The great room flows into the chef's kitchen featuring high-end Cafe appliances, gas range, and custom cast-in-place concrete countertops. A bespoke bar framed with antique doors creates the perfect spot to prepare a cocktail before stepping onto your private porch. Two inviting first-floor guest rooms share a luxurious bath with a deep 17'' soaking tub. The custom staircase leads to a serene primary suite offering a private balcony overlooking picturesque Simonton Street, a custom walk-in closet, and a spa-style en-suite bathroom with rain shower, jets, sprayer, and dual vanity. Step outside to your expansive tropical oasis featuring a new pool with waterfall, electric heater and chiller. Off-street parking accommodates 2-3 vehicles plus golf cart/UTV. The home boasts extensive upgrades including: new metal roof, impact windows and doors, beautiful Brazilian pecan floors, spray-foamed insulation, steel interior framing, new plumbing/electrical/HVAC systems, tankless gas water heater with instant-hot pump. The property maintains legal duplex zoning and can be easily returned to two units. A 3 bedroom 2 bathroom residence and a large, separately metered 1 bed 1 bath apartment. --with its own private side entrance, full kitchen, living room and bath. 3 electric meters, 2 water meters, located in the conditional transient receiver zone (buyer to verify uses with the City).
  1. Listed by Lisa Swanson • The Agency Florida Keys

Property Details for 529 Simonton Street

Waterfront
None
Waterfront
No
Zoning
HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Subdivision
Old Town - Unrecord (1.0)
Building Style
Conch
Vehicle Storage
Open Parking, Guest Parking
Pets
Pets Allowed
LISTING UPDATED: 12/19/2025 02:08 PM

Property Details for 529 Simonton Street

StatusActive
MLS #617467
Days on Market31
Taxes$10,431 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeMulti Family
MLS TypeResidential / Duplex
Year Built1889
Lot Size0.08 AC / 3,470 SF
CountyMonroe County

Location

Listing Courtesy of The Agency Florida Keys
Add your commute

Building Information for 529 Simonton Street

Stories-Residences-Year Built1889Building Size-Lot Size0.08 AC / 3,470 SF

Payment Calculator

$15,570 per month

30 year fixed, 6.28% Interest

Principal and Interest

$14,701

Property Taxes

$869

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 529 Simonton Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 01 - Key West
  • Absolute Longitude: 81.800741
  • Control Depth: 0
  • 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
  • Fee Includes: None
  • Tax Year: 2024
  • Tax Exemptions: None
Property
Lot Information
  • Acres: 0.08
  • Parcel #: 00009260-000000
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: KW PT LOT 4 SQR 49
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Flood Zone: X
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 84
  • Document Count: 0
  • Building Style: Above Flood: Yes
  • Security: Electric Gate
  • Title: Negotiable
Utilities
  • Utilities: FKAA, Propane, Elect Separate Meter, Water Separate Meter, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: In Ground, Concrete
  • Porch/Balcony: Open Porch/Balcony, Deck, Patio
Interior and Exterior Features
Interior Features
  • Floor: Wood
  • GF-Interior Features: Tankless Hot Wtr Htr, LED Lighting, Programmable Thermst
  • Interior Features: Cathedral Ceilings, Bar, Dade County Pine, Walk-in Closet(s)
  • Appliances: Washer, Wine Cooler, Gas Appliances, Microwave, Oven, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Construction: Frame
  • Dockage: None
  • Exterior Features: Fencing, Lighting
  • Windows/Doors: Impact Rstnce Window, Impact Rstnce Doors

Property History for 529 Simonton Street

DateEvent & SourcePriceAppreciation
Nov 25, 2025

Listed (Active)

FKMLS #617467

$2,975,000
Aug 9, 2023

Expired

FKMLS #604486

Aug 9, 2023

Expired

FKMLS #604487

Mar 20, 2023

Temp Off Market

FKMLS #604486

Mar 20, 2023

Temp Off Market

FKMLS #604487

Mar 9, 2023

Listed (Active)

FKMLS #604486

$2,700,000
Mar 9, 2023

Listed (Active)

FKMLS #604487

$2,700,000
Jul 16, 2021

Sold (Public Record)

Public Record #1467063041

$750,000
DateEvent & SourcePrice
11/25/2025

Listed (Active)

FKMLS #617467

$2,975,000
08/09/2023

Expired

FKMLS #604486

08/09/2023

Expired

FKMLS #604487

03/20/2023

Temp Off Market

FKMLS #604486

03/20/2023

Temp Off Market

FKMLS #604487

03/09/2023

Listed (Active)

FKMLS #604486

$2,700,000
03/09/2023

Listed (Active)

FKMLS #604487

$2,700,000
07/16/2021

Sold (Public Record)

Public Record #1467063041

$750,000

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

Public Records for 529 Simonton Street

Taxable ValueLand$807,065Additions$649,620Total$1,456,685
Tax Record2024$10,431 ($869 / month)
Home Facts
Baths3Total Finished SqFt1,800 SqFtAbove Grade Finished SqFt1,800 SqFtStories2Lot Size3,470 SqFtStyleMulti-Family Dwelling (2-4)Year Built1938Year Renovated2014CountyMONROEAPN00009260-000000

Schools near 529 Simonton Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - K to 12
Public - 9 to 12
Public - K to 5
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Monroe Virtual Instruction Program
PublicK to 12

Key West High School
Public9 to 12

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.

Similar Homes

Similar Sold Homes

529 Simonton Street is a multi-family home for sale in Key West, FL 33040. This property was listed for sale on November 25, 2025 by The Agency Florida Keys, it's currently listed at $2,975,000. It has been on the market for a total of 31 days and was last sold on July 16, 2021. This listing's school district is Monroe. Nearby schools include Gerald Adams Elementary School, Monroe Virtual Instruction Program and Key West High School. 529 Simonton Street is a 4-bed, 3-bath, 1,800 sqft multi-family home built in 1889.

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 The Agency Florida Keys

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.