525 Simonton St

Key West, FL 33040

$7,995,000
Price
11
Beds
3,034 Sq. Ft.
$2,635 / Sq. Ft.
3,034
Sq. Ft.
$2,635
per Sq. Ft.
a front view of a house with a yard
a view of a building with a porch
a view of a house with a yard and sitting area
a front view of a house with a garden
a living room with fireplace furniture wooden floor and a large window
a living room with furniture and a wooden floor
a living room with furniture and a wooden floor
a living room with furniture and a couch
a living room with furniture and a flat screen tv
a view of a dining room with furniture window and wooden floor
Dining Room
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a kitchen with stainless steel appliances granite countertop a stove a sink and a refrigerator
a bedroom with a large bed and a window
Bedroom #1 (fist floor)
a bathroom with a toilet a sink and a mirror
Bedroom #2 (1st Floor)
a bathroom with a bathtub shower sink vanity and toilet
a view of a hallway with wooden floor and windows
a spacious bedroom with a bed and a window
a bathroom with a sink and a mirror
a spacious bedroom with a bed and a chandelier
a bedroom with a bed and wooden floor
Balcony Overlooking pool
a bathroom with a granite countertop sink a mirror and a shower
a bedroom with a bed and wooden floor
a bathroom with a double vanity sink toilet and shower
a bedroom with a bed and a window
a bathroom with a sink a toilet and shower
a bedroom with a bed and a large window with outer view
a view of a two chair in the balcony
a kitchen with stainless steel appliances lots of counter top space
a living room with furniture bathtub and a chandelier
a living room with furniture and a large window
a living room with furniture a chandelier and a dining table
a view of livingroom with hardwood and furniture
a bedroom with a bed and wooden floor
a bathroom with a granite countertop shower a toilet and a sink
a living room with furniture and garden view
Main House Pool
a view of a backyard with pool and chairs
a view of swimming pool with outdoor seating and yard
Outdoor Dining
Parking
a living room with furniture a window and a flat screen tv
a kitchen with stainless steel appliances granite countertop a stove top oven a sink dishwasher a dining table and chairs with wooden floor
a bedroom with a bed and a window
a bedroom with a bed and a window
a bedroom with a bed and a window
a bathroom with a sink toilet and shower
a bedroom with a bed and a window
a bedroom with a bed and a view of bathroom
a bathroom with a sink toilet and shower
a bedroom with a large bed and a window
a bathroom with a sink toilet vanity and shower
a bedroom with a bed lamp and a large window
a bathroom with a sink toilet a mirror and shower
Outdoor Bar
Villa Pool
525 SIMONTON ST WEB-65

Description

A Rare Investment Opportunity in the Heart of Old Town Key West. NIGHTLY rentals allowed. Introducing The Watson House--one of the largest and most versatile TRANSIENTLY licensed estates in Key West. Situated just one block off Duval Street on iconic Simonton Street, this 11-bedroom, 11-bath compound spans two distinct residences: a stately 7-bedroom mansion and a sleek, modern 4-bedroom villa--each with its own private pool. Zoned with two transient licenses and off-street parking for 4+ vehicles,...A Rare Investment Opportunity in the Heart of Old Town Key West. NIGHTLY rentals allowed. Introducing The Watson House--one of the largest and most versatile TRANSIENTLY licensed estates in Key West. Situated just one block off Duval Street on iconic Simonton Street, this 11-bedroom, 11-bath compound spans two distinct residences: a stately 7-bedroom mansion and a sleek, modern 4-bedroom villa--each with its own private pool. Zoned with two transient licenses and off-street parking for 4+ vehicles, this exceptional property offers unmatched flexibility for luxury rentals or private use. The grand mansion was reimagined in July 2022 by a local designer, featuring fresh paint, stylish new furnishings, and 12-foot soaring ceilings. The main level includes two guest rooms with baths, formal living and dining rooms, a parlor, and a well-appointed kitchen that opens to the pool deck and outdoor dining area. Upstairs, four en suite bedrooms include two primary suites with private balconies--one overlooking Simonton Street, the other with views of the pool. A spacious third-floor suite, accessed via an interior or exterior staircase, offers a private living room, wet bar, and yet another balcony retreat. The villa, renovated to the studs in 2014, offers a clean, contemporary design with 4 bedrooms, 4 baths, full kitchen, living area, private pool, and outdoor bar--perfect for entertaining. Whether you choose to rent the estate in its entirety or as two separate homes, The Watson House is a rare asset in Key West's luxury rental market--highly sought-after and consistently booked well in advance.
  1. Listed by Paige Bethel • Island Home Realty Inc.

Property Details for 525 Simonton Street

Waterfront
None
Waterfront
No
Zoning
HRCC - Historic Residential Commercial Core
Subdivision
Old Town - Unrecord (1.0)
Vehicle Storage
Open Parking, Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 07/01/2025 03:01 AM

Property Details for 525 Simonton Street

StatusActive
MLS #615623
Days on Market180
Taxes$51,759 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1889
Lot Size0.19 AC / 8,269 SF
CountyMonroe County

Location

Listing Courtesy of Island Home Realty Inc.
Add your commute

Building Information for 525 Simonton Street

Stories3Year Built1889Building Size-Lot Size0.19 AC / 8,269 SF

Payment Calculator

$43,819 per month

30 year fixed, 6.28% Interest

Principal and Interest

$39,506

Property Taxes

$4,313

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 525 Simonton Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 01 - Key West
  • Absolute Longitude: 81.800775
  • 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
  • License Info: # of City License: 2
  • License Info: # of County License: 2
  • License Info: Transient Rntl Licns: Yes
  • Fee Includes: None
  • Furnished: Furnished
  • Tax Year: 2024
  • Tax Exemptions: None
Property
Lot Information
  • Parcel #: 00009240-000000
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: KW PT LOT 4 SQR 49 G8-444 OR885-189 OR890-2126 OR927-1164 OR2008-62 OR2555-1269 OR3147-0073 OR3164-0865
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Flood Zone: X
  • Rentals Allowed: Yes
  • Deed Restrictions: Unknown
  • Picture Count: 60
  • Document Count: 0
  • Building Style: Above Flood: Yes
  • Title: Negotiable
Utilities
  • Utilities: Buyer to Verify
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: Heated: Yes
  • Pool Info: In Ground, Decked, Concrete
Interior and Exterior Features
Interior Features
  • Interior Features: Drapes/Blinds Incl, Window Treatments, Storage, Smoke Alarms, Sky Light(s), Built-in Cabinets
  • Appliances: Dryer, Stainless Steel Appliance(s), Freezer, Microwave, Refrigerator, Dishwasher
Exterior Features
  • Construction: Frame, Hardi Board Siding
  • Dockage: None
  • Exterior Features: Fencing, Storage

Property History for 525 Simonton Street

DateEvent & SourcePriceAppreciation
Jul 1, 2025

Listed (Active)

FKMLS #615623

$7,995,000—
Jun 30, 2025

Expired

FKMLS #610247

—
Jun 3, 2024

Price Change

FKMLS #610247

$8,500,000—
Jun 3, 2024

Listed (Active)

FKMLS #610247

$7,999,000—
May 31, 2024

Expired

FKMLS #605218

—
May 8, 2023

Price Change

FKMLS #605218

$8,999,000—
May 8, 2023

Listed (Active)

FKMLS #605218

$8,500,000—
Dec 12, 2016

Expired

FKMLS #112885

—
Apr 28, 2010

Listed (Active)

FKMLS #112885

$1,999,000—
Sep 11, 2009

Expired

FKMLS #109259

—
Sep 11, 2008

Listed (Active)

FKMLS #109259

$2,399,000—
Sep 7, 2006

Temp Off Market

FKMLS #102476

—
Jul 22, 2006

Expired

FKMLS #529599

—
Jul 22, 2006

Expired

FKMLS #529610

—
Jul 22, 2006

Expired

FKMLS #529602

—
Nov 25, 2005

Listed (Active)

FKMLS #102476

$3,950,000—
Jul 22, 2005

Listed (Active)

FKMLS #529602

$2,195,000—
Jul 22, 2005

Listed (Active)

FKMLS #529610

$850,000—
Jul 22, 2005

Listed (Active)

FKMLS #529599

$1,495,000—
May 20, 2004

Sold

FKMLS #92760

$2,400,000—
May 20, 2004

Sold

FKMLS #518754

$2,400,000—
Mar 24, 2004

Pending

FKMLS #92760

—
Mar 24, 2004

Pending

FKMLS #518754

—
Oct 30, 2003

Listed (Active)

FKMLS #92760

$2,625,000—
Oct 30, 2003

Listed (Active)

FKMLS #518754

$2,625,000—
DateEvent & SourcePrice
07/01/2025

Listed (Active)

FKMLS #615623

$7,995,000
06/30/2025

Expired

FKMLS #610247

—
06/03/2024

Price Change

FKMLS #610247

$8,500,000
06/03/2024

Listed (Active)

FKMLS #610247

$7,999,000
05/31/2024

Expired

FKMLS #605218

—
05/08/2023

Price Change

FKMLS #605218

$8,999,000
05/08/2023

Listed (Active)

FKMLS #605218

$8,500,000
12/12/2016

Expired

FKMLS #112885

—
04/28/2010

Listed (Active)

FKMLS #112885

$1,999,000
09/11/2009

Expired

FKMLS #109259

—
09/11/2008

Listed (Active)

FKMLS #109259

$2,399,000
09/07/2006

Temp Off Market

FKMLS #102476

—
07/22/2006

Expired

FKMLS #529599

—
07/22/2006

Expired

FKMLS #529610

—
07/22/2006

Expired

FKMLS #529602

—
11/25/2005

Listed (Active)

FKMLS #102476

$3,950,000
07/22/2005

Listed (Active)

FKMLS #529602

$2,195,000
07/22/2005

Listed (Active)

FKMLS #529610

$850,000
07/22/2005

Listed (Active)

FKMLS #529599

$1,495,000
05/20/2004

Sold

FKMLS #92760

$2,400,000
05/20/2004

Sold

FKMLS #518754

$2,400,000
03/24/2004

Pending

FKMLS #92760

—
03/24/2004

Pending

FKMLS #518754

—
10/30/2003

Listed (Active)

FKMLS #92760

$2,625,000
10/30/2003

Listed (Active)

FKMLS #518754

$2,625,000

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

Schools near 525 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 525 Simonton Street, Key West, FL 33040

525 Simonton Street is a single family home for sale in Key West, FL 33040. This property was listed for sale on July 1, 2025 by Island Home Realty Inc., it's currently listed at $7,995,000. It has been on the market for a total of 180 days and was last sold on May 20, 2004. This listing's school district is Monroe. Nearby schools include Gerald Adams Elementary School, Monroe Virtual Franchise and Key West High School. 525 Simonton Street is a 11-bed, 11-bath, 3,034 sqft single 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 Island Home Realty Inc.

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.