Property details
About 525 Simonton St
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.
Highlights
Summary
- Full Bathrooms: 11
- Appliances: Dishwasher, Dryer, Freezer, Microwave, Refrigerator
- Total Bedroom Count: 11
- Garage Space: 4 spaces
- Private Pool: Yes
- Parking: Off Street
- Architectural Style: Single Family
- List Price: $7,995,000
- Price/SqFt: $2,635
- Year Built: 1889
- Living Area: 3,034 SqFt
- MLS Number: 615623
- MLS Name: KeyWest
- Office Name: Island Home Realty Inc.
- Office Phone: (305) 395-0550
- Listing Agent: Paige Bethel
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: 7/10/2025, 1:45:35 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Price information
Property sales
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Tax history
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Nearby schools
6
Poinciana Elementary School
Public District PK-5
2.3 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
28.8 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 $56,548. The majority of Key West, FL residents have income between $35k-100k annually. The most common type of family is single, no kids. The most common level of education of people living in this area is high school diploma.
How much money do the neighbors make?
What level of education do the neighbors have?
What types of families live nearby?
Are the neighbors home owners or renters?
How old are people in this area?
What do the neighbors do for fun?
Continuing Education Courses
Hiking/backpacking
Figure Skating
Where do the neighbors shop?
Express/Express For Men
Nordstrom Rack
Chico's
Where do the neighbors go to eat?
Qdoba
Chipotle
Bob Evans
What do the neighbors drive?
Volkswagen
Mazda
Oldsmobile
What do the neighbors listen to?
Urban Contemporary
Rock
News
Frequently asked questions
About 525 Simonton St
The listing price of 525 Simonton St property is $7,995,000.
The property 525 Simonton St is a house located in Key West, Florida, 33040.
Active Listing: 525 Simonton St is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 525 Simonton St are: Poinciana Elementary School (GreatSchools Rating 6/10), Gerald Adams Elementary School (GreatSchools Rating 2/10), Big Pine Academy (GreatSchools Rating 9/10), May Sands Montessori School (GreatSchools Rating 5/10), Horace O'Bryant School (GreatSchools Rating 3/10), Sigsbee Charter School (GreatSchools Rating 7/10), Monroe Virtual Instruction Program (GreatSchools Rating 2/10), Somerset Island Preparatory (GreatSchools Rating 6/10), Key West High School (GreatSchools Rating 5/10).
The property at 525 Simonton St has 11 bedrooms and 11 bathrooms.
The property 525 Simonton St is 3,034 SqFt (source: MLS/tax record).
The year of construction for 525 Simonton St is 1889.
This home is located at 525 Simonton St in Key West, FL and zip code 33040. This 3,034 square foot home was built in 1889. Features: 11 bedrooms, 11 bathrooms. It has been listed on Rocket Homes since July 1, 2025 and is currently priced at $7,995,000.
While more than 2 listings in Key West, FL in June 2025 were sold above asking price, there were more than 8 listings sold at asking price, and more than 35 were sold below. The number of homes for sale in Key West, FL increased by 2% between May and June 2025. The median list price of listings available in June 2025 was $1,100,000, while the average time on the real estate market was 91 days.