525 Simonton Street, Key West, FL 33040 (MLS# 615623)

525 Simonton Street, Key West, FL 33040

$6,500,000

Property Type: Residential Bedrooms: 11 Baths: 11 Square Footage: 3,034 Lot Size (sq. ft.): 8,269 Status: Closed

Current Price: $6,500,000 List Date: 7/01/2025 Last Modified: 6/17/2026

Overview

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, 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 priva ... (Read more)

Listing Details MLS# 615623

Location, Tax & Legal

Street #: 525
Street Name: Simonton
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Old Town - Unrecord (1.0)
Area: 01 - Key West

Contract Information

Listing Board: Key West Association

General Property Description

Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: No
Pool: Yes
Year Built: 1889
Lot SqFt: 8269
Living Apx SqFt: 3034
SqFt Source: Property Data Card
Total Bedrooms: 11
Full Baths: 11
Total Baths: 11
Rentals Allowed: Yes
Min Rental Days: Yes

Status Change Info

Under Contract Date: 2026-04-15
Leased Date: 2026-06-17

Association Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No

License Info

# of City License: 2
# of County License: 2
Transient Rntl Licns: Yes

More Information

Building Style

Above Flood: Yes
# Stories: 3 Stories

Vehicle Storage

Car(s): 4+

Pool Info

Heated: Yes

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: None Waterview: No Waterview Dockage: None Vehicle Storage: Off Street Parking; Open Parking Furnished: Furnished Cooling: Central Air; Ductless Utilities: Buyer to Verify Interior Features: Built-in Cabinets; Drapes/Blinds Incl; Sky Light(s); Smoke Alarms; Storage; Window Treatments Appliances: Dishwasher; Dryer; Freezer; Microwave; Refrigerator; Stainless Steel Appliance(s) Exterior Features: Fencing; Storage Pool Info: In Ground; Concrete; Decked Construction: Frame; Hardi Board Siding Pets: Pets Allowed Land Size: Less Than 1/4 Acre Title: Negotiable

Listing Office: Island Home Realty Inc.

Last Updated: June - 17 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.