1401 Simonton Street 16, Key West, FL 33040

$1,165,000

Virtual Tour

https://my.matterport.com/show/?m=stt1qAW6JET

Property Type: Residential Bedrooms: 2 Baths: 2 Square Footage: 958 Status: Closed

Current Price: $1,165,000 List Date: 1/29/2026 Last Modified: 3/31/2026

Overview

Description

Rare opportunity to own a luxury 2-bedroom, 2-bath condo-hotel residence with full transient nightly rental rights at the renowned Santa Maria Suites Resort. This turnkey property generated nearly $200,000 in actual gross rental revenue in 2025, offering strong income performance while preserving the flexibility of personal use. Located just one block from world-famous Duval Street, the resort blends a prime Old Town location with a private, resort-style atmosphere. Owners and guests enjoy walkability to dining and shopping while returning home to a quiet luxury setting. This residence is one of the few desirable single-level, pool-facing units in the complex. The layout features spacious living and dining areas, a well-equipped kitchen, and two comfortable bedroom suites.. Built in 2006 and consistently recognized as one of the island's premier resorts, the property offers amenities including off-street parking, 24-hour fitness center, and concierge services. Comprehensiv ... (Read more)

Listing Details MLS# 618368

Location, Tax & Legal

Street #: 1401
Street Name: Simonton
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Filer Boyle Sub (1.0)
Area: 01 - Key West
KW Neighborhood: Old Town-S of Truman
Unit #: 16
City: KEY WEST
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Ocean
Flood Zone: AE
Alternate Key #: 9087701
Parcel #: 00036231-001600
Zoning: HCT - Historic Commercial Tourist
Deed Restrictions: Unknown
Legal: UNIT 16 THE SANTA MARIA RESORT CONDOMINIUM OR2265-357/477 OR2272-1035 OR3126-1342
Taxes: 7984.55
Tax Year: 2025
Pub Sewer HkUp: Yes

Contract Information

Listing Board: Key West Association

General Property Description

Realtor.COM Type: Residential - Condo/Townhouse
Style: Condo
Waterfront: No
Pool: Yes
Year Built: 2006
Living Apx SqFt: 958
SqFt Source: Property Data Card
Total Bedrooms: 2
Full Baths: 2
Total Baths: 2
Rentals Allowed: Yes
Control Depth: 0
Lot SqFt: 0
Total Units: 0

Status Change Info

Under Contract Date: 2026-03-09
Sold Date: 2026-03-31

Association Info

Mandatory Home Owners Asc: Yes
1st Right of Refusal: No
Association Fee $: 3013.4
Assoc/Mnt Fee Per: Monthly

License Info

Transient Rntl Licns: Yes

More Information

Building Style

Above Flood: Yes

Vehicle Storage

Car(s): Yes
Guest Parking: Yes
Open Parking: Yes
Off Street Parking: Yes

Pool Info

Heated: Yes
In Ground: Yes
Lap: Yes

Remarks & Misc

Remarks – Consumer: Rare opportunity to own a luxury 2-bedroom, 2-bath condo-hotel residence with full transient nightly rental rights at the renowned Santa Maria Suites Resort. This turnkey property generated nearly $200,000 in actual gross rental revenue in 2025, offering strong income performance while preserving the flexibility of personal use. Located just one block from world-famous Duval Street, the resort blends a prime Old Town location with a private, resort-style atmosphere. Owners and guests enjoy walkability to dining and shopping while returning home to a quiet luxury setting. This residence is one of the few desirable single-level, pool-facing units in the complex. The layout features spacious living and dining areas, a well-equipped kitchen, and two comfortable bedroom suites.. Built in 2006 and consistently recognized as one of the island's premier resorts, the property offers amenities including off-street parking, 24-hour fitness center, and concierge services. Comprehensive interior renovations to the units, along with upgrades to the pool and gym, are planned for completion in 2027. The current owner has paid nearly the entire special assessment related to these improvements. Buyers may choose their own management company or negotiate with the existing on-site operator. All reservations within 180 days of closing must be honored. The property is being sold fully furnished and with future bookings in place, providing a seamless transition and immediate income continuity. Whether you are seeking a high-performing investment, a second home, or a hybrid ownership model, this residence delivers income potential in one of the most supply-constrained markets in the country. Own a piece of Key West that works for you — financially and personally.
Directions: Located on Corner of Simonton and South

Fee Includes

Bldg Exterior Mnt: Yes
Building Insurance: Yes
Common Area Mnt: Yes

Dockage

None: Yes

Tax Exemptions

None: Yes

Appliances

Dishwasher: Yes
Dryer: Yes
Microwave: Yes
Oven: Yes
Range: Yes
Refrigerator: Yes
Stainless Steel Appliance(s): Yes
Washer: Yes

Cooling

Central Air: Yes

Waterfront

None: Yes

Waterview

No Waterview: Yes

Neighborhood Feature

Beach: Yes
Bike Paths: Yes
Tennis Courts: Yes

Interior Features

Built-in Cabinets: Yes
Drapes/Blinds Incl: Yes
Fire Sprinkler: Yes
Granite Counter Top: Yes
Window Treatments: Yes

Property Condition

Updated/Remodeled: Yes

Construction

CBS: Yes
Concrete: Yes

Land Size

Less Than 1/4 Acre: Yes

Furnished

Furnished: Yes

Utilities

FKAA: Yes

Porch/Balcony

Open Porch/Balcony: Yes

Exterior Features

Lanai: Yes
Lighting: Yes

Pre-Wired

Cable: Yes

Property Features

Fee Includes: Bldg Exterior Mnt; Building Insurance; Common Area Mnt Tax Exemptions: None Waterfront: None Waterview: No Waterview Dockage: None Property Condition: Updated/Remodeled Vehicle Storage: Guest Parking; Off Street Parking; Open Parking Furnished: Furnished Cooling: Central Air Utilities: FKAA Interior Features: Built-in Cabinets; Drapes/Blinds Incl; Fire Sprinkler; Granite Counter Top; Window Treatments Pre-Wired: Cable Appliances: Dishwasher; Dryer; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer Exterior Features: Lanai; Lighting Pool Info: In Ground; Lap Construction: CBS; Concrete Neighborhood Feature: Beach; Bike Paths; Tennis Courts Land Size: Less Than 1/4 Acre

Listing Office: Suzanne Moore Real Estate

Last Updated: March - 31 - 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.

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