1401 Simonton St, Unit 16

Key West, FL 33040

$1,165,000
Last Sold Price
2
Beds
958 Sq. Ft.
$1,216 / Sq. Ft.
958
Sq. Ft.
$1,216
per Sq. Ft.
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Closed 3/31/26
Closed 3/31/26
a view of a chair and tables in the patio and a swimming pool
a kitchen with a stove a sink and a refrigerator
a living room with furniture and a large window
a view of a garden
a view of two chairs in the balcony
a kitchen with stainless steel appliances granite countertop sink stove and refrigerator
a large kitchen with kitchen island granite countertop a large window and stainless steel appliances
a large kitchen with a table and chairs
a kitchen with a sink and a refrigerator
a living room with furniture fireplace and a flat screen tv
a living room with furniture and a flat screen tv
a bedroom with a large bed and a chandelier
a bedroom with a large bed and a chandelier
a bedroom with a bed and window
a bedroom with a bed and a flat screen tv
a kitchen with a sink and cabinets
a bathroom with a granite countertop sink and a mirror
a bathroom with a shower and a sink
a view of swimming pool with outdoor seating and plants
a view of a swimming pool with chairs
a view of a room with gym equipment
a palm tree in front of a building
a couple of potted plants in front of a building
a view of a lobby with a porch
a view of outdoor space
a balcony with view of outdoor space
a view of a balcony
a utility room with dryer and washer
a picture of a bench in front of a door

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...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.
  1. Listed by Suzanne M Moore • Suzanne Moore Real Estate

Property Details for 1401 Simonton Street, Unit 16

Waterfront
None
Waterfront
No
Zoning
HCT - Historic Commercial Tourist
Subdivision
Filer Boyle Sub (1.0)
Directions
Located on Corner of Simonton and South
Vehicle Storage
Open Parking, Off Street Parking, Guest Parking
LISTING UPDATED: 03/31/2026 03:38 PM

Property Details for 1401 Simonton Street, Unit 16

StatusClosed
MLS #618368
Days on Market40
Taxes$7,985 / year
HOA Fees$3,013 / month
Condo/Co-op Fees-
Property TypeCondo
MLS TypeResidential / Condo
Year Built2006
CountyMonroe County
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Location

Listing Courtesy of Suzanne Moore Real Estate

Sold By Keller Williams Key West Compass Realty

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Building Information for 1401 Simonton Street, Unit 16

Building/Complex1401 Simonton StFloor-Stories3Residences1Pet PolicyNot AllowedPet Policy DetailsPets AllowedYear Built2006

Payment Calculator

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$9,545 per month

30 year fixed, 6.46% Interest

Principal and Interest

$5,866

Property Taxes

$665

HOA Dues

$3,013

The Payment Calculator is for illustrative purposes only.

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Property Information for 1401 Simonton Street, Unit 16

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 01 - Key West
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Ocean
  • KW Neighborhood: Old Town-S of Truman
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Neighborhood Feature: Tennis Courts, Bike Paths, Beach
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: Yes
  • Association Info: 1st Right of Refusal: No
  • License Info: Transient Rntl Licns: Yes
  • Fee Includes: Bldg Exterior Mnt, Common Area Mnt, Building Insurance
  • Furnished: Furnished
  • Tax Year: 2025
  • Tax Exemptions: None
Property
Lot Information
  • Lot Size: X
  • Parcel #: 00036231-001600
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: UNIT 16 THE SANTA MARIA RESORT CONDOMINIUM OR2265-357/477 OR2272-1035 OR3126-1342
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Flood Zone: AE
  • Rentals Allowed: Yes
  • Deed Restrictions: Unknown
  • Picture Count: 29
  • Document Count: 0
  • Building Style: Above Flood: Yes
  • Property Condition: Updated/Remodeled
Utilities
  • Utilities: FKAA
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: Heated: Yes
  • Pool Info: In Ground, Lap
  • Porch/Balcony: Open Porch/Balcony
Interior and Exterior Features
Interior Features
  • Interior Features: Drapes/Blinds Incl, Window Treatments, Fire Sprinkler, Granite Counter Top, Built-in Cabinets
  • Pre-Wired: Cable
  • Appliances: Washer, Stainless Steel Appliance(s), Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Construction: CBS, Concrete
  • Dockage: None
  • Exterior Features: Lighting, Lanai

Property History for 1401 Simonton Street, Unit 16

DateEvent & SourcePriceAppreciation
Mar 31, 2026

Sold

FKMLS #618368

$1,165,000—
Mar 9, 2026

Pending

FKMLS #618368

—
Mar 2, 2026

Backup Contract

FKMLS #618368

—
DateEvent & SourcePrice
03/31/2026

Sold

FKMLS #618368

$1,165,000
03/09/2026

Pending

FKMLS #618368

—
03/02/2026

Backup Contract

FKMLS #618368

—

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

Public Records for 1401 Simonton Street, Unit 16

Taxable ValueLand-Additions$902,146Total-
Tax Record2024$8,550 ($713 / month)
Home Facts
Baths2Total Finished SqFt958 SqFtAbove Grade Finished SqFt958 SqFtLot Size50,310 SqFtStyleHotel / MotelYear Built2006CountyMONROEAPN00036231-001600

Schools near 1401 Simonton Street, Unit 16

This home is within Monroe.
Rating
School
Type
Grades
Distance
Horace O'bryant School
Public - PK to 8
Key West High School
Public - 9 to 12
May Sands Montessori School
Charter - PK to 8
Keys Center
Public - 8 to 12
Rating
School
Distance
Horace O'bryant School
PublicPK to 8

Key West High School
Public9 to 12

May Sands Montessori School
CharterPK to 8

Keys Center
Public8 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.

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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 Suzanne Moore Real Estate

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.