1401 Simonton St, Unit 16

958 Sq. Ft.
$1,305 / Sq. Ft.
958
Sq. Ft.
$1,305
per Sq. Ft.

Description

Luxury Condo Hotel with rare Transient Nightly Rental Rights - Exceptional Key West Value. Discover a rare opportunity to own a luxury condo-hotel residence in the heart of Key West with full transient nightly rental privileges - an increasingly scare asset class in the Florida Keys. This turnkey Investment generated almost $200,000 in actual gross rental revenue in 2005, offering strong income potential while preserving the true joy of ownership. Located at the iconic Santa Maria Resort, built in...Luxury Condo Hotel with rare Transient Nightly Rental Rights - Exceptional Key West Value. Discover a rare opportunity to own a luxury condo-hotel residence in the heart of Key West with full transient nightly rental privileges - an increasingly scare asset class in the Florida Keys. This turnkey Investment generated almost $200,000 in actual gross rental revenue in 2005, offering strong income potential while preserving the true joy of ownership. Located at the iconic Santa Maria Resort, built in 2006 and consistently recognized as one of the Islands premier luxury resorts, this residence blends contemporary design with resort style comfort. This two bedroom, two bath residence is one of the few single-level units overlooking the resort style pool, capturing a serene sense of living rarely found in a condo hotel. Private poolside porch allows you to enjoy the relaxed sophistication of Island living - morning coffee, afternoon breezes and evenings wrapped in resort ambiance. Buyer can choose their own management company or choose to negotiate with the existing on-site company. All current reservations up to 180 days from closing must be honored. Being Sold Turn Key with all reservations in place allowing a seamless transition to the new owner. Resort Features include, Off Street Parking, 24 Hr Gym, Concierge, large Heated Pool and only One BLock To infamouns Duval St. This is not just an investment - it's a lifestyle-forward asset in one of the most supply-constrained markets in the country. Own a piece of Key West that pays you back, while still being yours to enjoy.
  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: 01/28/2026 06:13 PM

Property Details for 1401 Simonton Street, Unit 16

StatusActive
MLS #618368
Days on Market4
Taxes$7,985 / year
HOA Fees$3,013 / month
Condo/Co-op Fees-
Compass TypeCondo
MLS TypeResidential / Condo
Year Built2006
CountyMonroe County

Location

Listing Courtesy of Suzanne Moore Real Estate
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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

$9,771 per month

30 year fixed, 6.15% Interest

Principal and Interest

$6,092

Property Taxes

$665

HOA Dues

$3,013

The Payment Calculator is for illustrative purposes only.

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
Jan 28, 2026

Listed (Active)

FKMLS #618368

$1,250,000
May 6, 2025

Expired

FKMLS #613626

Feb 10, 2025

Price Change

FKMLS #613626

$1,495,000
Feb 10, 2025

Price Change

FKMLS #613626

$1,475,000
Feb 10, 2025

Listed (Active)

FKMLS #613626

$1,425,000
Sep 17, 2021

Sold

FKMLS #591127

$950,000
Sep 16, 2021

Sold (Public Record)

Public Record #1473068606

$950,000

-2.0% / yr

Aug 22, 2021

Pending

FKMLS #591127

Aug 22, 2021

Backup Contract

FKMLS #591127

Jun 4, 2020

Price Change

FKMLS #591127

$1,100,000
Jun 4, 2020

Price Change

FKMLS #591127

$1,050,000
Jun 4, 2020

Listed (Active)

FKMLS #591127

$999,000
Jan 16, 2009

Expired

FKMLS #107501

Jan 4, 2008

Listed (Active)

FKMLS #107501

$1,500,000
Nov 11, 2007

Expired

FKMLS #104983

Mar 12, 2007

Sold

FKMLS #105234

$1,275,000
Mar 12, 2007

Pending

FKMLS #105234

Feb 15, 2007

Listed (Active)

FKMLS #104983

$1,500,000
Feb 12, 2007

Sold (Public Record)

Public Record #216265795

$1,275,000
Mar 12, 2006

Listed (Active)

FKMLS #105234

$1,275,000
DateEvent & SourcePrice
01/28/2026

Listed (Active)

FKMLS #618368

$1,250,000
05/06/2025

Expired

FKMLS #613626

02/10/2025

Price Change

FKMLS #613626

$1,495,000
02/10/2025

Price Change

FKMLS #613626

$1,475,000
02/10/2025

Listed (Active)

FKMLS #613626

$1,425,000
09/17/2021

Sold

FKMLS #591127

$950,000
09/16/2021

Sold (Public Record)

Public Record #1473068606

$950,000

-2.0% / yr

08/22/2021

Pending

FKMLS #591127

08/22/2021

Backup Contract

FKMLS #591127

06/04/2020

Price Change

FKMLS #591127

$1,100,000
06/04/2020

Price Change

FKMLS #591127

$1,050,000
06/04/2020

Listed (Active)

FKMLS #591127

$999,000
01/16/2009

Expired

FKMLS #107501

01/04/2008

Listed (Active)

FKMLS #107501

$1,500,000
11/11/2007

Expired

FKMLS #104983

03/12/2007

Sold

FKMLS #105234

$1,275,000
03/12/2007

Pending

FKMLS #105234

02/15/2007

Listed (Active)

FKMLS #104983

$1,500,000
02/12/2007

Sold (Public Record)

Public Record #216265795

$1,275,000
03/12/2006

Listed (Active)

FKMLS #105234

$1,275,000

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
Public - PK to 8
Public - 9 to 12
Charter - PK to 8
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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1401 Simonton Street, Unit 16 is a condo for sale in Key West, FL 33040. This property was listed for sale on January 28, 2026 by Suzanne Moore Real Estate, it's currently listed at $1,250,000. It has been on the market for a total of 4 days and was last sold on September 17, 2021. This listing's school district is Monroe. Nearby schools include Horace O'bryant School, Key West High School and May Sands Montessori School. 1401 Simonton Street, Unit 16 is a 2-bed, 2-bath, 958 sqft condo built in 2006.

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.