419 Simonton St, Unit C

1,367 Sq. Ft.
$1,598 / Sq. Ft.
1,367
Sq. Ft.
$1,598
per Sq. Ft.

Description

Tucked discreetly behind one of Old Town's most storied addresses, 419 Simonton Street C is a hidden gem insiders hope no one else discovers. Completed in 2026 as a brand-new, ground-up construction, this private 2BD/2.5BA residence delivers modern island luxury within a lush, secluded enclave, featuring soaring cathedral ceilings in the bedrooms, impact-rated windows and doors, and a streamlined kitchen with Fisher & Paykel and Bosch appliances, a walk-in pantry, under-cabinet lighting, and refined...Tucked discreetly behind one of Old Town's most storied addresses, 419 Simonton Street C is a hidden gem insiders hope no one else discovers. Completed in 2026 as a brand-new, ground-up construction, this private 2BD/2.5BA residence delivers modern island luxury within a lush, secluded enclave, featuring soaring cathedral ceilings in the bedrooms, impact-rated windows and doors, and a streamlined kitchen with Fisher & Paykel and Bosch appliances, a walk-in pantry, under-cabinet lighting, and refined finishes throughout. Outdoors, a secluded patio is framed by vibrant tropical landscaping and includes a tranquil water-featured pool, outdoor shower, and dedicated golf cart parking--the preferred way to get around Old Town. Offered fully furnished with a curated interiors package by Ben Teague Design, the home is move-in ready and thoughtfully finished. Set within a well-structured HOA with no shared walls, and part of a three-residence property with two additional homes positioned at the front and parking conveniently located there, this residence represents Old Town living at its most refined--entirely new, intentionally designed, and quietly confident in every detail.
  1. Listed by Team Kaufelt • Truman & Co. (KW)

Property Details for 419 Simonton Street, Unit C

Waterfront
None
Waterfront
No
Zoning
HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Subdivision
Old Town - Unlisted (1.0)
Vehicle Storage
Assigned Parking
Pets
Pets Allowed

Open Houses

Sunday, Jan 25th

1:00 PM - 3:00 PM

Public

LISTING UPDATED: 01/22/2026 03:46 PM

Property Details for 419 Simonton Street, Unit C

StatusActive
MLS #618252
Days on Market1
Taxes$13,468 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeCondo
MLS TypeResidential / Condo
Year Built2026
CountyMonroe County

Location

Listing Courtesy of Truman & Co. (KW)
Add your commute

Building Information for 419 Simonton Street, Unit C

Building/Complex419 Simonton StFloor-Stories2Residences-Pet PolicyAllowedPet Policy Details-Year Built2026

Payment Calculator

$11,772 per month

30 year fixed, 6.15% Interest

Principal and Interest

$10,649

Property Taxes

$1,122

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 419 Simonton Street, Unit C

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 02 - Key West
  • Absolute Longitude: 81.801594
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Median
  • KW Neighborhood: Old Town-N of Truman
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: Yes
  • Association Info: Condo Doc's: Yes
  • Association Info: 1st Right of Refusal: Yes
  • Fee Includes: Common Area Mnt
  • Furnished: Furnished
  • Tax Year: 2025
  • Tax Exemptions: None
Property
Lot Information
  • Acres: 0.14
  • Parcel #: 00006340-000000
  • Land Size: Less Than 1/4 Acre
  • License Info: Non Trans Rntl Lic
Property and Assessments
  • Legal: KW PT LT 4 SQR 36 G9-593 OR153-170/71 OR377-65/66 OR773-1201 OR1097-1042/43 OR1298-1844/45 OR1432-2163/64 OR2272-2265 O
  • MLS Approved: Y
  • Bank Owned: No
  • SqFt Source: Seller
  • Flood Zone: X
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: No
  • Picture Count: 29
  • Document Count: 0
  • Building Style: Above Flood: Yes
  • Property Condition: New Construction
Utilities
  • Utilities: FKAA, Water Separate Meter, Elect Separate Meter, Buyer to Verify, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: Heated: Yes
  • Pool Info: In Ground
  • Porch/Balcony: Patio
Interior and Exterior Features
Interior Features
  • Floor: Wood
  • Interior Features: Drapes/Blinds Incl, Window Treatments, Built-in Cabinets, Walk-in Closet(s), Smoke Alarms, Pantry, Cathedral Ceilings
  • Appliances: Washer, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Construction: Frame, Hardi Board Siding
  • Dockage: None
  • Exterior Features: Fencing, Water Display, Privacy Wall/Fence, Outdoor Shower, Rain Gutters
  • Windows/Doors: Impact Rstnce Window, Impact Rstnce Doors

Property History for 419 Simonton Street, Unit C

DateEvent & SourcePriceAppreciation
Jan 22, 2026

Listed (Active)

FKMLS #618252

$2,185,000
DateEvent & SourcePrice
01/22/2026

Listed (Active)

FKMLS #618252

$2,185,000

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

Schools near 419 Simonton Street, Unit C

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - K to 12
Public - 9 to 12
Public - K to 5
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Monroe Virtual Instruction Program
PublicK to 12

Key West High School
Public9 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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419 Simonton Street, Unit C is a condo for sale in Key West, FL 33040. This property was listed for sale on January 22, 2026 by Truman & Co. (KW), it's currently listed at $2,185,000. This listing's school district is Monroe. Nearby schools include Gerald Adams Elementary School, Monroe Virtual Instruction Program and Key West High School. 419 Simonton Street, Unit C is a 2-bed, 3-bath, 1,367 sqft condo built in 2026.

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 Truman & Co. (KW)

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.