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$1,995,000 Just Listed

  • For Sale
  • Active
  • Condo
  • 2 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,409 Sq. Ft.
  • Updated 40 minutes ago
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Old Town has plenty of history. What it rarely has is a brand-new secret. Privately positioned behind one of Simonton Street's most storied facades, 419 Simonton Street C is a freestanding 2026 residence with no shared walls and a world of its own. Fully furnished with a curated interiors package by Ben Teague Design, this two-bedroom, two-and-a-half-bath home pairs clean-lined architecture with the relaxed rhythm of Key West. Cathedral ceilings elevate both bedrooms, while impact-rated windows and doors, wood flooring, built-in cabinetry, walk-in closets and thoughtful finishes bring refinement and ease to the approximately 1,409-square-foot interior. At the center of the home, a streamlined kitchen featuring Fisher & Paykel and Bosch appliances, a walk-in pantry and under-cabinet lighting is designed to transition effortlessly from morning coffee to evening cocktails. Outdoors, vibrant tropical landscaping surrounds a private heated pool with a tranquil water feature, secluded patio and outdoor shower. Dedicated parking for a golf cart or small vehicle, separate utility meters, a metal roof and an X flood-zone location provide the practical advantages buyers rarely find in Old Town. Part of an intimate three-residence setting, Unit C offers the privacy of a standalone home, the simplicity of condominium ownership and convenient access to Old Town's celebrated restaurants, galleries, waterfront and nightlife. Entirely new, quietly hidden and ready to enjoy from day one.

Full Property Details for 419 Simonton St #c

General

  • Price: $1,995,000
  • HOA FEE: $527
  • Taxes: $13,468 (2025)
  • Status: Active
  • Type: Condo
  • Source: 927
  • MLS ID: 621400
  • Updated: Today (9/25/2026)
  • Added to Site: Today

Interior

  • Interior Features: Walk-in Closet(s), Built-in Cabinets, Cathedral Ceilings, Drapes/Blinds Incl, Pantry, Smoke Alarms, Window Treatments
  • Appliances: Dishwasher, Disposal, Dryer, Freezer, Microwave, Oven, Range, Refrigerator, Washer
  • Flooring: Wood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 2

Additional Information

  • Pool: Yes
  • Pool Description: Heated, In Ground

Exterior

  • Exterior Features: Rain Gutters, Fencing, Outdoor Shower, Privacy Wall/Fence, Water Display
  • Deck/Patio: Patio
  • Porch/Patio/Deck: Patio

Parking

  • Parking Features: Assigned

Location

  • Area: 02 - Key West
  • County: Monroe
  • Subdivision: Old Town - Unlisted (1.0)

Community

  • Association: Yes
  • Assoc. Fees Include: Common Area Mnt
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Central Air, Ceiling Fans(s)

Structural Information

  • Architectural Style: Above Flood
  • Construction Status: New Construction
  • Construction: Frame, Hardi Board Siding
  • Roof: Metal
  • Windows/Doors: Impact Rstnce Doors, Impact Rstnce Window
  • Square Feet: 1,409
  • Sq. Ft. Source: Builder/Architect
  • Year Built: 2026
  • Property Condition: New Construction

Lot Features

  • Property View: No Waterview
  • Lot Size (Acres): 0.04
  • Lot Size (Sq. Ft.): 1,704
  • Lot Size Source: Property Data Card
  • Zoning: HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med

Water Features

  • Water View: Yes

Financial Considerations

  • Association Fee: Yes
  • Association Fee: $527
  • Tax Amount: $13,468.4
  • Tax Year: 2025
  • Terms: Cash, Conventional

Disclosures and Reports

  • Legal Description: 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 Or
  • Flood Zone: X
  • APN: 6340000000

Listed by Truman & Co. (KW), Team Kaufelt (305) 393-1267

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Listing agent

— 419 Simonton St #c —

  • Team Kaufelt

    Truman & Co. (KW)

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 419 Simonton St #c

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Horace O'bryant School
1105 Leon Street, Key West, FL 33040
6-81 mi
Gerald Adams Elementary School
5855 College Road, Key West, FL 33040
PK-53.9 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-121.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 419 Simonton St #c Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/25/2026
Listed
$1,995,000
50.57%
MLS
6/02/2026
Sold
$1,325,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 419 Simonton St #c

Year
Property Taxes
Change
Tax Assessment
Change
2025
$13,468
12%
$1,431,640
—
2024
$12,071
6%
$1,435,713
7%
2023
$11,335
22%
$1,346,829
48%
2021
$9,274
-7%
$912,475
-20%
2022
$10,024
8%
$1,138,871
31%
2021
$9,274
6%
$871,826
3%
2019
$8,724
-4%
$847,370
—
2018
$9,085
6%
$844,113
-1%
2017
$8,545
2%
$849,259
4%
2016
$8,410
5%
$815,283
29%
2015
$7,972
10%
$634,195
10%
2014
$7,247
2%
$576,541
4%
2013
$7,071
—
$553,353
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 419 Simonton St #c

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Truman & Co. (KW), Team Kaufelt (305) 393-1267

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419 Simonton Street #c, Key West, FL 33040 (MLS# 621400) is a Condo property with 2 bedrooms, 2 full bathrooms and 1 partial bathroom. 419 Simonton Street #c is currently listed for $1,995,000 and was received on September 25, 2026. Want to learn more about 419 Simonton Street #c? Do you have questions about finding other Condo real estate for sale in Key West? You can browse all Key West real estate or contact a Coldwell Banker agent to request more information.

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