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$3,180,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,373 Sq. Ft.
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Classic Key West charm and sophistication abound, with traditional grace yet modern conveniences, this wasn't just a simple remodel. This was a carefully thought out, complete and careful renovation of this Old Town treasure. A worry free and easily maintained 3 bedroom, 2 and & ½ bath home, master bath ensuite, on one of the most prestigious streets in Key West, this home is constantly photographed, whether it's the location, the style, or the carefully chosen color pallet by the current owners, we're not sure, but regardless, many are drawn to this home and its beautifully tailored look. Whether you want to people watch on the front porch and sip your coffee or cocktail, or withdraw to the secluded private back yard and lounge around the pool reading a Hemingway novel, who's legendary home is a mere stroll moments away out the gate one direction, or go the opposite direction to the Atlantic Ocean and the Southernmost Point Buoy, everything Key West is only minutes away from this front door, your front door. Your new home. And by new, that's what we mean-this home was carefully and completely renovated in the last couple years, essentially creating a classic Key West house, with all the comfort and benefits of a new home. A completely custom Bosch appliance filled kitchen, with virtually every modern convenience a new home would hold. Modern upscale interior, zoned central A/C system with whole-house ventilating dehumidifier, advanced internet modem and router system, maintenance free composite decking, complete security and camera system, are just a few of the extra steps the owners took when creating a time-honored but luxurious, self contained and above the norm renovation of this truly one of a kind Key West home. Lets set up your private showing today.

Full Property Details for 1019 Whitehead St

General

  • Price: $3,180,000
  • Taxes: $12,231 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 620747
  • Updated: 7/26/2026
  • Added to Site: 28 day(s) ago

Interior

  • Interior Features: Walk-in Closet(s), Cathedral Ceilings, Drapes/Blinds Incl, Quartz Countertops, Security System, Smoke Alarms, Window Treatments, Smart Thermostat
  • Appliances: Stainless Steel Appliance(s), Dishwasher, Disposal, Dryer, Microwave, Oven, Refrigerator, Washer
  • Flooring: Tile

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 3

Additional Information

  • Pool: Yes
  • Pool Description: Concrete, Heated, In Ground, Decked
  • Security/Safety: On Premises System

Exterior

  • Exterior Features: Rain Gutters, Fencing, Privacy Wall/Fence, Storage
  • Deck/Patio: Deck, Patio
  • Porch/Patio/Deck: Deck, Patio

Parking

  • Parking Features: Off Street

Location

  • Area: 01 - Key West
  • County: Monroe
  • Subdivision: Old Town - Unrecord (1.0)

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

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

Structural Information

  • Architectural Style: Above Flood, Conch
  • Construction Status: Updated/Remodeled
  • Construction: Frame
  • Roof: Metal
  • Windows/Doors: Double Hung Windows, French Doors, Glass Doors, Impact Rstnce Doors, Impact Rstnce Window, Shutters
  • Square Feet: 1,373
  • Sq. Ft. Source: Property Data Card
  • Year Built: 1928
  • Property Condition: Updated/Remodeled

Lot Features

  • Property View: No Waterview
  • Lot Size (Acres): 0.05
  • Lot Size (Sq. Ft.): 2,430
  • Lot Dimensions: 40 x 65
  • Zoning: HMDR - Historic Medium Density Residential

Water Features

  • Water View: Yes

Financial Considerations

  • Tax Amount: $12,231.1
  • Tax Year: 2025
  • Terms: Cash, Conventional, VA Loan, FHA

Disclosures and Reports

  • Legal Description: Kw Pt Subs 3 And 4 Pt Lt 4 Sqr 3 Tr 11 Or67-439/40 Or647-10 Or1183-2183/84 Or1199-594/95 Or1735-1231/33 Or1872-25/26 Or2
  • Flood Zone: X Flood Zone
  • APN: 27390000000

Listed by Real Estate Management of Key West, LLC, Wade J Meyer (305) 432-6373

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Listing agent

— 1019 Whitehead St —

  • Wade J Meyer

    Real Estate Management of Key West, LLC

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 1019 Whitehead St

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
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-121.5 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 1019 Whitehead St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/25/2026
Listed
$3,180,000
127.14%
MLS
9/27/2021
Sold
$1,400,000
—
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 1019 Whitehead St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$12,231
—
$1,418,446
-2%
2024
$12,248
5%
$1,448,096
1%
2023
$11,659
39%
$1,429,971
54%
2021
$8,376
-17%
$931,320
-21%
2022
$10,126
21%
$1,172,797
44%
2021
$8,376
6%
$812,252
-5%
2019
$7,932
3%
$852,363
6%
2018
$7,688
-2%
$807,741
-1%
2017
$7,868
22%
$813,037
31%
2016
$6,458
14%
$622,647
19%
2015
$5,656
1%
$524,960
5%
2014
$5,601
6%
$498,592
8%
2013
$5,275
—
$461,401
—
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.

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NMLS#: 1598647

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Listed by Real Estate Management of Key West, LLC, Wade J Meyer (305) 432-6373

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1019 Whitehead Street, Key West, FL 33040 (MLS# 620747) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 1019 Whitehead Street is currently listed for $3,180,000 and was received on July 25, 2026. Want to learn more about 1019 Whitehead Street? Do you have questions about finding other Single Family 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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