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3 Beds
4 Baths
3,104 sqft

$4,700,000

1014 Flagler Avenue, Key West FL, 33040

Price per sqft$1,514.18
Built in1998
Property size3,104 sqft
Property typeResidential

Overview

Active

Listed Oct 1, 2026

Updated 17h ago

A Key West original. 1014 Flagler Avenue is a storied Casa Marina residence shaped by legendary Key West developer David Wolkowsky and set behind privacy walls on an exceptional 11,730-square-foot corner double lot. Some homes are built. Others are authored. At its center: 40 feet of pool, surrounded by mature tropical landscaping and hardscape by Craig Reynolds Landscape Architecture, creating the feel of a private compound hidden in plain sight. Inside, the scale shifts again with 22-foot ceilings, walls of glass, 10-foot doors and sliders, custom teak, and a dramatic floor-to-ceiling library. The main residence offers two bedrooms and two-and-a-half baths, anchored by a chef's kitchen and expansive indoor-outdoor living. Extensive updates include new systems and impact-rated windows and doors. A completely separate one-bedroom guest house adds its own kitchen, laundry and private garden. 3 bedrooms. 3.5 baths. 3,104 square feet. 11,730 square feet of land. 40 feet of pool. In a market full of beautiful houses, 1014 Flagler offers something harder to replicate: a point of view.

$31,269/mo

Est. mortgage payment based on a $4,700,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
618577

Interior Features

Bedrooms
3
Bathrooms
4
Cooling
Yes
Basement
No

Exterior Features

Lot Size
0.27 Acres

Other Property Details

Taxes
$28,772
Tax Frequency
Annually
View
Yes
Pets Allowed
Yes
Pool
Yes
MLS provider logo

Listed by Team Kaufelt with Truman & Co. (KW)
Listing Contact: 305-393-1267 

The IDX display contains information sourced from the Florida Keys Board of REALTORS® as of 10/2/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

©2026 Florida Keys Board of REALTORS® all rights reserved.

Data last updated on 10/2/2026 at 5:08 AM UTC

 

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