1014 Flagler Avenue, Key West, FL 33040

bedrooms 3
bathrooms 4
|House
NZD $8,404,714
USD $4,700,000
Published on: 11 Feb 2026
Last updated on: 27 Oct 2026
1014 Flagler Avenue, Key West, FL 33040
1014 Flagler Avenue, Key West, FL 33040
1014 Flagler Avenue, Key West, FL 33040
+37
1014 Flagler Avenue, Key West, FL 33040
  • 37
Property ID: 110105522774
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Residential, Key West, FL

1014 Flagler Avenue, Key West, FL 33040
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.

Property Details

Basic Info

Property Type
House
Listing Status
Active
Land Size
1,089.82 m2
Building Size
288.37 m2
Year Built
1998
Rooms
3 bedroom(s), 4 bathroom(s)
Architecture Style
Other
County
Monroe
Parcel ID
00058260-000000
Provider
Key West Association of Realtors
Subdivision
Martello Towers (1.0)
Brokerage Office Name
Truman & Co. Real Estate Services
Brokerage Office Phone
(305) 292-2244
Neighbourhoods
Martello Towers (1.0)
Address
1014 Flagler Avenue, Key West, FL 33040

Tax History

YearTax amount
2025USD $28772NZD $51,451*

*Converted price in your currency provided by Open Exchange Rates. Exchange rates are subject to continuous change. Neither realestate.co.nz nor its affiliates guarantee that the conversion reflects current conversion rates and are not responsible for any inaccuracies. realestate.co.nz recommends that you independently verify any information before relying on it.

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Team Kaufelt
Truman & Co. (KW)
1205 Truman Avenue , Key West, FL 33040
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1205 Truman Avenue , Key West, FL 33040
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      Property ID: 110105522774

      Original Property ID: 3yd-KWARFL-618577
      Data provided by Key West Association of Realtors, MLS #: 618577
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      Copyright © 2026 Key West Association of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.