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1014 flagler avenue

Key West, FL 33040

$6,495,000

3 BEDS 4 BATHS
3,104 SQFT
Residential - Single Family
Image 1: 1014 FLAGLER AV HD-53
Image 2: 1014 FLAGLER AV HD-17
Image 3: 1014 FLAGLER AV HD-16
Image 4: 1014 FLAGLER AV HD-22
Bedrooms 3
Total Baths 4
Full Baths 3
Square Feet 3104
Status Active
MLS # 618577
County Monroe
More Info
Category Residential - Single Family
Status Active
Square Feet 3104
MLS # 618577
County Monroe
Some homes are built; others are authored. This is one of the latter--an architectural landmark shaped by David Wolkowsky, whose vision helped define Key West itself, with architecture by award-winning architect Rob Delaune that thoughtfully carries that legacy forward. This three-bedroom, three-and-a-half-bath estate, built in 1999 and comprehensively updated from the ground up, has been meticulously restored to museum-level standards with all-new systems, impact-rated windows and doors, and 10-foot doors and sliders throughout. The dramatic main living space is defined by soaring 22-foot ceilings, refinished custom teak columns and doors, expansive walls of glass, and a striking floor-to-ceiling built-in bookcase spanning the full height and length of the living room wall, complete with a concealed automatic disappearing television, while a thoughtfully designed chef's kitchen anchors the home with both beauty and functionality for everyday living and entertaining. Set on a rare, fully walled corner double lot spanning more than 11,700 square feet, the property is enveloped by indigenous and exotic landscaping and hardscape design by Craig Reynolds Landscape Architecture, creating a private, resort-style environment centered around an oversized 40′ x 20′ custom heated swimming pool and generous outdoor living areas--an extraordinary sense of scale and seclusion in the heart of Casa Marina. The main residence offers two bedrooms and two-and-a-half bathrooms, complemented by a separate one-bedroom, one-bath guest house with its own kitchen, washer and dryer, and private garden, providing ideal accommodations for guests, extended family, or additional flexibility, all located on one of the most desirable blocks in one of Key West's premier neighborhoods, where privacy, scale, architectural pedigree, and legacy converge.
Location not available

Exterior Features

  • Style Single Family
  • Construction Single Family
  • Siding CBS
  • Exterior Detached Guest Qtrs, Water Display, Sprinkler System, Privacy Wall/Fence, Lighting, Rain Gutters
  • Roof Metal Roof
  • Garage Yes
  • Water FKAA, Elect Separate Meter, Other - See Remarks, Cable Available, Municipal Sewer
  • Sewer FKAA, Elect Separate Meter, Other - See Remarks, Cable Available, Municipal Sewer

Interior Features

  • Appliances Washer, Stainless Steel Appliance(s), Wine Cooler, Gas Appliances, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
  • Cooling Central Air, Ceiling Fans(s), Wall/Window Unit(s)
  • Living Area 3,104 SQFT
  • Year Built 1998

Financial Information

  • Parcel ID 1058742
  • Zoning SF - Single Family

Additional Services

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Listing Information

Listing Provided Courtesy of Truman & Co. (KW)
Listing Agent Team Kaufelt
Florida Keys, MLS
Listing data is current as of 03/16/2026.

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