Residential

1014 Flagler Avenue, Key West

$4,700,000.00

Bedroom 3 bedrooms
Full Bathroom 3 full baths
Half Baths 1 half baths

  • MLS #: 618577
  • Address: 1014 Flagler Avenue, Key West, FL 33040
  • Date Listed: 2/10/2026
  • Days on Market: 245
  • SQFT: 3104
  • Acres: 0.27
  • Restrictions: No
  • Subdivision: Martello Towers (1.0)

Location Location

Agent Comments Agent Comments
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.

Amenities Amenities
  • Stainless Steel Appliance(s)
  • Dishwasher
  • Disposal
  • Dryer
  • Freezer
  • Gas Appliances
  • Microwave
  • Oven
  • Range
  • Refrigerator
  • Washer
  • Wine Cooler

Interior Features Interior Features
  • Cool System: Wall/Window Unit(s), Central Air, Ceiling Fans(s)
  • Rooms: Laundry Room
  • Interior: Walk-in Closet(s), Built-in Cabinets, Sky Light(s), Smoke Alarms, Split Bedroom, Tray Ceilings, Other

Exterior Features Exterior Features
  • Parking: Off Street
  • Roof: Metal
  • Pool: Yes
  • Exterior: Rain Gutters, Lighting, Detached Guest Qtrs, Privacy Wall/Fence, Sprinkler System, Water Display

Additional Features Additional Features
  • County: Monroe
  • Property Type: Single Family Residence
  • Tax Number: 00058260-000000
  • Water/Sewer: Cable Available, Elect Separate Meter, FKAA, Municipal Sewer, Other - See Remarks2
  • Stories: 1 Story
  • Year Built: 1998