About 1014 Flagler Avenue
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.
Features of 1014 Flagler Avenue
| MLS® # | 618577 |
|---|---|
| Price | $4,700,000 |
| Bedrooms | 3 |
| Bathrooms | 4.00 |
| Full Baths | 3 |
| Half Baths | 1 |
| Square Footage | 3,104 |
| Year Built | 1998 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Other Bldg Style |
| Status | Active |
Community Information
| Address | 1014 Flagler Avenue |
|---|---|
| Area | 02 - Key West |
| Subdivision | Martello Towers (1.0) |
| City | Key West |
| County | Monroe |
| State | FL |
| Zip Code | 33040 |
Amenities
| Amenities | Fire Hydrant, Beach, Bike Paths |
|---|---|
| Utilities | FKAA, Municipal Sewer, Elect Separate Meter, Cable Available, Other - See Remarks |
| Parking Spaces | 1 |
| Parking | Off Street Parking |
| View | No Waterview |
| Is Waterfront | No |
| Waterfront | None |
| Has Pool | Yes |
| Pool | In Ground |
Interior
| Interior Features | Split Bedroom, Built-in Cabinets, Sky Light(s), Smoke Alarms, Walk-in Closet(s), Other, Tray Ceilings |
|---|---|
| Appliances | Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Gas Appliances, Wine Cooler, Stainless Steel Appliance(s) |
| Cooling | Central Air, Wall/Window Unit(s), Ceiling Fans(s) |
| Fireplace | No |
| Has Basement | No |
Exterior
| Exterior Features | Detached Guest Qtrs, Rain Gutters, Lighting, Privacy Wall/Fence, Sprinkler System, Water Display |
|---|---|
| Lot Description | Less Than 1/4 Acre |
| Windows | Glass Doors, Sliding Glass Doors, Impact Rstnce Window, Impact Rstnce Doors |
| Roof | Metal Roof |
| Construction | CBS |
Additional Information
| Date Listed | February 10th, 2026 |
|---|---|
| Days on Market | 147 |
| Zoning | SF - Single Family |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Agent | Team Kaufelt |
|---|---|
| Office | Truman & Co. (KW) |