1014 Flagler Avenue 618577
Active 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. This three-bedroom, three-and-a-half-bath estate has been meticulously restored with exceptional care, reflecting the same restraint, intention, and pride that characterized Wolkowsky’s legacy. Built in 1999 and comprehensively updated from the ground up, the residence has been 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. A thoughtfully designed chef’s kitchen anchors the home, offering both beauty and functionality for everyday living and entertaining. Set on a rare, fully walled corner double lot over 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. Located on one of the most desirable blocks in one of Key West’s premier neighborhoods, this preserved architectural landmark stands among the island’s most exceptional residential offerings, where privacy, scale, and legacy converge.
| Price: | $4,995,000 |
|---|---|
| Address: | 1014 Flagler Avenue |
| City: | Key West |
| State: | Florida |
| Zip Code: | 33040 |
| Subdivision: | Martello Towers (1.0) |
| MLS: | 618577 |
| Year Built: | 1998 |
| Square Feet: | 3,104 |
| Bedrooms: | 3 |
| Bathrooms: | 4 |
| Half Bathrooms: | 1 |
| roof2: | Metal Roof |
|---|---|
| title: | Negotiable |
| cooling: | Central Air, Wall/Window Unit(s), Ceiling Fans(s) |
| dockage: | None |
| taxYear: | 2025 |
| landSize: | Less Than 1/4 Acre |
| preWired: | Cable |
| coolingYN: | yes |
| furnished: | Unfurnished |
| mlsStatus: | Active |
| utilities: | Elect Separate Meter, Cable Available, See Remarks |
| waterview: | No Waterview |
| appliances: | Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Gas Appliances, Wine Cooler, Stainless Steel Appliance(s) |
| postalCity: | KEY WEST |
| utilities2: | FKAA, Municipal Sewer, Elect Separate Meter, Cable Available, Other - See Remarks |
| waterfront: | None |
| lotSizeArea: | 11730 |
| petsAllowed: | Yes |
| listingTerms: | Cash, Conventional |
| lotSizeUnits: | Square Feet |
| mlsAreaMajor: | 02 - Key West |
| mlsAreaMinor: | 02 - Key West |
| poolFeatures: | In Ground |
| waterfrontYN: | no |
| windowsDoors: | Glass Doors, Sliding Glass Doors, Impact Rstnce Window, Impact Rstnce Doors |
| associationYN: | no |
| lotSizeSource: | Appraisal |
| poolPrivateYN: | yes |
| poolInfoHeated: | Yes |
| specialtyRooms: | Laundry Room |
| vehicleStorage: | Off Street Parking |
| laundryFeatures: | Laundry Room |
| taxAnnualAmount: | 28771.56 |
| attachedGarageYN: | no |
| exteriorFeatures: | Detached Guest Qtrs, Rain Gutters, Lighting, Privacy Wall/Fence, Sprinkler System, Water Display |
| interiorFeatures: | Built-in Cabinets, Sky Light(s), Walk-in Closet(s), Tray Ceilings |
| accessibilityFeat: | Wheelchair Ramp |
| communityFeatures: | Fire Hydrant, Beach, Bike Paths |
| interiorFeatures2: | Split Bedroom, Built-in Cabinets, Sky Light(s), Smoke Alarms, Walk-in Closet(s), Other, Tray Ceilings |
| lotSizeSquareFeet: | 11730 |
| newConstructionYN: | no |
| propertyCondition: | Updated/Remodeled |
| architecturalStyle: | Other Bldg Style |
| buildingAreaSource: | Appraisal |
| accessibilityFeatures: | Wheelchair Ramp |
| bathroomsTotalDecimal: | 3.5 |
| constructionMaterials: | CBS |
| patioAndPorchFeatures: | Open Porch/Balcony, Patio |
| associationFeeIncludes: | None |
| financialStatusBankOwned: | No |
| contractInformationBankOwned: | No |
| locationTaxLegalKwNeighborhood: | Casa Marina |
| associationInfo1stRightOfRefusal: | No |
| financialStatusPotentialShortSale: | No |
| locationTaxLegalMarathonNeighborhood: | N/A |
| contractInformationPotentialShortSale: | No |
©2026 Florida Keys MLS, Inc. The data relating to real estate for sale on this web site comes in part from the Florida Keys Multiple Listing Service. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Information is deemed reliable but not guaranteed. Data last updated: Monday, July 6th, 2026 at 03:41:19 PM.
Data services provided by IDX Broker
Listed by: Truman & Co. (KW) (305) 393-1267
