1014 Flagler Ave Key West, FL 33040
Casa Marina NeighborhoodEstimated payment $32,294/month
About This Home
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.
Map
Home Details
Home Type
Single Family
Year Built
1998
Lot Details
0.26 Acres
Listing Details
- Property Type: Residential
- Vehicle Storage Cars: 1
- Year Built: 1998
- Building Style Above Flood: Yes
- Property Condition: Updated/Remodeled
- Property Sub Type: Single Family Residence
- Co List Office Mls Id: kwa.10208
- Co List Office Phone: 305-292-2244
- Subdivision Name: Martello Towers (1.0)
- Special Features: VirtualTour
Interior Features
- Interior Amenities: Built-in Cabinets, Sky Light(s), Walk-in Closet(s), Tray Ceilings
- Appliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Gas Appliances, Wine Cooler, Stainless Steel Appliance(s)
- Full Bathrooms: 3
- Half Bathrooms: 1
- Total Bedrooms: 3
Exterior Features
- Waterfront: No
- Exterior Features: Detached Guest Qtrs, Rain Gutters, Lighting, Privacy Wall/Fence, Sprinkler System, Water Display
- Construction Type: CBS
- Waterfront: None
- Roof: Metal Roof
Utilities
- Utilities: Elect Separate Meter, Cable Available, See Remarks
- Laundry Features: Laundry Room
- Cooling: Central Air, Wall/Window Unit(s), Ceiling Fans(s)
- Utilities: FKAA, Municipal Sewer, Elect Separate Meter, Cable Available, Other - See Remarks
Condo/Co-op/Association
- Pets Allowed: Yes
Lot Info
- Parcel Number: 00058260-000000
- Lot Size Sq Ft: 11730.0
Rental Info
- Furnished: Unfurnished
Tax Info
- Tax Year: 2025
- Tax Annual Amount: 28771.56
Home Values in the Area
Average Home Value in this Area
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 05/01/2026 05/01/26 | Price Changed | $5,095,000 | -2.6% | $1,641 / Sq Ft |
| 04/21/2026 04/21/26 | Price Changed | $5,230,000 | -12.8% | $1,685 / Sq Ft |
| 03/25/2026 03/25/26 | Price Changed | $5,995,000 | -7.7% | $1,931 / Sq Ft |
| 02/10/2026 02/10/26 | For Sale | $6,495,000 | -- | $2,092 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $2,600,000 | -- | |
| Warranty Deed | $2,600,000 | -- | |
| Quit Claim Deed | -- | -- |
Source: Key West Association of REALTORS®
MLS Number: 618577
APN: 00058260-000000
- 924 Flagler Ave
- 906 Johnson St
- 1020 von Phister St
- 905 von Phister St
- 1421 Reynolds St
- 1420 Whalton St
- 1101 Casa Marina Ct
- 1126 von Phister St
- 1120 Washington St Unit SU
- 1416 White St
- 1501 White St
- 1100 South St
- 816 South St Unit 4
- 809 Washington St Unit 102
- 1006 Seminary St
- 1320 Grinnell St
- 804 South St Unit 3
- 1311 Grinnell St
- 1120 Seminary St
- 928 United St
- 1505 White St Unit Efficiency
- 1211 Varela St
- 634 Louisa St
- 1500-105 Atlantic Blvd
- 1209 Pearl St Unit 1209 Pearl Downstairs
- 1315 Whitehead St Unit SI ID1297834P
- 818 White St Unit 5
- 817 White St
- 1409 Olivia St
- 415 Julia St
- 1312 Petronia St
- 311 Amelia St Unit 1
- 816 Center St
- 710 Whitmarsh Ln
- 629 Elizabeth St Unit SI ID1297833P
- 918 Southard St Unit 205, Unit 205
- 725 Southard St
- 750 Fort St
- 536 Fleming St Unit SI FL2-ID1297611P
- 717 Emma St Unit C
Ask me questions while you tour the home.