1014 Flagler Avenue, Key West, FL 33040
$5,230,000
Property Type:
Residential
Bedrooms:
3
Baths:
4
Square Footage:
3,104
Lot Size (sq. ft.):
11,730
Status:
Active
Current Price:
$5,230,000
List Date:
2/10/2026
Last Modified:
4/21/2026
Overview
Description
...
(Read more)
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.
Open Houses
- Sunday, April 26, 12:00 pm - 2:00 pm
Listing Details MLS# 618577
Location, Tax & Legal
- Street #
- 1014
- Street Name
- Flagler
- Street Suffix
- Avenue
- Key/Island
- Key West
- State/Province
- FL
- Zip Code
- 33040
- County
- Monroe
- Subdivision
- Martello Towers (1.0)
- Area
- 02 - Key West
- KW Neighborhood
- Casa Marina
- City
- KEY WEST
- Off Shore Island
- No
- Mile Marker
- 1
- Marathon Neighborhood
- N/A
- Side
- Ocean
- Flood Zone
- AE
- Alternate Key #
- 1058742
- Parcel #
- 00058260-000000
- Zoning
- SF - Single Family
- Deed Restrictions
- No
- Legal
- KW MARTELLO TOWERS PB1-140 LOTS 1-2-3-4 AND PT LOTS 20 AND 21 SQ 2 TR 27 G31-441/444 OR470-742D/C OR1009-253(AFFD) OR10
- Taxes
- 28771.56
- Tax Year
- 2025
- Pub Sewer HkUp
- Yes
Contract Information
- Listing Board
- Key West Association
- Potential Short Sale
- No
- Bank Owned
- No
General Property Description
- Realtor.COM Type
- Residential - Single Family
- Style
- Single Family
- Waterfront
- No
- Pool
- Yes
- Year Built
- 1998
- Lot SqFt
- 11730
- Lot Sqft Source
- Appraisal
- Living Apx SqFt
- 3104
- SqFt Source
- Appraisal
- Total Bedrooms
- 3
- Full Baths
- 3
- Half Baths
- Yes
- Total Baths
- 4
- Rentals Allowed
- With Restrictions
- Control Depth
- 0
- Total Units
- 0
Association Info
- Mandatory Home Owners Asc
- No
- 1st Right of Refusal
- No
- Association Fee $
- 0
Building Style
- Above Flood
- Yes
- Stories
- 1 Story
- Other Bldg Style
- Yes
More Information
Vehicle Storage
- Car(s)
- Yes
- Off Street Parking
- Yes
Pool Info
- Heated
- Yes
- In Ground
- Yes
Financial Status
- Auction
- No
- Bank Owned
- No
- Potential Short Sale
- No
Remarks & Misc
- Remarks – Consumer
- 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.
License Info
- Non Trans Rntl Lic
- Yes
Fee Includes
- None
- Yes
Dockage
- None
- Yes
Tax Exemptions
- None
- Yes
Appliances
- Dishwasher
- Yes
- Disposal
- Yes
- Dryer
- Yes
- Freezer
- Yes
- Gas Appliances
- Yes
- Microwave
- Yes
- Oven
- Yes
- Range
- Yes
- Refrigerator
- Yes
- Stainless Steel Appliance(s)
- Yes
- Washer
- Yes
- Wine Cooler
- Yes
Pets
- Pets Allowed
- Yes
Cooling
- Ceiling Fans(s)
- Yes
- Central Air
- Yes
- Wall/Window Unit(s)
- Yes
Waterfront
- None
- Yes
Waterview
- No Waterview
- Yes
Neighborhood Feature
- Beach
- Yes
- Bike Paths
- Yes
- Fire Hydrant
- Yes
- Tennis Courts
- Yes
Interior Features
- Built-in Cabinets
- Yes
- Sky Light(s)
- Yes
- Smoke Alarms
- Yes
- Split Bedroom
- Yes
- Tray Ceilings
- Yes
- Walk-in Closet(s)
- Yes
- Other
- Yes
Property Condition
- Updated/Remodeled
- Yes
Specialty Rooms
- Laundry Room
- Yes
Windows/Doors
- Glass Doors
- Yes
- Impact Rstnce Doors
- Yes
- Impact Rstnce Window
- Yes
- Sliding Glass Doors
- Yes
Construction
- CBS
- Yes
Land Size
- Less Than 1/4 Acre
- Yes
Furnished
- Unfurnished
- Yes
Terms
- Cash
- Yes
- Conventional
- Yes
Utilities
- Cable Available
- Yes
- Elect Separate Meter
- Yes
- FKAA
- Yes
- Municipal Sewer
- Yes
- Other - See Remarks
- Yes
Porch/Balcony
- Open Porch/Balcony
- Yes
- Patio
- Yes
Title
- Negotiable
- Yes
Exterior Features
- Detached Guest Qtrs
- Yes
- Lighting
- Yes
- Privacy Wall/Fence
- Yes
- Rain Gutters
- Yes
- Sprinkler System
- Yes
- Water Display
- Yes
Pre-Wired
- Cable
- Yes
Roof
- Metal Roof
- Yes
Accessibility Feat
- Wheelchair Ramp
- Yes
Property Features
Fee Includes:
None
Tax Exemptions:
None
License Info:
Non Trans Rntl Lic
Waterfront:
None
Waterview:
No Waterview
Dockage:
None
Property Condition:
Updated/Remodeled
Building Style:
Other Bldg Style
Vehicle Storage:
Off Street Parking
Furnished:
Unfurnished
Cooling:
Ceiling Fans(s); Central Air; Wall/Window Unit(s)
Utilities:
Cable Available; Elect Separate Meter; FKAA; Municipal Sewer; Other - See Remarks
Interior Features:
Built-in Cabinets; Sky Light(s); Smoke Alarms; Split Bedroom; Tray Ceilings; Walk-in Closet(s); Other
Pre-Wired:
Cable
Specialty Rooms:
Laundry Room
Appliances:
Dishwasher; Disposal; Dryer; Freezer; Gas Appliances; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer; Wine Cooler
Exterior Features:
Detached Guest Qtrs; Lighting; Privacy Wall/Fence; Rain Gutters; Sprinkler System; Water Display
Accessibility Feat:
Wheelchair Ramp
Pool Info:
In Ground
Construction:
CBS
Roof:
Metal Roof
Pets:
Pets Allowed
Neighborhood Feature:
Beach; Bike Paths; Fire Hydrant; Tennis Courts
Land Size:
Less Than 1/4 Acre
Terms:
Cash; Conventional
Title:
Negotiable
Listing Office:
Truman & Co. (KW)
Last Updated: April - 21 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.
