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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

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, fu ...

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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.