1014 Flagler Avenue, KEY WEST, FL

$5,995,000

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3

Beds

4

Baths

3,104

Square feet

About 1014 Flagler Avenue

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.

Features of 1014 Flagler Avenue

MLS® # 618577
Price $5,995,000
Bedrooms 3
Bathrooms 4.00
Full Baths 3
Half Baths 1
Square Footage 3,104
Year Built 1998
Type Residential
Sub-Type Single Family
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 Tennis Courts, Bike Paths, Beach, Fire Hydrant
Utilities FKAA, Elect Separate Meter, Other - See Remarks, Cable Available, Municipal Sewer
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, Tray Ceilings, Built-in Cabinets, Other, Walk-in Closet(s), Smoke Alarms, Sky Light(s)
Appliances Washer, Stainless Steel Appliance(s), Wine Cooler, Gas Appliances, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Cooling Central Air, Ceiling Fans(s), Wall/Window Unit(s)
Fireplace No
Stories 1 Story

Exterior

Exterior Features Detached Guest Qtrs, Water Display, Sprinkler System, Privacy Wall/Fence, Lighting, Rain Gutters
Lot Description Less Than 1/4 Acre
Windows Glass Doors, Impact Rstnce Window, Impact Rstnce Doors, Sliding Glass Doors
Roof Metal Roof
Construction CBS

Additional Information

Date Listed February 10th, 2026
Days on Market 59
Zoning SF - Single Family
Short Sale No
RE / Bank Owned No
HOA Fees 0.00

Listing Details

AgentTeam Kaufelt
OfficeTruman & Co. (KW)

Listing Map

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