Ad #7253783
MLS #618577
Some homes are built; others are authored. This is one of the
1014 Flagler Ave, Key West, Florida, 33040
$4,995,000
3Beds
4Baths
3,104Sqft
0.269Acres
About this property
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.
Property Features
3 Beds
4 Baths
3,104 Sqft
Built in 1998
0.269 Acres
1 Story
Off Street
Siding: CBS
Metal Roof
Has Swimming Pool
$28,772 / yr property tax
Monroe County
Martello Towers (1) Community
Additional Photos
Contact Information
Team Kaufelt
Truman & Co. Real Estate Services
305-393-1267
Location
Listing Agent: Team Kaufelt 305-393-1267
Broker: Truman & Co. Real Estate Services 305-292-2244 Listing Site
Copyright © 2026 Key West Association of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Broker: Truman & Co. Real Estate Services 305-292-2244 Listing Site
Copyright © 2026 Key West Association of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
BarrierFreeHome.com
Printed Jun 9, 2026
Photo Gallery
$4,995,000
3
Beds
4
Baths
3,104
Sqft
1014 Flagler Ave, Key West, Florida, 33040
By contacting this agent you agree to these Terms and Conditions.
MLS# 618577
Some homes are built; others are authored. This is one of the
$4,995,000
1014 Flagler Ave, Key West, Florida, 33040
3
Beds
4
Baths
3,104
Sqft
0.269
Acres
$4,995,000
1014 Flagler Ave, Key West, Florida, 33040
3 Beds
4 Baths
3,104 Sqft
0.269 Acres
Accessibility Features
Accessible Approach with Ramp
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.
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Property Details
HOME DETAILS
3 Beds
4 Baths
3,104 Sqft
Built in 1998
0.269 Acres
1 Story
EXTERIOR
Off Street
Siding: CBS
Metal Roof
Has Swimming Pool
FINANCIAL & COMMUNITY
$28,772 / yr property tax
Monroe County
Martello Towers (1) Community
See More Details
Location
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Ad Statistics
Ad Number
7253783
Viewed
0 time
Listing Status
Active
Added
Feb 10, 2026
Last Refresh
Jun 08, 2026 09:04:43 PM
Listing Information
Data Source
Key West Association of Realtors
Source Property ID
618577
Listing Agent: Team Kaufelt 305-393-1267
Broker: Truman & Co. Real Estate Services 305-292-2244 Listing Site
Copyright © 2026 Key West Association of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Broker: Truman & Co. Real Estate Services 305-292-2244 Listing Site
Copyright © 2026 Key West Association of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
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