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Ad #7253783
MLS #618577
Listing photo

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

Additional listing photo 1
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Contact Information

Team Kaufelt

Truman & Co. Real Estate Services

305-393-1267

Location

Map
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.
BarrierFreeHome.com
Printed Jun 9, 2026

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$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.
Home Florida Key West
Some homes are built; others are authored. This is one of the
Some homes are built; others are authored. This is one of the
Some homes are built; others are authored. This is one of the
Some homes are built; others are authored. This is one of the
Some homes are built; others are authored. This is one of the
MLS# 618577
Home For Sale

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
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Listing Status
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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.

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Alabama Alaska Arizona Arkansas California Colorado Connecticut Delaware Florida Georgia Hawaii Idaho Illinois Indiana Iowa Kansas Kentucky Louisiana Maine Maryland Massachusetts Michigan Minnesota Mississippi Missouri Montana Nebraska Nevada New Hampshire New Jersey New Mexico New York North Carolina North Dakota Ohio Oklahoma Oregon Pennsylvania Rhode Island South Carolina South Dakota Tennessee Texas Utah Vermont Virginia Washington West Virginia Wisconsin Wyoming
SERVICES
Buy Buy Advertise
COMPANY
Testimonials About Us Office Locations
SUPPORT
Help Contact Us
ADDITIONAL MARKETS
LakeHouse.com BeachHouse.com GolfHomes.com
SUBSCRIBE
Receive notifications for new listings
Subscribe

Dream Home Network Inc.

is committed to ensuring digital accessibility and property listings for individuals with disabilities. All information provided is deemed reliable but is not guaranteed and should be independently verified. We are continuously working to improve the accessibility of our web experience for everyone, and we welcome feedback and accommodation requests. If you wish to report an issue or seek an accommodation, please let us know.

Dream Home Network Inc. Sells leads to DHN Realty Inc. who holds real estate brokerage licenses in Alabama. Listing agents will be sent notification copy of leads on their listings where Dream Home Network Inc. is provided listings via our Feed Provider as required.

© 1997 - 2026 Wheelchair-accessible Housing & Universal Design Homes at Barrier Free Home
Part of Dream Home Network, Inc.
Last updated on 2026.06.09
Terms & Policy