Ad #7253783
MLS #618577
A Key West original. 1014 Flagler Avenue is a storied Casa
1014 Flagler Ave, Key West, FL 33040
$4,700,000
3Beds
4Baths
3,104Sqft
0.27Acres
About this property
A Key West original. 1014 Flagler Avenue is a storied Casa Marina residence shaped by legendary Key West developer David Wolkowsky and set behind privacy walls on an exceptional 11,730-square-foot corner double lot. Some homes are built. Others are authored. At its center: 40 feet of pool, surrounded by mature tropical landscaping and hardscape by Craig Reynolds Landscape Architecture, creating the feel of a private compound hidden in plain sight. Inside, the scale shifts again with 22-foot ceilings, walls of glass, 10-foot doors and sliders, custom teak, and a dramatic floor-to-ceiling library. The main residence offers two bedrooms and two-and-a-half baths, anchored by a chef's kitchen and expansive indoor-outdoor living. Extensive updates include new systems and impact-rated windows and doors. A completely separate one-bedroom guest house adds its own kitchen, laundry and private garden. 3 bedrooms. 3.5 baths. 3,104 square feet. 11,730 square feet of land. 40 feet of pool. In a market full of beautiful houses, 1014 Flagler offers something harder to replicate: a point of view.
Property Features
3 Beds
4 Baths
3,104 Sqft
Built in 1998
0.27 Acres
View Type: Water
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 Oct 22, 2026
Photo Gallery
$4,700,000
3
Beds
4
Baths
3,104
Sqft
1014 Flagler Ave, Key West, FL 33040
By contacting this agent you agree to these Terms and Conditions.
MLS# 618577
$4,700,000
1014 Flagler Ave, Key West, FL 33040
3
Beds
4
Baths
3,104
Sqft
0.27
Acres
3 Beds
4 Baths
3,104 Sqft
0.27 Acres
Accessibility Features
Accessible Approach with Ramp
A Key West original. 1014 Flagler Avenue is a storied Casa
A Key West original. 1014 Flagler Avenue is a storied Casa Marina residence shaped by legendary Key West developer David Wolkowsky and set behind privacy walls on an exceptional 11,730-square-foot corner double lot. Some homes are built. Others are authored. At its center: 40 feet of pool, surrounded by mature tropical landscaping and hardscape by Craig Reynolds Landscape Architecture, creating the feel of a private compound hidden in plain sight. Inside, the scale shifts again with 22-foot ceilings, walls of glass, 10-foot doors and sliders, custom teak, and a dramatic floor-to-ceiling library. The main residence offers two bedrooms and two-and-a-half baths, anchored by a chef's kitchen and expansive indoor-outdoor living. Extensive updates include new systems and impact-rated windows and doors. A completely separate one-bedroom guest house adds its own kitchen, laundry and private garden. 3 bedrooms. 3.5 baths. 3,104 square feet. 11,730 square feet of land. 40 feet of pool. In a market full of beautiful houses, 1014 Flagler offers something harder to replicate: a point of view.
254 days
on BarrierFreeHome.com
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Property Details
HOME DETAILS
3 Beds
4 Baths
3,104 Sqft
Built in 1998
0.27 Acres
BARRIERFREE ACCESS & VIEW
View Type: Water
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
43 times
Listing Status
Active
Added
Feb 10, 2026
Last Refreshed
Oct 22, 2026 02:03:58 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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