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$4,700,000
Preferred partner

Kinsfolk Signature Realty
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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.
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Contact agent
| Date | Event | Price |
|---|---|---|
| 10/8/2026 | Listed for sale | $4,700,000$1514/sqft |
Team Kaufelt
Truman & Co. (KW)
Brokerage Phone: 305-292-2244
Source: Florida Keys MLS · MLS #618577
Data Powered by Home Junction, Inc.
KEY WEST MONTESSORI CHARTER SCHOOL, INC
Elementary · 0.3 mi
MAY SANDS MONTESSORI SCHOOL
Elementary · 0.4 mi
HORACE O'BRYANT SCHOOL
Elementary · 0.6 mi
Peanut Butter N What
0.0 mi
Artisan Sunday Market
0.3 mi
Fausto's Food Palace
0.4 mi
Tropical Watersports On The Beach
0.1 mi
The Hummus Factory
0.3 mi
Cafe Sole Office
0.3 mi
Astro City Playground
0.1 mi
Key West Garden Club
0.2 mi
CB Harvey Rest Beach Park
0.3 mi
Higgs Beach
0.2 mi
Dog Beach
0.3 mi
South Beach
0.5 mi
Nearby amenity locations include data © OpenStreetMap contributors.