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About This Home

This 3-bedroom, 4-bathroom single family at 1014 Flagler Avenue in Key West, FL is listed for $4,995,000 ($1,609 per sqft). Built in 1998, the home offers 3,104 sqft of living space on a 0.27 acres lot.

Agent Description

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.

Key Features

  • Built in 1998
  • 0.27 acre lot
  • Private pool

Property Details

1 story
3 full, 1 half
1998

Amenities

PoolViewA/C

Monthly Cost Estimate

$26,714/mo

20% down · 6.5% · 30 years

Principal$3,612
Interest$21,645
Insurance$1,457

Estimates only. Actual payments may vary.

Location

1014 Flagler Avenue

Key West, FL 33040

Martello Towers (1.0)

Features & Amenities

Interior Features

Built-in CabinetsSky Light(s)Walk-in Closet(s)Tray Ceilings

Exterior Features

Detached Guest QtrsRain GuttersLightingPrivacy Wall/FenceSprinkler SystemWater Display

Property Details

Construction

CBS

Views

Water

Pool Features

PorchPatio

Parking

Off Street

Cooling

Window Unit(s)Wall/Window Unit(s)Central Air

Appliances

WasherDryerDishwasherRefrigeratorRangeOvenMicrowaveDisposalFreezerGas AppliancesWine CoolerStainless Steel Appliance(s)

Questions & Answers

This 3-bedroom, 4-bathroom single family at 1014 Flagler Avenue is listed at $4,995,000 ($1,609/sqft). The estimated monthly payment is $21,645 based on 20% down at 6.5% interest.

Key features include: Built in 1998, 0.27 acre lot, Private pool. Interior Features: Built-in Cabinets, Sky Light(s), Walk-in Closet(s). Exterior Features: Detached Guest Qtrs, Rain Gutters, Lighting.

This property is listed by Team Kaufelt and can be reached at 3053931267 or teamkaufelt@trumanandcompany.com.

TK

Team Kaufelt

Agent at Truman & Co. (KW)

(305) 393-1267

Listed by Truman & Co. (KW) · View on Broker Site

MLS# 618577· Source: listhub· Updated 111 days ago

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.

1014 Flagler Avenue, Key West, FL 33040

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