About This Home

This 3-bedroom, 4-bathroom single family at 1014 Flagler Avenue in Key West, FL is listed for $4,700,000 ($1,514 per sqft). Built in 1998, the home offers 3,104 sqft of living space on a 0.27 acres lot.

Key Features

  • Built in 1998
  • 0.27 acre lot
  • Private pool

Property Details

3 full, 1 half
1998

Amenities

PoolViewA/C
Listing Description

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.

Monthly Cost Estimate

$25,137/mo

20% down · 6.5% · 30 years

Principal$3,399
Interest$20,367
Insurance$1,371

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

Pool

Outdoor Features

PorchPatio

Parking

Off Street

Cooling

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

Appliances

WasherDryerDishwasherRefrigeratorRangeOvenMicrowaveDisposalFreezerGas AppliancesWine CoolerStainless Steel Appliance(s)

Questions & Answers

This 3-bedroom, 4-bathroom single family at 1014 Flagler Avenue is listed at $4,700,000 ($1,514/sqft). The estimated monthly payment is $25,137 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

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.

TK

Team Kaufelt

Agent at Truman & Co. Real Estate Services

Listed by Truman & Co. Real Estate Services · Broker phone: (305) 292-2244 · View on Broker Site · Broker website

MLS# 618577· Source: Key West Association of Realtors· 264 days on PropertySimple

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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