About This Home

This 4-bedroom, 4-bathroom single family at 1028 Flagler Avenue in Key West, FL is listed for $4,650,000 ($1,296 per sqft). Built in 1958, the home offers 3,589 sqft of living space on a 0.27 acres lot.

Key Features

  • Built in 1958
  • 0.27 acre lot
  • Private pool

Property Details

3 full, 2 half
1958

Amenities

PoolViewA/C
Listing Description

A CASA MARINA ORIGINAL. Some houses capture a moment in time. Others seem to have understood, from the beginning, what makes Key West such an extraordinary place to live. Built in 1958, 1028 Flagler Avenue is a striking example of tropical mid-century modern architecture, set within a private three-building compound on 11,586 square feet in Casa Marina, one of the island's most distinguished neighborhoods.

Behind substantial privacy walls lies a world of its own. Winding pathways lead through lush native and tropical gardens that seem borrowed from a movie, connecting the main residence, separate two-bedroom guest quarters, and detached garage/workshop.

Mature palms, flowering gardens, shaded terraces, and a custom swimming pool create an extraordinary sense of seclusion. Inside, clean architectural lines, high ceilings, and generous proportions celebrate indoor-outdoor living. Expansive living and dining areas, a library, and a separate study offer room to gather or retreat.

Impact-rated windows and doors provide modern peace of mind without sacrificing the home's character. The guest quarters include their own living area and kitchen, ideal for family and visitors. Together, the three buildings offer 3,589 square feet of combined enclosed space: 3,173 square feet of living area plus a 416-square-foot garage/workshop.

Covered outdoor dining, an outdoor kitchen, and abundant off-street parking make this compound as practical as it is beautiful. Just two blocks from Higgs Beach and the Atlantic Ocean, with White Street Pier, waterfront parks, tennis, pickleball, and some of Key West's best-loved restaurants close at hand. Old Town is minutes away, yet the privacy and tranquility of Casa Marina remain entirely your own.

Monthly Cost Estimate

$24,869/mo

20% down · 6.5% · 30 years

Principal$3,363
Interest$20,150
Insurance$1,356

Estimates only. Actual payments may vary.

Location

1028 Flagler Avenue

Key West, FL 33040

Martello Towers (1.0)

Features & Amenities

Interior Features

Sky Light(s)

Exterior Features

Fruit Tree(s)LightingLanaiOutdoor ShowerPrivacy Wall/FenceSprinkler System

Property Details

Flooring

Tile

Construction

CBS

Views

Water

Pool Features

Pool

Outdoor Features

Porch

Parking

Open

Cooling

Central Air

Appliances

WasherDryerDishwasherRefrigeratorOvenDisposalFreezerGas Appliances

Questions & Answers

This 4-bedroom, 4-bathroom single family at 1028 Flagler Avenue is listed at $4,650,000 ($1,296/sqft). The estimated monthly payment is $24,869 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1958, 0.27 acre lot, Private pool. Interior Features: Sky Light(s). Exterior Features: Fruit Tree(s), Lighting, Lanai.

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# 621710· Source: Key West Association of Realtors· 10 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.

1028 Flagler Avenue, Key West, FL 33040

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