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1028 Flagler Avenue, Key West, FL 33040

$4,650,000
Property Type: Residential Bedrooms: 4 Baths: 5 Square Footage: 3,589 Lot Size (sq. ft.): 11,586 Status: Active
Current Price: $4,650,000 List Date: 10/20/2026 Last Modified: 10/20/2026

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.

More Information MLS# 621710

Contract Information

Current Price: $4,650,000 Listing Date: 2026-10-20 Listing Board: Key West Association List Price: $4,650,000 Potential Short Sale: No Bank Owned: No

Location Tax Legal

Street #: 1028 Street Name: Flagler Street Suffix: Avenue Key/Island: Key West State/Province: FL Zip Code: 33040 County: Monroe Subdivision: Martello Towers (1.0) Area: 02 - Key West

General Property Description

Realtor.COM Type: Residential - Single Family Style: Single Family Waterfront: No Pool: Yes Year Built: 1958 Lot SqFt: 11586 Living Apx SqFt: 3589 SqFt Source: Appraisal Total Bedrooms: 4 Full Baths: 3 Half Baths: 2 Total Baths: 5 Rentals Allowed: With Restrictions

Status Change Info

Status: Active

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No

Building Style

Above Flood: Unknown

Vehicle Storage

Car(s): 3

Pool Info

Heated: Yes

Financial Status

Auction: No Bank Owned: No Potential Short Sale: No

Property Features

Fee Includes: None Tax Exemptions: Homestead Waterfront: None Waterview: No Waterview Dockage: None Property Condition: Updated/Remodeled Vehicle Storage: Garage; Detached; Auto Door Opener; Guest Parking Furnished: Unfurnished Cooling: Ceiling Fans(s); Central Air Utilities: Buyer to Verify Interior Features: Entrance Foyer; Pantry; Sky Light(s); Split Bedroom; Window Treatments Appliances: Dishwasher; Disposal; Dryer; Freezer; Gas Appliances; Oven; Refrigerator; Washer Exterior Features: Fruit Tree(s); Lanai; Lighting; Outdoor Shower; Privacy Wall/Fence; Sprinkler System Pool Info: In Ground Construction: CBS Floor: Tile Roof: Metal Roof Pets: Pets Allowed Neighborhood Feature: Beach; Tennis Courts Land Size: Less Than 1/4 Acre Title: Negotiable
Listing Office: Truman & Co. (KW)
Last Updated: October - 20 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

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