1028 Flagler Avenue, Key West, FL 33040

New Listing

$4,650,000

Virtual Tour

https://my.matterport.com/show/?m=dLvow5iZFt8

Clean sidewalks and greener perimeter gr

Living Space leading to Covered Patio and kitchen and dining

Living Space connecting to hallway leading to primary suite and guest bedroom.

Primary Suite setup with office space and entryway to primary bathroom and outdoor shower

Walkway to separate building which is currently setup as a Studio and Office which can double as a garage.

Studio and Office which can double as a garage.

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

Overview

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 retrea ... (Read more)

Listing Details MLS# 621710

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
KW Neighborhood: Casa Marina
City: KEY WEST
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Ocean
Alternate Key #: 1058777
Parcel #: 00058290000000
Zoning: SF - Single Family
Deed Restrictions: Unknown
Legal: Kw Martello Towers Pb1-140 Lots 11-12-13-14 Sqr 2 Tr 27 Or262-233/234 Or629-263/264 Or1122-217 Or1164-1319 Or1392-1475/6
Taxes: 24851.55
Tax Year: 2025
Pub Sewer HkUp: Yes

Contract Information

Listing Board: Key West Association
Potential Short Sale: No
Bank Owned: No

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
Control Depth: 0

Association Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0

Building Style

Above Flood: Unknown

More Information

Vehicle Storage

Car(s): 3
Garage: Yes
Guest Parking: Yes
Detached: Yes
Auto Door Opener: Yes

Pool Info

Heated: Yes
In Ground: Yes

Financial Status

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

Remarks & Misc

Remarks – Consumer: 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.

Fee Includes

None: Yes

Dockage

None: Yes

Tax Exemptions

Homestead: Yes

Appliances

Dishwasher: Yes
Disposal: Yes
Dryer: Yes
Freezer: Yes
Gas Appliances: Yes
Oven: Yes
Refrigerator: Yes
Washer: Yes

Pets

Pets Allowed: Yes

Cooling

Ceiling Fans(s): Yes
Central Air: Yes

Waterfront

None: Yes

Waterview

No Waterview: Yes

Floor

Tile: Yes

Neighborhood Feature

Beach: Yes
Tennis Courts: Yes

Interior Features

Entrance Foyer: Yes
Pantry: Yes
Sky Light(s): Yes
Split Bedroom: Yes
Window Treatments: Yes

Property Condition

Updated/Remodeled: Yes

Windows/Doors

Impact Rstnce Window: Yes

Construction

CBS: Yes

Land Size

Less Than 1/4 Acre: Yes

Furnished

Unfurnished: Yes

Utilities

Buyer to Verify: Yes

Porch/Balcony

Open Porch/Balcony: Yes

Title

Negotiable: Yes

Exterior Features

Fruit Tree(s): Yes
Lanai: Yes
Lighting: Yes
Outdoor Shower: Yes
Privacy Wall/Fence: Yes
Sprinkler System: Yes

Roof

Metal Roof: Yes

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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