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Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

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$4,650,000
1028 Flagler Avenue
Key West, FL 33040
MLS# 621710
4 beds  |  5 baths  |  3589 sqft

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1028 Key West Real Estate_09 1028 Key West Real Estate_18 Walkway to Guest House 1028 Key West Real Estate_25 Primary Suite - Office and Closet Space Clean sidewalks and greener perimeter gr Off Street Parking 1028 Key West Real Estate_58 1028 Key West Real Estate_11 1028 Key West Real Estate_14 1028 Key West Real Estate_17 1028 Key West Real Estate_13 1028 Key West Real Estate_16 1028 Key West Real Estate_20 Living Space leading to Covered Patio and kitchen and dining Living Space connecting to hallway leading to primary suite and guest bedroom. 1028 Key West Real Estate_22 1028 Key West Real Estate_04 1028 Key West Real Estate_08 1028 Key West Real Estate_28 1028 Key West Real Estate_26 1028 Key West Real Estate_29 Primary Suite setup with office space and entryway to primary bathroom and outdoor shower Primary Suite Primary Suite Primary Bathroom Guest Bedroom in Main House Separate Guest House Separate Guest House 1028 Key West Real Estate_45 Guest House Kitchen Guest House Bedroom 1 Guest House Bedroom 2 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. Office Space in Studio

Property 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.

Details
Maps
Contract Information
Current Price: $4,650,000
Listing Date: 2026-10-20
Listing Board: Key West Association
Monthly Rent: $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
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
Status Change Info
Status: Active
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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David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)