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  • 1014 Flagler Avenue, Key West, FL 33040 (MLS# 618577)

1014 Flagler Avenue, Key West, FL 33040

$6,495,000
Property Type: Residential Bedrooms: 3 Baths: 4 Square Footage: 3,104 Lot Size (sq. ft.): 11,730 Status: Active
Current Price: $6,495,000 List Date: 2/10/2026 Last Modified: 2/25/2026

Description

Some homes are built; others are authored. This is one of the latter—an architectural landmark shaped by David Wolkowsky, whose vision helped define Key West itself, with architecture by award-winning architect Rob Delaune that thoughtfully carries that legacy forward. This three-bedroom, three-and-a-half-bath estate, built in 1999 and comprehensively updated from the ground up, has been meticulously restored to museum-level standards with all-new systems, impact-rated windows and doors, and 10-foot doors and sliders throughout. The dramatic main living space is defined by soaring 22-foot ceilings, refinished custom teak columns and doors, expansive walls of glass, and a striking floor-to-ceiling built-in bookcase spanning the full height and length of the living room wall, complete with a concealed automatic disappearing television, while a thoughtfully designed chef's kitchen anchors the home with both beauty and functionality for everyday living and entertaining. Set on a rare, fully walled corner double lot spanning more than 11,700 square feet, the property is enveloped by indigenous and exotic landscaping and hardscape design by Craig Reynolds Landscape Architecture, creating a private, resort-style environment centered around an oversized 40′ x 20′ custom heated swimming pool and generous outdoor living areas—an extraordinary sense of scale and seclusion in the heart of Casa Marina. The main residence offers two bedrooms and two-and-a-half bathrooms, complemented by a separate one-bedroom, one-bath guest house with its own kitchen, washer and dryer, and private garden, providing ideal accommodations for guests, extended family, or additional flexibility, all located on one of the most desirable blocks in one of Key West's premier neighborhoods, where privacy, scale, architectural pedigree, and legacy converge.

Open Houses

Sunday, March 01, 12:00 am - 2:00 pm

More Information MLS# 618577

Contract Information

Listing Board: Key West Association Potential Short Sale: No Bank Owned: No Current Price: $6,495,000 Listing Date: 2026-02-10 List Price: $6,495,000

Location, Tax & Legal

KW Neighborhood: Casa Marina City: KEY WEST Off Shore Island: No Mile Marker: 1 Marathon Neighborhood: N/A Side: Ocean Flood Zone: AE Alternate Key #: 1058742 Parcel #: 00058260-000000 Zoning: SF - Single Family Deed Restrictions: No Legal: KW MARTELLO TOWERS PB1-140 LOTS 1-2-3-4 AND PT LOTS 20 AND 21 SQ 2 TR 27 G31-441/444 OR470-742D/C OR1009-253(AFFD) OR10 Taxes: 28771.56 Tax Year: 2025 Pub Sewer HkUp: Yes Street #: 1014 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 Waterfront: No Control Depth: 0 Lot SqFt: 11730 Pool: Yes Lot Sqft Source: Appraisal Total Units: 0 SqFt Source: Appraisal Rentals Allowed: With Restrictions Style: Single Family Year Built: 1998 Living Apx SqFt: 3104 Total Bedrooms: 3 Full Baths: 3 Half Baths: 1 Total Baths: 4

Remarks & Misc

Remarks – Consumer: Some homes are built; others are authored. This is one of the latter—an architectural landmark shaped by David Wolkowsky, whose vision helped define Key West itself, with architecture by award-winning architect Rob Delaune that thoughtfully carries that legacy forward. This three-bedroom, three-and-a-half-bath estate, built in 1999 and comprehensively updated from the ground up, has been meticulously restored to museum-level standards with all-new systems, impact-rated windows and doors, and 10-foot doors and sliders throughout. The dramatic main living space is defined by soaring 22-foot ceilings, refinished custom teak columns and doors, expansive walls of glass, and a striking floor-to-ceiling built-in bookcase spanning the full height and length of the living room wall, complete with a concealed automatic disappearing television, while a thoughtfully designed chef's kitchen anchors the home with both beauty and functionality for everyday living and entertaining. Set on a rare, fully walled corner double lot spanning more than 11,700 square feet, the property is enveloped by indigenous and exotic landscaping and hardscape design by Craig Reynolds Landscape Architecture, creating a private, resort-style environment centered around an oversized 40′ x 20′ custom heated swimming pool and generous outdoor living areas—an extraordinary sense of scale and seclusion in the heart of Casa Marina. The main residence offers two bedrooms and two-and-a-half bathrooms, complemented by a separate one-bedroom, one-bath guest house with its own kitchen, washer and dryer, and private garden, providing ideal accommodations for guests, extended family, or additional flexibility, all located on one of the most desirable blocks in one of Key West's premier neighborhoods, where privacy, scale, architectural pedigree, and legacy converge.

Association Info

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

License Info

Non Trans Rntl Lic: 1

Fee Includes

None: 1

Dockage

None: 1

Tax Exemptions

None: 1

Appliances

Dishwasher: 1 Disposal: 1 Dryer: 1 Freezer: 1 Gas Appliances: 1 Microwave: 1 Oven: 1 Range: 1 Refrigerator: 1 Stainless Steel Appliance(s): 1 Washer: 1 Wine Cooler: 1

Pets

Pets Allowed: 1

Cooling

Ceiling Fans(s): 1 Central Air: 1 Wall/Window Unit(s): 1

Waterfront

None: 1

Waterview

No Waterview: 1

Neighborhood Feature

Beach: 1 Bike Paths: 1 Fire Hydrant: 1 Tennis Courts: 1

Interior Features

Built-in Cabinets: 1 Sky Light(s): 1 Smoke Alarms: 1 Split Bedroom: 1 Tray Ceilings: 1 Walk-in Closet(s): 1 Other: 1

Property Condition

Updated/Remodeled: 1

Specialty Rooms

Laundry Room: 1

Building Style

Above Flood: Yes Stories: 1 Story Other Bldg Style: 1

Windows/Doors

Glass Doors: 1 Impact Rstnce Doors: 1 Impact Rstnce Window: 1 Sliding Glass Doors: 1

Vehicle Storage

Car(s): 1 Off Street Parking: 1

Construction

CBS: 1

Land Size

Less Than 1/4 Acre: 1

Furnished

Unfurnished: 1

Terms

Cash: 1 Conventional: 1

Utilities

Cable Available: 1 Elect Separate Meter: 1 FKAA: 1 Municipal Sewer: 1 Other - See Remarks: 1

Porch/Balcony

Open Porch/Balcony: 1 Patio: 1

Title

Negotiable: 1

Exterior Features

Detached Guest Qtrs: 1 Lighting: 1 Privacy Wall/Fence: 1 Rain Gutters: 1 Sprinkler System: 1 Water Display: 1

Pool Info

In Ground: 1 Heated: Yes

Pre-Wired

Cable: 1

Roof

Metal Roof: 1

Financial Status

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

Accessibility Feat

Wheelchair Ramp: 1

Status Change Info

Status: Active

Property Features

Fee Includes: None Tax Exemptions: None License Info: Non Trans Rntl Lic Waterfront: None Waterview: No Waterview Dockage: None Property Condition: Updated/Remodeled Building Style: Other Bldg Style Vehicle Storage: Off Street Parking Furnished: Unfurnished Cooling: Ceiling Fans(s); Central Air; Wall/Window Unit(s) Utilities: Cable Available; Elect Separate Meter; FKAA; Municipal Sewer; Other - See Remarks Interior Features: Built-in Cabinets; Sky Light(s); Smoke Alarms; Split Bedroom; Tray Ceilings; Walk-in Closet(s); Other Pre-Wired: Cable Specialty Rooms: Laundry Room Appliances: Dishwasher; Disposal; Dryer; Freezer; Gas Appliances; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer; Wine Cooler Exterior Features: Detached Guest Qtrs; Lighting; Privacy Wall/Fence; Rain Gutters; Sprinkler System; Water Display Accessibility Feat: Wheelchair Ramp Pool Info: In Ground Construction: CBS Roof: Metal Roof Pets: Pets Allowed Neighborhood Feature: Beach; Bike Paths; Fire Hydrant; Tennis Courts Land Size: Less Than 1/4 Acre Terms: Cash; Conventional Title: Negotiable
Listing Office: Truman & Co. (KW)
Last Updated: February - 25 - 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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