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1014 Flagler Avenue AVENUE

KEY WEST, FL 33040
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Bed 3

Bed

Bath 4

Bath

SqFt3,104

Sqft

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.

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Detail Ic Property Details

Property Type : Residential - Single Family

Price : $4,995,000

AD Id : 75196889

MLS Id : 618577

Beds : 3

Living Area Size : 3,104

Year Built : 1998

County : Monroe

Subdivision: Old Town - Unlisted (1.0)

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Feature Features

  • Bedroom Information

    Total Bedrooms: 3 Laundry Room

    Bathroom Information

    Total Baths: 4 Full Baths: 3 Half Baths: 1
  • Interior Features

    Split Bedroom,Tray Ceilings,Built-in Cabinets,Other,Walk-in Closet(s),Smoke Alarms,Sky Light(s) Appliances: Washer,Stainless Steel Appliance(s),Wine Cooler,Gas Appliances,Freezer,Disposal,Microwave,Oven,Range,Refrigerator,Dishwasher,Dryer
  • Roofing Information

    Metal Roof

    Heating & Cooling

    Cooling: Central Air,Ceiling Fans(s),Wall/Window Unit(s) Water Front: No None No Waterview

    Window Information

    Window Treatments: Glass Doors,Impact Rstnce Window,Impact Rstnce Doors,Sliding Glass Doors

  • Building Information

    Year Built: 1998 Total Units: 0.00 Floor Location: 11730 Construction: CBS Roof: Metal Roof
  • Exterior Features

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

    Pool Information

    In Ground Heated: Yes

  • Lot Information

    Lot SqFt: 11,730 Lot SqFt Source: Appraisal 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
  • Property Information

    SQ ft (Living Area): 3,104 View: No Waterview Subdivision: Martello Towers (1.0) Stories: 1 Story

  • Listing Price Information

    List Price: $4,995,000
  • Listing Information

    Cash,Conventional

  • Tax Information

    Taxes: $28,772 Tax Year: 2025 Parcel Number: 00058260-000000 Tax Exemptions: None

  • Multi-Unit Information

    Pets Allowed: Pets Allowed
  • Homeowners Association Information

    Mandatory Home Owners Asc: No 1st Right of Refusal: No Association Fee: $0.00

  • Utility Information

    FKAA,Elect Separate Meter,Other - See Remarks,Cable Available,Municipal Sewer
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
1503 Johnson St, Key West, FL, 33040 $1,950,000 3 3 1,690 1,690 SqFt
231 E Shore Drive #UNIT 6, Key West, FL, 33040 $4,375,000 5 6 4,103 4,103 SqFt
231 E Shore Drive #UNIT 2, Key West, FL, 33040 $4,250,000 5 6 4,103 4,103 SqFt
4 Shore Drive, Key West, FL, 33040 $640,000 2 2 1,010 1,010 SqFt
6810 Front Street #SNL1.., Key West, FL, 33040 $1,000,000 2 5 1,200 1,200 SqFt
5435 5th Avenue, Stock Island, FL, 33040 $730,000 3 3 1,344 1,344 SqFt
60 Golf Club Drive, Key West, FL, 33040 $995,000 3 3 1,203 1,203 SqFt
90 Golf Club Drive, Key West, FL, 33040 $719,000 2 3 930 930 SqFt
236 Golf Club Drive, Key West, FL, 33040 $875,000 2 3 1,120 1,120 SqFt
263 Golf Club Drive, Key West, FL, 33040 $1,150,000 3 3 1,480 1,480 SqFt

ByOwner last updated this listing 06/07/2026 @ 16:38

MLS: 618577 LISTED BY: Team Kaufelt , Truman & Co. (KW) 305-292-2244 SOURCE: Florida Keys MLS, Inc.

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