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1014 Flagler Avenue, Key West, FL - photo 1

$4,700,000

1014 Flagler Avenue

Key West, FL 33040

Estimated payment $28,200/month

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3Beds
4Baths
3,104Sq Ft
$1514Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

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Highlights

No HOA
Built in 1998

About This Home

A Key West original. 1014 Flagler Avenue is a storied Casa Marina residence shaped by legendary Key West developer David Wolkowsky and set behind privacy walls on an exceptional 11,730-square-foot corner double lot. Some homes are built. Others are authored. At its center: 40 feet of pool, surrounded by mature tropical landscaping and hardscape by Craig Reynolds Landscape Architecture, creating the feel of a private compound hidden in plain sight. Inside, the scale shifts again with 22-foot ceilings, walls of glass, 10-foot doors and sliders, custom teak, and a dramatic floor-to-ceiling library. The main residence offers two bedrooms and two-and-a-half baths, anchored by a chef's kitchen and expansive indoor-outdoor living. Extensive updates include new systems and impact-rated windows and doors. A completely separate one-bedroom guest house adds its own kitchen, laundry and private garden. 3 bedrooms. 3.5 baths. 3,104 square feet. 11,730 square feet of land. 40 feet of pool. In a market full of beautiful houses, 1014 Flagler offers something harder to replicate: a point of view.

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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:3
  • •Bathrooms:4
  • •Full bathrooms:0

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:3,104 sqft
  • •Total interior livable area:3,104 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:N/A

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Single Family Residence
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:1998

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Price history

DateEventPrice
10/8/2026Listed for sale$4,700,000$1514/sqft

Listing Agent

Team Kaufelt

Truman & Co. (KW)

Brokerage Phone: 305-292-2244

Source: Florida Keys MLS · MLS #618577

Data Powered by Home Junction, Inc.

Nearby

Schools

KEY WEST MONTESSORI CHARTER SCHOOL, INC

Elementary · 0.3 mi

MAY SANDS MONTESSORI SCHOOL

Elementary · 0.4 mi

HORACE O'BRYANT SCHOOL

Elementary · 0.6 mi

Supermarkets

Peanut Butter N What

0.0 mi

Artisan Sunday Market

0.3 mi

Fausto's Food Palace

0.4 mi

Dining

Tropical Watersports On The Beach

0.1 mi

The Hummus Factory

0.3 mi

Cafe Sole Office

0.3 mi

Parks

Astro City Playground

0.1 mi

Key West Garden Club

0.2 mi

CB Harvey Rest Beach Park

0.3 mi

Beaches

Higgs Beach

0.2 mi

Dog Beach

0.3 mi

South Beach

0.5 mi

Nearby amenity locations include data © OpenStreetMap contributors.