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

1014 Flagler Avenue, Key West, FL 33040

$4,700,000
Property Type: Residential Bedrooms: 3 Baths: 4 Square Footage: 3,104 Lot Size (sq. ft.): 11,730 Status: Active
Current Price: $4,700,000 List Date: 10/01/2026 Last Modified: 10/01/2026

Overview

Description

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 mark ...

Listing Details MLS# 618577

Location, Tax & Legal

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

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
1998
Lot SqFt
11730
Lot Sqft Source
Appraisal
Living Apx SqFt
3104
SqFt Source
Appraisal
Total Bedrooms
3
Full Baths
3
Half Baths
Yes
Total Baths
4
Rentals Allowed
With Restrictions

Association Info

Mandatory Home Owners Asc
No
1st Right of Refusal
No

Building Style

Above Flood
Yes
# Stories
1 Story

More Information

Vehicle Storage

Car(s)
Yes

Pool Info

Heated
Yes

Financial Status

Auction
No
Bank Owned
No
Potential Short Sale
No

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: October - 01 - 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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