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
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 market full of beautiful houses, 1014 Flagler offers something harder to replicate: a point of view.
More Information MLS# 618577
Contract Information
Current Price: $4,700,000
Listing Date: 2026-02-10
Listing Board: Key West Association
List Price: $4,700,000
Potential Short Sale: No
Bank Owned: No
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
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: 1
Total Baths: 4
Rentals Allowed: With Restrictions
Status Change Info
Status: Active
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Building Style
Above Flood: Yes
Stories: 1 Story
Vehicle Storage
Car(s): 1
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
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