1014 Flagler Ave

Key West, FL 33040

$6,495,000
Price
3
Beds
3,104 Sq. Ft.
$2,092 / Sq. Ft.
3,104
Sq. Ft.
$2,092
per Sq. Ft.
a view of a backyard
a living room with furniture
a living room with furniture and a large window
a view of living room washer and dryer
a view of a city
an aerial view of a house with a yard and garden
a view of a yard with an outdoor space
an aerial view of a house with a yard and garden
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a view of a house with a yard and palm trees
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a view of a house with backyard and porch
a view of a patio with table and chairs potted plants and palm tree
a front view of a house
a view of a house with a swimming pool
a view of a house with a yard and tree s
a view of a house with pool and sitting area
a swimming pool with outdoor seating and yard
swimming pool with outdoor seating
a view of a yard with plants and trees
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a view of a house with a yard
a view of a balcony
a living room with fireplace furniture and a large window
a living room with furniture and a window
a living room with lots of furniture kitchen view and a large window
a kitchen with a refrigerator a sink and cabinets
a large white kitchen with stainless steel appliances granite countertop a stove and a sink
a large white kitchen with a lot of counter space and a sink
a view of a entryway with wooden floor and windows
a bed room with a bed and a couch
a bedroom with a bed and glass window
a bed room with a bed and a large window
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a view of a bathroom with a tub and shower
a bedroom with a bed and a chandelier
a bedroom with a bed and a window
a bathroom with a sink toilet and shower
a bed sitting in a bedroom next to a large window with yard view
a view of a backyard with plants
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a view of hallway with furniture and floor to ceiling window
a kitchen with a sink stainless steel appliances a refrigerator and a stove top oven
1014 FLAGLER AV HD-46
1014 FLAGLER AV HD-47
1014 FLAGLER AV HD-48

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...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.
  1. Listed by Team Kaufelt • Truman & Co. (KW)

Property Details for 1014 Flagler Avenue

Waterfront
None
Waterfront
No
Zoning
SF - Single Family
Subdivision
Martello Towers (1.0)
Building Style
Other Bldg Style
Vehicle Storage
Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 02/12/2026 03:43 PM

Property Details for 1014 Flagler Avenue

StatusActive
MLS #618577
Days on Market10
Taxes$28,772 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1998
Lot Size0.27 AC / 11,730 SF
CountyMonroe County

Location

Listing Courtesy of Truman & Co. (KW)
Add your commute

Building Information for 1014 Flagler Avenue

Stories1Year Built1998Building Size-Lot Size0.27 AC / 11,730 SF

Payment Calculator

$34,053 per month

30 year fixed, 6.15% Interest

Principal and Interest

$31,655

Property Taxes

$2,398

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 1014 Flagler Avenue

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 02 - Key West
  • Absolute Longitude: 81.788857
  • Control Depth: 0
  • Off Shore Island: No
  • Listing Board: Key West Association
  • Side: Ocean
  • KW Neighborhood: Casa Marina
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Accessibility Feat: Wheelchair Ramp
  • Neighborhood Feature: Tennis Courts, Bike Paths, Beach, Fire Hydrant
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Furnished: Unfurnished
  • Tax Year: 2025
  • Tax Exemptions: None
Property
Lot Information
  • Parcel #: 00058260-000000
  • Land Size: Less Than 1/4 Acre
  • License Info: Non Trans Rntl Lic
Property and Assessments
  • 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
  • MLS Approved: Y
  • Bank Owned: No
  • SqFt Source: Appraisal
  • Flood Zone: AE
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: No
  • Picture Count: 47
  • Document Count: 0
  • Building Style: Above Flood: Yes
  • Property Condition: Updated/Remodeled
  • Title: Negotiable
Utilities
  • Utilities: FKAA, Elect Separate Meter, Other - See Remarks, Cable Available, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: Heated: Yes
  • Pool Info: In Ground
  • Porch/Balcony: Open Porch/Balcony, Patio
Interior and Exterior Features
Interior Features
  • Interior Features: Split Bedroom, Tray Ceilings, Built-in Cabinets, Other, Walk-in Closet(s), Smoke Alarms, Sky Light(s)
  • Pre-Wired: Cable
  • Appliances: Washer, Stainless Steel Appliance(s), Wine Cooler, Gas Appliances, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Construction: CBS
  • Dockage: None
  • Exterior Features: Detached Guest Qtrs, Water Display, Sprinkler System, Privacy Wall/Fence, Lighting, Rain Gutters
  • Windows/Doors: Glass Doors, Impact Rstnce Window, Impact Rstnce Doors, Sliding Glass Doors
Room Information
  • Specialty Rooms: Laundry Room

Property History for 1014 Flagler Avenue

DateEvent & SourcePriceAppreciation
Feb 10, 2026

Listed (Active)

FKMLS #618577

$6,495,000—
Feb 5, 2020

Sold (Public Record)

Public Record #663168074

$2,600,000—
DateEvent & SourcePrice
02/10/2026

Listed (Active)

FKMLS #618577

$6,495,000
02/05/2020

Sold (Public Record)

Public Record #663168074

$2,600,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 1014 Flagler Avenue

Taxable ValueLand$1,381,325Additions$2,126,196Total$3,507,521
Tax Record2024$26,636 ($2,220 / month)
Home Facts
Beds4Baths3Total Finished SqFt2,816 SqFtAbove Grade Finished SqFt2,816 SqFtStories1Lot Size11,711 SqFtStyleSingle Family ResidenceYear Built1998Year Renovated2015CountyMONROEAPN00058260-000000

Schools near 1014 Flagler Avenue

This home is within Monroe.
Rating
School
Type
Grades
Distance
Horace O'bryant School
Public - PK to 8
Key West High School
Public - 9 to 12
May Sands Montessori School
Charter - PK to 8
Keys Center
Public - 8 to 12
Rating
School
Distance
Horace O'bryant School
PublicPK to 8

Key West High School
Public9 to 12

May Sands Montessori School
CharterPK to 8

Keys Center
Public8 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1014 Flagler Avenue, Key West, FL 33040

1014 Flagler Avenue is a single family home for sale in Key West, FL 33040. This property was listed for sale on February 10, 2026 by Truman & Co. (KW), it's currently listed at $6,495,000. It has been on the market for a total of 10 days and was last sold on February 5, 2020. This listing's school district is Monroe. Nearby schools include Horace O'bryant School, Key West High School and May Sands Montessori School. 1014 Flagler Avenue is a 3-bed, 4-bath, 3,104 sqft single family home built in 1998.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Truman & Co. (KW)

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.