Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$4,995,000 -$100,000 (-1.96%) Price Reduced

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,104 Sq. Ft.
  • Updated 7 hours ago
See This Home
Save This Home
See This Home
Save This Home
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.

Full Property Details for 1014 Flagler Ave

General

  • Price: $4,995,000
  • Taxes: $28,771 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 618577
  • Updated: 5/14/2026
  • Added to Site: 93 day(s) ago

Interior

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

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Fire Hydrant, Bike Paths, Beach, Tennis Court(s)
  • Pool: Yes
  • Pool Description: Heated, In Ground

Exterior

  • Exterior Features: Rain Gutters, Lighting, Detached Guest Qtrs, Privacy Wall/Fence, Sprinkler System, Water Display
  • Deck/Patio: Open Porch/Balcony, Patio
  • Porch/Patio/Deck: Open Porch/Balcony, Patio

Parking

  • Parking Features: Off Street

Location

  • Area: 02 - Key West
  • County: Monroe
  • Subdivision: Martello Towers (1.0)

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Wall/Window Unit(s), Central Air, Ceiling Fans(s)

Structural Information

  • Architectural Style: Above Flood, Other Bldg Style
  • Construction Status: Updated/Remodeled
  • Construction: CBS
  • Roof: Metal
  • Windows/Doors: Glass Doors, Impact Rstnce Doors, Impact Rstnce Window, Sliding Glass Doors
  • Square Feet: 3,104
  • Sq. Ft. Source: Appraisal
  • Year Built: 1998
  • Property Condition: Updated/Remodeled

Lot Features

  • Property View: No Waterview
  • Lot Size (Acres): 0.27
  • Lot Size (Sq. Ft.): 11,730
  • Lot Size Source: Appraisal
  • Zoning: SF - Single Family

Water Features

  • Water View: Yes

Financial Considerations

  • Tax Amount: $28,771.56
  • Tax Year: 2025
  • Terms: Cash, Conventional

Disclosures and Reports

  • Legal Description: 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
  • Flood Zone: AE
  • APN: 00058260-000000

Listed by Truman & Co. (KW), Team Kaufelt (305) 393-1267

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 1014 Flagler Ave —

  • Team Kaufelt

    Truman & Co. (KW)

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1014 Flagler Ave

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Horace O'bryant School
1105 Leon Street, Key West, FL 33040
6-80.6 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-120.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1014 Flagler Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/14/2026
Price Reduced
$4,995,000
-1.96%
MLS
2/10/2026
Listed
$5,095,000
95.96%
MLS
2/05/2020
Sold
$2,600,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1014 Flagler Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$28,772
8%
$3,507,521
4%
2024
$26,636
7%
$3,375,864
1%
2023
$25,003
25%
$3,358,175
50%
2021
$20,039
-9%
$2,239,543
-22%
2022
$21,951
10%
$2,859,813
30%
2021
$20,039
31%
$2,203,331
34%
2019
$15,269
6%
$1,645,020
10%
2018
$14,403
12%
$1,495,473
10%
2017
$12,881
-13%
$1,359,523
-8%
2016
$14,807
-3%
$1,481,929
3%
2015
$15,305
6%
$1,442,608
10%
2014
$14,461
7%
$1,311,462
10%
2013
$13,569
—
$1,192,239
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 1014 Flagler Ave

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Truman & Co. (KW), Team Kaufelt (305) 393-1267

Similar Properties near 1014 Flagler Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

720D Simonton St, Key West, FL 33040 - Photo 1
$4,990,000

720D Simonton St  Key West, FL 33040

  • Single Family
  • Active
  • Updated 18 hours ago
  • 4
    Beds
  • 4
    Total Baths
  • 2,441
    Sq. Ft.
Listed by Truman & Co. (KW), The Spottswood Team and Truman & Co. (KW), Terri Spottswood
1614 Washington St, Key West, FL 33040 - Photo 1
$4,495,000

1614 Washington St  Key West, FL 33040

  • Single Family
  • Active
  • Updated 12 hours ago
  • 4
    Beds
  • 5
    Total Baths
  • 2,806
    Sq. Ft.
Listed by Your Keys Real Estate, LLC, Richard Patten
1010 Olivia St, Key West, FL 33040 - Photo 1
$3,999,000
Open House

1010 Olivia St  Key West, FL 33040

  • Single Family
  • Active
  • Updated 23 hours ago
  • 3
    Beds
  • 4
    Total Baths
  • 2,421
    Sq. Ft.
Listed by Suzanne Moore Real Estate, Suzanne M Moore
600 Elizabeth St, Key West, FL 33040 - Photo 1
$4,500,000
Open House

600 Elizabeth St  Key West, FL 33040

  • Single Family
  • Active
  • Updated 7 hours ago
  • 4
    Beds
  • 6
    Total Baths
  • 3,092
    Sq. Ft.
Listed by Berkshire Hathaway HomeServices Knight & Gardner Realty, Lori Langton

Just Listed near 1014 Flagler Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

6800 Maloney Ave, Stock Island, FL 33040 - Photo 1 Just Listed
$534,000

6800 Maloney Ave  #13  Stock Island, FL 33040

  • Mobile Home
  • Active
  • Updated 7 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,222
    Sq. Ft.
Listed by Berkshire Hathaway HomeServices Knight & Gardner Realty, Forrest Shearin
4 Coral Dr, Lower Sugarloaf Key, FL 33040 - Photo 1 Just Listed
$450,000
Open House

4 Coral Dr  Lower Sugarloaf Key, FL 33040

  • Mobile Home
  • Active
  • Updated 7 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 873
    Sq. Ft.
Listed by RE/MAX Keys Connection (KW), Bobby W Coe IV and RE/MAX All Keys Real Estate, Kelly Randin
17286 Jamaica Ln, Sugarloaf Key, FL 33042 - Photo 1 Just Listed
$1,200,000
Open House

17286 Jamaica Ln  Sugarloaf Key, FL 33042

  • Single Family
  • Active
  • Updated 7 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,344
    Sq. Ft.
Listed by Coldwell Banker Schmitt Real Estate Co, Lisa H Ferringo
17387 Dolphin St E, Sugarloaf Key, FL 33042 - Photo 1 Just Listed
$3,750,000

17387 Dolphin St E  Sugarloaf Key, FL 33042

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 4
    Total Baths
  • 2,409
    Sq. Ft.

Price Reduced near 1014 Flagler Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

19267 Hansen Trail, Sugarloaf Key, FL 33042 - Photo 1 Price Reduced
-$100,000 (-9.1%)
$999,000

19267 Hansen Trail  Sugarloaf Key, FL 33042

  • Single Family
  • Active
  • Updated 10 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,968
    Sq. Ft.
Listed by Expert Realty LLC (HQ), Justyn Ewald and Expert Realty LLC (HQ), Mason C Kelly
154 Sebring Dr, Upper Sugarloaf Key, FL 33070 - Photo 1 Price Reduced
-$40,000 (-4.85%)
$785,000

154 Sebring Dr  Upper Sugarloaf Key, FL 33070

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,667
    Sq. Ft.
Listed by Harbour Residential Realty, Andres Navarro
74520 Overseas Hwy, Upper Sugarloaf Key, FL 33036 - Photo 1 Price Reduced
-$50,000 (-4.17%)
$1,149,000

74520 Overseas Hwy  Upper Sugarloaf Key, FL 33036

  • Lots/Land
  • Active
  • Updated 1 day ago
  • 0.31
    Acres
Listed by Coldwell Banker Schmitt Islamorada, Eddy Chamizo
130 N Hammock Rd, Upper Sugarloaf Key, FL 33036 - Photo 1 Price Reduced
-$35,000 (-5.15%)
$645,000

130 N Hammock Rd  Upper Sugarloaf Key, FL 33036

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,376
    Sq. Ft.
Listed by Berkshire Hathaway HomeServices Keys Real Estate - Islamorada, The Lindback Team and Berkshire Hathaway HomeServices Keys Real Estate - Islamorada, Brian Lindback Jr.

Recent Sales near 1014 Flagler Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1014 Southard St, Key West, FL 33040 - Photo 1 Sold
$4,700,000

1014 Southard St  Key West, FL 33040

  • Single Family
  • Closed
  • Updated 11 hours ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,026
    Sq. Ft.
Listed by Suzanne Moore Real Estate, Suzanne M Moore
Sold by Realty ONE Group Destination, Stacy Stahl
231 E Shore Dr, Key West, FL 33040 - Photo 1 Sold
$4,275,000

231 E Shore Dr  #Unit 7  Key West, FL 33040

  • Single Family
  • Closed
  • 5
    Beds
  • 6
    Total Baths
  • 4,103
    Sq. Ft.
231 E Shore Dr, Summerland Key, FL 33042 - Photo 1 Sold
$4,275,000

231 E Shore Dr  #7  Summerland Key, FL 33042

  • Single Family
  • Closed
  • Updated 1 day ago
  • 5
    Beds
  • 6
    Total Baths
  • 3,119
    Sq. Ft.
Listed by Serhant Florida LLC - Delray Beach Office, Stephanie Marie Muzzillo
Sold by Expert Realty LLC (HQ), Solaris Gregory

1014 Flagler Avenue, Key West, FL 33040 (MLS# 618577) is a Single Family property with 3 bedrooms, 3 full bathrooms and 1 partial bathroom. 1014 Flagler Avenue is currently listed for $4,995,000 and was received on February 10, 2026. Want to learn more about 1014 Flagler Avenue? Do you have questions about finding other Single Family real estate for sale in Key West? You can browse all Key West real estate or contact a Coldwell Banker agent to request more information.

Tour this property