Call Now:

Wade M. Berlin

ABR,BrkrAssc,CNE,CPM,FSSR,GAA,LLC,PMN,REALTOR ®,SRES
Tropic Shores Realty
The Real Estate Professional You Deserve
Active
Property Photos
1014 Flagler Avenue
  1. Image 1 of 47 For 1014 Flagler Avenue
  2. Image 2 of 47 For 1014 Flagler Avenue
  3. Image 3 of 47 For 1014 Flagler Avenue
  4. Image 4 of 47 For 1014 Flagler Avenue
  5. Image 5 of 47 For 1014 Flagler Avenue
  6. Image 6 of 47 For 1014 Flagler Avenue
  7. Image 7 of 47 For 1014 Flagler Avenue
  8. Image 8 of 47 For 1014 Flagler Avenue
  9. Image 9 of 47 For 1014 Flagler Avenue
  10. Image 10 of 47 For 1014 Flagler Avenue
  11. Image 11 of 47 For 1014 Flagler Avenue
  12. Image 12 of 47 For 1014 Flagler Avenue
  13. Image 13 of 47 For 1014 Flagler Avenue
  14. Image 14 of 47 For 1014 Flagler Avenue
  15. Image 15 of 47 For 1014 Flagler Avenue
  16. Image 16 of 47 For 1014 Flagler Avenue
  17. Image 17 of 47 For 1014 Flagler Avenue
  18. Image 18 of 47 For 1014 Flagler Avenue
  19. Image 19 of 47 For 1014 Flagler Avenue
  20. Image 20 of 47 For 1014 Flagler Avenue
  21. Image 21 of 47 For 1014 Flagler Avenue
  22. Image 22 of 47 For 1014 Flagler Avenue
  23. Image 23 of 47 For 1014 Flagler Avenue
  24. Image 24 of 47 For 1014 Flagler Avenue
  25. Image 25 of 47 For 1014 Flagler Avenue
  26. Image 26 of 47 For 1014 Flagler Avenue
  27. Image 27 of 47 For 1014 Flagler Avenue
  28. Image 28 of 47 For 1014 Flagler Avenue
  29. Image 29 of 47 For 1014 Flagler Avenue
  30. Image 30 of 47 For 1014 Flagler Avenue
  31. Image 31 of 47 For 1014 Flagler Avenue
  32. Image 32 of 47 For 1014 Flagler Avenue
  33. Image 33 of 47 For 1014 Flagler Avenue
  34. Image 34 of 47 For 1014 Flagler Avenue
  35. Image 35 of 47 For 1014 Flagler Avenue
  36. Image 36 of 47 For 1014 Flagler Avenue
  37. Image 37 of 47 For 1014 Flagler Avenue
  38. Image 38 of 47 For 1014 Flagler Avenue
  39. Image 39 of 47 For 1014 Flagler Avenue
  40. Image 40 of 47 For 1014 Flagler Avenue
  41. Image 41 of 47 For 1014 Flagler Avenue
  42. Image 42 of 47 For 1014 Flagler Avenue
  43. Image 43 of 47 For 1014 Flagler Avenue
  44. Image 44 of 47 For 1014 Flagler Avenue
  45. Image 45 of 47 For 1014 Flagler Avenue
  46. Image 46 of 47 For 1014 Flagler Avenue
  47. Image 47 of 47 For 1014 Flagler Avenue
Image Gallery

PRICED AT ONLY: $5,995,000

Address: 1014 Flagler Avenue, KEY WEST, FL 33040

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 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.
Payment Calculator
  •   Principal & Interest -
  •   Property Tax $
  •   Home Insurance $
  •   HOA Fees $
  •   Mortgage Insurance-

  •   Monthly -
For a Fast & FREE Mortgage Pre-ApprovalApply Now
  • MLS#: 618577 ( Single Family )
  • Street Address: 1014 Flagler Avenue
  • Viewed: 2
  • Price: $5,995,000
  • Price sqft: $1,931
  • Waterfront: No
  • Waterfront Type: None
  • Year Built: 1998
  • Bldg sqft: 3104
  • Bedrooms: 3
  • Total Baths: 4
  • Full Baths: 3
  • 1/2 Baths: 1
  • Days On Market: 48
Request More Information
  • All fields are required.
Features
Building and Construction
  • Absolute Longitude: 81.788857
  • Construction: CBS
  • Exterior Features: Detached Guest Qtrs, Water Display, Sprinkler System, Privacy Wall/Fence, Lighting, Rain Gutters
  • Porchbalcony: Open Porch/Balcony, Patio
  • Roof: Metal Roof
  • Sqft Source: Appraisal
  • Total Number Of Units: 0.00
Property Information
  • Property Condition: Updated/Remodeled
  • Property Group Id: 19990816212109142258000000
Garage and Parking
  • Vehicle Storage: Off Street Parking
Eco-Communities
  • Off Shore Island: No
  • Pool Info Heated: Yes
  • Pool Info: In Ground
  • Water View: No Waterview
Utilities
  • Cooling: Central Air, Ceiling Fans(s), Wall/Window Unit(s)
  • Kw Neighborhood: Casa Marina
  • Pets: Pets Allowed
  • Pub Sewer Hkup: Yes
  • Utilities: FKAA, Elect Separate Meter, Other - See Remarks, Cable Available, Municipal Sewer
  • Windowsdoors: Glass Doors, Impact Rstnce Window, Impact Rstnce Doors, Sliding Glass Doors
Amenities
  • Neighborhood Feature: Tennis Courts, Bike Paths, Beach, Fire Hydrant
Finance and Tax Information
  • Association Info Association Fee: 0.00
  • Fee Includes: None
  • Tax Year: 2025
Rental Information
  • Rentals Allowed: With Restrictions
Other Features
  • Accessibility Feat: Wheelchair Ramp
  • Alternate Key Num: 1058742
  • Appliances: Washer, Stainless Steel Appliance(s), Wine Cooler, Gas Appliances, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
  • Association Info 1st Right Of Refusal: No
  • Association Info Mandatory Home Owners Asc: No
  • Deed Restrictions: No
  • Dockage: None
  • Flood Zone: AE
  • Furnished: Unfurnished
  • Interior Features: Split Bedroom, Tray Ceilings, Built-in Cabinets, Other, Walk-in Closet(s), Smoke Alarms, Sky Light(s)
  • 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
  • Mile Marker: 1.00
  • Parcel Num: 00058260-000000
  • Pre Wired: Cable
  • Side: Ocean
  • Style: Single Family
  • Zoning: SF - Single Family
Similar Properties

Active
Details for 30 Cannon Royal Drive, Shark Key, FL 33040
$5,750,000.00 ($1,110.04 / sqft )

30 Cannon Royal Drive Virtual Tour More Like This

European Elegance! Recently updated and freshly painted, this 4BD/5BA Mediterranean villa in gated Shark Key offers 5,180 SF with soaring ceilings, Viking kitchen, office, game room, and breathtaking

  1. Bedrooms: 4
  2. Baths: 5
  3. Approx. 5180 sqft
  1. MLSID: 612702
  2. Provided by Berkshire Hathaway HomeServices Knight & Gardner R
  3. Contact Joanne Allen
  4. (305) 294-5155
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
Active
Details for 317 Whitehead Street, KEY WEST, FL 33040
$6,895,000.00 ($2,013.14 / sqft )

317 Whitehead Street More Like This

Discover unparalleled luxury in the heart of Old Town, Key West. Comprised of a main house and guest cottage, this newly built ''Smart'' property infuses casual island elegance with modern sophisticat

  1. Bedrooms: 6
  2. Baths: 7
  3. Approx. 3425 sqft
  1. MLSID: 617122
  2. Provided by RE/MAX Keys Connection (KW)
  3. Contact Bobby W Coe IV
  4. (305) 296-1400
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
Active
Details for 411 Louisa Street, KEY WEST, FL 33040
$6,750,000.00 ($1,842.75 / sqft )

411 Louisa Street More Like This

Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa Street, located in the heart of Old Town Key West, less than a block from Duval Street's top dining and entertainment.This st

  1. Bedrooms: 5
  2. Baths: 5
  3. Approx. 3663 sqft
  1. MLSID: 617175
  2. Provided by RE/MAX Keys Connection (KW)
  3. Contact Bobby W Coe IV
  4. (305) 296-1400
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
Active
Details for 42 Cannon Royal Drive, Shark Key, FL 33040
$6,200,000.00 ($1,550.00 / sqft )

42 Cannon Royal Drive Virtual Tour More Like This

Motivated Seller! Discover luxury living in this stunning 4 Bedroom ,Office/or Fifth bedroom,three and half baths custom home in the exclusive gated community on Shark Key. Featuring 4000 SF of refine

  1. Bedrooms: 4
  2. Baths: 4
  3. Approx. 4000 sqft
  1. MLSID: 613209
  2. Provided by Berkshire Hathaway HomeServices Knight & Gardner R
  3. Contact Joanne Allen
  4. (305) 294-5155
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
Active
Details for 36 Cannon Royal Drive, Shark Key, FL 33040
$6,200,000.00 ($1,340.83 / sqft )

36 Cannon Royal Drive More Like This

Don't miss this rare and exceptional opportunity to have your dream waterfront masterpiece begin construction in 2026! Located in the prestigious, gated community of Shark Key, 36 Cannon Royal is an e

  1. Bedrooms: 5
  2. Baths: 5
  3. Approx. 4624 sqft
  1. MLSID: 617894
  2. Provided by Brenda Donnelly Real Estate LLC
  3. Contact Brenda J Donnelly
  4. (305) 304-1116
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
Active
Details for 910-914 Watson Street, KEY WEST, FL 33040
$5,995,000.00 ($1,366.54 / sqft )

910-914 Watson Street Virtual Tour More Like This

More than a residence and rarer than legend, 910 914 Watson Street stands as one of the most iconic private estates in all of Key West a once in a generation offering where historic gravitas, tropica

  1. Bedrooms: 5
  2. Baths: 7
  3. Approx. 4387 sqft
  1. MLSID: 617923
  2. Provided by Truman & Co. (KW)
  3. Contact Team Kaufelt
  4. (305) 292-2244
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
Active
Details for 719 Washington Street, KEY WEST, FL 33040
$6,295,000.00 ($1,998.41 / sqft )

719 Washington Street More Like This

Luxury Estate A Masterpiece of Light, Space & DesignA new benchmark for modern island living is rising in the coveted Casa Marina district, with completion set for March 2026. Crafted by renowned b

  1. Bedrooms: 4
  2. Baths: 5
  3. Approx. 3150 sqft
  1. MLSID: 618070
  2. Provided by Truman & Co. (KW)
  3. Contact Elizabeth E Chamberlain
  4. (305) 292-2244
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
Active
Details for 906 Johnson Street, KEY WEST, FL 33040
$5,750,000.00 ($1,532.92 / sqft )

906 Johnson Street Virtual Tour More Like This

Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front po

  1. Bedrooms: 6
  2. Baths: 6
  3. Approx. 3751 sqft
  1. MLSID: 618573
  2. Provided by Truman & Co. (KW)
  3. Contact Regan Enouen
  4. (305) 292-2244
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
Active
Details for 1101 Casa Marina Court, KEY WEST, FL 33040
$6,965,000.00 ($1,492.71 / sqft )

1101 Casa Marina Court More Like This

Rarely does a property of such storied provenance and grand scale grace the Key West market. This is a residence where history breathes. Commanding nearly half a city block in the prestigious Casa Mar

  1. Bedrooms: 5
  2. Baths: 5
  3. Approx. 4666 sqft
  1. MLSID: 619169
  2. Provided by Brenda Donnelly Real Estate LLC
  3. Contact Brenda J Donnelly
  4. (305) 304-1116
  5. Florida Keys Board of REALTORS
  6. DMCA Notice

Contact Info

  1. The Real Estate Professional You Deserve
  2. Mobile: 904.248.9848
  3. phoenixwade@gmail.com
Wade M. Berlin