Call Now:

Wade M. Berlin

ABR,BrkrAssc,CNE,CPM,FSSR,GAA,LLC,PMN,REALTOR ®,SRES
Tropic Shores Realty
The Real Estate Professional You Deserve
  1. Home
  2. Property Search
  3. Search results
  4. 720d Simonton Street, KEY WEST, FL 33040
Contact Wade M. Berlin
Contacting Wade M. Berlin
  • All fields are required.
Schedule A Showing
Schedule a Showing.
  • All fields are required.
Check this box to Register with us:
Submit an Offer Now!
Submit an Offer Now!
All fields are required.
Print Flyer
Active
Property Photos
720d Simonton Street
  1. Image 1 of 59 For 720d Simonton Street
  2. Image 2 of 59 For 720d Simonton Street
  3. Image 3 of 59 For 720d Simonton Street
  4. Image 4 of 59 For 720d Simonton Street
  5. Image 5 of 59 For 720d Simonton Street
  6. Image 6 of 59 For 720d Simonton Street
  7. Image 7 of 59 For 720d Simonton Street
  8. Image 8 of 59 For 720d Simonton Street
  9. Image 9 of 59 For 720d Simonton Street
  10. Image 10 of 59 For 720d Simonton Street
  11. Image 11 of 59 For 720d Simonton Street
  12. Image 12 of 59 For 720d Simonton Street
  13. Image 13 of 59 For 720d Simonton Street
  14. Image 14 of 59 For 720d Simonton Street
  15. Image 15 of 59 For 720d Simonton Street
  16. Image 16 of 59 For 720d Simonton Street
  17. Image 17 of 59 For 720d Simonton Street
  18. Image 18 of 59 For 720d Simonton Street
  19. Image 19 of 59 For 720d Simonton Street
  20. Image 20 of 59 For 720d Simonton Street
  21. Image 21 of 59 For 720d Simonton Street
  22. Image 22 of 59 For 720d Simonton Street
  23. Image 23 of 59 For 720d Simonton Street
  24. Image 24 of 59 For 720d Simonton Street
  25. Image 25 of 59 For 720d Simonton Street
  26. Image 26 of 59 For 720d Simonton Street
  27. Image 27 of 59 For 720d Simonton Street
  28. Image 28 of 59 For 720d Simonton Street
  29. Image 29 of 59 For 720d Simonton Street
  30. Image 30 of 59 For 720d Simonton Street
  31. Image 31 of 59 For 720d Simonton Street
  32. Image 32 of 59 For 720d Simonton Street
  33. Image 33 of 59 For 720d Simonton Street
  34. Image 34 of 59 For 720d Simonton Street
  35. Image 35 of 59 For 720d Simonton Street
  36. Image 36 of 59 For 720d Simonton Street
  37. Image 37 of 59 For 720d Simonton Street
  38. Image 38 of 59 For 720d Simonton Street
  39. Image 39 of 59 For 720d Simonton Street
  40. Image 40 of 59 For 720d Simonton Street
  41. Image 41 of 59 For 720d Simonton Street
  42. Image 42 of 59 For 720d Simonton Street
  43. Image 43 of 59 For 720d Simonton Street
  44. Image 44 of 59 For 720d Simonton Street
  45. Image 45 of 59 For 720d Simonton Street
  46. Image 46 of 59 For 720d Simonton Street
  47. Image 47 of 59 For 720d Simonton Street
  48. Image 48 of 59 For 720d Simonton Street
  49. Image 49 of 59 For 720d Simonton Street
  50. Image 50 of 59 For 720d Simonton Street
  51. Image 51 of 59 For 720d Simonton Street
  52. Image 52 of 59 For 720d Simonton Street
  53. Image 53 of 59 For 720d Simonton Street
  54. Image 54 of 59 For 720d Simonton Street
  55. Image 55 of 59 For 720d Simonton Street
  56. Image 56 of 59 For 720d Simonton Street
  57. Image 57 of 59 For 720d Simonton Street
  58. Image 58 of 59 For 720d Simonton Street
  59. Image 59 of 59 For 720d Simonton Street
Image Gallery

PRICED AT ONLY: $4,990,000

Address: 720d Simonton Street, KEY WEST, FL 33040

Description

KEY WEST'S UNLIKELY SANCTUARY | DUAL TRANSIENT LICENSES While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE COMPOUND | Built in 2008 on a generous 5,220sf lot, this 2,441sf property features two distinct units, a front house and back house, connected by a heated pool oasis. Four bedrooms, four full baths, soaring two story ceilings, and thoughtfully curated interiors showcase warm mid century touches against clean architectural lines. Wood and tile floors, built in cabinetry, walk in closets, and abundant natural light through expansive glass doors create spaces that are both meditative and functional. | THE SANCTUARY | High privacy walls enclose a tranquil pool courtyard with tropical landscaping, outdoor shower, and ample off street parking. Electric gate entry ensures complete seclusion while downtown's energy pulses just steps away. | THE OPPORTUNITY | Two active transient rental licenses with 1 day minimum stays unlock exceptional income in Key West's most sought after location. The property's distinctive design aesthetic attracts discerning guests seeking something different, proven by outstanding reviews and strong rental performance. HNC zoning supports flexible commercial use, while X flood zone designation offers insurance advantages. | THE LOCATION | Heart of Old Town, steps from Duval's legendary dining, nightlife, galleries, and waterfront. Close enough to all the action, far enough from the noise. This is investment grade real estate with soul, where architectural distinction drives premium rates and occupancy.

Property Location and Similar Properties

All
Similar
Payment Calculator
  •   Principal & Interest -
  •   Property Tax $
  •   Home Insurance $
  •   HOA Fees $
  •   Mortgage Insurance-
  •   Monthly -
For a Fast & FREE Mortgage Pre-ApprovalApply Now
Virtual Tour
More Like This
  • MLS#: 618363 ( Single Family )
  • Street Address: 720d Simonton Street
  • Viewed: 2
  • Price: $4,990,000
  • Price sqft: $2,044
  • Waterfront: No
  • Waterfront Type: None
  • Year Built: 2008
  • Bldg sqft: 2441
  • Bedrooms: 4
  • Total Baths: 4
  • Full Baths: 4
  • Days On Market: 60

Description

KEY WEST'S UNLIKELY SANCTUARY | DUAL TRANSIENT LICENSES While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE COMPOUND | Built in 2008 on a generous 5,220sf lot, this 2,441sf property features two distinct units, a front house and back house, connected by a heated pool oasis. Four bedrooms, four full baths, soaring two story ceilings, and thoughtfully curated interiors showcase warm mid century touches against clean architectural lines. Wood and tile floors, built in cabinetry, walk in closets, and abundant natural light through expansive glass doors create spaces that are both meditative and functional. | THE SANCTUARY | High privacy walls enclose a tranquil pool courtyard with tropical landscaping, outdoor shower, and ample off street parking. Electric gate entry ensures complete seclusion while downtown's energy pulses just steps away. | THE OPPORTUNITY | Two active transient rental licenses with 1 day minimum stays unlock exceptional income in Key West's most sought after location. The property's distinctive design aesthetic attracts discerning guests seeking something different, proven by outstanding reviews and strong rental performance. HNC zoning supports flexible commercial use, while X flood zone designation offers insurance advantages. | THE LOCATION | Heart of Old Town, steps from Duval's legendary dining, nightlife, galleries, and waterfront. Close enough to all the action, far enough from the noise. This is investment grade real estate with soul, where architectural distinction drives premium rates and occupancy.
Request More Information
  • All fields are required.
Features
Building and Construction
  • Absolute Longitude: 81.799736
  • Construction: CBS, Combo Construction, Concrete
  • Exterior Features: Detached Guest Qtrs, Water Display, Storage, Privacy Wall/Fence, Outdoor Shower, Lighting
  • Floor: Tile, Wood
  • Porchbalcony: Open Porch/Balcony, Patio
  • Roof: Metal Roof
  • Sqft Source: Property Data Card
  • Total Number Of Units: 2.00
Property Information
  • Property Condition: Updated/Remodeled
  • Property Group Id: 19990816212109142258000000
Garage and Parking
  • Vehicle Storage: Off Street Parking
Eco-Communities
  • Pool Info Heated: Yes
  • Pool Info: In Ground, Concrete
  • Water View: No Waterview
Utilities
  • Cooling: Central Air, Ceiling Fans(s)
  • Kw Neighborhood: Old Town-N of Truman
  • Pets: Pets Allowed
  • Pub Sewer Hkup: Yes
  • Security: Electric Gate
  • Utilities: FKAA, Buyer to Verify, Municipal Sewer
  • Windowsdoors: Glass Doors, Aluminum Windows, Sliding Glass Doors
Finance and Tax Information
  • Association Info Association Fee: 0.00
  • Fee Includes: None
  • Tax Year: 2025
Rental Information
  • Min Rental Days: 1.00
  • Rentals Allowed: Yes
Other Features
  • Add L Parcel Num1: 00015880-000000
  • Alternate Key Num: 1016268
  • Appliances: Washer, Wine Cooler, Freezer, Microwave, Range, Refrigerator, Dishwasher, Dryer
  • Association Info 1st Right Of Refusal: No
  • Association Info Mandatory Home Owners Asc: No
  • Deed Restrictions: Unknown
  • Dockage: None
  • Flood Zone: X FLOOD ZONE
  • Interior Features: Drapes/Blinds Incl, Window Treatments, Walk-in Closet(s), Storage, Built-in Cabinets, Pantry
  • Legal Description: KW PT LOT 3 SQR 2 TR 4 OR172-109/10 OR190-476/77 OR333-396/97
  • Mile Marker: 1.00
  • Side: Median
  • Style: Single Family
  • Zoning: HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Nearby Subdivisions
Bay Manor (3.0)   Benj Alburys Subd (2.0)   Calle Uno 9.0   Carletons Compound (1.0)   Casa Gato (2.0)   East Martello Towers (2.0)   Gardens Of Key West (1.0)   George W Nichols Sub (1.0)   Gg Watson Sub (1.0)   Gwynn Sub (1.0)   Hilton Haven Sec 2 A (2.0)   Island City Land Sub (1.0   Island City Land Sub (1.0)   Kamien Plat #1 (2.0)   Kamien Plat #2 (2.0)   Key Estates (3.0)   Key West Estates (4.0)   Key West Fwdn Sub (4.0)   Key West Golf Club Dev (4.0)   Key West Investment Co Sub (1.   Key West Realty Cos Sub (3.0)   Knights Sub (2.0)   Kw All Sub   Land Buyers Assn (3.0)   Lime Grove (3.0)   Macros Subd (2.0)   Martello Towers (1.0)   Moffats Sub (2.0)   Monroe Investement Co Sub (2.0   New Town - Unlisted (2.0)   Nuevo Progresso (2.0)   Old Town - Unlisted (1.0)   Old Town - Unrecord   Old Town - Unrecord (1.0)   Old Town- Unrecord (1.0)   Pearlman Est (4.0)   Pearlman Heights (4.0)   Pearlmans Subd (2.0)   Prog Land Imp Co Diag (2.0)   Riviera Shores (3.0)   Riviera Shr Amd Plat (3.0)   Robyn Sub (5.0)   Southernmost Hidaways (1.0)   Summerland Estates   Sunrise Shores (4.0)   Sunset Key (tank) Island Unrcd   Sunshine Sub Plat 1 (3.0)   Sunshine Sub Plat 3 (3.0)   The Foundry (1.0)   The Seven Palms - A Key West O   Tropical Bldt & Investment Co    Vista Del Mar (4.0)   Waddells Subdivision (2.0)   Webb Realty Co Sub (1.0)   White & Pierce Diagram (1.0)  
Similar Properties

Active
Details for 18 Hilton Haven Road, KEY WEST, FL 33040
$5,195,000.00 ($1,444.26 / sqft )

18 Hilton Haven Road More Like This

Double waterfront MM 2 in Key West. Presenting a rare opportunity to acquire a distinguished single family waterfront home on highly desired Hilton Haven Drive, a truly unique private Key West Street

  1. Request Information
  1. Bedrooms: 5
  2. Baths: 6
  3. Approx. 3597 sqft
  1. MLSID: 616896
  2. Provided by Keller Williams Key West Compass Realty
  3. Contact The Behmke Group
  4. (305) 292-0020
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
34 Pictures and Information
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. Request Information
  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
39 Pictures and Information
Active
Details for 1006-1008 Fleming Street, KEY WEST, FL 33040
$4,898,000.00 ($1,468.23 / sqft )

1006-1008 Fleming Street Virtual Tour More Like This

MOTIVATED SELLERS! Exceptional Old Town estate with pool, gardens, and 2 guest houses in the heart of Key West. This impeccable property blends timeless architecture with modern updates across three b

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 5
  3. Approx. 3336 sqft
  1. MLSID: 617020
  2. Provided by Truman & Co. (KW)
  3. Contact Terri Spottswood
  4. (305) 292-2244
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
48 Pictures and Information
Active
Details for 1014 Southard Street, KEY WEST, FL 33040
$4,995,000.00 ($1,650.69 / sqft )

1014 Southard Street Virtual Tour More Like This

Nestled in the storied heart of Old Town Key West, this grand estate is a masterpiece of luxury & history. Spanning a majestic 8,397 sq. ft. lot, the property at 1014 Southard St. Invites you into a w

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 4
  3. Approx. 3026 sqft
  1. MLSID: 617209
  2. Provided by Suzanne Moore Real Estate
  3. Contact Suzanne M Moore
  4. (305) 797-0699
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
71 Pictures and Information
Active
Details for 600 Elizabeth Street, KEY WEST, FL 33040
$4,799,000.00 ($1,552.07 / sqft )

600 Elizabeth Street More Like This

Elegantly positioned beneath the sweeping canopy of its namesake tree, Casa Sapodilla introduces itself with the kind of presence that feels both storied and serene. Built in 1996, the residence pays

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 6
  3. Approx. 3092 sqft
  1. MLSID: 617513
  2. Provided by Berkshire Hathaway HomeServices Knight & Gardner R
  3. Contact Lori Langton
  4. (305) 294-5155
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
90 Pictures and Information
Active
Details for 709 Eaton Street, KEY WEST, FL 33040
$4,750,000.00 ($1,748.90 / sqft )

709 Eaton Street More Like This

Step into the enchanting world of Key West history at 709 Eaton Street, a meticulously preserved gem built circa 1847 in the iconic Seaport neighborhood. Historic charm and modern comfort, this home d

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 5
  3. Approx. 2716 sqft
  1. MLSID: 618470
  2. Provided by Berkshire Hathaway HomeServices Knight & Gardner R
  3. Contact Will Langley
  4. (305) 294-5155
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
37 Pictures and Information
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. Request Information
  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
65 Pictures and Information
Active
Details for 3300 Riviera Drive, KEY WEST, FL 33040
$4,785,000.00 ($1,337.71 / sqft )

3300 Riviera Drive More Like This

Welcome to 3300 Riviera Drive an exceptional, turn key, waterfront, residential estate featuring 4 bedrooms and 4.5 bathrooms. Nestled on three lots in a serene enclave just minutes from Old Town, th

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 5
  3. Approx. 3577 sqft
  1. MLSID: 614999
  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
56 Pictures and Information
Active
Details for 1614 Washington Street, KEY WEST, FL 33040
$4,495,000.00 ($1,601.92 / sqft )

1614 Washington Street More Like This

Architect designed and purpose built for modern island living, 1614 Washington Street delivers a rare combination of durability, intelligence, and refined restraint. This is a luxury home defined not

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 5
  3. Approx. 2806 sqft
  1. MLSID: 618937
  2. Provided by Your Keys Real Estate, LLC
  3. Contact Richard Patten
  4. (305) 680-6720
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
59 Pictures and Information
Active
Details for 24 Cannon Royal Drive, Shark Key, FL 33040
$4,695,000.00 ($1,124.28 / sqft )

24 Cannon Royal Drive Virtual Tour More Like This

Tucked behind swaying palms and lush tropical landscaping, this elegant waterfront estate captures the very best of Florida Keys living. From breathtaking sunset views to exceptional outdoor spaces, e

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 4
  3. Approx. 4176 sqft
  1. MLSID: 619136
  2. Provided by Ocean Sotheby's International Realty
  3. Contact Jenna Stauffer
  4. (305) 294-1117
  5. Florida Keys Board of REALTORS
  6. DMCA Notice
65 Pictures and Information

Contact Info

Skip to Main Content
  2. The Real Estate Professional You Deserve
  3. Mobile: 904.248.9848
  4. phoenixwade@gmail.com
Wade M. Berlin

Looking To Sell Your Property ?

Connecting agents, buyers, and sellers
Call Us Now Get In Touch
Featured Listings
5321 24th Terrace 203a
223 Arbor Avenue
31018 Satinleaf
30 Jewfish Avenue
18801 Orange Hill Drive
29172 Rose Drive
12514 Coffee Hill Row

Copyright ©2006-2026 brokerIDXsites.com   |   All Rights Reserved.