Exquisite Tri-Level Waterfront Estate in Islamorada! Step into

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Home For Sale

153 Stromboli Drive

Upper Matecumbe Key, Florida 33036

Monroe County

Waterfront: Yes

Community: Venetian Shores (86)

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$4,650,000 6 br, 5.0 bath 4964 sq. ft. 0.230 acres

Exquisite Tri-Level Waterfront Estate in Islamorada! Step into luxury with this remarkable home in the prestigious Venetian Shores, designed for the most discerning buyer. Offering six bedrooms, five bathrooms, and a spacious 5000sqft of magnificently designed living space, this residence offers an open-concept floor plan with soaring ceilings, a fireplace and a grand living area. Enjoy seamless indoor-outdoor living with an expansive wraparound veranda, perfect for soaking in the breeze and relaxing water views. The beautifully landscaped 10,000sqft lot provides privacy and tranquility, while the salt swimming pool offers the ultimate relaxation. For boating enthusiasts, this property is a dream come true! Featuring 100' of deep-water concrete dockage equipped with a 20,000lb catamaran width elevator boat lift and a 5500lb set of davits you will enjoy immediate access to both the Atlantic Ocean and Florida Bay for excellent offshore and backcountry fishing. A two-car garage with a new A/C unit, plus additional covered carport parking, ensures ample space for vehicles and storage along with a beautifully paved drivewaye experience the best of the Florida Keys lifestyle in this exceptional waterfront retreat! Updates.... 1. NEW 2-car Air Conditioning Split with 10-year warranty 2. New Dock and Stair Brick Pavers 3. New third-floor Impact Windows 4. Two New third-floor Impact French Doors 5. Two New third-floor electric Rolladen Hurricane Shutters 6. Swimming poll resurfacing with new glass edge surround 7. Dock has a 220-volt pedestal to service dock-side marine electric needs

Interior:
  • Bedrooms: 6
  • Baths: 5.0
  • Sq Ft: 4964
  • Year Built: 1998
  • Utilities: 
  • Fireplaces: Has Fireplace
  • Stories: 3
  • Heat/AC: 
  • Garage: Carport, Covered, Garage, Open
Exterior:
  • Lot Size: 0.230 acre
  • Lot Dimensions: 
  • Waterfront: Yes
  • View Types: 
  • Yard: 
  • Siding: Concrete
  • Roof: Metal
  • Property Taxes: $15,133
  • MLS #: 617415
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Contact Information:
Beach Home For Sale in Upper Matecumbe Key, Florida
Listing Agent: Lisa Frins P.A., Berkshire Hathaway HomeServices Freewheeler Realty, 305-522-1479, 305-664-4444 Listing Site, Listing Status: Active
Copyright © 2025 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Ad Number: 6864740
Viewed 17 times.
Updated: Nov 21, 2025

This property is a Home located at 153 Stromboli Drive, Upper Matecumbe Key, Florida 33036, and is currently For Sale at $4,650,000. This Home has 6 bedrooms, 5.0 baths, 4964 sq ft.