Spectacular Bayfront Estate with Guesthouse in the Heart of

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Home For Sale

1101 Mastic St

Upper Matecumbe Key, Florida 33036

Monroe County

Waterfront: Yes

Water View: Yes

Community: Strattons (825)

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$8,490,000 8 br, 6.0 bath 3649 sq. ft. 0.550 acres

Spectacular Bayfront Estate with Guesthouse in the Heart of IslamoradaExperience luxury coastal living at its finest in this exceptional Gated bayfront estate, ideally situated in the heart of Islamorada. Set on a rare peninsula with over 225 feet of prime waterfront, this property offers unmatched privacy, panoramic views, and direct access to both the Florida Bay and Atlantic Ocean.The main residence features 7 spacious bedrooms and 5 beautifully appointed bathrooms designed with both elegance and comfort in mind--perfect for entertaining or hosting large gatherings. A dramatic third-floor Birds Nest Sky Lounge features 360-degree glass walls and a walkout rooftop deck, capturing breathtaking vistas in every direction. Expansive living areas and thoughtfully designed spaces capture stunning water views from every angle.A private 1-bedroom, 1-bathroom guesthouse provides the ideal retreat for visitors, accommodating extended family, or potential rental income or creating a secluded retreat. For boating enthusiasts, the estate includes an impressive 85+ foot deep-water yacht slip and four boat lifts, offering seamless access to both the Bay and Ocean--an unparalleled fishing advantage in the Florida Keys.Step outside to your own waterfront oasis, where a gorgeous heated bayfront pool invites relaxation while you take in breathtaking sunset views and the tranquil surroundings.Blending luxury, comfort, and premier waterfront access, this remarkable estate presents a rare mixed-use opportunity in one of Islamorada's most coveted locations.

Interior:
  • Bedrooms: 8
  • Baths: 6.0
  • Sq Ft: 3649
  • Year Built: 1984
  • Utilities: 
  • Fireplaces: Has Fireplace
  • Stories: 2
  • Heat/AC: 
  • Garage: Carport, Guest, Open, RV
Exterior:
  • Lot Size: 0.550 acre
  • Lot Dimensions: 
  • Waterfront: Yes
  • View Types: Water
  • Yard: 
  • Siding: Concrete
  • Roof: Concrete
  • Property Taxes: $16,658
  • MLS #: 619673
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Contact Information:
Beach Home For Sale in Upper Matecumbe Key, Florida
Listing Agent: Tracey E. Petrusha, Venture Realty Group, 305-896-1080, 954-545-5583 Listing Site, Listing Status: Active
Copyright © 2026 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: 7641243
Viewed 19 times.
Updated: May 03, 2026

This property is a Home located at 1101 Mastic St, Upper Matecumbe Key, Florida 33036, and is currently For Sale at $8,490,000. This Home has 8 bedrooms, 6.0 baths, 3649 sq ft.