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8 Beds
6 Baths
3,649 sqft

$6,999,000

1101 Mastic Street, Upper Matecumbe Key Islamorada FL, 33036

Price per sqft$1,918.06
Built in1984
Property size3,649 sqft
Property typeResidential

Overview

Active

Listed Apr 28, 2026

Updated 16h ago

Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available. Experience 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 Whole House Generator for peace of mind. 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. Seller will consider all reasonable offers.

$46,565/mo

Est. mortgage payment based on a $6,999,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
619673

Interior Features

Bedrooms
8
Bathrooms
6
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
0.55 Acres

Other Property Details

Taxes
$16,658
Tax Frequency
Annually
View
Yes
Pets Allowed
Yes
Pool
Yes
Waterfront
Yes
MLS provider logo

Listed by Tracey E. Petrusha with LoKation Real Estate
Listing Contact: 305-896-1080 

The IDX display contains information sourced from the Florida Keys Board of REALTORS® as of 10/4/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

©2026 Florida Keys Board of REALTORS® all rights reserved.

Data last updated on 10/4/2026 at 7:09 AM UTC

 

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