Skip links
MLS #A12009440 image #0
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. Seller will consider all reasonable offers.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 Bird’s 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.
Current real estate data for Single Family in Islamorada as of Nov 05, 2026
30
Single Family Listed
125
Avg DOM
1,701
Avg $ / SqFt
$7,986,533
Avg List Price
Listing Provided Courtesy of LoKation at 954-545-5583

Property Details

Price:
$5,999,000
MLS #:
A12009440
Status:
Active
Beds:
8
Baths:
6
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Strattons Subdivision Pb2-
Neighborhood:
5940otherfloridacounty
Listed Date:
Apr 27, 2026
Finished Sq Ft:
3,649
Total Sq Ft:
24,004
Year Built:
1984
WaterfrontOutbuildingPoolCommunity 55 Plus5940 – Other Florida County5940otherfloridacountyStrattons Subdivision Pb2-Plantation KeyCoral Shores

Schools

Elementary School:
Plantation Key
High School:
Coral Shores

Interior

Appliances
Gas Water Heater, Dishwasher, Disposal, Dryer, Free-Standing Freezer, Gas Range, Microwave, Refrigerator, Washer
Bathrooms
6 Full Bathrooms
Cooling
Ceiling Fan(s), Central Air, Wall/Window Unit(s), Zoned
Flooring
Tile
Heating
Central
Interior Features
Built-in Features, Elevator, Kitchen Island, Pantry, Storage, Walk-In Closet(s)
Levels
Two

Exterior

Association Amenities
None
Community
55+
Construction Materials
CBS
Covered Spaces
2
Direction Faces
Southeast
Exterior Features
Lighting
Fencing
Fenced
Other Structures
Outbuilding, Shed(s)
Parking Features
Boat, Circular Driveway, Covered, Driveway, Golf Cart Garage, Guest, Paver Block, RV Access/Parking
Patio And Porch Features
Porch – Open, Porch, Patio
Roof
Concrete
Security Features
Smoke Detector(s)
Senior Community YN
1
Spa Features
Heated, In Ground
View
Bay, Water
Waterfront Features
Ocean Access, Bay, Rip Rap, Other

Financial

Tax Year
2025
Taxes
$16,657

Map

Contact Us

Send
  

Mortgage Calculator

 

Community

Property Summary

    Located in the Strattons Subdivision Pb2- subdivision, 1101 Mastic Street Islamorada FL is a Single Family for sale in Islamorada, FL, 33036. It is listed for $5,999,000 and features 8 beds, 6 baths, and has approximately 3,649 square feet of living space, and was originally constructed in 1984. The current price per square foot is $1,644. The average price per square foot for Single Family listings in Islamorada is $1,701. The average listing price for Single Family in Islamorada is $7,986,533. To schedule a showing of MLS#a12009440 at 1101 Mastic Street in Islamorada, FL, contact your Trust House Realty agent at 9543362003.

Similar Listings Nearby

broker reciprocity
MLS# A12095140broker reciprocity
115 Villa Bella
Islamorada, FL

$4,899,000

4.1 miles away

1101 Mastic Street
Islamorada, FL
This website uses cookies to improve your web experience.