$8,490,000
1101 Mastic Street
Islamorada, FL, 33036
Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada
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 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 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.
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 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 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.
Property Details
Price:
$8,490,000
MLS #:
A12009440
Status:
Active
Beds:
8
Baths:
6
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Strattons Subdivision Pb2-
Neighborhood:
strattonssubdivisionpb2
Listed Date:
Apr 28, 2026
Year Built:
1984
Schools
Interior
Appliances
Dishwasher, Disposal, Dryer, Free-Standing Freezer, Microwave, Gas Range, Refrigerator, Washer
Bathrooms
6 Full Bathrooms
Cooling
Ceiling Fan(s), Central Air, Wall/Window Unit(s), Zoned
Flooring
Tile
Heating
Central
Interior Features
First Floor Entry, Built-in Features, Cooking Island, Pantry, Walk-In Closet(s), Den/Library/Office, Other, Storage, Utility Room/Laundry, Workshop
Laundry Features
Utility Room/Laundry
Exterior
Architectural Style
Detached, Two Story
Community Features
None
Construction Materials
CBS Construction
Covered Spaces
2
Direction Faces
Southeast
Exterior Features
Lighting
Fencing
Fenced
Lot Features
1/2 To Less Than 3/4 Acre Lot
Open Parking YN
1
Other Structures
Extra Building/Shed, Shed(s)
Parking Features
Additional Spaces Available, Circular Driveway, Covered, Driveway, Golf Cart Parking, Guest, Other, Paver Block, Rv/Boat Parking
Patio And Porch Features
Open Porch, Patio
Roof
Concrete
Security Features
Smoke Detector
View
Bay, Water
Waterfront Features
Ocean Access, Waterfront, Rip Rap
Window Features
Complete Accordian Shutters, Complete Impact Glass, Hurricane Shutters
Financial
Tax Year
2025
Taxes
$16,657
Mortgage Calculator
Map
Current real estate data for Single Family in Islamorada as of Jun 19, 2026
25
Single Family Listed
168
Avg DOM
1,657
Avg $ / SqFt
$8,626,236
Avg List Price
Community
- Address1101 Mastic Street Islamorada FL
- SubdivisionStrattons Subdivision Pb2-
- CityIslamorada
- CountyMonroe County
- Zip Code33036
Subdivisions in Islamorada
- Anglers Reef Un 111
- INDIAN WATERWAYS
- Islamorada
- ISLAMORADA SOUTH
- ISLAMORADA, TOWNSITE OF
- Lower Matecumbe
- Mat Ocean Bay
- Mat Ocean View
- MATE OCEAN BAY SUBD SEC 1
- MATECUMBE OCEAN BAY SEC 2
- MATECUMBE OCEAN BEACH SEC
- MATECUMBE OCEAN VIEW
- MATECUMBE SANDY BEACH
- Ocean Harbour
- Palms of Isla 80.0
- PEARL CITY
- PLANTATION BEACH
- PLANTATION BY THE SEA
- Plantation Lake Estates
- PLANTATION VILLAS I CONDO
- PORT ANTIGUA PLAT NO 2
- PORT ANTIGUA PLAT NO 5 &,Port Antigua
- Safety Harbor
- SAFETY HARBOR SEC 1
- Strattons 82.5,Coral Cove
- STRATTONS SUBD
- Strattons Subdivision Pb2-
- Upper Matecumbe
- VENETIAN SHORES NO 2
- WHITE MARLIN BEACH SEC 1
- WHITE MARLIN BEACH SEC 2
- WINDLEY KEY MOBILE HOME P
Similar Listings Nearby
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 $8,490,000 and features 8 beds, 6 baths, and has approximately 0 square feet of living space, and was originally constructed in 1984. The average price per square foot for Single Family listings in Islamorada is $1,657. The average listing price for Single Family in Islamorada is $8,626,236.

1101 Mastic Street
Islamorada, FL




































































































