$2,750,000
122 Court Contessa
Islamorada, FL, 33036
Rarely available, turnkey Deepwater Boater’s Retreat with Private Beach Access in the Heart of Islamorada
Tucked away on a quiet cul-de-sac in one of the most desirable enclaves in Islamorada, this fully designer-updated 3+ bedroom, 3.5-bath home delivers the ultimate Florida Keys lifestyle–where luxury, durability, and world-class boating converge.
Built for peace of mind and longevity, the home features solid concrete construction and a concrete roof, offering superior storm resilience and insurance advantages rarely found in the Keys. The interior staircase provides easy access to the home’s main living areas.
The property boasts 90 feet of deep-water dockage with immediate access to both the bay and the Atlantic Ocean–no bridges.
The oversized paved driveway provides ample parking for guests, trailers, or multiple vehicles — an uncommon convenience in this area.
What truly sets this property apart is access to a rare, highly coveted private beach area, widely regarded by locals as one of the finest in the Florida Keys, offering a unique blend of boating and beach lifestyle.
Whether you’re seeking a primary residence, a luxury second home, or an income-producing waterfront asset, this property delivers unmatched versatility and strong potential for high-end monthly rentals. Some Exterior Photos are AI-generated.
Tucked away on a quiet cul-de-sac in one of the most desirable enclaves in Islamorada, this fully designer-updated 3+ bedroom, 3.5-bath home delivers the ultimate Florida Keys lifestyle–where luxury, durability, and world-class boating converge.
Built for peace of mind and longevity, the home features solid concrete construction and a concrete roof, offering superior storm resilience and insurance advantages rarely found in the Keys. The interior staircase provides easy access to the home’s main living areas.
The property boasts 90 feet of deep-water dockage with immediate access to both the bay and the Atlantic Ocean–no bridges.
The oversized paved driveway provides ample parking for guests, trailers, or multiple vehicles — an uncommon convenience in this area.
What truly sets this property apart is access to a rare, highly coveted private beach area, widely regarded by locals as one of the finest in the Florida Keys, offering a unique blend of boating and beach lifestyle.
Whether you’re seeking a primary residence, a luxury second home, or an income-producing waterfront asset, this property delivers unmatched versatility and strong potential for high-end monthly rentals. Some Exterior Photos are AI-generated.
Property Details
Price:
$2,750,000
MLS #:
A11857499
Status:
Active
Beds:
3
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
PORT ANTIGUA PLAT NO 5 &,Port Antigua
Neighborhood:
portantiguaplatno5
Listed Date:
Aug 20, 2025
Finished Sq Ft:
2,374
Total Sq Ft:
3,858
Year Built:
2021
Schools
Interior
Appliances
Dishwasher, Disposal, Dryer, Electric Water Heater, Free-Standing Freezer, Ice Maker, Microwave, Electric Range, Refrigerator, Self Cleaning Oven, Wall Oven, Washer
Bathrooms
3 Full Bathrooms
Cooling
Ceiling Fan(s), Central Air
Flooring
Concrete
Heating
Central
Interior Features
Second Floor Entry, Closet Cabinetry, Cooking Island, Pantry, Vaulted Ceiling(s), Walk-In Closet(s), Den/Library/Office, Family Room, Utility Room/Laundry
Laundry Features
Utility Room/Laundry, Washer/Dryer Hook-Up
Exterior
Architectural Style
Detached, Three Or More Stories
Attached Garage YN
1
Community Features
Boating, Maintained Community, Management On Site, Paved Road, Picnic Area, Street Lights
Construction Materials
Concrete Block Construction, CBS Construction, Elevated Construction
Covered Spaces
1
Direction Faces
East
Exterior Features
Open Balcony, Outdoor Shower, Room For Pool
Garage Spaces
1
Green Energy Efficient
Appliances, Doors, HVAC, Lighting, Roof, Ventilation, Water Heater, Windows
Lot Features
Less Than 1/4 Acre Lot
Open Parking YN
1
Parking Features
Additional Spaces Available, Covered, Driveway, Golf Cart Parking, Guest, Paver Block
Patio And Porch Features
Awning(s), Open Balcony, Open Porch, Patio
Roof
Concrete
Security Features
Curr Owner Wind Mitig Cert Avail, Fire Alarm, Smoke Detector
View
Bay, Canal, Intracoastal View, Ocean, Direct Ocean, Water
Waterfront Features
WF/Ocean Access, Canal Front, Ocean Access
Window Features
Clear Impact Glass, Complete Impact Glass, Blinds, High Impact Windows, Impact Glass, Picture Window
Financial
HOA Fee
$500
HOA Fee Frequency
Annually
Tax Year
2024
Taxes
$13,927
Mortgage Calculator
Map
Current real estate data for Single Family in Islamorada as of Jul 31, 2026
24
Single Family Listed
193
Avg DOM
1,913
Avg $ / SqFt
$10,140,204
Avg List Price
Community
- Address122 Court Contessa Islamorada FL
- SubdivisionPORT ANTIGUA PLAT NO 5 &,Port Antigua
- 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 PORT ANTIGUA PLAT NO 5 &,Port Antigua subdivision, 122 Court Contessa Islamorada FL is a Single Family for sale in Islamorada, FL, 33036. It is listed for $2,750,000 and features 3 beds, 3 baths, and has approximately 2,374 square feet of living space, and was originally constructed in 2021. The current price per square foot is $1,158. The average price per square foot for Single Family listings in Islamorada is $1,913. The average listing price for Single Family in Islamorada is $10,140,204.

122 Court Contessa
Islamorada, FL
















































































