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$13,750,000
Upper Matecumbe Key Islamorada, FL 33036
MLS# 620590
5 beds | 7 baths | 5489 sqft
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Property Description
Situated on one of Islamorada's premier and most sought-after bayfront streets, in the heart of Islamorada, this custom-designed poured concrete waterfront estate by renowned architect Charles Vincent George occupies 1.27 private acres with panoramic open-water views, spectacular year-round sunsets, protected boat basin, solar panels and a rare sandy beach area. Designed to maximize its exceptional setting, the residence offers seamless indoor-outdoor living with floor-to-ceiling impact-rated glass, expansive covered terraces, and walls of retractable sliders that frame breathtaking bay views from every room. A dramatic floating staircase, 12-foot interior doors, engineered hardwood flooring, and superb designer finishes define the home's clean contemporary design. The main residence features 4 bedrooms all ensuite, and 1 half bath. It is complemented by a detached 1-bedroom, 1-bath guest house. The kitchen features quartz countertops, premium Miele and Thermador appliances, and a hidden walk-in pantry. Upstairs is a spacious family/media or fitness room that leads onto a large deck with exquisite views of Florida Bay. Separate laundry/storage room. Fully integrated Loxone Smart Home system controls lighting, security, audio, and six independent HVAC climate zones. Outdoor amenities include an elevated heated and chilled 50FT saltwater lap pool, expansive entertaining terraces, mature tropical fruit trees & landscaping, an air conditioned garden shed, architectural landscape lighting, and a gated entrance ensuring exceptional privacy. The protected boat basin features a composite dock, 12,000 lb boat lift, with immediate access to world-class fishing & diving. At the front is an oversized air-conditioned garage with EV charging & a half bath. A covered carport is adjacent to the main house. A rare opportunity to acquire one of Islamorada's premier contemporary bayfront estates, combining exceptional architecture, outstanding construction and spectacular sunsets.
Details
Maps
Contract Information
Listing Board: Key West Association
Current Price: $13,750,000
Listing Date: 2026-07-10
List Price: $13,750,000
Location, Tax & Legal
City: ISLAMORADA
Mile Marker: 82
Marathon Neighborhood: N/A
Side: Bay/Gulf
Flood Zone: AE,AE,AE,VE
Alternate Key #: 1494682
Parcel #: 00402330-000000
Zoning: R1 - Residential Single Family
Deed Restrictions: Unknown
Legal: LT 5 AND LT 19 ISLAMORADA PB1-48 UPPER MATECUMBE AND PT MARKED RES
Taxes: 35593.82
Tax Year: 2025
Pub Sewer HkUp: Yes
Street #: 19
Street Name: Avacado
Street Suffix: Street
Key/Island: Upper Matecumbe Key Islamorada
State/Province: FL
Zip Code: 33036
County: Monroe
Subdivision: Misc Upper Matacumbe (82.0)
Area: 23 - Upper Matecumbe
General Property Description
Realtor.COM Type: Residential - Single Family
Waterfront: Yes
Control Depth: 3
Lot SqFt: 55125
Pool: Yes
Lot Sqft Source: Property Data Card
Total Units: 0
Acres: 1.27
SqFt Source: Property Data Card
Rentals Allowed: With Restrictions
Min Rental Days: 28
Style: Single Family
Year Built: 2019
Living Apx SqFt: 5489
Total Bedrooms: 5
Full Baths: 5
Half Baths: 2
Total Baths: 7
Remarks & Misc
Remarks – Consumer: Situated on one of Islamorada's premier and most sought-after bayfront streets, in the heart of Islamorada, this custom-designed poured concrete waterfront estate by renowned architect Charles Vincent George occupies 1.27 private acres with panoramic open-water views, spectacular year-round sunsets, protected boat basin, solar panels and a rare sandy beach area. Designed to maximize its exceptional setting, the residence offers seamless indoor-outdoor living with floor-to-ceiling impact-rated glass, expansive covered terraces, and walls of retractable sliders that frame breathtaking bay views from every room. A dramatic floating staircase, 12-foot interior doors, engineered hardwood flooring, and superb designer finishes define the home's clean contemporary design. The main residence features 4 bedrooms all ensuite, and 1 half bath. It is complemented by a detached 1-bedroom, 1-bath guest house. The kitchen features quartz countertops, premium Miele and Thermador appliances, and a hidden walk-in pantry. Upstairs is a spacious family/media or fitness room that leads onto a large deck with exquisite views of Florida Bay. Separate laundry/storage room. Fully integrated Loxone Smart Home system controls lighting, security, audio, and six independent HVAC climate zones. Outdoor amenities include an elevated heated and chilled 50FT saltwater lap pool, expansive entertaining terraces, mature tropical fruit trees & landscaping, an air conditioned garden shed, architectural landscape lighting, and a gated entrance ensuring exceptional privacy. The protected boat basin features a composite dock, 12,000 lb boat lift, with immediate access to world-class fishing & diving. At the front is an oversized air-conditioned garage with EV charging & a half bath. A covered carport is adjacent to the main house. A rare opportunity to acquire one of Islamorada's premier contemporary bayfront estates, combining exceptional architecture, outstanding construction and spectacular sunsets.
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
Fee Includes
None: 1
Dockage
Dock: Composite
Basin: 1
Boat Lift: 1
Seawall: Rip Rap
Tax Exemptions
None: 1
Appliances
Dishwasher: 1
Disposal: 1
Dryer: 1
Freezer: 1
Microwave: 1
Oven: 1
Refrigerator: 1
Washer: 1
Water Purification: 1
Wine Cooler: 1
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Central Air: 1
Heating
Central: 1
Waterfront
Bay Front: 1
Gulf Front: 1
Open Water: 1
Waterview
Bay/Gulf View: 1
Open Water View: 1
Floor
Tile: 1
Wood: 1
Interior Features
Built-in Cabinets: 1
Drapes/Blinds Incl: 1
Entrance Foyer: 1
Pantry: 1
Quartz Countertops: 1
Security System: 1
Smoke Alarms: 1
Walk-in Closet(s): 1
Property Condition
New Construction: 1
Building Style
Above Flood: Yes
Stories: 2 Stories
Windows/Doors
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
Vehicle Storage
Car(s): 4+
Covered Parking: 1
Garage: 1
Detached: 1
Security
Electric Gate: 1
On Premises System: 1
Construction
Concrete: 1
Land Size
1 Less Than 2 Acres: 1
Furnished
Negotiable: 1
Utilities
FKAA: 1
Municipal Sewer: 1
Propane: 1
Porch/Balcony
Deck: 1
Open Porch/Balcony: 1
Patio: 1
Title
Title Ins - Buyer: 1
Exterior Features
Detached Guest Qtrs: 1
Fruit Tree(s): 1
Lighting: 1
Outdoor Shower: 1
Privacy Wall/Fence: 1
Sandy Beach: 1
Storage: 1
Pool Info
In Ground: 1
Salt Water: 1
Lap: 1
Concrete: 1
Decked: 1
Pre-Wired
Other: Loxone Smart System
Surround Sound: 1
Roof
Concrete Roof: 1
GF-Utilities
Solar Panels: 1
Status Change Info
Status: Active
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: Bay Front; Gulf Front; Open Water
Waterview: Bay/Gulf View; Open Water View
Dockage: Basin; Boat Lift
Property Condition: New Construction
Vehicle Storage: Garage; Detached; Covered Parking
Furnished: Negotiable
Cooling: Ceiling Fans(s); Central Air
Heating: Central
Utilities: FKAA; Municipal Sewer; Propane
Interior Features: Built-in Cabinets; Drapes/Blinds Incl; Entrance Foyer; Pantry; Quartz Countertops; Security System; Smoke Alarms; Walk-in Closet(s)
Pre-Wired: Surround Sound
Appliances: Dishwasher; Disposal; Dryer; Freezer; Microwave; Oven; Refrigerator; Washer; Water Purification; Wine Cooler
Exterior Features: Detached Guest Qtrs; Fruit Tree(s); Lighting; Outdoor Shower; Privacy Wall/Fence; Sandy Beach; Storage
Pool Info: In Ground; Salt Water; Lap; Concrete; Decked
Construction: Concrete
Floor: Tile; Wood
Roof: Concrete Roof
Pets: Pets Allowed
Security: Electric Gate; On Premises System
Land Size: 1 Less Than 2 Acres
Title: Title Ins - Buyer
GF-Utilities: Solar Panels
Listing Office: The Agency Florida Keys
Last Updated: July - 10 - 2026
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