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$8,490,000
Upper Matecumbe Key Islamorada, FL 33036
MLS# 619673
8 beds | 6 baths | 3649 sqft
1 / 3
Property Description
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 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 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.
Details
Contract Information
Listing Board: Florida Keys
Potential Short Sale: No
Bank Owned: No
Current Price: $8,490,000
Listing Date: 2026-04-28
List Price: $8,490,000
Location, Tax & Legal
City: ISLAMORADA
Mile Marker: 82.5
Marathon Neighborhood: N/A
Side: Bay/Gulf
Alternate Key #: 1491519
Parcel #: 00399130000000
Zoning: SC - Sub Urban Commercial District
Deed Restrictions: Unknown
Legal: Strattons Subdivision Pb2-38 Ne 10 Ft Lot 10 & All Lot 11 Bk 1 G24-94 G49-592 Or366-6/7 Or397-476Qc Or411-520/23 Or455-6
Taxes: 16657.96
Tax Year: 2025
Pub Sewer HkUp: Yes
Street #: 1101
Street Name: Mastic
Street Suffix: Street
Key/Island: Upper Matecumbe Key Islamorada
State/Province: FL
Zip Code: 33036
County: Monroe
Subdivision: Strattons (82.5)
Area: 23 - Upper Matecumbe
General Property Description
Realtor.COM Type: Residential - Single Family
Waterfront: Yes
Control Depth: 7
Lot Size: X
Lot SqFt: 24004
Pool: Yes
Lot Sqft Source: Property Data Card
Acres: 0.55
SqFt Source: Property Data Card
Rentals Allowed: With Restrictions
Style: Single Family
Year Built: 1984
Living Apx SqFt: 3649
Total Bedrooms: 8
Full Baths: 6
Total Baths: 6
Remarks & Misc
Remarks – Consumer: 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 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 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.
Directions: US 1 Bay Side.
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
Fee Includes
None: 1
Dockage
Dock: Wood
Basin: 1
Boat Lift: 1
Davits: 1
Tax Exemptions
None: 1
Appliances
Dishwasher: 1
Disposal: 1
Dryer: 1
Freezer: 1
Gas Appliances: 1
Microwave: 1
More Appliances: 1
Oven: 1
Range: 1
Refrigerator: 1
Washer: 1
Wine Cooler: 1
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Central Air: 1
Ductless: 1
Wall/Window Unit(s): 1
Heating
Central: 1
Fireplace(s): 1
Waterfront
Bay Front: 1
Open Water: 1
Waterview
Bay/Gulf View: 1
Open Water View: 1
Floor
Tile: 1
Neighborhood Feature
Community Boat Ramp: 1
Other Area Features: 1
Interior Features
Built-in Cabinets: 1
Elevator: 1
Fireplace(s): 1
Pantry: 1
Smoke Alarms: 1
Storage: 1
Walk-in Closet(s): 1
Wet Bar: 1
Specialty Rooms
Guest/Servant Qtrs: Legal
Gym: 1
Laundry Room: 1
Utility Room: 1
Workshop: 1
Other: 1
Building Style
Above Flood: Unknown
Stories: 2 Stories
Windows/Doors
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
Vehicle Storage
Car(s): 4+
Carport: 1
Guest Parking: 1
Open Parking: 1
RV Parking Open: 1
Trailer Storage: 1
Security
Electric Gate: 1
Other: 1
Construction
CBS: 1
Concrete: 1
Land Size
1/2 - Less Than 1 AC: 1
Furnished
Negotiable: 1
Terms
Cash: 1
Conventional: 1
FHA: 1
VA: 1
Utilities
Buyer to Verify: 1
Cable Available: 1
FKAA: 1
Municipal Sewer: 1
Propane: 1
Whole House Generatr: 1
Porch/Balcony
Open Porch/Balcony: 1
Title
Title Ins - Buyer: 1
Exterior Features
Fencing: 1
Lighting: 1
Shed: 1
Sprinkler System: 1
Storage: 1
Pool Info
In Ground: 1
Heated: Yes
Concrete: 1
Pre-Wired
Cable: 1
Roof
Concrete Roof: 1
Financial Status
Auction: No
Bank Owned: No
Potential Short Sale: No
Standard Sale: Yes
Shutters
Accordion: 1
Status Change Info
Status: Active
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: Bay Front; Open Water
Waterview: Bay/Gulf View; Open Water View
Dockage: Basin; Boat Lift; Davits
Vehicle Storage: Carport; Guest Parking; Open Parking; RV Parking Open; Trailer Storage
Furnished: Negotiable
Cooling: Ceiling Fans(s); Central Air; Ductless; Wall/Window Unit(s)
Heating: Central; Fireplace(s)
Utilities: Buyer to Verify; Cable Available; FKAA; Municipal Sewer; Propane; Whole House Generatr
Interior Features: Built-in Cabinets; Elevator; Fireplace(s); Pantry; Smoke Alarms; Storage; Walk-in Closet(s); Wet Bar
Pre-Wired: Cable
Specialty Rooms: Gym; Laundry Room; Utility Room; Workshop; Other
Appliances: Dishwasher; Disposal; Dryer; Freezer; Gas Appliances; Microwave; More Appliances; Oven; Range; Refrigerator; Washer; Wine Cooler
Exterior Features: Fencing; Lighting; Shed; Sprinkler System; Storage
Pool Info: In Ground; Concrete
Construction: CBS; Concrete
Shutters: Accordion
Floor: Tile
Roof: Concrete Roof
Pets: Pets Allowed
Neighborhood Feature: Community Boat Ramp; Other Area Features
Security: Electric Gate; Other
Land Size: 1/2 - Less Than 1 AC
Terms: Cash; Conventional; FHA; VA
Title: Title Ins - Buyer
Listing Office: Venture Realty Group
Last Updated: April - 28 - 2026
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