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1101 Mastic Street, Upper Matecumbe Key Islamorada, FL 33036

New Listing
$8,490,000
Property Type: Residential Bedrooms: 8 Baths: 6 Square Footage: 3,649 Lot Size (sq. ft.): 24,004 Status: Active
Current Price: $8,490,000 List Date: 4/28/2026 Last Modified: 4/28/2026

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.

More Information MLS# 619673

Contract Information

Current Price: $8,490,000 Listing Date: 2026-04-28 Listing Board: Florida Keys List Price: $8,490,000 Potential Short Sale: No Bank Owned: No

Location Tax Legal

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 Style: Single Family Waterfront: Yes Control Depth: 7 Pool: Yes Year Built: 1984 Lot Size: X Lot SqFt: 24004 Lot Sqft Source: Property Data Card Acres: 0.55 Living Apx SqFt: 3649 SqFt Source: Property Data Card Total Bedrooms: 8 Full Baths: 6 Total Baths: 6 Rentals Allowed: With Restrictions

Status Change Info

Status: Active

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No

Dockage

Dock: Wood

Building Style

Above Flood: Unknown Stories: 2 Stories

Vehicle Storage

Car(s): 4+

Specialty Rooms

Guest/Servant Qtrs: Legal

Pool Info

Heated: Yes

Financial Status

Auction: No Bank Owned: No Potential Short Sale: No Standard Sale: Yes

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
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

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