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1101 Mastic Street, Upper Matecumbe Key Islamorada, FL 33036

$6,999,000
Property Type: Residential Bedrooms: 8 Baths: 6 Square Footage: 3,649 Lot Size (sq. ft.): 24,004 Status: Active
Current Price: $6,999,000 List Date: 4/28/2026 Last Modified: 8/30/2026

Overview

Description

Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available. 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 Whole House Generator for peace of mind. A private 1-bedroom, 1-bathroom guesthouse provides the ...

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Listing Details MLS# 619673

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

Contract Information

Listing Board
Florida Keys
Potential Short Sale
No
Bank Owned
No

General Property Description

Realtor.COM Type
Residential - Single Family
Style
Single Family
Waterfront
Yes
Control Depth
7
Pool
Yes
Year Built
1984
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

Association Info

Mandatory Home Owners Asc
No
1st Right of Refusal
No

Dockage

Dock
Wood

More Information

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; Loft; 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 Accessibility Feat: Other See Remarks 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; Seller Finance Psble; VA Title: Title Ins - Buyer
Listing Office: Venture Realty Group
Last Updated: August - 30 - 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.