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
...
(Read more)
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 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. Seller will consider all reasonable offers.
Open Houses
- Sunday, August 30, 1:00 pm - 3:00 pm
- Tomorrow, 4:00 pm - 6:00 pm
- Tomorrow, 4:00 pm - 6:00 pm
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.
