Open House Fri, Sep 11th 04:00 PM - 06:00 PM - Waterfront - Seller Financing
Address
1101 Mastic Street, Upper Matecumbe Key Islamorada, FL
Price
$ 6,999,000
Property Attributes
- MLS#619673
- TypeSingle Family
- Listing Status Active
- CountyMONROE
- CityUpper Matecumbe Key Islamorada
- AreaUpper Matecumbe
- NeighborhoodStrattons
- Zip33036
- StyleSingle Family
- Year Built1984
- Taxes$ 16657
- Price$ 6,999,000
- Bedrooms8
- Full Bathrooms6
- Half Bathrooms0
- Sqr Footage3649
- Lot Size0.55 Acres
Data Source:
Florida Keys MLS (FLKMLS)
Property 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 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.
| Price History | |
|---|---|
| 4/28/2026 | Listed $8,490,000 |
| 6/13/2026 | 12$7,495,000 |
| 7/21/2026 | 7$6,999,000 |
General Features
| Living Area | 3649.00 |
|---|---|
| Construction | CBS,Concrete |
| Utilities | FKAA,Propane,Cable Available,Whole House Generatr,Buyer to Verify,Municipal Sewer |
| Roof | Concrete Roof |
| Appliances | More Appliances,Wine Cooler,Gas Appliances,Freezer,Disposal,Microwave,Oven,Range,Refrigerator,Dishwasher,Dryer,Washer |
| Zoning | SC - Sub Urban Commercial District |
| HOA Fee | 0.00 |
| Pets Allowed Y/N | Pets Allowed |
| Status | Active |
| Full Baths | 6 |
| Year Built | 1984 |
| Subdivision | Strattons (82.5) |
| Style | Single Family |
| View | Bay/Gulf View,Open Water View |
| Property Type | A |
| Neighborhood Feature | Community Boat Ramp,Other Area Features |
| Fee Includes | None |
| Acres | 0.55 |
| Lot Sqft | 24004.00 |
| Bank Owned | No |
| Rental Allowed | With Restrictions |
| Accessibility Features | Other See Remarks |
| Building Style: Above Flood | Unknown |
| Building Style: Stories | 2 Stories |
| Control Depth | 7 |
| Dockage | Davits,Basin,Boat Lift |
| Dockage: Dock | Wood |
| Virtual Tour | https://www.zillow.com/view-imx/56397a77-06d5-4cd7-aed1-51be86a27854?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard |
Interior Features
| Interior Amenities | Wet Bar,Built-in Cabinets,Walk-in Closet(s),Storage,Smoke Alarms,Elevator,Pantry,Fireplace(s) |
|---|---|
| Furnished Y/N | Negotiable |
| Flooring | Tile |
| Specialty Rooms | Gym,Other,Workshop,Utility Room,Loft,Laundry Room |
| Pre-Wired | Cable |
| Specialty Rooms: Guest/Servant Qtrs | Legal |
Exterior Features
| Exterior Amenities | Fencing,Storage,Sprinkler System,Shed,Lighting |
|---|---|
| Pool | Yes |
| Waterfront | Bay Front,Open Water |
| Lot Size | X |
| Land Size | 1/2 - Less Than 1 AC |
| Pool Info | In Ground,Concrete |
| Pool Info: Heated | Yes |
| Porch/Balcony | Open Porch/Balcony |
| Public Sewer Hookup | Yes |
| Shutters | Accordion |
| Side | Bay/Gulf |
| Vehicle Storage | Carport,Trailer Storage,RV Parking Open,Guest Parking,Open Parking |
| Vehicle Storage: Car(s) | 4+ |
| Windows/Doors | Impact Rstnce Window,Impact Rstnce Doors |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 33036
Price
Taxes
Year Built
Visits
In The Neighborhood
Reduced
Upper Matecumbe Key Islamorada
$ 4,499,500
- Type
- Single Family
- Size
- 946 SqFt
- Rooms
- 1 Beds + 1 Baths
Waterfront
Upper Matecumbe Key Islamorada
$ 2,495,000
- Type
- Single Family
- Size
- 1,829 SqFt
- Rooms
- 3 Beds + 3.5 Baths
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Data Last Updated: September 11, 2026 3:21 PM UTC
Information is deemed to be reliable, but is not guaranteed. © 2026 MLS and FBS. Prepared by Florida Keys MLS, Inc. on September 11, 2026 3:16 PM UTC The information on this sheet has been made available by the MLS and may not be the listing of the provider. 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
All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating
