Home in 1101 Mastic Street, Islamorada, FL 33036 for sale with MLS# A12009440

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. Seller will consider all reasonable offers.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 Bird's 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.

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1101 Mastic Street, Islamorada, FL 33036

Price
Price:
$6,999,000.00
Original List Price:
$8,490,000.00
List Price per Sq Ft (Calculated, Approx.):
$1,918.05
Property Status and Type
Listing Type:
For Sale
Status:
Active
Listing Category:
Residential
Property Type:
Single Family House
Description of Last Important Update:
Price Reduced
Last Major Update on:
July 21, 2026 10:32 pm
Other Special Conditions:
Sold As-is
Rooms Distribution
Bedrooms:
8
Bathrooms Total:
6
Full Bath:
6
Room Type:
Laundry, Other, Den, Workshop
Master Bedroom Bath:
Master Bdrm - Upstairs, Master Bdrm - Ground, Other
Measures
Living Area:
3,649 Sqft
Built-Up Area:
0.55 Acre
Property Features
View from the Property:
Water, Bay
Waterfront:
Yes
Waterfront Features:
Ocean Access, Other, Bayfront, Riprap
Frontage Length:
85
Private Pool
Swimming Pool Features:
In Ground
Spa Features:
Heated, In Ground
Guest House Features:
1 Bath, 1 Bedrooms
Security:
Smoke Detector(s)
Appliances:
Dryer, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Gas Range, Gas Water Heater, Free-Standing Freezer
Interior:
Pantry, Walk-In Closet(s), Kitchen Island, Built-in Features, Elevator, Storage
Exterior:
Lighting
Patio and Porch:
Patio, Porch, Porch - Open
Other Structures:
Shed(s), Outbuilding
Fireplace:
Decorative
Air Conditioning
Air Conditioning System:
Zoned, Central Air, Ceiling Fan(s), Wall/window Unit(s)
Heating
Heating System:
Central
Fence:
Fenced
Boat and Dock Features:
Private Dock, Lift, Marina, Ramp
Property Entrance Faces:
Southeast
Storm Protection Impact Glass:
Complete
Storm Protection Permanent Generator:
Whole House
Storm Protection Accordian Shutters:
Complete
Construction
Year Built:
1984
Roof:
Concrete
Levels:
Two
Entry Level (floor):
1
Construction Materials:
CBS
Flooring:
Tile
Number of stories:
2
Property Condition:
Resale
Taxes and Expenses
Tax Annual Amount:
$16,657.00
Tax Year:
2025
Parking
Garage Spaces:
0
Carport Spaces:
2
Covered Spaces:
2
Parking Features:
Driveway, Covered, Circular Driveway, Guest, Paver Block, Rv Access/parking, Golf Cart Garage, Boat Access/parking
Carport
Utilities
Sewer:
Public Sewer
Water Source:
Public
Community
Subdivision Name:
Strattons Subdivision Pb2-
Senior Community:
Yes
Restrictions:
Lease Restrictions
Community Dock
Leasing Permitted
Leasing Permitted Details:
Okay To Lease With Restrictions
Terms
Listing Terms Considered by Seller:
Cash, Conventional, FHA, VA Loan
Buyer Possession:
Negotiable, Close Of Escrow
Zoning and Legal
Tax Legal Description:
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
Real Estate Folio Number (Parcel Number):
00399130000000
Zoning:
SC Sub Urban Commer
Public Schools Assigned
Elementary School:
Plantation Key
High School:
Coral Shores
Listing History
Active on the market since:
April 28, 2026
Listing Agreement executed on:
April 28, 2026
Price change occurred on:
July 21, 2026 10:32 pm
Listing Status Last Changed On:
April 28, 2026 4:00 am
Photos updated on:
August 6, 2026 4:20 pm
Last Modified:
August 6, 2026 4:20 pm
Additional Information
Courtesy of:
LoKation
Attribution:
Not provided
Location
Street Name:
Mastic
Street Number:
1101
City:
Islamorada
State:
Florida
Zip Code:
33036
County:
Monroe
Latitude:
N24° 55' 12''
Longitude:
W81° 21' 52.8''
Street Suffix:
Street
Property Map

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Neighborhood Stats

Source: U.S. Census Bureau, ACS 5-Year Estimates

Median Household Income $88,214
Median Home Value $995,600
Median Rent $1,846/mo
Median Age 56
Population 3,632
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Association of REALTORS®
Disclaimer: IDX listing information is presented by Rebonus Brokerage LLC for consumer informational purposes only. The information provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed by the MLS or the real estate broker. This page presents structured listing information sourced directly from the MLS via the RESO Web API feed. Rebonus prioritizes maximum field coverage and data completeness, displaying the most granular MLS-provided attributes available.