Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

$6,999,000
1101 Mastic Street
Upper Matecumbe Key Islamorada, FL 33036
MLS# 619673
8 beds  |  6 baths  |  3649 sqft
 | 
1101 Mastic St
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Matecumbe Key, FL 1101 Mastic St., Upper Matecumbe Key, FL 1101 Mastic St., Upper Matecumbe Key, FL
Open House (10/11/2026 - 12:00 pm - 3:00 pm)

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.

Details
Contract Information
Current Price: $6,999,000
Listing Date: 2026-04-28
Listing Board: Florida Keys
Monthly Rent: $6,999,000
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
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Dockage
Dock: Wood
Specialty Rooms
Guest/Servant Qtrs: Legal
Building Style
Above Flood: Unknown
# Stories: 2 Stories
Vehicle Storage
Car(s): 4+
Pool Info
Heated: Yes
Financial Status
Auction: No
Bank Owned: No
Potential Short Sale: No
Standard Sale: Yes
Status Change Info
Status: Active
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: LoKation Real Estate

Last Updated: October - 11 - 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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