1101 Mastic Street, Islamorada, FL 33036

$5,999,000 — Active

Property Features

Map Map It    Virtual Tour

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.

▼ Price Reduced — originally listed at $8,490,000

Property Details

  • Listing ID: A12009440
  • Status: Active
  • Listing Date: 2026-04-28
  • Property Type: Single Family Residence
  • Subdivision: Strattons Subdivision Pb2-
  • County: Monroe
  • MLS Area: 5940 - Other Florida County
  • Bedrooms: 8
  • Full Bathrooms: 6
  • Living Area Sq Ft: 3,649
  • Year Built: 1984

Financial

  • List Price: $5,999,000
  • Original List Price: $8,490,000
  • HOA Fee: None
  • Taxes: $16,657/yr

Features & Amenities

  • View: Water, Bay
  • 55+ Community (HOPA): Yes
  • Parking: Circular Driveway, Covered, Driveway, Golf Cart Garage, Guest, Paver Block, RV Access/Parking, Boat
  • Cooling: Central Air, Ceiling Fan(s), Wall/Window Unit(s), Zoned
  • Heating: Central
  • Flooring: Tile
  • Construction: CBS
  • Roof: Concrete
  • Interior Features: Built-in Features, Elevator, Kitchen Island, Pantry, Walk-In Closet(s), Storage
  • Exterior Features: Lighting
  • Community Amenities: None

Courtesy of LoKation
Contact Starfish Real Estate to schedule an appointment or call .

RAPB

© 2026 Starfish Real Estate. Listings updated Nov 9, 2026 5:00 am. Listing data is derived from the Broker Reciprocity Program of the Realtor Association of Indian River County (RAIRC) and BeachsMLS. Properties listed by brokers other than Starfish Real Estate are identified with the applicable MLS logo and include the listing broker's name. Not all properties available through either MLS may be displayed. All MLS data is the copyrighted property of the respective MLS and its participants. Data is deemed reliable but is not guaranteed accurate and should be independently verified prior to entering into any transaction.