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1101 Mastic Street, Upper Matecumbe Key Islamorada, FL - photo 1

$6,999,000

1101 Mastic Street

Upper Matecumbe Key Islamorada, FL 33036

Estimated payment $41,994/month

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8Beds
6Baths
3,649Sq Ft
$1918Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

No HOA
Built in 1984
23,958 sqft Lot

About This Home

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.

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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:8
  • •Bathrooms:6
  • •Full bathrooms:0

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:3,649 sqft
  • •Total interior livable area:3,649 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:23,958 sqft

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Single Family Residence
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:1984

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Price history

DateEventPrice
10/13/2026Listed for sale$6,999,000$1918/sqft

Listing Agent

Tracey E. Petrusha

LoKation Real Estate

Brokerage Phone: 954-545-5583

Source: Florida Keys MLS · MLS #619673

Data Powered by Home Junction, Inc.

Nearby

Supermarkets

Florida Keys Farmers Market

1.0 mi

Publix

1.5 mi

Dining

Lorelei Restaurant & Cabana Bar

0.2 mi

Kaiyo Grill & Sushi

0.2 mi

Cheeca Lodge Coffee Stand

0.3 mi

Parks

Green Turtle Hammock Preserve

0.9 mi

Beaches

Anne's Beach

8.3 mi

North Beach

18.9 mi

South Beach

19.1 mi

Nearby amenity locations include data © OpenStreetMap contributors.