1101 Mastic Street, Upper Matecumbe Key Islamorada, FL 33036

$7,495,000

Virtual Tour

https://www.zillow.com/view-imx/56397a77-06d5-4cd7-aed1-51be86a27854?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard

Property Type: Residential Bedrooms: 8 Baths: 6 Square Footage: 3,649 Lot Size (sq. ft.): 24,004 Status: Active

Current Price: $7,495,000 List Date: 4/28/2026 Last Modified: 6/13/2026

Description

Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. 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 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.

Open Houses

Saturday, June 13, 5:00 pm - 6:00 pm

More Information MLS# 619673

Contract Information

Listing Board: Florida Keys Potential Short Sale: No Bank Owned: No Current Price: $7,495,000 Listing Date: 2026-04-28 List Price: $7,495,000

Location, Tax & Legal

City: ISLAMORADA Mile Marker: 82.5 Marathon Neighborhood: N/A Side: Bay/Gulf Alternate Key #: 1491519 Parcel #: 00399130000000 Zoning: SC - Sub Urban Commercial District Deed Restrictions: Unknown Legal: 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 Taxes: 16657.96 Tax Year: 2025 Pub Sewer HkUp: Yes 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 Waterfront: Yes Control Depth: 7 Lot Size: X Lot SqFt: 24004 Pool: Yes Lot Sqft Source: Property Data Card Acres: 0.55 SqFt Source: Property Data Card Rentals Allowed: With Restrictions Style: Single Family Year Built: 1984 Living Apx SqFt: 3649 Total Bedrooms: 8 Full Baths: 6 Total Baths: 6

Remarks & Misc

Remarks – Consumer: Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. 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 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. Directions: US 1 Bay Side.

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No Association Fee $: 0

Fee Includes

None: 1

Dockage

Dock: Wood Basin: 1 Boat Lift: 1 Davits: 1

Tax Exemptions

None: 1

Appliances

Dishwasher: 1 Disposal: 1 Dryer: 1 Freezer: 1 Gas Appliances: 1 Microwave: 1 More Appliances: 1 Oven: 1 Range: 1 Refrigerator: 1 Washer: 1 Wine Cooler: 1

Pets

Pets Allowed: 1

Cooling

Ceiling Fans(s): 1 Central Air: 1 Ductless: 1 Wall/Window Unit(s): 1

Heating

Central: 1 Fireplace(s): 1

Waterfront

Bay Front: 1 Open Water: 1

Waterview

Bay/Gulf View: 1 Open Water View: 1

Floor

Tile: 1

Neighborhood Feature

Community Boat Ramp: 1 Other Area Features: 1

Interior Features

Built-in Cabinets: 1 Elevator: 1 Fireplace(s): 1 Pantry: 1 Smoke Alarms: 1 Storage: 1 Walk-in Closet(s): 1 Wet Bar: 1

Specialty Rooms

Guest/Servant Qtrs: Legal Gym: 1 Laundry Room: 1 Utility Room: 1 Workshop: 1 Other: 1

Building Style

Above Flood: Unknown Stories: 2 Stories

Windows/Doors

Impact Rstnce Doors: 1 Impact Rstnce Window: 1

Vehicle Storage

Car(s): 4+ Carport: 1 Guest Parking: 1 Open Parking: 1 RV Parking Open: 1 Trailer Storage: 1

Security

Electric Gate: 1 Other: 1

Construction

CBS: 1 Concrete: 1

Land Size

1/2 - Less Than 1 AC: 1

Furnished

Negotiable: 1

Terms

Cash: 1 Conventional: 1 FHA: 1 VA: 1

Utilities

Buyer to Verify: 1 Cable Available: 1 FKAA: 1 Municipal Sewer: 1 Propane: 1 Whole House Generatr: 1

Porch/Balcony

Open Porch/Balcony: 1

Title

Title Ins - Buyer: 1

Exterior Features

Fencing: 1 Lighting: 1 Shed: 1 Sprinkler System: 1 Storage: 1

Pool Info

In Ground: 1 Heated: Yes Concrete: 1

Pre-Wired

Cable: 1

Roof

Concrete Roof: 1

Financial Status

Auction: No Bank Owned: No Potential Short Sale: No Standard Sale: Yes

Shutters

Accordion: 1

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; 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 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; VA Title: Title Ins - Buyer

Listing Office: Venture Realty Group

Last Updated: June - 13 - 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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