1101 Mastic Street, Upper Matecumbe Key Islamorada, FL 33036 (MLS# 619673)

1101 Mastic Street, Upper Matecumbe Key Islamorada, FL 33036

New Listing

$8,490,000

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

Current Price: $8,490,000 List Date: 4/28/2026 Last Modified: 4/29/2026

Overview

Description

Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada 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 ... (Read more)

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Listing Details MLS# 619673

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
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

Contract Information

Listing Board: Florida Keys
Potential Short Sale: No
Bank Owned: No

General Property Description

Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 7
Pool: Yes
Year Built: 1984
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
Association Fee $: 0

Dockage

Dock: Wood
Basin: Yes
Boat Lift: Yes
Davits: Yes

More Information

Building Style

Above Flood: Unknown
Stories: 2 Stories

Vehicle Storage

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

Specialty Rooms

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

Pool Info

Heated: Yes
In Ground: Yes
Concrete: Yes

Financial Status

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

Remarks & Misc

Remarks – Consumer: Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada 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.

Fee Includes

None: Yes

Tax Exemptions

None: Yes

Appliances

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

Pets

Pets Allowed: Yes

Cooling

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

Heating

Central: Yes
Fireplace(s): Yes

Waterfront

Bay Front: Yes
Open Water: Yes

Waterview

Bay/Gulf View: Yes
Open Water View: Yes

Floor

Tile: Yes

Neighborhood Feature

Community Boat Ramp: Yes
Other Area Features: Yes

Interior Features

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

Windows/Doors

Impact Rstnce Doors: Yes
Impact Rstnce Window: Yes

Security

Electric Gate: Yes
Other: Yes

Construction

CBS: Yes
Concrete: Yes

Land Size

1/2 - Less Than 1 AC: Yes

Furnished

Negotiable: Yes

Terms

Cash: Yes
Conventional: Yes
FHA: Yes
VA: Yes

Utilities

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

Porch/Balcony

Open Porch/Balcony: Yes

Title

Title Ins - Buyer: Yes

Exterior Features

Fencing: Yes
Lighting: Yes
Shed: Yes
Sprinkler System: Yes
Storage: Yes

Pre-Wired

Cable: Yes

Roof

Concrete Roof: Yes

Shutters

Accordion: Yes

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: April - 29 - 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.