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1101 Mastic Street
Upper Matecumbe Key Islamorada FL 33036 US

$8,490,000

Active Listing ID 619673
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8 bed
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6.00 Bath (6 Full)
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Lot: 0.55 Acres
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Single Family Residence

$8,490,000

Active Listing ID 619673
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1101 Mastic Street Spectacular Bayfront Estate with Guesthouse in the Heart of IslamoradaExperience 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.

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Property Features

  • Facts
  • Lot Size: 0.55 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 6
  • Cooling System: Ceiling Fan(s)
  • Exterior Finish: Fencing, Storage, Sprinkler System, Shed, Lighting
  • Floor Covering: Tile
  • Roof Type: Concrete
  • Additional Features
  • Fireplace
  • Waterfront

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 8490000
  • unparsedaddress: 1101 Mastic Street
  • postalcity: Upper Matecumbe Key Islamorada
  • stateorprovince: FL
  • country: US
  • postalcode: 33036
  • bathroomsfull: 6
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.55
  • lotsizeunits: Acres
  • lotsizearea: 0.55
  • livingarea: 3649
  • livingareaunits: Square Feet
  • listagentfullname: Tracey E. Petrusha
  • listagentemail: traceypetrusha.realtor@gmail.com
  • listagentkey: 3yd-FLKEYSMLSFL-20150128180500728507000000
  • listagentmlsid: 20150128180500728507000000
  • listagentpreferredphone: 3058961080
  • listagentofficephone: 9545455583
  • listofficekey: 3yd-FLKEYSMLSFL-20210726194710435795000000
  • listagentstatelicense: 651549
  • listofficemlsid: 20210726194710435795000000
  • disclaimer: Copyright © 2026 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: FLKEYSMLSFL
  • yearbuilt: 1984
  • countyorparish: Monroe
  • parcelnumber: 00399130000000
  • appliances: Dishwasher, Dryer, Freezer, Garbage Disposer, Microwave, Range, Refrigerator, Washer
  • cooling: Ceiling Fan(s)
  • constructionmaterials: Concrete
  • flooring: Tile
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 2
  • parkingtotal: 0
  • parkingfeatures: Carport, Guest, Open, RV
  • roof: Concrete
  • view: Water
  • waterfrontyn: True
  • interiorfeatures: Wet Bar, Built-in Cabinets, Walk-in Closet(s), Storage, Smoke Alarms, Elevator, Pantry, Fireplace(s)
  • exteriorfeatures: Fencing, Storage, Sprinkler System, Shed, Lighting
  • waterfrontfeatures: Waterfront
  • architecturalstyle: Other
  • rooms: Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bathroom 5, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5
  • otherstructures: Packing Shed, Shed(s), Storage
  • accessibilityfeatures: Accessible Elevator Installed
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • fencing: Fenced
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • openhouse: { "AppointmentRequiredYN": false, "ListingKey": "3yd-FLKEYSMLSFL-619673", "OpenHouseEndTime": "2026-05-02T20:00:00+00:00", "OpenHouseId": "619673", "OpenHouseRemarks": null, "OpenHouseStartTime": "2026-05-02T19:00:00+00:00", "OpenHouseType": null, "VirtualOpenHouseURL": null }
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Venture Realty Group", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"traceypetrusha.realtor@gmail.com", "ListBrokerageCity":"Pompano Bch", "ListBrokerageCountry":"US", "ListBrokerageEmail":null, "ListBrokerageLogoUrl":null, "ListBrokerageName":"Venture Realty Group", "ListBrokeragePhone":"(954) 545-5583", "ListBrokeragePostalCode":null, "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":"Ste B", "ListBrokerageUnparsedAddress":"1500 E Atlantic Blvd.", "ListBrokerageWebsiteUrl":null, "ListOfficeAddress1":"1500 E Atlantic Blvd.", "ListOfficeAddress2":"Ste B", "ListOfficeBrokerMlsId":"20210727172247877295000000", "ListOfficeCity":"Pompano Bch", "ListOfficeCountry":"US", "ListOfficeEmail":"mls+venture@lokationre.com", "ListOfficePostalCode":"33060", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential - Single Family - Upper Matecumbe Key Islamorada, FL", "ListingURL":"https://listings.listhub.net/pages/FLKEYSMLSFL/619673/?channel=rexren", "MLSModificationTimestamp":"2026-04-29T15:58:05Z", "Neighborhoods":[{"Description":null, "Name":"23 - Upper Matecumbe"}], "PostalCode":null, "RawPropertySubType":"Residential - Single Family", "RawPropertyType":"Residential", "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":16657.96, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 4/29/2026 11:00:44 PM GMT
Source Updated Date: 4/30/2026 9:05:19 AM GMT

Courtesy of: Tracey E. Petrusha, Venture Realty Group, traceypetrusha.realtor@gmail.com

Copyright © 2026 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.