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101 Oleander Circle
Key Largo FL 33037 US

$7,750,000

Active Under Contract Listing ID 618417
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7 bed
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6.00 Bath (5 Full , 2 Half)
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Lot: 1.62 Acres
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Single Family Residence

$7,750,000

Active Under Contract Listing ID 618417
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101 Oleander Circle Welcome to the iconic Key Largo Lighthouse, a one-of-a-kind oceanfront landmark set on 1.6 acres of lushly landscaped tropical paradise in Key Largo. With over 300 feet of seawalled waterfront, this private compound delivers an unmatched resort-style lifestyle in the Florida Keys. Surrounded by mature palms, the property offers an extraordinary array of amenities, including a private boat basin, pickleball court, working lighthouse, and a spectacular water-park-style infinity pool complete with a lazy river, grotto, hot tub, waterslide, and multiple cascading waterfalls. Designed for grand-scale entertaining or quality family time, the estate features three main buildings with accommodations for up to 20 guests. The main residence showcases a stunning great-room layout anchored by a chef's kitchen with a Wolf gas range, Sub-Zero refrigerator and six under-counter refrigerated drawers, full-size wine fridge, expansive pantry, and an oversized island ideal for gatherings. Additional living spaces include two separate units, each with full kitchens and bedrooms, along with three detached guest bedrooms with cabana baths, offering exceptional privacy and flexibility. Throughout the grounds, Old Chicago brick walkways, seven tiki huts, and thoughtfully designed lounging areas invite relaxation at every turn. Enjoy breathtaking ocean sunrises from the point and entertain under the cabana bar overlooking Pennekamp National Park, the Atlantic Ocean, and your private, secure boat basin-equipped with a boat lift, floating jet-ski lift, and kayak/paddleboard launch. The property is fully outfitted with impact windows and doors, a metal roof, and a standby generator capable of powering the entire estate, providing peace of mind year-round. This rare and irreplaceable oceanfront compound is the ultimate setting for unforgettable entertaining and luxurious island living. Simply too many impeccable details to capture-come see it in person and schedule your private showing toda

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Property Features

  • Facts
  • Lot Size: 1.62 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 5
  • 1/2 Bathrooms: 2
  • Cooling System: Ductless, Central Air, Heat Pump
  • Exterior Finish: Bar, Built-in Grill, Chickee Hut, Fencing, Gazebo, Detached Guest Qtrs, Lighting, Outdoor Kitchen, Outdoor Shower, Privacy Wall/Fence, Tennis Court(s)
  • Floor Covering: Tile
  • Roof Type: Metal
  • Heating Fuels: Ductless (Heating), Central, Electric (Heating)
  • Additional Features
  • Patio
  • Pool
  • Waterfront

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 7750000
  • unparsedaddress: 101 Oleander Circle
  • postalcity: Key Largo
  • stateorprovince: FL
  • country: US
  • postalcode: 33037
  • bathroomsfull: 5
  • bathroomshalf: 2
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 1.62
  • lotsizeunits: Acres
  • lotsizearea: 1.62
  • livingarea: 4460
  • livingareaunits: Square Feet
  • latitude: 25.087143
  • longitude: -80.43452
  • listagentfullname: Timothy Lloyd
  • listagentemail: timlloydsells@gmail.com
  • listagentkey: 3yd-FLKEYSMLSFL-20171017205012086052000000
  • listagentmlsid: 3315887
  • listagentpreferredphone: 9544480781
  • listofficekey: 3yd-FLKEYSMLSFL-20150116200618864204000000
  • listagentstatelicense: 3315887
  • listofficemlsid: 272569
  • 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: 1959
  • listingcontractdate: 2026-02-01
  • countyorparish: Monroe
  • parcelnumber: 00503800-000000
  • appliances: More Appliances, Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Freezer, Gas Appliances, Ice Machine, Wine Cooler, Stainless Steel Appliance(s)
  • cooling: Ductless, Central Air, Heat Pump
  • constructionmaterials: CBS
  • flooring: Tile
  • heating: Ductless (Heating), Central, Electric (Heating)
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: RV
  • roof: Metal
  • view: Ocean, Water
  • waterfrontyn: True
  • franchiseaffiliation: None
  • interiorfeatures: Built-in Cabinets, Granite Counter Top, Storage, Walk-in Closet(s), Bar, Wired for Sound
  • exteriorfeatures: Bar, Built-in Grill, Chickee Hut, Fencing, Gazebo, Detached Guest Qtrs, Lighting, Outdoor Kitchen, Outdoor Shower, Privacy Wall/Fence, Tennis Court(s)
  • waterfrontfeatures: Ocean Front
  • rooms: Bedroom 6, Bathroom 7, Bathroom 4, Bedroom 2, Bathroom 6, Bedroom 5, Bedroom 4, Bathroom 3, Family Room, Bathroom 1, Bedroom 7, Bedroom 1, Bathroom 5, Bathroom 2, Bedroom 3
  • otherstructures: Gazebo, Outdoor Kitchen, Storage
  • utilities: Cable Available
  • patioandporchfeatures: Porch, Deck
  • accessibilityfeatures: Accessible Approach with Ramp
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • fencing: Privacy, Fenced
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -80.43452, 25.087143
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Illustrated Properties Real Estate", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"timlloydsells@gmail.com", "ListBrokerageCity":"Palm Beach Gardens", "ListBrokerageCountry":"US", "ListBrokerageEmail":null, "ListBrokerageLogoUrl":null, "ListBrokerageName":"Illustrated Properties Real Estate", "ListBrokeragePhone":"(561) 626-7000", "ListBrokeragePostalCode":null, "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"2725 PGA Blvd.", "ListBrokerageWebsiteUrl":null, "ListOfficeAddress1":"700 E Atlantic Blvd ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"20150116200618864204000000", "ListOfficeCity":"Del Ray Bch", "ListOfficeCountry":"US", "ListOfficeEmail":null, "ListOfficePostalCode":"33483", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Key Largo, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/101-Oleander-Cir_Key-Largo_FL_33037_M68888-67498?f=listhub&s=FLKEYSMLSFL&m=618417&c=rexren", "MLSModificationTimestamp":"2026-03-19 16:20:36", "Neighborhoods":[{"Description":null, "Name":"Key Largo Beach Addition (100.0)"}], "PostalCode":null, "RoomCount":1, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":54417, "TaxDescription":"LOT 11 AND ADJ ACCRETED LAND (PT GOV LOT 3 AND BOAT BASIN KEY LARGO BEACH ADDITION PB4-22 KEY LARGO OR47-160 OR544-76", "TaxYear":"2024"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 5/23/2026 11:30:08 AM GMT
Source Updated Date: 5/26/2026 6:40:34 PM GMT

Courtesy of: Timothy Lloyd, Illustrated Properties, LLC, timlloydsells@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.