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101 Oleander Circle, 
Key Largo, FL 33037

$7,750,000


7

Beds


7

Baths


4,460

Sq Ft


Single Family


Virtual Tour

Active

Listed by

Timothy Lloyd

Illustrated Properties, LLC.

Last updated:

May 29, 2026, 02:52 PM

MLS#

618417

Source:

FL FKBOR

About This Home

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 today!

Home Facts

Single Family

7 Baths

7 Bedrooms

Built in 1959

Price Summary

7,750,000

$1,737 per Sq. Ft.

MLS #:

618417

Last Updated:

May 29, 2026, 02:52 PM

Added:

4 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

7

Bathrooms

Total Bathrooms:

7


Structure

Structure

Building Area:

4,460 Sq. Ft.

Year Built:

1959


Lot

Lot Size (Sq. Ft):

70,567


Finances & Disclosures

Finances

Price:

$7,750,000

Price per Sq. Ft:

$1,737 per Sq. Ft.

Source:FL FKBOR
The information being provided by Florida Keys Board Of REALTORS®, Inc. is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Florida Keys Board Of REALTORS®, Inc. All rights reserved. FL FKBOR Member Broker: Brian Schmitt

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.