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$7,750,000 Contingent

  • For Sale
  • Contingent
  • Single Family
  • 7 Beds
  • 5 Full Baths
  • 2 Partial Baths
  • 4,460 Sq. Ft.
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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!

Full Property Details for 101 Oleander Cir

General

  • Price: $7,750,000
  • Taxes: $54,417 (2024)
  • Status: Contingent
  • Type: Single Family
  • Source: 927
  • MLS ID: 618417
  • Updated: 5/13/2026
  • Added to Site: 128 day(s) ago

Interior

  • Number of Rooms: 1
  • Interior Features: Workshop, Walk-in Closet(s), Bar, Built-in Cabinets, Granite Counter Top, Pantry, Storage, Wired for Sound
  • Appliances: Other, Stainless Steel Appliance(s), Dishwasher, Dryer, Freezer, Gas Appliances, Ice Machine, Microwave, More Appliances, Oven, Range, Refrigerator, Washer, Wine Cooler
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 7
  • Full Bathrooms: 5
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 7

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Pool: Yes
  • Pool Description: Heated, Salt Water, In Ground, Decked

Exterior

  • Exterior Features: Tennis Court(s), Lighting, Bar, Built-in Grill, Chickee Hut, Detached Guest Qtrs, Fencing, Gazebo, Outdoor Kitchen, Outdoor Shower, Privacy Wall/Fence, Boat Slip
  • Deck/Patio: Open Porch/Balcony, Deck
  • Porch/Patio/Deck: Open Porch/Balcony, Deck

Parking

  • Parking Features: Off Street, Covered, Carport

Location

  • Area: 27 - Key Largo MM 97-107
  • County: Monroe
  • Subdivision: Key Largo Beach Addition (100.0)
  • Driving Directions: US 1 then Left on Atlantic Ave, then Right on Homestead Way, then Left on Ocean, All the way to the End and Left on Oleander Circle, the Home is Last House on Right

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Heat Pump, Ductless, Central Air, Ceiling Fans(s)
  • Heating Type: Central, Electric, Ductless

Structural Information

  • Construction Status: Updated/Remodeled
  • Construction: CBS
  • Roof: Metal
  • Windows/Doors: Impact Rstnce Doors, Impact Rstnce Window, Sliding Glass Doors
  • Square Feet: 4,460
  • Sq. Ft. Source: Property Data Card
  • Year Built: 1959
  • Property Condition: Updated/Remodeled

Lot Features

  • Property View: Canal, Open Water View, Ocean
  • Lot Size (Acres): 1.62
  • Lot Size (Sq. Ft.): 70,613
  • Lot Size Source: Property Data Card
  • Zoning: SF - Single Family

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Canal Front, Oceanfront, Open Water

Financial Considerations

  • Tax Amount: $54,417
  • Tax Year: 2024
  • Terms: Cash, Conventional

Disclosures and Reports

  • Legal Description: 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
  • APN: 00503800-000000

Listed by Illustrated Properties, LLC, Timothy Lloyd (954) 448-0781

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Listing agent

— 101 Oleander Cir —

  • Timothy Lloyd

    Illustrated Properties, LLC

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 101 Oleander Cir

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Key Largo School
104801 Overseas Highway, Key Largo, FL 33037
PK-85.5 mi
Coral Shores High School
89901 Old Highway, Tavernier, FL 33070
9-129.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 101 Oleander Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/01/2026
Listed
$7,750,000
302.6%
MLS
9/27/2021
Sold
$1,925,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 101 Oleander Cir

Year
Property Taxes
Change
Tax Assessment
Change
2024
$55,514
—
$7,930,270
5%
2024
$55,514
9%
$7,571,120
9%
2023
$50,961
54%
$6,960,976
61%
2021
$33,195
-21%
$4,319,159
-20%
2022
$42,139
27%
$5,389,557
39%
2021
$33,195
54%
$3,873,020
55%
2019
$21,625
25%
$2,503,057
31%
2018
$17,240
5%
$1,914,892
-2%
2017
$16,382
11%
$1,960,528
24%
2016
$14,824
2%
$1,582,555
4%
2015
$14,586
5%
$1,526,339
35%
2014
$13,852
29%
$1,131,599
10%
2013
$10,730
—
$1,028,727
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 101 Oleander Cir

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Illustrated Properties, LLC, Timothy Lloyd (954) 448-0781

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101 Oleander Circle, Key Largo, FL 33037 (MLS# 618417) is a Single Family property with 7 bedrooms, 5 full bathrooms and 2 partial bathrooms. 101 Oleander Circle is currently listed for $7,750,000 and was received on February 01, 2026. Want to learn more about 101 Oleander Circle? Do you have questions about finding other Single Family real estate for sale in Key Largo? You can browse all Key Largo real estate or contact a Coldwell Banker agent to request more information.

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