101 Oleander Cir

Key Largo, FL 33037

$7,750,000
Price
7
Beds
4,460 Sq. Ft.
$1,738 / Sq. Ft.
4,460
Sq. Ft.
$1,738
per Sq. Ft.
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a living room with furniture and a flat screen tv
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a kitchen with appliances a sink a counter top space and a center island
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a kitchen with stainless steel appliances granite countertop a dining table chairs sink and wooden floor
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a bedroom with a bed and a flat screen tv
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a bathroom with a glass shower door and a bathtub
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a bedroom with a large bed a flat tv screen and dresser
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a bedroom with a bed dresser and a window
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a kitchen with stainless steel appliances granite countertop a stove and a sink
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a kitchen with stainless steel appliances granite countertop a stove a refrigerator and a cabinets
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Description

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...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!
  1. Listed by Timothy Lloyd • Illustrated Properties, LLC

Property Details for 101 Oleander Circle

Waterfront
Oceanfront, Open Water, Canal Front
Waterfront
Yes
Zoning
SF - Single Family
Subdivision
Key Largo Beach Addition (100.0)
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
Vehicle Storage
Carport, Trailer Storage, Covered Parking, RV Parking Open, Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 02/02/2026 12:18 PM

Property Details for 101 Oleander Circle

StatusActive
MLS #618417
Days on Market6
Taxes$54,417 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1959
Lot Size1.62 AC / 70,613 SF
CountyMonroe County

Location

Listing Courtesy of Illustrated Properties, LLC
Add your commute

Building Information for 101 Oleander Circle

Stories-Year Built1959Building Size-Lot Size1.62 AC / 70,613 SF

Payment Calculator

$42,307 per month

30 year fixed, 6.15% Interest

Principal and Interest

$37,772

Property Taxes

$4,535

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 101 Oleander Circle

Summary
Location and General Information
  • Waterview: Ocean View, Open Water View, Canal View
  • Area: 27 - Key Largo MM 97-107
  • Absolute Longitude: 80.43452
  • Control Depth: 5
  • Off Shore Island: No
  • Listing Board: Florida Keys
  • Side: Ocean
  • Mile Marker: 100.0
  • Marathon Neighborhood: N/A
  • Accessibility Feat: Accessible Full Bath, Wheelchair Ramp, Accessible Kitchen, Grab Bars
  • Key/Island: Key Largo
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Furnished: Furnished
  • Tax Year: 2024
  • Tax Exemptions: None
Property
Lot Information
  • Acres: 1.62
  • SqFt Remarks: *Information to be verified by buyers and buyers agent
  • Parcel #: 00503800-000000
  • Add'l Parcel #1: 00503800-000100
  • Add'l Parcel #2: 00503800-000200
  • Land Size: 1 Less Than 2 Acres
Property and Assessments
  • Legal: 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
  • MLS Approved: Y
  • Bank Owned: No
  • SqFt Source: Property Data Card
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 126
  • Document Count: 0
  • Building Style: Above Flood: No
  • Property Condition: Updated/Remodeled
Utilities
  • Utilities: FKAA, Propane, Cable Available, Whole House Generatr, Buyer to Verify, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Handicap Access: Yes
  • Pool Info: Heated: Yes
  • Pool Info: Other Surroundings: Grotto Hot Tub Slide
  • Pool Info: In Ground, Decked, Salt Water
  • Porch/Balcony: Open Porch/Balcony, Deck
Interior and Exterior Features
Interior Features
  • Floor: Tile
  • Interior Features: Pantry, Built-in Cabinets, Bar, Walk-in Closet(s), Storage, Granite Counter Top
  • Pre-Wired: Cable, Surround Sound
  • Appliances: Other: wood pizza oven
  • Appliances: More Appliances, Stainless Steel Appliance(s), Wine Cooler, Ice Machine, Gas Appliances, Freezer, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer, Washer
Exterior Features
  • Roof: Metal Roof
  • Dockage: Dock Length: 300
  • Dockage: Dock: Concrete
  • Dockage: Seawall: Concrete
  • Construction: CBS
  • Dockage: Boat Lift, Basin, Boat Slip
  • Exterior Features: Bar, Tennis Court(s), Privacy Wall/Fence, Outdoor Shower, Outdoor Kitchen, Lighting, Detached Guest Qtrs, Gazebo, Fencing, Chickee Hut, Built-in Grill
  • Windows/Doors: Sliding Glass Doors, Impact Rstnce Window, Impact Rstnce Doors
Room Information
  • Specialty Rooms: Laundry Room, Workshop
Room Information
Room 1 Information
  • Room Type: Family Room
  • Area: 340.0
  • Level: M
  • Dimensions: 20 x 17
  • Length: 20.0
  • Width: 17.0

Property History for 101 Oleander Circle

DateEvent & SourcePriceAppreciation
Feb 1, 2026

Listed (Active)

FKMLS #618417

$7,750,000—
Sep 27, 2021

Sold (Public Record)

Public Record #1477348025

$1,925,000

-92.1% / yr

Apr 27, 2021

Sold (Public Record)

Public Record #1460728296

$5,565,000—
Apr 27, 2021

Sold

FKMLS #590864

$5,565,000—
Mar 1, 2021

Backup Contract

FKMLS #590864

—
Feb 24, 2021

Pending

FKMLS #590864

—
May 13, 2020

Price Change

FKMLS #590864

$6,450,000—
May 13, 2020

Listed (Active)

FKMLS #590864

$5,999,000—
Sep 19, 2014

Sold

FKMLS #562896

$2,900,000—
Jul 19, 2014

Pending

FKMLS #562896

—
Dec 16, 2013

Listed (Active)

FKMLS #562896

$2,995,000—
Oct 17, 2007

Expired

FKMLS #541691

—
May 17, 2007

Listed (Active)

FKMLS #541691

$6,600,000—
Nov 17, 2006

Expired

FKMLS #531706

—
Nov 17, 2005

Listed (Active)

FKMLS #531706

$6,600,000—
DateEvent & SourcePrice
02/01/2026

Listed (Active)

FKMLS #618417

$7,750,000
09/27/2021

Sold (Public Record)

Public Record #1477348025

$1,925,000

-92.1% / yr

04/27/2021

Sold (Public Record)

Public Record #1460728296

$5,565,000
04/27/2021

Sold

FKMLS #590864

$5,565,000
03/01/2021

Backup Contract

FKMLS #590864

—
02/24/2021

Pending

FKMLS #590864

—
05/13/2020

Price Change

FKMLS #590864

$6,450,000
05/13/2020

Listed (Active)

FKMLS #590864

$5,999,000
09/19/2014

Sold

FKMLS #562896

$2,900,000
07/19/2014

Pending

FKMLS #562896

—
12/16/2013

Listed (Active)

FKMLS #562896

$2,995,000
10/17/2007

Expired

FKMLS #541691

—
05/17/2007

Listed (Active)

FKMLS #541691

$6,600,000
11/17/2006

Expired

FKMLS #531706

—
11/17/2005

Listed (Active)

FKMLS #531706

$6,600,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 101 Oleander Circle

Taxable ValueLand$5,994,621Additions$1,935,649Total$7,930,270
Tax Record2024$55,514 ($4,626 / month)
Home Facts
Beds4Baths6Total Finished SqFt2,176 SqFtAbove Grade Finished SqFt2,176 SqFtStories1Lot Size73,662 SqFtStyleSingle Family ResidenceYear Built1959Year Renovated2019CountyMONROEAPN00503800-000000

Schools near 101 Oleander Circle

This home is within Monroe.
Rating
School
Type
Grades
Distance
Key Largo School
Public - PK to 8
Coral Shores High School
Public - 9 to 12
Ocean Studies Charter
Charter - K to 8
Upper Keys Academic Connections for Excellence
Public - 6 to 12
Rating
School
Distance
Key Largo School
PublicPK to 8

Coral Shores High School
Public9 to 12

Ocean Studies Charter
CharterK to 8

Upper Keys Academic Connections for Excellence
Public6 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 101 Oleander Circle, Key Largo, FL 33037

101 Oleander Circle is a single family home for sale in Key Largo, FL 33037. This property was listed for sale on February 1, 2026 by Illustrated Properties, LLC, it's currently listed at $7,750,000. It has been on the market for a total of 6 days and was last sold on September 27, 2021. This listing's school district is Monroe. Nearby schools include Key Largo School, Coral Shores High School and Ocean Studies Charter. 101 Oleander Circle is a 7-bed, 7-bath, 4,460 sqft single family home built in 1959.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Illustrated Properties, LLC

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.