$7,750,000

101 Oleander Cir Key Largo, FL 33037

Estimated payment $44,460/month

Total Views 2,113
7 Beds
7 Baths
4,460 Sq Ft
$1,738 Price per Sq Ft

Highlights

  • Very Popular Property
  • Ocean Front
  • Detached Guest House
  • Coral Shores High School Rated A
  • Dock made with concrete
  • 1-minute walk to Schwingggg

About This Home

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!

Listing Agent

Timothy Lloyd

Illustrated Properties, LLC License #3315887 Listed on: 02/01/2026

Illustrated Properties, LLC

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $54,417

Year Built

  • Built in 1959 | Remodeled

Lot Details

  • 1.62 Acre Lot
  • Ocean Front
  • Home fronts a canal
  • Privacy Fence
  • Fenced

Property Views

  • Ocean
  • Canal

Home Design

  • Metal Roof

Interior Spaces

  • 4,460 Sq Ft Home
  • Furnished
  • Bar
  • Ceiling Fan
  • Sliding Doors
  • Workshop
  • Storage
  • Tile Flooring
  • Impact Glass

Kitchen

  • Oven
  • Range
  • Microwave
  • Sub-Zero Refrigerator
  • Freezer
  • Ice Maker
  • Dishwasher
  • Wine Cooler
  • Wolf Appliances
  • Stainless Steel Appliances
  • Granite Countertops
  • Built-In or Custom Kitchen Cabinets

Bedrooms and Bathrooms

  • 7 Bedrooms
  • Walk-In Closet

Laundry

  • Laundry Room
  • Dryer
  • Washer

Parking

  • 4 Parking Spaces
  • Carport
  • Off-Street Parking
  • RV or Boat Parking

Accessible Home Design

  • Accessible Full Bathroom
  • Grab Bars
  • Accessible Kitchen
  • Handicap Accessible
  • Accessible Ramps

Pool

  • Heated In Ground Pool
  • Saltwater Pool
  • Pool Deck
  • Outdoor Shower

Outdoor Features

  • Seawall
  • Boat Lift
  • Boat Slip
  • Dock made with concrete
  • Tennis Courts
  • Balcony
  • Deck
  • Outdoor Kitchen
  • Exterior Lighting
  • Gazebo
  • Tiki or Chickee Hut
  • Attached Grill

Additional Homes

  • Detached Guest House

Utilities

  • Central Heating and Cooling System
  • Ductless Heating Or Cooling System
  • Heat Pump System
  • Whole House Permanent Generator
  • Propane
  • Public Hookup Available For Sewer
  • Cable TV Available

Community Details

  • No Home Owners Association
  • Key Largo Beach Addition Subdivision
  • Rental Restrictions
  • RV Parking in Community

Listing and Financial Details

  • Assessor Parcel Number 00503800-000000

Home Details

Home Type

Single Family

Est. Annual Taxes

$54,417

Year Built

Built in 1959 | Remodeled

Lot Details

1.62 Acres

Listing Details

  • Property Type: Residential
  • Style: Single Family
  • Additional Assessor Parcel Number 1: 00503800-000100
  • Additional Assessor Parcel Number 2: 00503800-000200
  • As Is Right To Inspect: Yes
  • First Right of Refusal: No
  • Mandatory HOA: No
  • Dockage Dock: Concrete
  • Dockage Seawall: Concrete
  • Fee Includes: None
  • Financial Status Bank Owned: No
  • Financial Status Potential Short Sale: No
  • Handicap Access: Yes
  • Key Island: Key Largo
  • Limited Representation: No
  • Marathon Neighborhood: N/A
  • Mile Marker: 100.00
  • M L S Identifier: 20060123165453488875000000
  • Off Shore Island: No
  • Pets: Pets Allowed
  • Property Group I D: 19990816212109142258000000
  • Side: Ocean
  • State Province: FL
  • Taxes: 54417.00
  • Vehicle Storage: Carport, Trailer Storage, Covered Parking, RV Parking Open, Off Street Parking
  • Vehicle Storage Cars: 4+
  • Year Built: 1959
  • Alternate Key Number: 1621684
  • Cooling Heating: Central Air, Ductless, Ceiling Fans(s), Heat Pump
  • Lot Sq Ft: 70613.00
  • Pool Info: In Ground, Decked, Salt Water
  • Pool Info Heated: Yes
  • Porch Balcony: Open Porch/Balcony, Deck
  • Tax Exemptions: None
  • Building Style Above Flood: No
  • Estimated Living Sq Ft: 4460.00
  • Pool Info Other Surroundings: Grotto Hot Tub Slide
  • Pre Wired: Cable, Surround Sound
  • Financial Status Standard Sale: Yes
  • Property Condition: Updated/Remodeled
  • Sewer Hook Up: Yes
  • Statistical Purposes Only: No
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Interior Amenities: Pantry, Built-in Cabinets, Bar, Walk-in Closet(s), Storage, Granite Counter Top
  • Total Bathrooms: 7.00
  • Full Bathrooms: 5
  • Appliances: More Appliances, Stainless Steel Appliance(s), Wine Cooler, Ice Machine, Gas Appliances, Freezer, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer, Washer
  • Floor: Tile
  • Half Bathrooms: 2
  • Specialty Rooms: Laundry Room, Workshop
  • Windows/Doors: Sliding Glass Doors, Impact Rstnce Window, Impact Rstnce Doors
  • Appliances Other: wood pizza oven
  • Total Bedrooms: 7
  • Accessibility Features: Accessible Full Bath, Wheelchair Ramp, Accessible Kitchen, Grab Bars
  • Sq Ft Remarks: *Information to be verified by buyers and buyers agent

Exterior Features

  • Dockage: Boat Lift, Basin, Boat Slip
  • Waterfront: Oceanfront, Open Water, Canal Front
  • Waterfront: Yes
  • Construction: CBS
  • Exterior Features: Bar, Tennis Court(s), Privacy Wall/Fence, Outdoor Shower, Outdoor Kitchen, Lighting, Detached Guest Qtrs, Gazebo, Fencing, Chickee Hut, Built-in Grill
  • Roof: Metal Roof
  • Waterview: Ocean View, Open Water View, Canal View
  • Pool: Yes

Utilities

  • Utilities: FKAA, Propane, Cable Available, Whole House Generatr, Buyer to Verify, Municipal Sewer
  • Heating: Central, Electric, Ductless

Lot Info

  • Deed Restrictions: Unknown
  • Parcel Number: 00503800-000000
  • Land Size: 1 Less Than 2 Acres
  • Acres: 1.62

Rental Info

  • Rentals Allowed: With Restrictions
  • Furnished: Furnished

Tax Info

  • Tax Year: 2024

Map

Range of Values:

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Value Increase
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Percent Increase
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Adjusted for Inflation
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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $55,514 $7,930,270 $5,994,621 $1,935,649
2024 $50,961 $7,571,120 $5,659,458 $1,911,662
2023 $50,961 $6,960,976 $5,082,685 $1,878,291
2022 $42,139 $5,389,557 $3,480,537 $1,909,020
2021 $33,195 $4,319,159 $2,541,346 $1,777,813
2020 $30,286 $3,873,020 $2,366,399 $1,506,621
2019 $21,625 $2,503,057 $1,461,384 $1,041,673
2018 $17,240 $1,947,843 $1,397,845 $549,998
2017 $16,382 $1,960,528 $0 $0
2016 $14,824 $1,582,555 $0 $0
2015 $14,586 $1,526,339 $0 $0
2014 $13,852 $1,803,534 $0 $0
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft Prior Sale
02/01/2026 02/01/26 For Sale $7,750,000 +39.3% $1,738 / Sq Ft
04/27/2021 04/27/21 Sold $5,565,000 -29.6% $1,926 / Sq Ft View Prior Sale
02/24/2021 02/24/21 Pending -- -- --
05/13/2020 05/13/20 For Sale $7,900,000 +172.4% $2,734 / Sq Ft
09/19/2014 09/19/14 Sold $2,900,000 -3.2% $1,189 / Sq Ft View Prior Sale
07/19/2014 07/19/14 Pending -- -- --
12/16/2013 12/16/13 For Sale $2,995,000 -- $1,228 / Sq Ft
Source: Florida Keys Board of REALTORS®

Purchase History

Date Type Sale Price Title Company
Quit Claim Deed -- None Listed On Document
Quit Claim Deed -- None Listed On Document
Quit Claim Deed -- None Listed On Document
Warranty Deed $1,925,000 Accommodation
Warranty Deed $1,925,000 None Listed On Document
Warranty Deed -- Attorney
Warranty Deed -- None Listed On Document
Warranty Deed $5,565,000 Attorney
Warranty Deed $5,565,000 None Listed On Document
Quit Claim Deed -- Attorney
Warranty Deed $2,900,000 Attorney
Interfamily Deed Transfer -- Attorney
Interfamily Deed Transfer -- Attorney
Interfamily Deed Transfer -- Attorney
Interfamily Deed Transfer -- Attorney
Warranty Deed $1,300,000 --
Quit Claim Deed $100 --
Warranty Deed $600,000 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Previous Owner $500,000 New Conventional
Previous Owner $2,000,000 Adjustable Rate Mortgage/ARM
Previous Owner $480,000 New Conventional
Source: Public Records

Source: Florida Keys Board of REALTORS®

MLS Number: 618417

Florida Keys Board of REALTORS®

APN: 00503800-000000

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