101 Oleander Circle, Key Largo, FL 33037

$7,750,000

Virtual Tour

https://www.zillow.com/view-imx/13405de7-0877-4cc6-b5ee-d3139ced40e3?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard

Property Type: Residential Bedrooms: 7 Baths: 7 Square Footage: 4,460 Lot Size (sq. ft.): 70,613 Status: Active

Current Price: $7,750,000 List Date: 2/01/2026 Last Modified: 2/02/2026

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 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!

More Information MLS# 618417

Contract Information

Listing Board: Florida Keys As is Rght to Inspct: Yes Potential Short Sale: No Bank Owned: No Current Price: $7,750,000 Listing Date: 2026-02-01 List Price: $7,750,000

Location, Tax & Legal

City: KEY LARGO Off Shore Island: No Mile Marker: 100 Marathon Neighborhood: N/A Side: Ocean Alternate Key #: 1621684 Handicap Access: Yes Add'l Parcel #1: 00503800-000100 Parcel #: 00503800-000000 Add'l Parcel #2: 00503800-000200 Zoning: SF - Single Family Deed Restrictions: Unknown 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 Taxes: 54417 Tax Year: 2024 Pub Sewer HkUp: Yes Street #: 101 Street Name: Oleander Street Suffix: Circle Key/Island: Key Largo State/Province: FL Zip Code: 33037 County: Monroe Subdivision: Key Largo Beach Addition (100.0) Area: 27 - Key Largo MM 97-107

General Property Description

Realtor.COM Type: Residential - Single Family Waterfront: Yes Control Depth: 5 Lot SqFt: 70613 Pool: Yes Lot Sqft Source: Property Data Card Total Units: 0 Acres: 1.62 SqFt Source: Property Data Card Rentals Allowed: With Restrictions Style: Single Family Year Built: 1959 Living Apx SqFt: 4460 Total Bedrooms: 7 Full Baths: 5 Half Baths: 2 Total Baths: 7

Remarks & Misc

Remarks – Consumer: 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! 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

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No Association Fee $: 0

Fee Includes

None: 1

Dockage

Dock Length: 300 Dock: Concrete Basin: 1 Boat Lift: 1 Boat Slip: 1 Seawall: Concrete

Tax Exemptions

None: 1

Appliances

Dishwasher: 1 Dryer: 1 Freezer: 1 Gas Appliances: 1 Ice Machine: 1 Microwave: 1 More Appliances: 1 Oven: 1 Range: 1 Refrigerator: 1 Stainless Steel Appliance(s): 1 Washer: 1 Wine Cooler: 1 Other: wood pizza oven

Pets

Pets Allowed: 1

Cooling

Ceiling Fans(s): 1 Central Air: 1 Ductless: 1 Heat Pump: 1

Heating

Central: 1 Ductless: 1 Electric: 1

Waterfront

Canal Front: 1 Oceanfront: 1 Open Water: 1

Waterview

Canal View: 1 Ocean View: 1 Open Water View: 1

Floor

Tile: 1

Interior Features

Bar: 1 Built-in Cabinets: 1 Granite Counter Top: 1 Pantry: 1 Storage: 1 Walk-in Closet(s): 1

Property Condition

Updated/Remodeled: 1

Specialty Rooms

Laundry Room: 1 Workshop: 1

Building Style

Above Flood: No

Windows/Doors

Impact Rstnce Doors: 1 Impact Rstnce Window: 1 Sliding Glass Doors: 1

Vehicle Storage

Car(s): 4+ Carport: 1 Covered Parking: 1 RV Parking Open: 1 Off Street Parking: 1 Trailer Storage: 1

Construction

CBS: 1

Land Size

1 Less Than 2 Acres: 1

Furnished

Furnished: 1

Terms

Cash: 1 Conventional: 1

Utilities

Buyer to Verify: 1 Cable Available: 1 FKAA: 1 Municipal Sewer: 1 Propane: 1 Whole House Generatr: 1

Porch/Balcony

Deck: 1 Open Porch/Balcony: 1

Exterior Features

Bar: 1 Built-in Grill: 1 Chickee Hut: 1 Detached Guest Qtrs: 1 Fencing: 1 Gazebo: 1 Lighting: 1 Outdoor Kitchen: 1 Outdoor Shower: 1 Privacy Wall/Fence: 1 Tennis Court(s): 1

Pool Info

In Ground: 1 Salt Water: 1 Heated: Yes Decked: 1 Other Surroundings: Grotto Hot Tub Slide

Pre-Wired

Cable: 1 Surround Sound: 1

Roof

Metal Roof: 1

Financial Status

Bank Owned: No Potential Short Sale: No Standard Sale: Yes

Accessibility Feat

Accessible Full Bath: 1 Accessible Kitchen: 1 Grab Bars: 1 Wheelchair Ramp: 1

Status Change Info

Status: Active

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: Canal Front; Oceanfront; Open Water Waterview: Canal View; Ocean View; Open Water View Dockage: Basin; Boat Lift; Boat Slip Property Condition: Updated/Remodeled Vehicle Storage: Carport; Covered Parking; Off Street Parking; RV Parking Open; Trailer Storage Furnished: Furnished Cooling: Ceiling Fans(s); Central Air; Ductless; Heat Pump Heating: Central; Ductless Utilities: Buyer to Verify; Cable Available; FKAA; Municipal Sewer; Propane; Whole House Generatr Interior Features: Bar; Built-in Cabinets; Granite Counter Top; Pantry; Storage; Walk-in Closet(s) Pre-Wired: Cable; Surround Sound Specialty Rooms: Laundry Room; Workshop Appliances: Dishwasher; Dryer; Freezer; Gas Appliances; Ice Machine; Microwave; More Appliances; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer; Wine Cooler Exterior Features: Bar; Built-in Grill; Chickee Hut; Detached Guest Qtrs; Fencing; Gazebo; Lighting; Outdoor Kitchen; Outdoor Shower; Privacy Wall/Fence; Tennis Court(s) Accessibility Feat: Accessible Full Bath; Accessible Kitchen; Grab Bars; Wheelchair Ramp Pool Info: In Ground; Salt Water; Decked Construction: CBS Floor: Tile Roof: Metal Roof Pets: Pets Allowed Land Size: 1 Less Than 2 Acres Terms: Cash; Conventional

Room Information

Family Room Length: 20.00 Level: Main Length: 20.00 Width: 17.00 Width: 17.00

Listing Office: Illustrated Properties, LLC

Last Updated: February - 02 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

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