About 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!
Features of 101 Oleander Circle
| MLS® # | 618417 |
|---|---|
| Price | $7,750,000 |
| Bedrooms | 7 |
| Bathrooms | 7.00 |
| Full Baths | 5 |
| Half Baths | 2 |
| Square Footage | 4,460 |
| Acres | 1.62 |
| Year Built | 1959 |
| Type | Residential |
| Sub-Type | Single Family |
| Status | Contingent |
Community Information
| Address | 101 Oleander Circle |
|---|---|
| Area | 27 - Key Largo MM 97-107 |
| Subdivision | Key Largo Beach Addition (100.0) |
| City | KEY LARGO |
| County | Monroe |
| State | FL |
| Zip Code | 33037 |
Amenities
| Utilities | FKAA, Propane, Cable Available, Whole House Generatr, Buyer to Verify, Municipal Sewer |
|---|---|
| Parking Spaces | 4 |
| Parking | Carport, Trailer Storage, Covered Parking, RV Parking Open, Off Street Parking |
| View | Ocean View, Open Water View, Canal View |
| Is Waterfront | Yes |
| Waterfront | Oceanfront, Open Water, Canal Front |
| Has Pool | Yes |
| Pool | In Ground, Decked, Salt Water |
Interior
| Interior Features | Pantry, Built-in Cabinets, Bar, Walk-in Closet(s), Storage, Granite Counter Top |
|---|---|
| Appliances | More Appliances, Stainless Steel Appliance(s), Wine Cooler, Ice Machine, Gas Appliances, Freezer, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer, Washer |
| Heating | Central, Electric, Ductless |
| Cooling | Central Air, Ductless, Ceiling Fans(s), Heat Pump |
| Fireplace | No |
Exterior
| Exterior Features | Bar, Tennis Court(s), Privacy Wall/Fence, Outdoor Shower, Outdoor Kitchen, Lighting, Detached Guest Qtrs, Gazebo, Fencing, Chickee Hut, Built-in Grill |
|---|---|
| Lot Description | 1 Less Than 2 Acres |
| Windows | Sliding Glass Doors, Impact Rstnce Window, Impact Rstnce Doors |
| Roof | Metal Roof |
| Construction | CBS |
Additional Information
| Date Listed | February 1st, 2026 |
|---|---|
| Days on Market | 76 |
| Zoning | SF - Single Family |
| Short Sale | No |
| RE / Bank Owned | No |
| HOA Fees | 0.00 |
Listing Details
| Agent | Timothy Lloyd |
|---|---|
| Office | Illustrated Properties, LLC |