About 109 Columbus Drive
Iconic Islamorada Oceanfront Retreat. Welcome to The Last Resort, a one-of-a-kind oceanfront estate offering rare privacy and breathtaking natural beauty in the heart of Islamorada. Set on over an acre of lush tropical land, this coastal retreat boasts 165 feet of private sandy Atlantic beach, where you can launch a kayak or paddleboard right from your backyard and soak in endless turquoise views. Expansive covered verandahs, a 15' x 30' heated seaside pool, and beachside hammocks invite slow, sun-filled days and relaxed gatherings. Across the street, a separate canalfront parcel with a 37.5' concrete dock provides protected deep-water dockage and space for boats, trailers, and water toys — an extraordinary pairing of true beachfront living and convenient boating access. Inside, the home's 3,860 square feet is designed for easy Keys living with generous main-level living areas and bedrooms, plus a spacious upstairs suite with private bath and roof-top deck capturing panoramic ocean vistas. Four bedrooms and five baths accommodate family and guests comfortably, while breezy porches and open gathering spaces make entertaining effortless. Highlights you'll love: 165' of private sandy Atlantic beach with direct ocean entry, 37.5' private concrete dock on canalfront lot for boating convenience, 15' x 30' heated seaside swimming pool with expansive sun decks, over one acre of tropical privacy and mature landscaping, 4 bedrooms | 5 baths | 3,860 sq. ft. with thoughtful single-level layout plus upstairs suite and roof deck. A true Keys treasure, The Last Resort delivers a rare mix of sandy beach, deep-water dockage, and timeless coastal charm. Ann exceptional opportunity to create your own island legacy!
Features of 109 Columbus Drive
| MLS® # | 616619 |
|---|---|
| Price | $6,700,000 |
| Bedrooms | 4 |
| Bathrooms | 5.00 |
| Full Baths | 5 |
| Square Footage | 3,860 |
| Acres | 1.14 |
| Year Built | 1922 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Status | Active |
Community Information
| Address | 109 Columbus Drive |
|---|---|
| Area | 22 - Lower Matecumbe |
| Subdivision | Mat Ocean View (76.5) |
| City | Lower Matecumbe |
| County | Monroe |
| State | FL |
| Zip Code | 33036 |
Amenities
| Amenities | Community Boat Ramp |
|---|---|
| Utilities | FKAA, Municipal Sewer, Buyer to Verify |
| Parking | Open Parking, Guest Parking, Off Street Parking, Trailer Storage |
| View | Ocean View, Canal View, Open Water View |
| Is Waterfront | Yes |
| Waterfront | Oceanfront, Canal Front, Open Water |
| Has Pool | Yes |
| Pool | In Ground, Concrete, Decked |
Interior
| Interior Features | Built-in Cabinets, Dade County Pine, Smoke Alarms, Storage, Walk-in Closet(s) |
|---|---|
| Appliances | Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Wine Cooler, Stainless Steel Appliance(s) |
| Heating | Central |
| Cooling | Central Air, Ceiling Fans(s) |
| Fireplace | No |
| Stories | 2 Stories |
| Has Basement | No |
Exterior
| Exterior Features | Fencing, Lighting, Lanai, Sandy Beach, Storage |
|---|---|
| Lot Description | 1 Less Than 2 Acres |
| Windows | French Doors, Glass Doors, Impact Rstnce Window, Impact Rstnce Doors |
| Roof | Metal Roof |
| Construction | Frame |
Additional Information
| Date Listed | September 26th, 2025 |
|---|---|
| Days on Market | 203 |
| Zoning | R1 - Residential Single Family |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Agent | Kelly K Shaw Pa |
|---|---|
| Office | American Caribbean Real Estate, Christie's International Real Estate |