Home » Properties » 109 Columbus Dr, Islamorada FL 33036

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Iconic Oceanfront Estate in Islamorada with Private Beach

Discover The Last Resort, a unique oceanfront home in Islamorada featuring 4 bedrooms, 5 bathrooms, private beach access, and a heated seaside pool.

$6,700,000

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MLS #A11885559

Listing Updated: 2026-07-21 00:24:54

Listed By: American Caribbean Real Estate

Overview

Welcome to The Last Resort, a distinguished oceanfront estate located at 109 Columbus Dr in Islamorada, FL. This historic residence, built in 1922, offers four bedrooms and five bathrooms, combining classic charm with coastal living. Situated on over an acre of lush tropical land, the property features 165 feet of private sandy Atlantic beach, perfect for kayaking or paddleboarding directly from your backyard. Expansive covered verandahs and a 15' x 30' heated seaside pool provide inviting spaces for relaxation and entertaining.Across the street, a separate canalfront parcel includes a 37.5-foot concrete dock, offering protected deep-water dockage and ample space for boats, trailers, and water toys. This rare combination of beachfront privacy and convenient boating access makes The Last Resort a distinctive retreat in the heart of Islamorada’s vibrant coastal community.

Property Highlights

4 Bedrooms, 5 Bathrooms, Private Sandy Beach, Heated Seaside Pool, 165 ft Beachfront, Canalfront Dock with Deep-Water Access, Built in 1922, Over an Acre of Tropical Land

Property Details

City: Islamorada

State: FL

Zip Code: 33036

Address: 109 Columbus Dr, Islamorada FL 33036

Year Built: 1922

Property Type: Residential

Property Sub Type: Single Family Residence

Listing Office Name: American Caribbean Real Estate

County: Monroe County

Garage Spaces: 0

Parking Features: Guest, Other, Rv/Boat Parking

Interior Features: First Floor Entry, Built-in Features, Other, Walk-In Closet(s), Utility Room/Laundry

Exterior Features: Lighting

Waterfront: Yes

Pool: No

HOA Fee: $0

Annual Tax: $30,786

Days On Market: 253 Days

Original Listing Description

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.

Property Location

Explore the surrounding area, nearby amenities, and neighborhood access for this property.

109 Columbus Dr, Islamorada FL 33036

About This Neighborhood

Islamorada is renowned for its scenic beauty and vibrant coastal lifestyle. The neighborhood combines tranquil residential areas with easy access to local dining, shopping, and recreational activities. Residents enjoy a strong sense of community alongside the natural charm of the Florida Keys, making it a desirable location for those seeking both relaxation and convenience.

Walkability & Lifestyle

The property enjoys a coastal setting with nearby access to restaurants, shops, and waterfront areas. Walking along the beach or to local amenities is an integral part of the lifestyle in Islamorada. Residents appreciate the blend of natural surroundings and daily conveniences within a short distance.

Things To Do Nearby

Islamorada offers abundant outdoor activities including boating, fishing, kayaking, and paddleboarding. The area features marinas, parks, and dining options that cater to a relaxed yet active lifestyle. Cultural events and nightlife add to the vibrant community atmosphere, making it a well-rounded destination for residents and visitors alike.

Nearby Schools

Islamorada provides access to local educational institutions within reasonable commuting distance. Families benefit from nearby schools offering a range of programs, contributing to the community’s family-friendly environment. The area supports convenient access to educational resources alongside its coastal lifestyle.

Why Buyers Like This Area

Buyers are drawn to this area for its exceptional oceanfront properties, privacy, and access to boating facilities. The combination of natural beauty and community amenities creates a compelling lifestyle. The property’s unique features, including a private beach and heated pool, align with the desires of those seeking a premium coastal residence.

Investment Potential

This oceanfront estate in Islamorada offers a rare combination of privacy and direct beach access, appealing to buyers seeking a distinctive coastal residence. Its expansive land and deep-water dock enhance usability for boating enthusiasts. The property's unique location and amenities support sustained interest from buyers looking for exclusive waterfront living in a sought-after Florida Keys community.

Market Trends

The Islamorada real estate market continues to attract buyers interested in waterfront properties with unique features. Limited inventory of oceanfront homes contributes to steady demand, especially for properties offering private beach access and boating facilities. Long-term interest remains strong due to the area's lifestyle appeal and natural surroundings.

Rental Income Potential

Properties like this oceanfront estate in Islamorada tend to attract tenants interested in seasonal and vacation rentals due to the location’s natural beauty and recreational opportunities. The combination of private beach access and boating amenities enhances rental appeal, although rental income can vary with market conditions and seasonal demand.