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The tropical arrival and main residence at Palm Paradise on Plantation Key

Plantation Key, Islamorada, Florida

In the Florida Keys, privacy is the rarest amenity.

Behind oceanfront gates on Plantation Key, this $26.4 million estate brings shoreline, guest accommodations, and extensive recreation into a private retreat.

Active$26,400,000Verified October 30, 2026

Palm Paradise

The Florida Keys are built around proximity to water. Palm Paradise offers something harder to reproduce: distance from everything else. The oceanfront offering at 89505 Old Highway occupies a gated Plantation Key setting with 369 feet of shoreline and open Atlantic views.

At the center is an 8,988-square-foot main residence designed with two residential wings. A dramatic two-story primary suite with a private office occupies one side; four additional bedrooms and four baths are arranged across the opposite wing. A separate two-bedroom guest house gives visitors genuine independence and brings the total accommodation to seven bedrooms, six full baths, and four partial baths.

The interiors include custom woodwork, coffered ceilings, a chef’s kitchen, wine cellar, private gym, and elevator. Outside, a custom pool, tiki bar, outdoor kitchen, beachside fire pit, observation pier, putting green, and lighted tennis court with its own cabana allow the property to move easily between family retreat, extended gathering place, and executive escape.

Offered at $26.4 million, Palm Paradise is not selling a single dramatic room. It is selling control over an entire island experience: acreage, shoreline, recreation, guest capacity, and the ability to arrive in the Florida Keys without surrendering privacy. Leslie Leopold and Cheri Tindall of Ocean Sotheby’s International Realty represent the offering.

The ownership perspective

The separate guest house is an important part of Palm Paradise’s composition. It allows the property to host beyond the main residence without requiring every visitor to share the same domestic rhythm. The two residential wings add another layer of separation inside the principal building. Together, those arrangements give the offering a clear compound character.

The outdoor program extends that idea. Tennis, a putting green, poolside entertaining, and ocean-facing destinations offer several ways to use the property at once. The strongest editorial reading is therefore about variety within a private setting. Its appeal is the ability to move between a family residence, guest retreat, and recreational environment without leaving the property.

Source and photography: Ocean Sotheby’s International Realty / MLS 620022. Property details reflect the verification date and may change.

THE DIGITAL EDITION

October 2026

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