88041 Old Hwy: $42 Miliion Spectacular Tropical Retreat in Plantation Key

Date of Publishing: April 8, 2025

Nestled on a rare 5.07-acre peninsula in the heart of the Florida Keys, 88041 Old Hwy redefines tropical luxury with its unmatched privacy, architectural pedigree, and resort-style amenities. This extraordinary estate, listed at $42 million, is not just the most exclusive home in Plantation Key for sale – it’s a legacy waiting to be written.

$42M tropical retreat at 88041 Old Hwy featuring lagoon pool and boat basin

Built in 2017, the home spans 9,843 square feet of interior space and over 17,800 square feet in total, including covered verandas that blur the line between inside and out. Designed by legendary architects Bruce Carlson and Steve Siskind, and enhanced by the interior mastery of Sam Robin, this residence is a celebration of light, landscape, and livable luxury.

Where Architecture Embraces Nature

From the moment one enters the estate via a crushed coral drive flanked by native landscaping, it’s evident this home is different. Lush tropical greenery, designed by landscape architect Raymond Jungles, frames each vista like a painting.

“The house was designed not to dominate the land but to disappear into it,” noted listing agent Eric M. Rizzo in a comment to Luxury Houses Magazine. “The connection between the structure and its surroundings is immediate and intimate.”

Inside, every material was chosen for both form and function: cool marble floors, soaring cathedral ceilings, custom quartz countertops, and floor-to-ceiling impact-resistant windows. An expansive open-plan living room with fireplace anchors the home, while six ensuite bedrooms and nine total bathrooms accommodate guests in total comfort.

SEE MORE: $38.5 Million Resort-Style Masterpiece Redefines Lakefront Luxury Living in Odessa, Florida

The Outdoor Life, Redefined

This Plantation Key home for sale was conceived as an all-encompassing retreat. The backyard alone could rival any Caribbean resort: a gas-heated lagoon pool, built-in swim-jet therapy, hot tub, and a waterfall grotto make up the aquatic centerpiece.

Nearby, an elevated outdoor kitchen features a pizza oven, wet bar, and pop-up TV, while tiki torches light the night with a romantic glow. There’s also a beach-entry saltwater pond, teeming with native sea life, and a grassy knoll ideal for events – or even helipad landings.

“This is where barefoot luxury and five-star amenities intersect,” said co-listing agent Russell A. Post of Ocean Sotheby’s International Realty. “From the moment you arrive, it’s like stepping into a private island experience.”

SEE MORE: $19.9 Million Coastal Retreat with Gulf Access and Designer Interiors in Naples

A Boater’s Dream With Unmatched Dockage

Positioned directly on the Atlantic Ocean, 88041 Old Hwy is one of the few home in Plantation Key for sale offering a 450-foot dock, complete with two boat lifts and a protected boat basin. For boating and yachting enthusiasts, this is an irreplaceable asset in the Florida Keys.

A four-bay air-conditioned garage caters to collectors, while additional portico parking accommodates guests and staff with ease. “The estate is designed not just for luxury, but for functionality at scale,” Post added.

SEE MORE: Waterfront Masterpiece in Miami Beach Asks $59.9 Million With Rooftop Terraces & Private Dock

A Rare Legacy on the Rise

According to public records, this Plantation Key real estate gem was last sold in 2011 for just $3,000,000. Over the past decade, the estate has been completely reimagined – its current Zestimate® now exceeds $36,000,000, reflecting the property’s escalating prestige and the scarcity of such offerings in the Upper Keys.

“Everything here was built with intention,” Rizzo remarked. “This isn’t just a home – it’s a life statement.”

Luxury Houses Magazine reached out to the owners for insights on the estate’s evolution and their vision. While they declined to comment, citing privacy concerns, the property’s curated design speaks volumes.

Plantation Key: A Jewel of the Upper Keys

Located just 90 minutes south of Miami, Plantation Key offers a harmonious balance between seclusion and accessibility. Residents benefit from world-class diving and fishing, easy access to Founders Park, and proximity to excellent dining – from the iconic Marker 88 to hidden culinary gems known only to locals.

For those seeking shopping, the charming boutiques of Islamorada are minutes away, offering fine art, handmade jewelry, and island-style luxury. Add in top-tier schools and secure gated estates, and it’s clear why Plantation Key real estate continues to rise in demand.

With its world-class pedigree, pristine private beach, and one-of-a-kind amenities, 88041 Old Hwy is more than a home in Plantation Key for sale – it is a sanctuary for those who crave both privacy and prestige.

This rare offering is not expected to remain on the market long. For those ready to invest in the finest that Florida homes for sale have to offer, this estate offers an opportunity that’s as secure as it is spectacular.

For more information or to arrange a private tour, visit the listing on Zillow or contact the official representatives at Ocean Sotheby’s International Realty.

For inquiries or to schedule a private showing, please contact:

Eric M. Rizzo
305-394-3062
Ocean Sotheby’s International Realty

Russell A. Post
305-712-8888
Ocean Sotheby’s International Realty

* This property might not for sale at the moment you read this post; please check property status at the above Zillow or Agent website links*