The five highest-priced home sales reported in the Florida Keys for the week ending October 25, 2026, came to a combined $21.85 million. All five were single-family homes in Monroe County, and the list followed the Overseas Highway up the Upper Keys, with two sales in Key Largo and one each in Tavernier, Plantation Key and Islamorada.
Islamorada had the top sale at $10,000,000. Below it, two homes tied at $3,600,000, and the group closed out with Key Largo sales at $2,450,000 and $2,200,000.
No. 1 — $10,000,000 · 186 & 165 Bayview Dr, Islamorada, Florida
The week’s top sale was a waterfront home in Islamorada’s Safety Harbor, and it came with two separate parcels. For a boater, the setting is the draw. The property has more than 220 linear feet of concrete dock and three boat lifts, with room for large vessels and a run to Florida Bay, the Gulf or the ocean by way of the Channel 5 bridge.
Built in 1991, the home was completely renovated in 2020 in a clean, contemporary style, with Viking appliances, custom finishes and a quiet, neutral palette drawn from the turquoise water outside. Floors are tile and marble. The home has an elevator and a gym, and with six bedrooms it has the most of any home in this week’s group. There are five bathrooms, four full and one half, in 4,394 square feet on 0.56 acres.
The saltwater pool was custom built and has both a heater and a chiller, so it can be used in any season. There is also a gazebo and an outdoor bar, along with fruit trees and an outdoor shower.
Sabrina Wampler & Sarah Ewald of Ocean Sotheby’s International Realty listed the home. Lisa Frins P.A. of Berkshire Hathaway HomeServices Keys Real Estate – Islamorada represented the buyer.
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No. 2 — $3,600,000 · 87950 Overseas Hwy, Plantation Key, Florida
The oldest home in this week’s Top 5, built in 1973, sits on the bay on Plantation Key behind fully fenced grounds. It has wide views across the water, and a tiki hut stands at the end of its dock.
Upstairs, an open living area leads through sliding glass doors to a large screened terrace. That level also has three bedrooms and two baths. The ground floor adds two more bedrooms, a bath and a second, more casual living area. Steps lead down from the terrace to the pool, the yard, a sandy beach and the dock. In all, the home has five bedrooms and three bathrooms in 2,464 square feet on 0.52 acres.
Restaurants such as Marker 88 and City Hall CafΓ© are within walking distance. The property last sold for $600,000 in 1999, 27 years ago.
Alina Davis of Coldwell Banker Schmitt Islamorada was the listing agent, and Margaret Jones Gonzalez of Coldwell Banker Schmitt Islamorada represented the buyer.
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No. 3 — $3,600,000 · 154 Redwing Rd, Tavernier, Florida
This bayfront home in the Sunshine Estates community was laid out in a V shape, a plan meant to give the rooms privacy and turn most of them toward the water. The property has 100 feet of frontage on the open bay and 50 feet of deep-water dock, with a short trip to the ocean through Tavernier Creek. It sold furnished.
Inside the concrete block home, built in 1977, the open living area rises to a vaulted ceiling with exposed wood beams over oak floors, and marble finishes run through the bedrooms and baths. Built-in shelving lines the living space, and the laundry room and pantry share a dumbwaiter. Of the four bedrooms, three have their own baths, and the home has five bathrooms in total, four full and one half, in 2,320 square feet on 0.25 acres.
The ground level is given over to entertaining, with a recreation room, a cabana bath and a summer kitchen that open the home to the outdoors. The home is near Mile Marker 91, a few minutes from shops, restaurants and schools.
Noemi Camps of Keller Williams Capital Realty – Coral Gables was the listing agent. Karan Moeller, PA of Ocean Sotheby’s International Realty represented the buyer.
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No. 4 — $2,450,000 · 55 Ocean Front Dr, Key Largo, Florida
Land sets this Key Largo property apart. At 1.09 acres it has the largest lot in this week’s group, landscaped with mature plantings and lit at night, and it is zoned to allow one horse. Its 4,446 square feet of living area is also the most of the five, and at 1998 it is the newest home on the list.
The concrete home was remodeled in 2020 and 2021. Its main living space measures 3,069 square feet, and another 1,377 square feet of enclosed space is set aside for entertaining. The custom kitchen has a large center island and opens to the main living area, and a big screened porch sits off the living room. The primary suite has a walk-in closet and access to a balcony, and its bath has a private balcony of its own. There are four bedrooms and three bathrooms, along with a media room, a gym and a bar. The home sold furnished.
Outside, a 450-square-foot pool is heated and chilled and has a spa, next to a summer kitchen and patio. A hookup with power, sewer and water serves an RV of up to 45 feet. Key Largo Park is nearby. The property last sold for $899,000 in 2020.
Sunne Rego of Coastal Realty of the Florida Keys was the listing agent.
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No. 5 — $2,200,000 · 1502 Shaw Dr, Key Largo, Florida
The smallest home of the five, at 1,605 square feet, sits on a gated 0.26-acre waterfront lot in Key Largo that has been rebuilt for life on the water. A concrete dock added in 2024 has a 20,000-pound boat lift, and the yard has artificial turf, a new heated pool and an outdoor kitchen. A six-foot metal gate closes off the property, and there is paved parking for more than ten vehicles.
Built in 1976, the concrete home was fully remodeled, with new impact windows and doors, new plumbing and electrical, and custom built-ins in every closet. It has three bedrooms and three bathrooms and is wired for sound. The property last sold for $1.14 million in 2023.
Hanler Portal of Florida Realty of Miami listed the home and also represented the buyer, so the same agent was on both sides of the sale.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 25, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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