The five highest-priced home sales reported in the Florida Keys for the week ending November 8, 2026, totaled $30.24 million. The list runs the length of the island chain, with two sales in Key Largo, one on Sunset Key off Key West, one in Islamorada and one in Tavernier. All five are single-family homes in Monroe County, built between 1980 and 1998, and the group ranges from canal-front homes made for fishing and boating to an oceanfront property with its own beach.
No. 1 — $9,300,000 · 48 Sunrise Cay Dr, Key Largo, Florida
The week’s top sale was 48 Sunrise Cay Drive in Key Largo, a waterfront home that sold for $9,300,000. Built in 1988 and sold furnished, the three-story home has four bedrooms, four bathrooms and 5,031 square feet of living space on a 0.45-acre lot. Its exterior is clad in corrugated metal panels, and inside are a private elevator and an office.
The water shapes the way the home is lived in. Views from the second floor take in both the bay and the ocean, and the primary suite looks out over the water as well. Breezes move from the front of the home through to a back deck with sunset views. The large screened lower level is built around boating and fishing, with an extensive tackle room. Along the canal, 72 feet of frontage and a 38-foot dock can take a 42-foot boat. The grounds also include a pool, a Jacuzzi, a terrace and a garden. The property last sold for $3.35 million in 2019.
Wendy Brainard of Ocean Reef Club Sotheby’s International Realty was the listing agent, and Roberta Watson of Watson Luxury Properties at Ocean Reef represented the buyer. The home went under contract 24 days after it was listed and finished the week at No. 1.
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No. 2 — $8,750,000 · 11 Sunset Key Dr, Key West, Florida
Sunset Key can be reached only by private ferry, yet Old Town Key West is a few minutes away. The home at 11 Sunset Key Drive sits on the island’s Crescent Beach, and it sold for $8,750,000, the second-highest price of the week.
Built in 1998, the home was completely renovated in 2018. That work brought hurricane-impact doors and windows, new electrical systems, white oak engineered wood floors and an interior fire sprinkler system. The kitchen was redone with a Sub-Zero refrigerator, stainless appliances, new countertops and custom cabinetry. Outside, the pool and spa were rebuilt to the plumbing and finished in handcrafted, hand-painted tile, with lighting and equipment controlled by an app. The saltwater pool sits near a deck, an open porch and an outdoor shower, and the home also has a gym.
The home has three bedrooms, two full baths and a half bath in 2,905 square feet on a 6,098-square-foot lot, the smallest lot among the five. It sold furnished, with pieces from Restoration Hardware. Owners on Sunset Key have access to an oceanfront restaurant and a full-service spa, as well as tennis courts and private beaches. The property last sold for $5.3 million in 2018.
Dan R Serban of Key West Luxury Real Estate Inc (KW) was the listing agent, and the Cardenas & Krug Team of Coastal Collection Real Estate Inc. represented the buyer.
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No. 3 — $4,950,000 · 165 S Harbor Dr, Key Largo, Florida
A second Key Largo sale came in at No. 3, as 165 South Harbor Drive sold for $4,950,000. The lakefront home looks out over open water from most of its rooms, and an extra side yard planted with lush landscaping gives it privacy from the neighbors. Inside, an extra-large playroom adds room for family and guests. The home is close to the new member fitness center and pool.
Built in 1988, the home has three bedrooms, three full baths and a half bath in 2,587 square feet on a 0.41-acre lot. It sold furnished. The property last sold for $1.76 million in 2019.
Roberta Watson of Watson Luxury Properties at Ocean Reef, who also represented the buyer of the week’s top sale, was the listing agent. Cassy Everhart, Morgan Smith of Ocean Reef Club Sotheby’s International Realty represented the buyer. The home went under contract 21 days after it was listed.
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No. 4 — $4,022,375 · 75761 Overseas Hwy, Islamorada, Florida
In Islamorada, 75761 Overseas Highway sold for $4,022,375. The oceanfront property sits behind its own gated entrance on 0.65 acres, the largest lot among the five, with a sandy beach and long views over the ocean. The concrete block home was built in 1998 and has four bedrooms, four bathrooms and 3,001 square feet, plus a bonus room.
Hardwood floors run through an open plan that takes in a breakfast nook, a dining bar and the living area. The kitchen has a gas stove and stainless steel appliances. The primary suite opens to a private balcony above the updated saltwater pool, and there is a heated spa as well. The property also has room for RV parking. It last sold for $2.835 million in 2022.
Stephany Duvall of Engel & VΓΆlkers Marathon was the listing agent.
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No. 5 — $3,220,000 · 141 Canal St, Tavernier, Florida
The fifth sale of the week, 141 Canal Street in Tavernier, is the largest home of the group at 5,061 square feet and also the oldest, built in 1980. It sold for $3,220,000. Set on a canal on Plantation Key, the all-concrete home is elevated above potential flooding and has five bedrooms, five full baths and a half bath, the most bedrooms and bathrooms among the five.
An exotic wood staircase rises from the entry to a spacious primary suite with views of the surroundings. Marble floors lead out to a private concrete rooftop deck with panoramic views of the ocean. The kitchen centers on a large granite island. On the first level are a theater room, a tackle room and a legal guest suite with its own bedroom and bath.
Outside, the pool is both heated and chilled, and a 24,000-pound boat lift serves the canal. Tavernier Creek is a few minutes away, with access to the Atlantic Ocean and Florida Bay. The home sold furnished on a 6,969-square-foot lot. The property last sold for $1.75 million in 2020.
Kim Bagnell Thaler of Ocean Sotheby’s International Realty was the listing agent, and Leslie Leopold, also of Ocean Sotheby’s International Realty, represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, November 8, 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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