Location: Casey Key, Longboat Key, and Siesta Key
Discover the 10 most expensive homes ever built in Sarasota. The Sarasota-Manatee luxury home market remains humble, compared to East-Coast markets like New York, Boston, and Miami, where luxury home sales can reach $100-250 million.
While Sarasota’s luxury real estate landscape continues to evolve, the most expensive homes in Sarasota remain remarkably consistent. Surprisingly, with all the luxury new construction being built, seven properties that ranked among the area’s most valuable homes three years ago still appear in today’s top 10—and ownership has largely stayed the same.
Unsurprisingly, these estates share a common thread: premier waterfront settings, exceptional privacy, and expansive living spaces. Below is an updated look at Sarasota County’s most valuable residences and the individuals behind them. If you want to see the most expensive homes currently for sale in Sarasota, this list is updated daily.
Lido Shores | A five-acre New Pass estate on one of Sarasota's most prestigious streets
No. 1 Most expensive Home in Sarasota – 1127 Westway Dr, Sarasota (Lido Shores)
Current Value: $27,341,011
2021 Value: $15,573,800
The most expensive home in Sarasota sits on a five acres in Lido Shores. The land was a tactful assemblage by one of the nation’s top female CEOs and her husband. The home and additional land were purchased in 2003 for $11 million, making it the largest waterfront residence on Lido Key.
The owners built a 19,658-square-foot edifice (7,151 square feet under air) with four bedrooms, seven bathrooms, and a pool hidden from view. The owners appreciate privacy, so we’ll forgo mentioning them by name. That said, it’s safe to say the home was thoughtfully designed with comfort and efficiency in mind.
Bay Point Park | A 16,016-square-foot hôtel particulier modeled on Paris's Hôtel Biron, built in 2012
No. 2 - 1420 Bay Point Drive, Sarasota
Current Value: $26,144,316
2021 Value: $15,135,200
Set along the bay in the exclusive Bay Point Park neighborhood, this 16,016-square-foot estate was custom-built in 2012 by former Congresswoman and Florida Secretary of State Katherine Ebbeson. The home is Inspired by 18th century french architecture, the home reflects Old World European design with formal symmetry and monumental proportions. A fun fact about this home is that Katherine asked her Architect to take inspiration from Paris's Hôtel Biron, also known as the Musée Rodin.
The property includes six bedrooms, 11 bathrooms, a resort-style pool, boathouse, and private dock—features that take full advantage of its direct bay frontage. Bay Point Park is prized for its gated privacy and proximity to downtown Sarasota while maintaining a secluded residential atmosphere.
Harbor Acres | A 28,182-square-foot home built on land once owned by Dow Jones heiress Jane Bancroft Cook
No. 3 - 1253 Hillview Drive, Sarasota (Harbor Acres)
Current Value: $25,017,104
2021 Value: $16,211,300
Located in one of Sarasota’s most sought-after neighborhoods, this 28,000 -square-foot estate was completed in 2018 by investment executive David Grain and his wife, Dr. Lisa Butler Grain. The four-bedroom residence sits on a property once owned by philanthropist Jane Bancroft Cook before being sold at auction.
Harbor Acres is particularly attractive for deepwater boating access, oversized lots, and proximity to downtown, making it a consistent performer at the top end of the market.
St. Armands Key | Owned by Jeffrey and Mary Penny Vinik, this stark-white modern estate is nicknamed the "S.S. Magellan" for its scale
No. 4 - 132 N. Washington Drive, Sarasota (St. Armands Key)
Current Value: $23,248,946
2021 Value: $15,382,000
Hedge fund pioneer and Tampa Bay Lightning owner Jeffrey Vinik and his wife own one of Sarasota’s largest private residences. The striking, ultra-modern waterfront estate spans more than 24,000 square feet.
The residence includes eight bedrooms, multiple entertaining spaces, and a pool overlooking Sarasota Bay with direct views of the Ringling Bridge. Vinik remains active in large-scale development projects, including the multibillion-dollar Water Street Tampa district.
Casey Key | A 14,898-square-foot Mediterranean estate built on the former site of a Ralph Twitchell–designed Sarasota School home
No. 5 - 2209 Casey Key Road, Casey Key
Current Value: $20,369,129
2021 Value: $16,332,700
Another standout on Casey Key, this Mediterranean-style residence sits on a large waterfront parcel. Purchased in 1999 for nearly $4 million, the original home, designed by Ralph Twitchell of the Sarasota School, was razed to make way for this Mediterranean-style estate, which sits on a prime Casey Key parcel and offers nearly 15,000 square feet of living space.
Designed as a private coastal compound, the home features a beach cabana, a boat dock, and expansive terraces positioned to capture views of both the Gulf and the bay. Casey Key’s limited inventory and strict development controls contribute to its enduring appeal among luxury buyers seeking privacy and natural beauty.
Longboat Key | Known as "Serenissima," this nearly 20,000-square-foot Gulf-front estate holds Sarasota County's residential sale record
No.6 - 845 Longboat Club Road, Longboat Key
Current Value: $22,947,131
2021 Value: $14,406,500
Known as Serenissima, this Venetian-style estate made headlines when it was listed in 2017 at a record-setting price. The home ultimately sold in 2020 and remains one of the most expensive residential transactions in Sarasota County history. Located within the Longboat Key Club, ownership adds access to golf, dining, and marina amenities.
Spanning nearly 20,000 square feet, this unmatched architectural splendor is a masterful craftsmanship, that offers panoramic views of sea, sand, and sky from nearly every room. This lavish residence invites both an entertaining and tranquil retreat. Featuring six bedrooms, expansive terraces, hand-painted ceilings, a custom birdcage elevator, and many more details to reinforce the property’s Old World European influence. It also serves as the base for the James and Laura Rogers Foundation, which supports arts and youth initiatives.
Sarasota Bay | A 21,192-square-foot Beaux-Arts residence with 10 bedrooms and 17 bathrooms
No.7 - 4449 Bay Shore Road, Sarasota
Current Value: $21,589,329
2021 Value: $15,358,900
Overlooking Sarasota Bay, this 21,000 -square-foot baroque-style mansion is owned by the former AM General CEO James Armour and his wife, Maryann. After purchasing the unfinished home in 2008, the Armours invested heavily to resolve construction issues and complete the estate.
The three-story residence -inspired by Parisian architecture- includes 10 bedrooms, 17 bathrooms, and extensive renovations that transformed the property into one of the largest single-family residences on Bay Shore Road—a corridor known for panoramic bay views and proximity to cultural institutions.
Casey Key | A 19,674-square-foot Spanish-style home built in 2007, with an award-winning 1.2-acre pagoda garden
No.8 - 2309 Casey Key Road, Nokomis
Current Value: $19,353,606
2021 Value: $17,094,600
This rare Gulf-to-bay estate occupies a prime stretch of Casey Key, offering both beachfront and bayfront access. The Spanish-style residence was completed in 2007. It encompasses nearly 20,000 square feet and was designed to function as a private compound.
In addition to expansive living spaces, the property is notable for its landscaped grounds, including a meticulously designed garden spanning more than an acre. Casey Key remains one of the most supply-constrained barrier islands in the region, contributing to the long-term value of estates of this caliber.
iesta Key | Nearly 10,000 square feet across two buildings, on the site of Harry Higel's historic Hotel Higelhurst
No.9 - 3332 Gulfmead Drive, Siesta Key
Current Value: $18,548,291
2021 Value: $3,074,700
This newly constructed waterfront compound occupies nearly an acre at the northern tip of Siesta Key. The estate includes two separate structures with nearly 10,000 square feet of combined living space, with expansive seawalls along both Bayou Louise and Big Pass.
The location offers wide-open water views and boating access. The site adds historical significance as it once hosted the Higelhurst Hotel, an early Sarasota resort developed by pioneer Harry Higel in the early 1900s.
Lido Key | Over 100 feet of direct Gulf beachfront on one of Lido Shores' most coveted stretches
No.10 - 1067 Westway Dr, Sarasota (Lido Shore)
Current Value: $18,625,303
2021 Value: $8,872,400
This Mediterranean-inspired beachfront is situated along the iconic shores of Lido Beach. Purchased in 1999, the original residence—designed by Sarasota School architect Ralph Twitchell—was removed to make way for a nearly 15,000-square-foot custom estate with a beach cabana and private dock.
Key features include a beach cabana, boat dock, and expansive outdoor entertaining areas designed for both Gulf sunsets and bay views.
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