Welled inventory, new construction persisted, prices softened and buyers grew more selective.

Despite all that, Sarasota County still produced a record-setting outlier: a $30.3 million, all-cash sale on Longboat Key, the most expensive residential transaction ever recorded in the county.

The contrast between the top and bottom of this year’s expanded list is sharper than it was in 2024. The lowest sale to make the 2025 ranking closed at $9.5 million, roughly 25.8 percent lower than last year’s cutoff of $12.8 million, underscoring how much pricing pressure filtered into the lower edge of the ultra-luxury market.

At the same time, the very top of the list moved in the opposite direction. This year’s $30.3 million Longboat Key sale was 42.6 percent higher than 2024’s most expensive transaction, which closed at $21,244,000—a reminder that truly singular properties continue to operate on a different curve.

Of the 11 sales included, at least four closed below their most recent asking prices, often after extended time on the market. By contrast, a small subset—including a new-construction St. Armands Key home and select St. Regis condominium sales—sold at or near full ask, showing demand for newer or turnkey inventory.

Among the transactions where both list and sale prices were disclosed, homes sold at an average discount of roughly 19 percent from ask—wide enough to signal real leverage for buyers, but still narrow enough to keep prices in record territory.

All of the sales were cash transactions–a clean sweep that underscores how detached the highest tier of the market remains from interest rates and financing conditions. The only one we can't say that for is 40 N. Washington Drive, which appears to have been handled as a private sale.

Timing tells a more nuanced story. Among the top MLS-listed sales, 30 percent went under contract within 30 days, including two new-construction St. Regis condominium units that sold at launch. Forty percent secured buyers within 60 days, while the remaining 30 percent took more than 90 days to go under contract, in some cases stretching close to a year. The faster deals tended to involve newer or turnkey properties, while longer times clustered around larger legacy estates that sold below their most recent asking prices—evidence that even in a fully cash market, patience still matters.

Geography tells one of the quieter but more revealing stories. In 2024, the county’s most expensive sales were spread across Longboat Key, St. Armands Key, Casey Key, Siesta Key and the mainland bayfront. In 2025, that map tightened noticeably. Longboat Key dominates the upper tier, turning this year’s list into less of a countywide tour and more of a concentrated stretch of coastline where price sensitivity thins quickly.

Still, no matter the year or the zip code, the formula rarely changes: more square footage than anyone strictly needs, water views in every direction and neighborhoods chosen for their long track records of converting sunshine into a commodity, even when the rest of the market takes a breath.

This list reflects residential property sales recorded in Sarasota County based on publicly available deed records and sale prices reported by the Sarasota County Property Appraiser and Clerk of Court. Data is also based on Multiple Listing Service (MLS) data.

Tie

No. 11: $9.5 Million

3336 Old Oak Drive, Sarasota

The home at 3336 Old Oak Drive is a bayfront property situated on roughly two acres. The residence spans just under 6,000 square feet and includes a primary suite with bay views, multiple fireplaces and a home gym.

The property includes an attached four-car garage and a detached carriage garage accommodating at least six additional vehicles. Outdoor elements include a heated pool, landscaped grounds and multiple patio areas oriented toward the bay.

The buyer is Elizabeth A. Coughlin, trustee of the Elizabeth A. Coughlin Revocable Trust, with a mailing address in Wenham, Massachusetts. The seller was Northern Trust Co., trustee, which acquired the property in 2013 for $2.3 million, according to recorded property records.

TIE

No. 10: $9.5 Million  

1378 Harbor Drive, Sarasota

The bayfront home at 1378 Harbor Drive changed hands in June for $9.5 million after being listed earlier in the year for $11.35 million. The home was sold by the Duoos Family Trust—with Lynn M. Duoos listed as a co-trustee—to Charles D. Sizemore after an original listing of $14 million in 2022. Built in 2003, the three-story home spans 6,238 square feet on a .33-acre waterfront lot. It has four bedrooms and eight bathrooms and is oriented toward Sarasota Bay, with extensive indoor and outdoor living areas designed to take advantage of the water views and boating access. There's a private dock and lift, along with multiple terraces and a pool positioned along the bayfront edge. Sizemore is an entrepreneur and executive best known as the founder of The Memory Company, a consumer products business he started in 1998 that designs and distributes branded drinkware and home décor to major retailers. In 2025, private equity firm Fruition Partners acquired The Memory Company, with Sizemore staying on as an investor and leader associated with the business. He's also listed in corporate directories as a partner at Transcend Health, LLC, a company that manages the financial side of healthcare for hospitals and medical providers.

TIE

No. 9: $9.5 Million

1580 Harbor Cay Lane, Longboat Key

Located at the heart of Longboat Key’s Bay Isles Harbor, this contemporary bayfront home essentially fetched its original list price of $9,495,000 after arriving on the market earlier that spring. Originally built in 1981 and updated over time, the residence spans 6,349 square feet of interior space with five bedrooms and six bathrooms, set on a .34-acre bayfront lot with about 100 feet of deep-water frontage. It's got panoramic water views, clean architectural lines and expansive terraces that blur indoor and outdoor living. The gated Bay Isles community offers 24-hour security and deeded access to the private Bay Isles Beach Club. Todd and Elizabeth Rieke, trustees, of Lake Geneva, Wisconsin, sold the property to Bryan Martin of Larchmont, New York. Seems he likes the neighborhood; Martin also appears as the owner of a nearby Longboat Key address on Gulf of Mexico Drive. A longtime energy sector executive, Martin is the executive chairman and co-founder of DESRI–D. E. Shaw Renewable Investments—a company that develops, owns and operates renewable energy projects, primarily utility-scale solar and wind. 

No. 8: $9.75 Million

40 N. Washington Drive, Sarasota

George Duke, with a mailing address in Bradford, Pennsylvania, bought this home from Susan Kellaway in a rare 2025 moment: it received the full listing price. Built in 2021, it's a newer generation of construction on St. Armands Key, where much of the housing stock dates to earlier decades. The transaction followed a period in which luxury sellers were adjusting expectations after late-2024 storm activity reshaped insurance costs and buyer scrutiny, even though 2025 itself passed without major hurricanes. In that context, the Washington Drive sale reflected continued demand for newer homes on St. Armands Key. As for getting along with his neighbors, that's a cinch. Duke—the chairman and sole family owner of Zippo Manufacturing Company, the privately held company founded by his grandfather, George Blaisdell, in 1932—also owns the home next door.

No. 7: $9,795,000

1561 Gulf of Mexico Drive, Unit 302, Longboat Key

This condo was sold by S.R. LBK, LLC, the development entity behind the St. Regis project, to Mark Byrne for the full listing price. Completed in 2024, it spans 4,917 square feet of living area. It's a three-bedroom condominium with three and a half bathrooms arranged around expansive living and dining spaces oriented toward the Gulf of Mexico. The unit includes a private elevator entry and broad terraces designed to extend living space outdoors, consistent with the scale and layout of the building’s upper-tier residences. And as a developer sale rather than a resale, the transaction reflects a direct handoff from builder to end user. Unit 302’s sale price aligns with other top-floor and corner-unit transactions within the development during its initial sellout phase.

No. 6: $10.25 Million

801 Longboat Club Road, Longboat Key

The home at 801 Longboat Club Road, located within the gated Regent’s Court enclave of the Longboat Key Club, sold after being listed at $11.9 million in December 2024. The property spent 134 days on the market and sold for 86 percent of its asking price.

The Gulf-front residence sits on a site with 150 feet of beach frontage and includes five bedrooms and five and a half bathrooms. The layout includes a gallery-style entry, a formal dining room with a service kitchen, and multiple living and family rooms. The first-floor owner’s suite is configured with two separate sleeping and bathroom areas, while the second floor includes four guest suites and an additional family room opening to a covered verandah.

Outdoors sees a pool and spa set within landscaped grounds, along with direct beach access via a nearby shared walkover. The home also includes an elevator and garage space for up to eight vehicles.

The current owner is ADJ Texas Property Inc., which lists a mailing address at 2068 Piper Lane, London, Ontario, Canada. The address is linked to ADJ Industries Inc., a Canadian manufacturing and fabrication firm that specializes in large-scale machining and welding for locomotive, power generation, oil and gas, mining, trucking and defense industries. The same entity owns 1540 Hillview Drive on the mainland. The seller was Northern Trust Bank. This home is one of two located on the same street on this year's list.

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No. 5: $10.25 Million

435 L’Ambiance Drive, PH-J, Longboat Key

The buyers of this Longboat Key penthouse are Scott Dols and Vicki Dols, purchasing as trustees of the Scott Dols Irrevocable Trust, with a mailing address in Lutz, Florida. The condo sits within L’Ambiance at the Longboat Key Club, a Gulf-front condominium community known for its large floor plans and full-width beach views. Built in 1994, Penthouse J is among the building’s most prominent units, with direct access to expansive Gulf-facing terraces. Dols is the founder of Big Truck Rental, an equipment rental company serving the waste and environmental services industry, and has served on the board of OPAL Fuels, a renewable natural gas company. Since 2020, the couple has also owned another luxury condo nearby on Gulf of Mexico Drive.

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No. 4: $10.5 Million

26 Sandy Hook Road S., Siesta Key

The home at 26 Sandy Hook Road S. is a Gulf-front property in the private Sandy Hook community on Siesta Key. The residence sits on roughly one acre and includes just over 5,000 square feet of interior living space, along with more than 3,000 square feet of covered outdoor areas. The layout includes five bedrooms with en-suite bathrooms, two half baths and a three-car garage.

Built in 2003, the house has since been fully renovated and includes impact-rated floor-to-ceiling windows facing the Gulf. Interior and exterior finishes include hardwood decking and custom millwork. Outdoors includes a heated saltwater pool and spa, multiple covered seating and dining areas, a built-in outdoor kitchen and a fire pit. Included is direct access to a private, resident-only beach. 

No. 3: $13 Million

1561 Gulf of Mexico Drive, Unit 502, Longboat Key

No. 2: $14.8 Million

1490 Hillview Drive, Harbor Acres

The home at 1490 Hillview Drive is a new construction home that sits on roughly half an acre with approximately 100 feet of waterfront and south-facing bay views. The house spans about 6,500 square feet and includes five bedrooms, five and a half bathrooms and a three-car side-entry garage.

The layout includes an elevator, a primary suite and study on the main floor and a second-level family room with four additional en-suite bedrooms. Interior living spaces open to outdoor terraces, an infinity-edge pool and spa, and a covered patio area. The home also includes a whole-house generator.

The property sold for $14.8 million on March 10, according to Sarasota County Construction was by Sarasota-based builder Voigt Brothers and it was designed by architect Stephen Balut of MHK Architects. The seller was SRQ Home Holdings LLC, which purchased the property in 2022 for $12 million.

The buyer is listed as 1490 Hillview Dr LLC and property records link it to a residential address in Libertyville, Illinois, owned by Allyson D. Cayce.

No. 1: $30.3 Million

845 Longboat Club Road, Longboat Key

The Gulf-front estate known as La Serenissima set a new record as the most expensive residential sale ever recorded in Sarasota County. It was an all cash deal. Set behind the gates of the Longboat Key Club, the Venetian-inspired estate sits on roughly 1.18 acres with about 145 feet of direct Gulf frontage. It spans nearly 19,300 square feet of living space and is organized around a two-story grand salon, with formal rooms extending toward terraces and the beach beyond. Architectural details include a birdcage-style glass elevator, hand-painted Venetian murals, frescoed and coffered ceilings, limestone-clad walls, a mahogany-wrapped library, and multiple interior staircases and elevators. The property last changed hands in 2020 for $16.5 million, which at the time also set a regional record. In 2025, the home was listed at $35 million and went under contract within weeks, closing in less than a month 25 days and underscoring how singular properties at the very top of the market continue to operate on a different timeline. The buyer was Vicki James, purchasing through a trust. James is president of the James Foundation and is based in Auburn, Indiana. She has been honored by former vice president and Indiana Gov. Mike Pence for her civic and philanthropic work and serves on several nonprofit boards in northeast Indiana, including organizations focused on parks, libraries and Special Olympics. James is already familiar with Sarasota’s barrier island luxe-Italian style. In 2021, she purchased 139 S. Washington Drive on St. Armands Key for $10.6 million, also through a trust. Earlier this summer, she listed that property—known as Casa del Carnavale—for $17.5 million, where it remains on the market. Even with that listing unsold, James was able to close on La Serenissima in cash.