Longbeach Village, Longboat Key

The Village, as it’s called, lies at the extreme northern end of 12-mile Longboat Key, and unlike the tall, resort-feeling condominiums that line much of the southern end, it has more of an older, single-family home vibe (although there are certainly some smaller, low-rise beachfront condos here, too). Take a turn off Gulf of Mexico Drive onto Broadway Street and you’ll wind up at the Mar Vista Dockside Restaurant, a piece of Longboat Key history. The original docking spot on Sarasota Bay was built in 1912; destroyed in a hurricane and rebuilt in the 1920s, Mar Vista also has undergone a more recent renovation and expansion without losing its rustic charm—the perfect spot to enjoy waterfront dining. Coming soon nearby: The Shore, an expansive new eatery on the spot of the iconic Moore’s Stone Crab Restaurant. Recently gone and much lamented: the 60-year-old Longboat Key Center for the Arts, long a key gathering spot for artists and art lovers. New development awaits at its location.

St. Armands Key

Shopping destination St. Armands Circle, originally laid out by circus king John Ringling as part of his development plans for St. Armands Key, is the hub of the island, with shops and restaurants galore. But there are plenty of quieter residential streets, too, where fairly low-key homes of a certain vintage, often set on canals, poke out between more recent multimillion-dollar mansions, like the imposing one Tampa Bay Lightning owner Jeff Vinik recently built. It’s an easy stroll to beautiful Lido Beach from the key, and maybe even to the colorful tiki bar hidden behind the Ritz-Carlton’s exclusive members’ Beach Club. (The tiki bar is open to the public.)

Lido Shores

Tucked away on streets with names like Morningside and Westway, between St. Armands Key and Longboat Key, this is a neighborhood of true architectural distinction. You’ll find homes from the famed modernist Sarasota School of Architecture that have been carefully restored and refurbished, along with newer residences that reflect their owners’ more diverse architectural styles, from classic to contemporary. An enclave for those who really care about design, and occasionally the site of architecture tours.

Longboat Key Club

Behind the gates of the Longboat Key Club at the very south end of the key are some of the most expensive and opulent homes in the county—including the very highest real estate listing of all, an Italianate mansion with almost 20,000 square feet under air that’s currently on the market for $26.5 million. Not every home here reaches that stratospheric height, but this is definitely a case of lifestyles of the rich, if not always famous. With 45 holes of championship golf, 20 Har-Tru tennis courts, fine dining, a spa and a marina close at hand, residents and members here can satisfy just about every need without ever leaving the island. 

Country Club Shores, Longboat Key

Country Club Shores promised the ultimate in Florida living when it was built back in the early 1960s. Practically all of the houses are on canals and have a dock in the back yard. The location at the southern end of Longboat Key makes Country Club Shores close to the bridge and city. There’s golf, beach and tennis at the Longboat Key Club, right across the street.  

The property feels a little dated. But it’s waterfront in a great location, and that’s attracting buyers. Older ranch homes are being replaced by multistoried new homes that are exactly what the luxury buyer wants.

What that buyer wants is evident in one of the largest of the newer homes, located at the end of Ranger Lane. It’s a two-story Mediterranean-style home that boasts over 6,000 square feet. Priced at $5.85 million, it has all the features of a home that expensive—home theater, elevator, several fireplaces, heated infinity pool, not to mention drop-dead views from virtually every room.

More ordinary new construction generally goes for between $1.5 million and $2 million. And there are plenty of older homes left. Some can hold their own with new construction, particularly when the buyer doesn’t want something enormous. Others are sitting there waiting. During a recent visit I was taken with the idea of buying one, living in it for a while, then selling it as a teardown in say, five years when it will really be valuable. One recent buyer has done exactly that. He got a nice 1960s home for just under $700,000. He plans to live there at first, then perhaps have his parents live there. When he retires, he’ll replace it with a new luxury model.—Robert Plunket

Beauty Queens

Two of Sarasota Magazine’s 10 most beautiful homes are on upscale Lido Shores.

 1300 Westway Drive

Our panelists were unanimous in choosing famed architect Paul Rudolph’s 1953 Umbrella House in Lido Shores as the most striking in our treasure trove of Sarasota School of Architecture residences. Current owners have meticulously restored its namesake “umbrella”—a novel shade roof originally made, believe it or not, of tomato stakes; it was damaged by a windstorm in the 1960s and removed. (The new one is made of aluminum.) Architect Greg Hall earned a Florida Trust for Historic Preservation award this year for his work on the project.

1255 Westway Drive

Internationally renowned fashion designer Adrienne Vittadini took a different professional turn with her husband, Gigi, in the early 2000s when they developed three grand, classically inspired residences in Lido Shores with architect Cliff Scholz. Our panelists picked this home at 1255 Westway Drive as their favorite because of its spot-on proportions and scale, and its infinity-edge pool that spills over into New Pass.

Most Expensive Homes

And…maybe you can’t afford one of Sarasota’s most expensive homes, but it’s nice to know who can. These Lido Key/Longboat homes made our listing in late 2016.

No. 1

$16,857,400 | 1127 Westway Drive | Owners: Carrie and Kenneth Cox

The most expensive home in Sarasota sits on five acres on New Pass on Lido Key on Westway Drive. Owned by pharmaceutical executive Carrie Cox and her husband, Kenneth, a developer, the home and additional land were purchased in 2003 for $11 million. The Coxes built a 19,658-square-foot edifice (7,151 square feet under air) with four bedrooms, seven bathrooms and a pool hidden from view. Carrie Cox, who has been named one of the nation’s top female CEOs and was a global president at Schering-Plough, Merck & Company, is now the CEO of Humacyte, Inc., a small North Carolina-based biotech firm that creates soft tissue parts for regenerative medicine.

No. 5

$14,471,300 | 845 Longboat Club Road | Owners: Mike B. and Michele P. McKee

Located inside the gates of the Longboat Key Club on the Gulf of Mexico, this modern Venetian palace is the first of four homes on our list located in the exclusive enclave Regent Court. Owned by Mike and Michele McKee, the property was purchased in 1998 for $2.15 million. The couple moved here after selling their manufacturing company in the Midwest and “stumbled upon the lot at Regent Court,” Michele says. The 17,714-square-foot residence has six bedrooms, eight baths and a pool. Details include a grand salon, hand-painted ceilings, stone columns, Palladian windows and a sun-drenched atrium.

No. 8

$12,967,200 | 857 Longboat Club Road | Owner: Pleasant Real Estate LLC

The second Regent Court home on the list is a 15,954-square-foot home with six bedrooms, 12 bathrooms and a pool built in 2008. The home was purchased in 2000 by Clayton Lee Mathile and his wife Mary; they transferred the deed to Pleasant Real Estate in 2003. Mathile is a well-known businessman and philanthropist who built the Iams pet food company into a powerhouse and sold it to Proctor & Gamble for $2.3 billion.

No. 9

$12,720,600 | 825 Longboat Club Road | Owner: P & W Charters, LLC

This home—also in Regent Court—is owned by P & W Charters, LLC, which has an address in Great Britain that shows ownership by British businessman William Archer and his wife Shirley. Archer, who regularly makes the lists of the U.K.’s richest, founded retailer Focus DIY—a home and garden store—with a partner in 1987. The Longboat Key property was purchased for $12.5 million—a record at the time—in 2011. It’s a two-story, six-bedroom, seven-bathroom home of 12,095 square feet.

No. 11

$9,713,000 | 1067 Westway Drive, Sarasota |Owners: Thomas and Paula McInerney 

This secluded property is set on the northern edge of North Lido Beach. The 7,400-square-foot, two-story home was built in 1996 and sold for $13 million a decade later to Thomas and Paula McInerney of New York City. The couple together founded Connecticut’s Bluff Point Associates with a portfolio concentrated in health care, information technology and wealth management. In addition to their main home, the McInerneys also own a pair of adjacent vacant properties to the south, together worth another $4.1 million.

No. 15

$9,008,900 | 835 Longboat Club Road, Longboat Key | Owners: Vern and Sandy Buchanan

Vern and Sandy Buchanan built their 9,900-square-foot Mediterranean Revival manse in 1998, shortly after buying the beachfront Longboat Key lot for $1.8 million. Vern earned his fortune in Michigan by founding American Speedy Printing, a franchise print shop. He bought and ran automobile dealerships after moving to Florida and is involved in dozens of other businesses. In 2006, he was elected to the United States Congress as a Republican. Now in his fifth term, he serves on the powerful House Ways and Means Committee. In 2015, he was ranked the ninth-wealthiest member of Congress, with a net worth of $49.86 million.

No. 16

$8,634,300 | 1333 Westway Drive, Sarasota | Owner: Colleen Ofield

As the trustee for the Craig Ofield Florida Trust, named for her husband, Colleen Ofield purchased this 8,800-square-foot Lido Key home overlooking New Pass for $8.4 million in 2010, shortly after the original owners built the structure, which included a movie theater, wine bar and wine room, two swimming pools and a guest house. Craig is the president of Bulk Barn, Canada’s largest bulk food retailer, with 250-plus locations, and the son of the chain’s founder, Carl. Colleen is an executive vice president in the company, headquartered in Aurora, Ontario.

No. 19

$8,369,400 | 1157 Westway Drive, Sarasota | Owner: Ira Barsky

The former home of Joseph and Grace Penner, a prominent Sarasota couple in the 1980s, this 10-room contemporary-style Lido Shores house, built in 1974, is nestled into the curve of north Lido Key, with a swimming pool just steps away the Gulf of Mexico. In 1991, Ira Barsky and his wife Lee retired here from the Northeast, where he had been involved in finance and industrial companies. Drawn to the Lido Shores area, they rented a house two doors away from their current home. Soon afterwards, he says, the Penner home became available and they purchased it. In 1999, Ira Barsky co-founded the Animal Rescue Coalition, bringing together leaders from local animal welfare organizations to help end the killing of the region’s adoptable dogs and cats.