Just about everyone agrees that Sarasota is the perfect place for a second home. Our beautiful year-round weather—OK, forget September—means year-round outdoor recreation. The arts are flourishing as never before, with Sarasota Ballet, Asolo Rep and Westcoast Black Theatre Troupe scaling new heights. Eating out is a major pastime, with your choice of fancy local restaurants, all the top chains and even some sensational taco trucks.

And oh, yes, one more thing—the beach. Siesta Beach has been officially rated the top beach in the country. That says everything.

We’ve been catering to second-home owners ever since Chicago socialite Bertha Palmer moved here in 1910, and by now we have it down to a science. All sorts of communities designed for their needs have sprung up, and continue to do so. But it’s not just the specialized communities. On every block in town, no matter where, some homes and apartments are only occupied for part of the year. (No prizes for guessing which part of the year.)

But how much do you have to spend to get the Sarasota vacation home you’ve been dreaming about? Here’s a look at what your money can buy.

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Colony Cove in Ellenton has water views and a variety of older and new mobile homes.

$100,000 or Less

Think Bradenton—or a Mobile Home

 It’s easy to find the perfect Sarasota getaway if you’re a multimillionaire, but what if your disposable income is more limited? You’re still in luck. Entry-level second homes can start at under $100,000. For that you’ll get a decent condo in a nice community. It won’t be glamorous, but it will be Sarasota.

Actually, it’s more likely to be Bradenton. I’ve long been fascinated by a place off Cortez Road called Bayshore on the Lake. There you’ll find two-bedroom condos for as little as $59,000. They are around 1,000 square feet and probably haven’t been renovated since they were built in 1980. (The updated ones cost more, but not that much more.) The monthly fees are $222. If you put 20 percent down and use conventional financing, you’ll be paying another $313 or so a month. Keep in mind you’ll be paying this every month, whether you’re there or not.

The atmosphere at Bayshore on the Lake is pleasant, with lots of wide open space, big, well-maintained swimming pools and pretty lawns. Many units have views of a large lake. Some sections are age-restricted, requiring one owner to be 55 or over. If you qualify, these are a little better, in my opinion, unless you enjoy lots of children hogging the elevators.

Perhaps the best thing about Bayshore on the Lake is the location—an easy 20-minute drive to downtown Sarasota, with the beaches about as close. You can walk to everyday shopping on Cortez Road. The actual buildings themselves are unadorned and graceless, but the price is certainly right.

A better low-budget choice may be a mobile home. Back in the old days, these were called trailers, and they had a bad rap. Now they’re called mobile or manufactured or park homes, and the newer, nicer ones are extraordinary: roomy, well-designed and full of features you won’t get in a cheap condo, such as vaulted ceilings, beautiful kitchens, elaborate master baths, full-size laundry rooms and on-trend décor.

And if you’re thinking, gee, I couldn’t live in a trailer park with a bunch of old people who leave every summer and play bingo all day, think again. I once lived in a very nice trailer park in Palmetto when I was between houses, and I was amazed at how much I liked the people. Everybody wants to be your friend. When my cat disappeared, the entire park was on the lookout. In fact, one thing about a good mobile home park is the built-in support system that comes with it. You get an instant community.

Mobile home prices are confusing. There are two different systems. System One is where you own the land under your home. System Two is where you own the trailer but not the land. You pay “lot rent” to the owner of the park, often an enormous company that owns similar parks all over the country and runs them with impressive efficiency.

Let’s say you find an older but perfectly nice home in a “lot-rent” park for $25,000. The same home in a land-owned park might cost $89,000. But at the lot-rent park you’ll be paying $600 a month (and it goes up every year; they make no bones about that). In the park where you own the land your monthly HOA fees will be $120 a month and won’t go up as often. Which works out better? I’ve been trying to figure it out for years. It’s like a nightmarish math question on the SATs.

The best mobile home parks at the moment seem to be found in Ellenton. I love the waterside portion of Colony Cove, with its mix of old and new homes, its winding streets and the beautiful setting. And The Gardens in Parrish is also very well done, about as prosperous-looking as a trailer park can be. Both of those parks are lot-rent.

My favorite land-owned park is Tri-Par Estates right here in Sarasota. The housing stock is mostly older but beautifully maintained. Some even retain the form of trailers of the classic era, when they weren’t designed to mimic houses but were their own wonderful thing, with sloping roofs and fins and odd embellishments.

Every time you fly into Sarasota you get a good look at Tri-Par Estates because it’s that big trailer park right underneath the wing of the plane, the one you’re hoping you’re not going to crash into. I was there recently when the tables were turned. A plane flew right over me at what seemed like 30 or 40 feet. Oddly enough, it was kind of thrilling. “What an exciting trailer park,” I thought to myself.

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Paired villas at University Village are aimed at pre-retirement boomers and start at $250,000.

$200,000-$400,000

Your Paired Villa Awaits 

Let’s move up the price range a notch or two. At $200,000 to $300,000 you begin to find homes that show what Sarasota is all about. Style kicks in, and living becomes more gracious. Some will be single-family homes, but you’ll find more options with a villa or condo in a community. Most will be a gated community, even at this price.

The big buys here at the moment are brand-new “paired villas”—meaning you’re attached at one side to a similar unit. There are two such places right near my house (in the University Park area), and I’ve seen them change from cow pastures to housing developments in a matter of months. One is called University Village and the other is called Villa Amalfi. They are built by different builders, yet they are both exactly the same: small gated communities with one-story paired villas of around 1,500 square feet. Each villa has two bedrooms and two baths, plus a room that could be used as a den (most likely) or a dining room or even, in a pinch, a third bedroom. Stylistically, they are mini-versions of big fancy homes, with pillars and moldings and recessed lighting and porcelain tile, most of which, I get the feeling, cost extra.

University Village was built by Carlos Beruff, who recently ran in the Republican primary for the U.S. Senate on a right-wing platform. (He lost to Marco Rubio.) Villa Amalfi was built by Pat Neal, another local power player in Republican politics, although more moderate. So which politician is the better builder? Villa Amalfi seems more smoothly run, but University Village grabbed me more. It has a lighter touch. Whether or not you agree with Beruff’s politics, he sure knows how to design a paired villa.

These communities—and more are popping up all over town—are aimed at pre-retirement boomers who will use their villa as a second home and then retire here at some future date. They are not family homes; they are couple homes. You could probably pack in grandkids on air mattresses for a week at Christmas, but the place is too small to have a lot of people visiting. Of course, that may be the point—your cousins will have to stay at Homewood Suites because there just isn’t room.

If you want a place for the whole family, cousins included, you’ll have to increase your budget a bit. Once you get above $400,000 the paired villas separate themselves and become single-family homes, with plenty of bedrooms, big family rooms, and—probably—your own pool. Homes like this can be found all over town, and there’s no reason one won’t make the perfect second home.

But there are challenges. Leaving a single-family home unattended for months on end can be a pain in the neck. You have to get somebody to check on it regularly. You have to get the grass cut and your oleanders trimmed, make sure raccoons don’t invade the attic, and replace the air filters, since the air conditioning must be left on to prevent mold. And when an aging water heater breaks or the roof leaks, you have to hire workers and oversee the job long-distance. All this can add up to quite a few headaches and considerable expense. So if you’re going to go this route, you might consider buying a new home, which is likely to have fewer problems. Unfortunately, new single-family homes are in short supply in many parts of Sarasota. 

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Homes like this $565,000 listing in the Country Club neighborhood of Lakewood Ranch often have lavish touches and outdoor living areas.

$500,000-$600,000

Head East to the Ranch

That’s one of the reasons they built Lakewood Ranch. It’s a giant planned community out to the northeast of town, on the other side of the interstate. It’s only 20 years old, and they keep building new neighborhoods like crazy, so it’s filled with pretty new and brand-new homes. (And the new homes usually come with a builder’s warranty that covers many problems for a number of years.) The homes come in all sizes and types, from condos to mansions, and many are second homes, so as a part-time resident, you’ll fit right into the Lakewood Ranch community.

And that sense of community is one of Lakewood Ranch’s biggest draws. It has recreational facilities galore, a slew of country clubs (and hundreds of other clubs), good shopping and restaurants, and, with its green space and jogging paths, a feeling of peace, order and security. The best second home buys here are in the $500,000 to $600,000 range. You’ll get a new or newer three- or four-bedroom place of around 3,000 square feet with lots of luxury touches. The next-door-neighbors may be close, but the homes are usually situated to have a nice view of a greenbelt or a lake from the lanai in the rear. The most important feature to check out is the outdoor living area. Some achieve near-perfection with their caged pools, spas, outdoor kitchens and even outdoor fireplaces.

But let’s get real. Having a half million dollars tied up in a second home that’s costing you money each month—at this point, it becomes an investment, and not necessarily a good one. Most of the time it sits there empty. What if you could make a little money by renting it out when you’re not there?

In most communities, that’s not encouraged. The neighbors don’t want transients moving in and out and there are strict rules about rentals. But that’s where our next category comes up. 

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$700,000-$900,000

Your Place on Siesta Beach

Siesta Key is full of condominium complexes, and in most of them, renting out your unit is permitted and even facilitated. Many people buy them not as second homes but as an investment. You can get a decent apartment for under $500,000, but the nice ones start around $700,000. For that, expect a two-bedroom, two-bath unit with a direct Gulf view. These condos are often sold turnkey furnished. The complex will have good if not great resort amenities. People come here for the vacation lifestyle, and condos within walking distance of the village’s bars and restaurants have an advantage. (Not too close, though. Noise from the bars can be a problem.)

Rental policies vary from building to building, with the frequency of allowed rentals a dead giveaway of how classy the building is. If they allow daily rentals, forget about it. That’s a hotel. The better buildings have a one-month minimum, and there may be other limits as to how many times a year you can rent it. The dilemma, of course, is that in the winter you can get a fortune for these places: $4,000 to $6,000 a month.  But that’s when you want to be there. In the summer, renters are harder to find. Summer vacationers spend a week, not a month.

 And because you’re renting it to all sorts of different strangers, it can’t be very personal. The furniture must be sturdy and practical, no white rug, no Sleep Number bed, and there’s a checklist of items, such as dishes, that you must have on hand. It will always be a vacation rental rather than a family home. Of course, this may be a plus to those who want their second home clean and simple, not full of life’s baggage.

These apartments are on the beach. That forgives everything, including the fact that many of them were built at the wrong time—the 1970s—and seem bland and dated by today’s standards. A good decorator can do wonders bringing one up to date, but it’s hard to find a Siesta condo that has inherent style. It doesn’t matter. They are right on the best beach in the country. That’s all they need.

Currently, there’s a great unit in a premium building called Casarina, where the site is pleasantly wooded. It’s got two bedrooms but with 1,700 square feet, it feels bigger, with features like a real laundry room and a fancy—but dated—master bath. The price is $799,000.

The one I’d probably buy, though, is in a bland mid-rise building called the Siesta Gulf View. It’s also two bedrooms, two baths, and as apartments go, nothing special. But that view! You see a greenbelt of sea oats waving on the dunes, then an impossibly wide white sand beach dotted with beach umbrellas and sailboats, then a glittering expanse of blue-green water. Nothing obstructs it, no buildings hem it in. There are several units for sale in this building, all priced around $800,000 to $900,000. And it’s a five-minute walk to the Daiquiri Deck.

The problem with expecting income from your second home is that it turns the experience into a business. You have a lot of money tied up and every time a hurricane forms you start to worry. You have to keep track of the local economy and the rental competition and what the tourist season is going to be like. You find yourself obsessing about global warming. How many years do I have before the water starts lapping at the base of my building? And what if a renter dies in my unit? Or even worse, throws a week-long frat party?

Still, it’s your very own second home on the best beach in the country. 

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Sarasota's Aquadisia, listed at $18 million, is a waterfront mansion in a class of its own.

$1 Million and Up

The Sky’s the Limit

Once you get over a million dollars, a new dynamic takes over. Forget about economy or compromise. Now we’re in the land of serious wealth. It’s one thing to have a million-dollar home. Lots of people do. But to have a second home that you paid 2, or 5, or even $11 million for—just think how rich you have to be.

Sarasota is full of homes that fill this rarefied niche. In the neighborhoods near the hospital and downtown, builders have been tearing down older homes and replacing them with fancier new homes priced at $1 million and a little more. And all those new buildings going up downtown have apartments aimed at the highest of the high-end market, and they’re selling fast, even before completion. The massive new Vue has been much maligned for its overwhelming scale, but the flip side of this is some pretty incredible apartments.

The smaller ones, which begin at just over a million, run around 1,700 square feet. For this you get a large, open-plan great room with the kitchen, dining and living areas combined, a nice but hardly lavish master bedroom (the master bath has no tub), a guest room and bath, and perhaps a small den without a closet. Not really big enough for a family, but for a vacation getaway for a couple, it’s ideal. Factor in the incredible view and being at the epicenter of the downtown action—and you’ve got a great Sarasota home.

If that sounds small, there’s still a penthouse unit for sale on the 18th floor, with three bedrooms and three baths in 3,415 square feet. It’s got 11-foot-high ceilings and an outdoor kitchen on one of the terraces. Here the master bathroom is lavish, with a walk-in closet that measures 20 feet by 12 feet. It’s priced at $3,399,000.

But the penthouses, as nice as they are, are still a cut below the grandest second homes here. From Casey Key to Anna Maria, waterfront mansions stand out for their luxury and style.

The great ones are created by master architects and have strong visual impact. Aquadisia on Siesta Key (currently on the market for $18 million) is a fantasy South Beach fashion set, complete with geometric lawns and several stand-alone rooms, some all glass. Ohana, at the north end of Longboat, is a series of interconnected Indonesian-inspired pavilions, sited so you don’t see the neighbors. It’s listed for $19.9 million. 

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Michael Kors

Image: Shutterstock

But now one is taking shape that may become the greatest second home of all. This is the Longboat Key mansion being built by Michael Kors and his husband Lance La Pere. Imagine—a billionaire fashion designer famous for his taste and sense of design is building his dream home right here. It’s a game changer.

I drove by it the other day. I’d guess it’s a little more than halfway finished. At the moment you can see it from the road; I assume vegetation will eventually block everything. The home is long and low-slung. You can already tell it’s got great lines and proportions. It’s from the New York firm of Stelle Lomont Rouhani, famous for elegant beach houses that—to me, anyway—suggest Paul Rudolph at his best.

Including the land, the place is setting Michael and Lance back $8.2 million. (By the way, this is actually a third home; the second one is on Fire Island, and home itself is a $20 million penthouse in Greenwich Village.)

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Image: Staff

From the construction documents on file, you can get a pretty good idea of what to expect. It’s large but not freakishly so (6,300 square feet), set on 2.25 acres. The master bedroom is over 400 square feet with the bath coming in at 225. There are four guest rooms, each with bath, and a second-floor suite for the staff that includes three bedrooms and a living room. The swimming pool is enormous: 70 feet long and 20 feet wide. Other features include mahogany privacy panels and retractable insect screens. Expect the décor to be monochromatic. “People are the color,” says Kors about interior decoration.

To make peace with the neighbors for all the inconvenience of construction, Kors and La Pere have been sending them gift baskets. Way to go, guys, and welcome to Sarasota. Thanks to you, the sky’s now the limit for Sarasota’s second homes. From trailer parks to a sprawling celebrity mansion, now there really is something for everyone.

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