Oldforestlakes 025 xuytl9

A classic low-slung ranch in Old Forest Lakes.

IN REAL ESTATE PARLANCE, a neighborhood is occasionally described as a “best-kept secret.” This often means it’s a dog and there’s a reason nobody ever heard of it. But that’s not always true. There are some little enclaves that are unique unto themselves, places with charm or character or well-designed houses at bargain rates, which have somehow remained under the radar. Seek them out and you may be rewarded with your perfect new neighborhood. Best-kept-secret neighborhoods share certain traits. They are old or oldish. Their locations are usually excellent—scenic or convenient—and sometimes spectacular. They’re beautiful, though not necessarily in a conventional sense. Their style is understated; homes built for show are usually built in more prominent neighborhoods. And often residents want to keep things just the way they are. They dread change and will fight it even though it might be financially beneficial. Let’s take a look at five of our region’s best-kept secrets. Chances are you’re familiar with a couple. But it’s a rare Sarasotan who knows all five.

Old Forest Lakes

Not to be confused with regular Forest Lakes or all the other Forest Lake variations, this upscale development dates back to the 1950s. It’s east of Beneva Road between Webber Street and Bee Ridge Road. Back then it was on the edge of town. Now it’s in the middle of everything.

With its large lots—they range from half an acre to just over two—and winding streets, Old Forest Lakes is the very picture of upper-middle-class family life. The architecture is an interesting mix of custom homes from every decade, the most typical being a low-slung ranch. But you’ll see midcentury modern, too, and some beautiful newer homes, very few of which are McMansions.

And yes, there is a lake, one of the prettiest in town. It’s a perfect size—no real boating, just canoes and such—and the homes that line it are prizes.

Old Forest Lakes is also Old Sarasota, and has been home to many prominent local people over the years. You’re always meeting second- and third-generation townspeople who grew up here. Their parents were the charter members of the local establishment—lawyers and well-to-do business owners.

Today the names are different but the feeling remains the same. True, there is no gate. The surrounding area is nice but unexceptional, pure white-bread suburbia, in fact. Old Forest Lakes remains an unlikely enclave of social cachet in this middle-class environment, an old dowager who keeps herself looking great in a timeless, discreet way.

There are just 72 homes in Old Forest Lakes, so you may have to wait until the right one comes on the market. At the moment you can find a newish (1999) 3,000-square-foot contemporary with three bedrooms and two baths, set on three quarters of an acre with a secluded pool and gazebo (3415 E. Forest Lake Drive). It’s priced at $895,000.

But for a glimpse of classic Old Forest Lakes style, take a look at 3425 W. Forest Lake Circle. It dates back to 1954 and was originally built by David Miller, who developed the subdivision. He soon sold it to Maxwell and Vivian Cooke. Max owned Cooke Cadillac—now Coastal Cadillac—and Vivian is still remembered by old-timers as the driving force behind the annual Debutante Ball.

Updating is needed, true, but it’s easy to picture white-gloved debutante teas in the big living room overlooking the lake. The property is set on two acres and is gated. You will even have your own little island in the lake, accessed by a wooden bridge.

“I’ve been selling homes in Sarasota for 25 years and this may be the most unique property of them all,” says Alison Menke, who’s listing the house for ReMax Alliance. It’s an important part of Sarasota’s social history, and at a great price: $999,000.

Myakkavalleyranches 010 lch55y

A starter ranch; homeowners have miles of trails for riding.

Myakka Valley Ranches

There are fancier communities east of I-75 than Myakka Valley Ranches. Gator Creek suggests a tony suburb in Connecticut somehow magically transported to the tropics. Saddle Creek is for wealthy gentleman ranchers who want to keep a horse or two. But Myakka Valley Ranches is the wild card and definitely the one I’d pick. Tractors and farm equipment are very much in evidence and the aesthetic is practical rather than picturesque. The website brags about the fire station “conveniently located at the entrance.”

Myakka Valley Ranches is located off State Road 70, on the way to Arcadia, maybe five miles past the interstate. When you first drive in, it doesn’t seem very imposing. But keep going. Head for the northwest portion, around Vanderipe Road.

Here there’s a little bit of a roll to the land and the vegetation suggests a cowboy movie. You’ll see miles of riding trails, and Myakka State Park is directly to the east. The area abounds with wildlife—foxes, deer and even bald eagles.

Myakka Valley specializes in what might be called the “starter ranch.” For under half a million you can get a nice, somewhat simple three-bedroom home, often with a pool, set on a parcel of over five acres. Chances are there will also be a barn of sorts and other outbuildings, maybe even a pond.

“It’s wonderful for children,” says insurance broker Jennifer Peeples, who along with her husband is raising two boys on 10 acres. “And critters, too. We have dogs, bunnies, reptiles, guinea pigs. And the schools are great.”

The Peeples’ barn is bigger than their house. Although they don’t keep horses, many of their neighbors do. Jennifer particularly appreciates the family atmosphere. “The volunteerism is amazing. And every Christmas Santa arrives in a horse and carriage.”

If you’re looking for acreage, check out 6008 Shepps Island Road. It used to be a miniature horse farm and has an asking price of $445,000. There are larger, more elaborate properties available, but what makes Myakka Valley Ranches so attractive is that it offers a country lifestyle for a reasonable price.

And for a real bargain, wait for one of the fixer-uppers that come on the market from time to time. A large two-story home on almost six acres, shabby but with lots of possibilities and interesting touches (stone walls and several fireplaces), just sold for $307,000.

Longboatvillage 044 sdvlpm

Longboat Village occupies the northern tip of the island and was founded in 1885.

Longboat Village

Of all the picturesque coastal villages in the region, Longboat Village, also known as Long Beach, might be the best. It’s the oldest settlement on Longboat Key, founded in 1885, and occupies the northern tip of the island. It’s always been a resort community, and the old cottages from the vacation colonies that existed back in the 1940s and ’50s are prized homes today.

Remodeled and enlarged, they still exude the charm of bygone lazy days in the sun. Look for one from the Robinson Colony—there are seven left—or one of the Waverly Colony ones, instantly recognizable by their distinctive wavy siding. Realtor Bobbie Banan snagged a Robinson cottage when she moved from mid-key several years ago. “It has a full attic and a front porch,” she says, “and though it’s been upgraded it still has all the character of the original.”

The Village might be termed the “anti-Longboat Key.” Unlike the multimillion-dollar mansions and glamorous high-rise condos that give the key its reputation, homes in the Village tend to be small but impeccably maintained and boast charm worth many times their price tag. Life moves slowly; aside from the Mar Vista restaurant—diners can arrive by boat—there is no commercial activity.

“The Village is a real neighborhood where people sit on their front porches,” Banan says. “People stop and chat when you’re walking your dog.”

Local mega-realtor Michael Saunders grew up in Longboat Village, in a cottage her mother and father built right over the water. Her great-uncle ran a pair of steamboats down from Tampa, and she and her siblings worked in the marina, flipping burgers.

But things are changing—a little. Some of the older, larger homes at the southern end of the village are now gated and called Bayou Hammock. New homes are going up on the acre-plus lots, and prices are reaching the $5 million mark. And a property that was the popular Longboat Key Center for the Arts is being developed, along with a nearby piece of land; soon a total of 19 new homes, all priced well over a million, will hit the market.

But the charm is still there. Check out the Waverly Cottage at 6989 Longboat Drive S.  It’s been expanded over the years and now has three bedrooms and three baths in just over 2,400 square feet. Much of the interior is charming, and the layout would work for a variety of situations. Currently, it includes a full mother-in-law suite. Some renovation is needed to bring it up to speed. But the price ($549,000) is right, and you could easily end up with one of the nicest cottages in a village full of charmers.

Sandyhook 004 vagcsz

A beachy home on a shell street.

Sandy Hook

The most understated of Sarasota’s prestigious communities may well be Sandy Hook on Siesta Key. Most of the road is still shell, and many of the homes are original, from the 1960s. But these are very sophisticated 1960s homes—cypress, beachy in feeling, yet done with style and panache. Practically all the Sarasota School’s great architects have examples of their work here.

The homes have been remodeled over the years, of course, but there is still a simplicity to them that reminds you of an old WASP-y community where discretion is valued more than display.

The setting helps. It’s just a short walk to the hubbub of Siesta Village, but once you make the turn onto Sandy Hook Road, you’re in a different world. You’ll find densely packed bamboo groves and banyan trees and tropical hedges, all striking the perfect balance between wild and manicured. Many of the homes are on the water and there is a private beach for residents.

Sandy Hook is so special that its newer homes tend to be very big and expensive—much more stylish than McMansions and even grander. Though its residents would probably squirm at the term, the neighborhood exudes “class.”

It certainly has a classy past. It’s the creation of a remarkable woman named Mary Hook, who was a pioneering female architect. She designed a whole slew of homes in Kansas City that are on the National Register. In the 1930s, she and her family bought a piece of property on Siesta Key, just to the north of what is now Sandy Hook, and built a hotel called the Whispering Sands Inn. (The name lives on in what is now a much more middle-class retirement community than Sandy Hook, referred to by generations of snarky teenagers as Withering Glands.) After she sold the inn in 1945, she bought the Sandy Hook parcel and designed its first two homes in the early 1950s. Paul Rudolph, then a young architect living in Sarasota, designed the third home.

Hook was a Wellesley graduate and had great taste. She loved artists and other architects, and it was her plan to start a sort of boutique architecture school on the property. That never happened, but her aesthetic vision of modern-feeling homes that fit into the tropical environment has stayed intact after all these years.

At a recent dinner party in the neighborhood, the conversation revolved around the New York theater scene, where to stay in Bali and a first-hand account of the ins and outs of Bitcoin investing. “That’s what I love about Sandy Hook,” said the host, a retired educator and art collector. “In a sophisticated town, it’s about as sophisticated as you can get.”

With only 42 homes, listings are pretty slim. Only one house is officially on the market (16 Sandy Hook Road S.), but it’s a doozy: a five-bedroom, five-bath, 6,300-square-foot mansion built in 2008. It’s directly on the Gulf, with spectacular views from most of the rooms and terraces. It has a price tag as big as almost any home in town—$6.9 million—but the style, a sort of contemporary coastal, blends well with the older Sandy Hook homes, making it a perfect addition to this very understated neighborhood.

Bayouoaks 025 ntp8yx

Bayou Oaks is artsy, cheap, diverse and eccentric.

Bayou Oaks

Every town needs a neighborhood like Bayou Oaks. It’s artsy, cheap, diverse and eccentric. The demographic is working class, but it’s also full of professors, artists and college students sharing rented homes. And it’s immensely helped by its namesake trees. Many of the streets have a canopy of towering oaks, giving them an Old Florida look as authentic as any place in town.

One of the city’s oldest neighborhoods, Bayou Oaks didn’t even have a name until 20 years ago. It was just that somewhat scruffy part of town that ran from Ringling College up to the dog track. On paper it didn’t look so good. Income and housing were below average; crime was above. Many fastidious homebuyers would take one look and dismiss it.

But concerned residents and a certain tenacity have turned things around. A giant radio tower (“as big as the Eiffel Tower,” says one resident) was blocked, and that led to other improvements. Old Bradenton Road was enhanced by a good-looking median, and the neighborhood’s convenient location began to draw new residents.

With more than 1,300 homes, Bayou Oaks has a wide variety of housing choices. There are even some World War II army barracks, converted into pleasant rental apartments. Noted architect Carl Abbott lives in one of the most unusual homes—a Spanish-style residence that dates back to the Ringling era—and has long been one of the area’s boosters. “It doesn’t feel urban,” he marvels. “It’s full of native plants but nothing formal or manicured. It reminds me of where I grew up in south Georgia.”

Your housing dollar will go a long way in Bayou Oaks. There’s a nice newer cottage at 1344 40th St. that’s priced at $349,900. It has many premium features and an attractive lot that borders Whitaker Bayou. Most homes will be considerably less, and it’s easy to find something under $200,000. Check out the two-bedroom 1960s-era cottage at 1177 38th St. The current owner is an architect who gutted the interior and replaced everything with state-of-the-art mechanicals and tasteful modern design. The price? $185,000.

Bayou Oaks is sandwiched between the town’s two leading colleges, New College to the north and Ringling College of Art and Design to the south. That means you’ll be in the heart of intellectual Sarasota. So it’s only appropriate to find certain blocks a little gritty and unpolished. College students—and professors—have to live somewhere. But if you have a creative spirit, the atmosphere becomes a plus. There are some beautiful one-of-a-kind homes tucked away here and there, all under the shelter of the towering oaks.

Show Comments

Related Content