Constitution Park: Chelsea Piner with her dog Boudro beneath the Constitution Oak, which is approximately 135 years old.

Dear readers, if it seems that you saw these three wonderful places to live in Central Florida already profiled in these very pages not too long ago, you’re not mistaken.  However, we were. A bit. The cover story of Orlando’s July 2023 issue explored 10 Great Places to Live, a feature we run annually. After publication, some of our readers contacted us with suggestions on how the stories could have better reflected their neighborhood and towns.

We took your concerns to heart and sent writer Cynthia Van Gaasbeck out to explore for herself and interview community leaders for three new features on Oviedo, South Eola and Windermere.

*Photos by Roberto Gonzalez

Oviedo

Social spaces and foodie favorites are basis of town’s pride

A free-wheeling, cordial conversation at The Factory Bar revealed several facts about Oviedo:

1. It’s a secret foodie hub. 
2. It’s also a secret recreation hub.
3. Oviedo pride is a thing and it is robust. 

In a recent interview, Oviedo Mayor Megan Sladek and Communications Manager Lisa McDonald dove right into what makes that former cow town north of UCF so special.

“Oviedo is a great place for families. There is something for everyone of all ages in this town,” Sladek says. 

“The city offers an aquatic center, which has a giant pool and a splash zone for kids. It has a skate park for skaters and kids on BMX bikes. It has a huge arcade in the Alafaya Square,” she says.

About that secret foodie hub claim, Sladek had the stats to back it up.“We have 118 restaurants in Oviedo city limits with a 42,000 population. It’s an extraordinary amount of foodie opportunities in this little place,” she says.

“Turkish, Venezuelan (the only Venezuelan food in Orange and Seminole counties). You go around to some of the restaurants around town, they are all family-owned, little shops. They are making home cooking,” Sladek says.

Continuing in the underground vein, she says Oviedo is also a secret recreation hub and can back up that claim with one impressive figure: 

“We have more land per capita dedicated to parks than any other city in Central Florida.”

These parks aren’t there just to look pretty, either.

“We offer a variety of activities at the parks,” McDonald says.

Sladek joins in: “We do have a half-size Olympic pool. Hardly any cities have even one Olympic-size pool but we have one plus another half. We have 1½ pools!”

The story behind the abundance of large pools is that the Oviedo Gymnasium & Aquatic Facility on Oviedo Boulevard is home to the Blue Dolphins, a highly successful USA Swimming team.

Oviedo is surrounded by the real Florida. Thousands of square acres of Central Florida are in near-pristine condition and much of it is accessible through trails that traverse Oviedo. 

McDonald looks across the spacious, industrial bar within The Food Factory Foodie Collective, a just-opened gathering spot with individual eateries and an outdoor social space. “You don’t have to go to other downtown areas anymore,” she says.

Sladek says: “We have serious townie spirit. Not to be down on other places but . . . we weren’t always the cool kids. We used to be the place to go to cow tip and everybody felt sorry for you if you were from Oviedo.”

“You see that Oviedo Pride everywhere,” McDonald adds.

A feature of her town’s layout and planning that is especially useful to Sladek is the ability to walk or bike pretty much wherever she needs and she supposes this is just as useful for other residents.

“For people who are living here in this area, which is slated to get a little more dense, it is hypothetically possible for you to live and work and relax here,” she says.

The town celebrates its 100th anniversary in 2025 and it already sounds pretty nice but what is on Oviedo’s wish list?

“We’d love to have a hotel,” Sladek says.

South Eola

The Heart of Downtown Orlando

South Eola is arguably the most identifiable of Orlando’s neighborhoods, being the home of the crown jewel that is Lake Eola.

But the chic, modern high-rises and traditional homes and the eminently walkable streets leading to entrepreneurial offices, specialty shops and innovative eateries sends a vibe that this is a living, breathing, dog-loving social hub.

South Eola is proof that an urban living experience can be convenient and exciting, with an unmistakable community pride forged through active organizations such as the South Eola Neighborhood Association.

The association represents the residents who are proud of their neighborhood and who are vigilant about keeping its identity separate from its neighbor to the east, Thornton Park. The two neighborhoods happen to enjoy each other’s company but are distinct and proud of their origins.

Their vibes are complementary and that’s where there was a mixing of identities. Thornton Park was the neighborhood originally profiled in the feature but it was credited with having some features that actually belong in South Eola.

An 11-minute walk south from Lake Eola’s Southeast Lawn to the neighborhood’s other urban park, Constitution Green, takes you past some of Orlando’s favorite restaurants, such as The Stubborn Mule and RusTeak Thornton Park. Yes, even some of the businesses take into consideration the neighborhoods’ proximity to each other.

South Eola’s strong sense of community is just one of the wonderful reasons it’s a great place to call home.

But South Eola truly is the heart of downtown, with an active social, business, shopping and dining scene among its 2,300 residents and in no way could be described as a bedroom community. The neighborhood has the only grocery store serving Downtown Orlando, the Publix Super Market at The Paramount on Lake Eola.

For a more social shopping and entertainment experience, residents and visitors have made the Orlando Farmers Market a Sunday tradition since moving to the neighborhood from Heritage Square in 2004. 

From its location on the corner of East Central Boulevard and North Eola Drive, the dog-friendly market has matured into a spirited social scene where hours may be spent with friends.

Simply put, it is the kind of atmosphere one hopes to find in a city and it’s just one aspect of South Eola’s charming personality.

Website niche.com ranks South Eola the second-best neighborhood of 88 ranked in the Orlando area for Best Neighborhoods for Young Professionals in Orlando. The top spot went to downtown itself. 

To determine rankings, Niche analyzes federal and local government datasets. Check the website for some more interesting metrics regarding South Eola and other Orlando neighborhoods.

One unnamed resident gives the neighborhood five stars in a review on the site: 

“Multimillion-dollar condos and luxury apartments, all in the most walkable neighborhood in Orlando. Lake Eola, Publix, dozens of restaurants, this is Orlando’s best kept secret. I walk to work, have a gym, pool, and security 24/7 in the lobby. Keep your historic shoebox houses, this is the place to be downtown!” 

That sums up the elements that bring people to South Eola but it is the people who give South Eola its soul.

Windermere

A small town rich in natural beauty 

Admit it. When you think of Windermere, posh homes and jet-setting celebrities come to mind.

Which is a shame, because the Windermere you should be visualizing is one of natural beauty and fiery pride in a resident-led community.

We sat down with Diane Edwards, who was communications director for The Town of Windermere at the time of the interview, to discuss the confusion over what some residents call “Windernearians” — those whom the outside world incorrectly consider its residents — and to explore the 2.2-square-mile isthmus that sits amid the Butler Chain of Lakes in Southwest Orange County.

We can blame some of the confusion on a zip code (34786) and a post office in unincorporated Windermere. And to be clear, Isleworth Golf & Country Club, the community of multimillion-dollar homes with a world-class golf course alluded to in the first paragraph, shares nothing but a boundary line and a zip code with The Town of Windermere.

Downtown Windermere is charm personified.

“The zip code 34786 encompasses about 30,000 homesites,” Edwards says. “In reality, Windermere is only 2.2 square miles and it’s centered here in downtown. We have about 3,000 residents.”

Edwards explains that the post office on Conroy sorts the mail for this whole area. So even though Isleworth and other expensive neighborhoods such as Keene’s Pointe are separate from Windermere, the town name is used in their addresses. Also important to note is that Windermere Prep, a private college preparatory academy, is actually on the west side of Lake Butler, about five miles from Windermere town limits.

The town really is worth getting to know. Coming in from S.R. 435, past countless subdivisions and shopping centers, where the traffic is often bumper-to-bumper, the personality of the area starts to change. It calms down.

The chains and support businesses for the many neighborhoods start to slip away and a rural feel takes over. Once on Main Street, this could be a hamlet far from the world’s finest theme parks. Literally 20 minutes from Walt Disney World and Universal Orlando, The Town of Windermere quietly exists.

Incorporated in 1925, Windermere has a significant anniversary coming up next year.

“This is a very close-knit community. They take a lot of pride in their community and are very focused and involved. Our Town Council meetings are always packed,” Edwards notes, nodding her head.

They do get their money’s worth out of their town government. 

While Windermere isn’t exactly a one-horse town, neither is it a pop-up suburb with the requisite fast-food restaurants, mattress shops and gas stations. Edwards says the downtown area is its sole business district so unless it’s homebased, what you see is what you get along Main Street.

They do have the Farmers Market, from 9 a.m. to 1:30 p.m. Fridays at Town Square Park. It’s attractive and full of a variety of goods, such as meat and seafood, ready-to-eats, art, pet products, home goods, jewelry, kitchen wares and more.

As far as social activities go, the lakes are good for private and public gatherings and the town organizes holiday events such a Halloween Costume Parade and Hayride and the 5K/10K Run Among the Lakes.

The residents are proud of their community, she says, evidenced by a facet of the town’s government that is rare, to say the least:

“All of our boards and committees, even our town council and our mayor, are volunteers,” noted Edwards.