The Coolest Neighborhoods in Orlando

Lake Eola Park
Lake Eola Park | © Courtesy City of Orlando
Michele Marin

If images of mouse ear headbands and a world of wizardry permeate your mind at the mere mention of Orlando, chances are you have yet to see the “real” Orlando. Beyond the theme park gates lie an enclave of alluring neighborhoods. To truly experience the culture, history and charm of the “real” Orlando venture out to where the locals hang.

Park Lake Highland

Once a well-kept secret, word is quickly spreading about this hidden gem. In fact, the area northeast of Downtown Orlando was recently named #1 Best Neighborhood to Live in Orlando, by Niche. Stunning views of the city skyline serve as a backdrop to a mix of historic clap board lake front homes and impressive modern designs. Anchored by the pristine campus of the affluent private school, Lake Highland Preparatory School, the safety and walkability of the neighborhood only adds to the appeal. Popular among joggers and cyclists, the nearby Urban Trail winds by several lakes and the area’s cultural center Loch Haven Park. Not to mention the gamut of restaurants, bars and indie shops of the nearby Mills 50 District.

From BBQ, Pig Floyds, to farm to table, The Strand, and of course authentic Vietnamese fare (as the stretch of Mills, known as Mills 50 District, is home to one of Orlando’s largest Vietnamese populations) dining options are endless. Friday evenings are bustling with tatted up hipsters hanging outside Lil Indies and Will’s pub. Quantum Leap Winery, Florida’s only sustainable winery offers a tasting room and free tours.

Park Lake Highland is also conveniently next to the up and coming Ivanhoe Village. What was once dubbed Antique Row, offers vintage shopping and breathtaking lake views. Grab dinner and and catch those amazing views at Mesa 21 or a cold beer at Lucky Lure. Or jump in on the fun and play a game of beach volleyball, try stand up paddleboarding or even waterskiing just like a local.

Sunset at Lake Ivanhoe

Baldwin Park

What was once home to an army and airforce base, followed by a naval training center, is now a quintessential American neighborhood. With 50 miles of walking paths, residents jog along Lake Baldwin, walk their dog or practice soccer in one of the many green parks. Perfectly manicured lawns and safe streets make the neighborhood one of The Best Neighborhoods For Trick-or-Treating, according to Home Union Research Services. New Broad Street serves as the epicenter of the community. For tasty eats locals indulge on Limoncello Mussels and sip Tipsy Tea at the Lake at Provisions and Buzz Steak Co., and fill the patio at Gators Dockside where they watch the latest televised sporting event.

Lake Baldwin Park

College Park

Much like its moniker, the streets of this cozy and charming neighborhood are named after famous colleges such as Harvard, Yale and Princeton. Despite Orlando’s growing population, College Park manages to maintain a small-town feel. In fact, the façade of the 1950s era Publix grocery chain graces the neighborhood’s main street, Edgewater Drive. “The Drive” is filled with great eats like local hot spots, K restaurant, RusTeak , and even the casual Doghouse. Catch locals cooling off with ice cream at the old-fashioned Soda Fountain or catching some shade at Albert Park. Bungalows line streets littered with oversized oaks and bougainvillea. One bungalow in particular served as a short-term home for Jack Kerouac from 1957-1958, where he typed the original manuscript to his sequel, Dharma Buns. Today the writer’s home provides four residencies a year to aspiring writers. For more culture, venture to nearby Lock Haven Park, home to the Orlando Museum of Art, Shakespeare Theater and the Orlando Repertory Theatre.

Jack Kerouac House College Park

Thornton Park

Nestled one city block from Lake Eola Park, this lively neighborhood is popular among young professionals who reside in a myriad of early 1900s bungalow style homes or new brownstones. In true upscale urbanism, the area offers residents walking convenience to hip hangouts like Dexters of Thorton Park and Benjamin French Bakery and Café. Locals shop at the trendy, indie boutique Zou Zou and practice sun salutations along the lake, while tourists pedal the iconic swan boats around the Lake Eola Fountain. If you’re visiting the quaint EO Inn & Urban Spa, be sure to check out the Sunday farmers market brimming with crafts, local produce, music and treats. On the second Thursday of the month the area beckons the well-heeled for Thortons Second Thursday Wine and Art Walk.

Lake Eola Park coutesy City of Orlando

Milk District

East of Thornton Park, this edgy little neighborhood derives its name from nearby T.G. Lee Dairy. Known for its small World War II era homes, funky bars and eclectic shops, the area is a throwback to all things vintage. Catch a show at The Plaza Live, dubbed the Rocking Chair Theatre, by locals as its one of the area’s oldest theatres turned musical and theatrical venues in the area. Common scenes include food truck gatherings and street parties, but if you miss the outdoor entertainment, there’s always other well-known eateries, Se7en Bites, featured on Diners, Drive-Ins, and Dives, the long standing Beefy King, and Pom Pom’s Teahouse and Sandwicheria.

Outdoor Street Party in the Milk District

Winter Park

Originally created as a winter destination among wealthy northerners, the upscale neighborhood north of Orlando has maintained its well-manicured lawns, beautiful estates and flourishing culture. The main street, Park Avenue houses more than 140 shops, boutiques and cafes along its pristine tree lined street. Slightly off the Avenue, don’t miss a meal at the James Beard Award nominee, The Ravenous Pig. Take a stroll near Rollins College and admire the picturesque grounds, and for a bit of culture, the area boasts a few noteworthy museums including Albin Polasek Museum & Sculpture Gardens, The Charles Hosmer Morse Museum, and a few others.

Courtesy City of Winter Park Communications Department

Audubon Park

This hipster haunt north of downtown is known among locals as the Garden District. The city’s first Eco District strives to create a sustainability initiative within the community. The program is focused on Habitat and Ecosystem Function, Transportation, Materials Management, Community Identity, and Equitable Development. As a perfect example of local culture, East End Market serves as a culinary hub among local farmers and food artisans, with 10 locally owned food enterprises, including the Orlando Sentinel Award Winner for Best Dessert, Gideon’s Bakehouse. Nature abounds throughout the district, so it’s no surprise that the 50-acre botanical oasis Harry P. Leu Gardens is located in Audubon Park. Recently, the city planted over 500 native plants in the area. Besides the natural beauty of the area, a unique selection of shops, bars, and out of this world bakeries make Audubon Park a sought-after place to dwell.

Leu Gardens

Dr. Phillips

Named after Dr. Phillip Phillips, one of the largest citrus producers in the world, the area’s close proximity to the theme parks and Sand Lake and Butler Chain of Lakes, make it a desirable place to live. The suburban area overflows with upscale gated communities, waterfront estates, and the esteemed Bay Hill community and Golf Club. Nearby Restaurant Row draws locals and visitors to a plethora of eateries and nightlife. Between upscale shopping at Mall of Millenia, fabulous dining at popular hot spots, Ocean Prime, Rocco’s’ Tacos and Seasons 52, as well as endless opportunities for outdoor enthusiasts, Dr. Phillips is one of Orlando’s most desirable neighborhoods.

Dr.Phillips Community Park

Winter Garden

Located 20 miles west of downtown along Lake Apopka, the former citrus town has recently experienced a revival. The city’s historic downtown, listed on the national register of historic places, charms not only residents but bikers traveling along the popular West Orange Trail, soon to be a part of the 250-mile Coast to Coast Trail. The Farmers Market draws a lively crowd on a Saturday for locally grown produce, handmade soaps, fresh flowers, and live music. If you miss the market, you can still check out The Downtown Plant Street Market open seven days a week featuring over 20 vendors in one building where patrons can grab locally sourced farm to table fare at Five Thymes Five, a custom juice creation at Press’d, or even a cold brew at Crooked Can Brewing Company. Not only does the nostalgic Garden Theatre, constructed in 1935, fit in with the ambiance, but it also showcases some of the best local talent.

Winter Garden


Formed to be the all-American neighborhood, the community originally developed by the Walt Disney company, denotes a storybook image of all things American; que apple pie, 4th of July parades, and neighbors chatting on their perfectly mantained lawns. Colonia, Victorian and Mediterranean homes sprawl amongst parks and postcard worthy town landmarks. Creating a community reminiscent of the 1930s, Disney commissioned many well-known architects to build the town’s post office, theatre, town hall and other landmarks. A sampling of great restaurants includes the vastly popular Columbia Restaurant and Celebration Town Tavern. Accordingly, as one would expect of the quintessential American neighborhood, boutiques, dog bakery and of course the children’s store Once Upon a Time, line the main street. Not only does Celebration connect to Walt Disney World via a main road, but the magic of Disney resonates into the community. For example, each year a snow falls nightly in December, despite the subtropical climate, during the Now Snowing Event. With Disney, anything is possible.

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