Orlando. The name, to most people, means more than a dozen theme parks, the first of which was Walt Disney World. That theme park put Orlando on the map for the rest of America and the world, actually. But long before the theme park mania, normal people lived in Orlando and its surrounding communities, and they still do. Some of the neighborhoods and small towns and villages surround Orlando proper are quaint, eclectic, quite hip and major draws for folks wishing to relocate in Florida or just heading there for vacation.

4 Counties

The metropolitan area of Orlando actually includes the counties of Orange, Seminole, Lake, and Osceola. Within each country are a wide variety of cities, towns, and smaller communities – some old, some new, some in-between. Each county has some very cool neighborhoods depending upon the lifestyle you may want – young and single; young married; middle-class families with children, empty nesters, or senior citizens. Here are some of the coolest neighborhoods in the metro area that most visitors to Orlando have never visited.

Downtown Orlando

image by Russ Sanderlin via Flickr Creative Commons

Also known as the Business District, this is the financial and business hub of the area. For those who like apartment dwelling and a less “responsible” lifestyle, the business district is a perfect choice. Shops, theater, museums and the Sports Center are all located in the Business District.


Adjacent to the Business District is Lake Eola and Lake Eola Heights, a great historic district. Here, you can have the best of both worlds – live around a lake and be just a short jaunt to the Business District. Older housing or new condos are options. Lake Eola Park is a great place for walking, paddling, enjoying lots of wild life and letting the kids just run.

Altamonte Springs


Image by jinjian liang via Flickr Creative Commons

This historic town was founded in 1880 and has come a long way since, with both older and newer residential areas. It has two major attractions:

1. Crane Roost Park: This is a huge venue offering free events all year round. Its center is a large lake with a mile-long walkway around it.


2. Uptown Altamonte: While Altamonte is dotted with lots of shopping options, Uptown is a favorite outdoor walkway with small shops, large stores, and restaurants.

Baldwin Park


Image by Manuel Lora via Flickr Creative Commons

Baldwin Park is one of the trendiest neighborhoods in the Orlando area. Until 1968, it was home to Army and Air Force bases and then the Orlando Naval Training Center. After that, the town underwent a “renaissance” of sorts and is a sought after place to live, along with 50 miles of walking paths, and parks that together number 200 acres.

One of the most popular activities is bike-riding along the Cady Trail, a 3 ½ mile ride ending at Blue Jacket Park, housing one of the most diverse sports complexes in the Orlando area.


College Park

Image by Camron Flanders via Flickr Creative Commons

This quaint town is one of the best-kept real estate secrets in the Orlando area. There are still bargains to be found in homes, but prices are rising rapidly. Pristine streets, all named after well-known colleges are lined with bungalows.


College Park’s “main street” is actually an intersection of two main roads, but you can find any type of food, shopping and just interesting older architecture.

For outdoor activities, College Park is dotted with lakes with paved paths around them; for the cultural you, there is Loch Haven Park with the Orlando Science Center, Orlando Shakespeare Theatre, and the Museum of American Art

Ivanhoe Village


Image via 10Best

This town is just north of the Business District and is most famous for its art galleries, its small boutique shops and lots of just green space. It was formerly known as “Antiques Row,” but is now probably far more famous for its “First Friday” events with outdoor musicians lining the sidewalks and an Art Walk to all of the small galleries.

Ivanhoe Village has some of the most unique shopping in the Orlando area, if you are into vintage goods. 1618Something Different is just example of an eclectic shopping experience. Also quite famous is Boom-Art by Rogers, a shop featuring pop art. And don’t miss meeting the owner/artist – certainly a character.


Loch Haven

Image by Chad Miller via Flickr Creative Commons

Situated right next to Ivanhoe Village, Loch Haven is a continuation of art and culture, with its galleries, antique shops, and sidewalks, Loch Haven hosts a number of annual events, to include an Antiques Show, the International Fringe Festival, VegFest, Festival of the Trees, and the PlayFest.


A restaurant not to miss is the White Wolf Café on Orange Avenue, offering great food and antiques for sale. This village is a walker’s and art aficionados’ paradise.



Image by Daniel Piraino via Flickr Creative Commons

Sanford sits on Lake Monroe, and has been the subject of a huge re-gentrification, maintaining its old buildings and brick streets. Both residents and visitors walk the shores of the Lake and shop along the quaint main street, in sight of beautifully restored historic homes.

There is never a lack for things to do in Sanford. Cultural events every evening along the streets, the Saturday farmer’ market, and the Sanford Art Walk are all huge draws as are the local musicians and artists everywhere.


Night life in Sanford also lack nothing. All types of bars and wine rooms provide a variety for any taste. Probably most famous is “Little Fish, Huge Pond,” a combination beer and wine bar, along with an art gallery, music, a hookah room and other strange goings on.

Thornton Park


Just a few blocks from the Business District, Thornton Park is one of the most eclectic neighborhoods in the metro area. If you are looking for an abundance of sidewalk shops, along cobblestone streets lined with pristine bungalows, you have found your personal paradise. In between the sidewalk shops are small cafes and restaurants with live music, day and night. The architecture is period, and the town just exudes urban hip.

Within walking distance of the quaint downtown area is CityArts, a nest of art galleries featuring local, national and international art. For those not into art, there is the SAK Comedy Lab, a standup comedy club with many “claims to fame” of comedians who got their start there.

Right in the middle of the Thornton Park Neighborhood is Lake Eola, with a paved path all around for walkers and joggers alike. Yoga and Tai Chi are practiced on the green space, and there is a farmer’s market every Sunday.


Eating in Thornton Park is just as eclectic as its residents – barbeque, huge burritos at a place called “Tijuana Flats,” sushi, and French café and bakery items.

Winter Park


Image via Inside Florida

This is a more affluent and beautiful town, with cobblestone streets and homes and condos that are the winter retreats of many “snowbirds.” One of the most popular activities is to take the Scenic Boat Ride to view some of the beautiful old and new homes, but also the rich plant life.

As expected for a winter haven of the affluent, there are very tony eateries, a myriad of shops, wine rooms, and a modern version of a “Speak Easy.”


Other attractions include the Charles Hosmer Morse Museum and the Enzian Theatre, which shows independent films, some classics with a cult following, and sports a great restaurant and bar right inside – probably the most modern structure in all of Winter Park.

Park Ave. is this town’s answer to Rodeo Drive in Los Angeles – high end clothiers and boutiques – a big draw from downtown Orlando all year long.



Image via ExperienceKissmmee

Situated on the bank of Lake Toho (shortened from its Native American name), Kissimmee is often overlooked as a cool neighborhood, because its outskirts has become an overflow hotel/motel/restaurant venue for the theme park visitors. People forget that Kissimmee has a historic district in the center of town with a rich history, period architecture and lots of annual events and festivals.

The Osceola Center for the Arts is a hub of art and festivals year-round. In addition, there is the annual “sculpture experience” and pub crawl. Artists create sculptures which are placed around the town until the next year’s event.


Mount Dora

Image by Daniel Piraino via Flickr Creative Commons

A bit further out from the city, Mount Dora is just a quaint small town famous for its bed and breakfasts and it cobblestone streets. It sits on the shore of Lake Dora and was founded in 1880.


Activities in Mount Dora include sailing and other water sports, visiting a large cadre of antique shops and boutiques, and spending time in any of its numerous parks.

The town is listed in the National Registry of Historic Places, as is the Lakeside Inn, the town’s oldest structure.

In terms of cultural events and activities, Mount Dora has it all – an annual Art Festival featuring over 200 artists from across the country and a famous Sailing Regatta each April.


Residents of Mount Dora enjoy being a bit farther away from the city and the theme parks and the drive into the Business District for work is really minor. They love the 19th century “feel” of their town and have the best of both worlds historic and contemporary.