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Are you feeling overwhelmed on figuring out which area to move to in Orlando? This short blog and video will help you gain a really good understanding of some of the more popular places to live in greater Orlando. You will see and hear about the neighborhoods, the lifestyle, and the home prices for many of the most ideal places to live in Orlando.

If you look at the map of Orlando, you will notice it is quite expansive with about a 20-mile radius around downtown Orlando. This area is actually made up of a handful of different cities and municipalities.

Downtown Orlando

Living in downtown Orlando is extremely convenient and has lots of lifestyle options.

There are luxury high rise and low rise condominiums. There are historic single-family craftsmen style homes, and occasional new construction homes as well. When living in or near downtown Orlando, you’ll be walking distance to many local restaurants, exciting nightlife, plenty of businesses, and much more. Lake Eola Park has a nice walking path lined with sculptures that give a taste of Orlando’s vibrant art culture.

A few of the closest walkable neighborhoods to Downtown Orlando include Lake Eola Heights, Thornton Park, and Delaney Park. Traveling to and from the downtown Orlando area is fast and easy since two major highways, Interstate 4 and State Road 408, run nearby. The condo sale prices average about $300,000 while single-family homes average about $500,000.

The location, the affordably, and the walkability help put Downtown Orlando on this list of the most popular neighborhoods. Now let’s take a look at the next area, Winter Park.

Winter Park

Winter Park is one of the most unique and established areas in Central Florida. Winter Park is actually its own city and located just a few miles north of downtown Orlando. The diversity of homes can range from lakefront estates to modern new construction to historic craftsmen style bungalows. The SF home prices here average about $600,000 while new construction is averaging about $850,000 or $275/sq ft at the time of this video.  

If you live in or near Winter Park, then Park Ave will quickly become one of your go-to places to visit. Park Ave boasts unique restaurants, great shopping, and a nice central park where art festivals and farmers' markets are held. The Winter Park Golf Course is one of the few nicer public courses in Orlando.  Winter Park is home to the respected Rollins College and many of the public schools are highly rated as well. Winter Park truly has a little something for everyone and is one of the nicest places to live in not just Orlando but in all of Florida. Next on the list is Winter Park’s neighbor, College Park.

College Park:

College Park is one of Orlando’s oldest neighborhoods, initially developed during the early 1900s around Dubsdread, an 18-hole public golf course that is lined with old and new homes. Like many established areas near downtown Orlando, College Park has been undergoing a renaissance as smaller homes are being replaced with new construction, typically larger two-story houses. Located just a few minutes from downtown, with easy access to Interstate 4, College Park has its own shopping and dining district that is within easy walking and biking distance for most residents. There is a wide variety of housing options, from 2-bedroom, 1-bath bungalows to condominiums to spacious four and five-bedroom houses. People love living here because of the close proximity to major attractions, affordability, and highly-rated schools. If you prefer neighborhoods with a bit more consistency in the home styles, then you want to see the next neighborhood, Baldwin Park.

Baldwin Park:

Baldwin Park is a redeveloped planned community that is known for its amenities, convenient location, and picturesque charm. This community borders Winter Park and is only a 20 min drive to OIA. Formerly a military base, Baldwin Park features single-family homes and townhomes that range in price from the mid 200’s to about $3,000,000. The HOA dues and taxes are very reasonable for the value. Baldwin Park is one of the most unique planned communities because it was designed to mimic more historic Orlando neighborhoods such as College Park — where many of the homes are craftsmen style with small garages or with small second-floor garage apartments. While most of the homes were constructed between 2005 to 2007, the community planners successfully avoided the cookie-cutter feel that you find in many newer planned communities. You will find almost everything you need in Baldwin Park, from grocery stores, schools, unique dining options, fitness facilities, and more.

Baldwin Park is exceedingly walkable and bike-able. There are two public swimming pools, a small community gym, and a 2.5-mile bike/pedestrian path that encircles Lake Baldwin, where the main street through the downtown takes you to this beautiful area. Another fantastic planned community is Lake Nona, our next location.

Lake Nona:

Lake Nona is a master-planned community of some 7,000 acres just to the east of Orlando International Airport. Lake Nona’s roots go back to the 1980s. It has grown exponentially over the years, spawning a variety of neighborhoods along with three well-regarded golf courses.

When it comes to homes, there is something for everyone, be it single-family homes to estate properties to condos and apartments. Named after a large lake on its northern edge, Lake Nona also has been building an employment base, most prominently the Lake Nona Medical City, a 650-acre health and life sciences campus. The United States Tennis Association (USTA) has also relocated its national campus to Lake Nona in 2017.

This community was planned from the start for active, healthy lifestyles, with golf courses, country clubs, and bike and walking paths. Lake Nona has worked hard to create a place where there is plenty to keep residents occupied.

Home prices range from the $200,000’s for resales and go well into the $1,000,000’s. There is plenty of opportunities to secure new construction here in Lake Nona. If you like the idea of lakefront living, then you want to see the next area, Windermere.


The town of Windermere is known for its luxury lakefront and golf course living. Windermere is located about 10 miles north of Disney and 12 miles west of Downtown Orlando. The Isleworth Golf and Country club is one of Windermere’s most well-known properties.  Various professional athletes and business execs play there. Some of the largest estates in Central Florida are found in Windermere. Nearby is the Bay Hill golf and country club, where the PGA holds the annual Arnold Palmer Classic.

There is a quaint town square in Windermere with a small handful of local restaurants and shops. If you’re looking for more to do in the neighborhood, then you can find plenty of great options at restaurant row on Sand Lake Road, which is only a short drive away.

Lake butler and the chain of lakes weave throughout Windermere and offer a fantastic boating experience as well as some of the best lakefront living you’ll find in Florida. Windermere also hosts a weekly farmer's market, along with a food truck night every 4th Friday of the month in the town square. Some of the neighboring areas to Windermere include Dr. Phillips and Bay Hill.

Homes prices on the Windermere Chain of Lakes can start AT just over $1,000,000 and can go way up in price, such as former NBA star Shaquille O’Neal’s home, which is listed for $19,500,000. If you’re looking for a large relatively newer estate with lakefront living options, then Windermere is certainly worth considering.

Located just north of Windermere is our next area, Winter Garden which has a much more comfortable price tag.

Winter Garden:  

Winter Garden has grown quite a bit during the last 20 years and is one of the fastest-growing areas in central Florida. There are mostly single-family homes in the Winter Garden, with plenty of new construction homes available. Many of the homes were built in the ’90s and early 2000’s, however, you can find homes built in the 1940s and 50’s and everything in between.

Winter Garden can even be an occasional destination to visit for locals from other parts of Central Florida. Centennial Plaza area has a quaint downtown with lots of local shops and restaurants. Lake Apopka, one of the largest lakes in FL, is just north of Winter Garden.

Lakefront homes average about $900,000 to $1,000,000, while Single-family homes not on the water average about $400,000 to $450,000.

The west orange trail runs through Winter Garden’s quaint downtown. It’s a 22-mile long bike/pedestrian-only trail. After a nice ride, you can grab a pint at the local Crooked Can Brewery or something to eat at Plant St Market located on the western edge of downtown, Winter garden.

There are other really nice communities in Orlando that are not mentioned here, but they will be on future blogs and videos.

Feel free to call or email if you have questions about any of the homes or relocating to any of these areas.

Kris Kennedy