3 Best Neighborhoods to Live in Winter Park

3 Best Neighborhoods to Live in Winter Park

Would you like to be one of 30,000 people lucky enough to call Winter Park home? Centrally located five miles north of downtown Orlando, Winter Park is a sprawling city with plenty of open spaces, pristine golf courses, and beautiful sunny weather. If you are considering relocating and buying a new home in Winter Park but aren’t sure which neighborhood to move to, this guide is for you. Read on to learn about the three best neighborhoods in Winter Park.

1. Dixie Terrace

What makes Dixie Terrace unique?

Dixie Terrace consists of beautiful tree-lined streets with spacious homes. The neighborhood comprises two sections across North Park Avenue, which is just seven miles away from the busy business district filled with the most eclectic array of restaurants, shops, and other attractions.

Things to do

Many residents like to visit Kraft Azalea Garden, with many cypress trees offering plenty of shade and beautiful azaleas blooming in the spring. In addition, this botanical garden is located along the shore of the 449-acre Lake Maitland, which offers an abundance of fishing, boating, and camping activities.


Less than a mile from many Dixie Terrace homes for sale, you can find The Hangry Bison, which offers locally sourced ingredients. Locals love the handcrafted burgers and beer at this casual restaurant. There are more dining options located just a few miles from Dixie Terrace.


Families send their kids to the top-rated public schools in the area. Many students attend Winter Park High School, which has received a College Success Award for academic excellence. Many parents also send their children to the Cornerstone Charter Academy, which offers an exemplary STEM-focused education that will prepare students for college and beyond.

Real estate in Dixie Terrace

There are a variety of single-family homes of many different architectural styles. Many of the homes for sale in Dixie Terrace offer plenty of space, around 2,000 square footage. The homes are typically listed anywhere from $400,000 to nearly $2 million.

What else should you know about Dixie Terrace?

Dixie Terrace is a pedestrian-friendly neighborhood with a walk score of 66 and a bike score of 57. Residents can easily walk or bike to parks, restaurants, and other local attractions.

2. Cortland Park

What makes Cortland Park unique?

Surrounded by the natural landscape, the Cortland Park neighborhood is ideally located to offer its residents an abundance of opportunities to enjoy the outdoors.

Things to do

Located at the junction between two lakes and a park, there is an abundance of outdoor activities that many residents enjoy in Cortland Park. Families with kids love visiting Frederick Detmar Trismen Park for the immersive playground experience. In addition, residents can visit Lakes Sylvan and Mizell for countless boating, fishing, swimming, and other water activities.


Drive just a few miles outside the Cortland Park neighborhood, and you can find many restaurants that fit nearly every need. For example, consider dining at Reyes Mezcaleria, which offers an elegant and lively atmosphere that is perfect whether you are seeking a romantic night or a casual outing with friends. At Reyes, you can enjoy uniquely crafted Mexican dishes.
Consider also visiting Pop Thai, which seeks to bring an authentic experience where patrons can enjoy all the different flavors of Thai cuisine.


Parents can send their kids to highly-rated local schools such as Brookshire Elementary, Maitland Middle, and Winter Park High Schools. Students can also elect to attend the prestigious Cornerstone Charter Academy.

Real estate in Cortland Park

There are many large single-family homes with anywhere from three to five bedrooms. Homes for sale in Cortland Park typically range from $695,000 to $1,850,000.

What else should you know about Cortland Park?

As an open and spacious neighborhood with many public parks and picturesque lakes, it is hard to get around on foot in Cortland Park. Most residents commute by car for work, school, and other attractions.

3. Cypress Reserve

What makes Cypress Reserve unique?

Cypress Reserve is a gated lakefront neighborhood that was first developed between 1997 and 1999. With approximately 45 single-family homes within this small and tight-knit community, this neighborhood continues to attract residents far and wide.

Things to do

Residents have access to a playground, resort-style pool, and a clubhouse on-site. They can also drive just a few miles away to enjoy a variety of parks and nature trails. For even more fun things to do, residents can drive to the historic Winter Garden, where they can find many more options for dining and shopping.


Travel a few miles north, and you can find a large selection of exquisite dining establishments. One notable place you need to visit is Chef’s Table which has been voted one of the most romantic restaurants in the country. In an intimate and warmly-lit setting, you can find classic American fare that you can enjoy with your loved ones. For a more decidedly casual vibe, consider visiting Market To Table, which offers American cuisine with creative cocktails. Visit the Winter Garden for more fabulous dining options.


There are excellent school options for residents who choose to live in this neighborhood. Many families send their children to Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High School. As a recipient of the College Success Award, Lake Howell High School does an exemplary job of preparing students for the rigors of university.

Real estate in Cypress Reserve

In Cypress Reserve, you can find majestic mansions across 4,000 square footage. Many of these properties have five to six bedrooms. Homes in Cypress Reserve often sell between $670,000 and $750,000.

What else should you know about Cypress Reserve?

Cypress Reserve is located along the southern portion of the 136-acre Bear Gully Lake. Cypress Reserve offers an unparalleled lifestyle filled with all of the amenities associated with lakefront living. If you are interested in living in any one of the gorgeous lakefront homes in Cypress Reserve, get pre-approved for a mortgage today to find out how much you qualify for.

Ready to find your dream home in one of the neighborhoods in Winter Park?

If so, schedule a consultation with realtor Florence Zimmerman of the ZMRMN Group, who can provide expert guidance on everything from neighborhood insights to negotiation tactics. Florence and her top-notch team can make the buying process as seamless as possible!

*Header photo courtesy of Shutterstock

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