Dr. Phillips and Windermere, Florida: A perfect area for families among the lakes


Dr. Phillips and Windermere Florida

When we moved to Orlando 9 years ago there was only one place we wanted to be: the Dr. Phillips and Windermere, Florida area. My husband’s aunt and uncle have lived here for over 30 years and we have always felt like this area “among the lakes,” was a second home with its beautiful surroundings as well as sense of community. 

With some of the best schools in Central Florida, proximity to major highways, and plenty to do, it’s a wonderful place to raise a family.

Dr Phillips Windermere FloridaDining

Known for its amazing variety of eateries, Restaurant Row (Sand Lake Road) is a wonderful spot for date night, lunch with your girlfriends, or a quick bite with the kids.

Dr. Phillips and Windermere Florida Restaurant Row

One of our favorite locations to take the kids is Bar Taco. It may not sound kid-friendly from the name, but they are wonderful with kids, offering a great kids menu, kid-friendly cups/coloring books, and awesome gelato and churros for dessert.

For your Sunday brunch, avoid chain restaurants and head to Dixie Cream Cafe in Downtown Windermere; a wonderful small business with amazing food. 

If you’re a mini-van Mom, with an infant asleep in the car, waiting for lessons to be over, or for the school bell to ring, the Panera Bread on the corner of Apopka Vineland/Conroy Road has a drive-thru. Other drive-thrus in the area include Chick-Fil-a, McDonald’s and Wendy’s. 


For groceries, my go to is Whole Foods on Sand Lake Road. They have an amazing hot bar as well as a wonderful selection of produce. The staff there is always so friendly too. I run through, grab some groceries, keep them cold in insulated bags I leave in the car, and it’s location is close enough, leaving me plenty of time to get my daughter from preschool.

Trader Joes has great kid-friendly offerings too, and our local Publix stores are so accommodating. My favorite is the one in The Marketplace at Dr. Phillips. They have a wonderful catering desk to take your party orders and a cooking school that is perfect for date nights!

For gifts, I love to go to The Pink Chalet in Phillips Crossing — their selection of jewelry is wonderful, and their personalized service is wonderful! They will help you find the perfect gift for your friend (or yourself!)

When it comes to your home, HomeGoods in the Marketpalce at Dr. Phillips has a large selection of well… home goods! And when it comes to taking care of your home, landscape or patio, the new Orchard Hardware Store is stocked with everything I want. It’s a hardware store I love to peruse!

Dr. Phillips and Windermere Florida

When you need to pamper yourself, the Woodhouse Day Spa at the Dellagio Town Center is the best around. And when you need a quick brow touch-up, mom-owned business, Waxing the City, gives the best waxings around!

Dr. Phillips and Windermere FloridaCommunity and Activities

The Dr. Phillips/Windermere community and its plethora of activities is one of the best in the southwest. As a new mom, I ventured to the Dr. Phillips library for storytime with my then 7 month old. I quickly made friends with other moms and 4 years later, our girls are still all best friends. There are lots of Mom meetup groups in the area, both online, through activities, preschools and churches.  

Mommy and Me Class

Here are some of my favorite activities in the area:

  • Music with Mar with Ms. Becky: Held at the Church of Ascension on Tuesdays, she currently has 2 class times, 9:30 and 10:30. The moms (dads and grandparents welcome too!) I see here, I typically see at other activities/preschool as well, so it is very community-based. It’s not only a great class for your child, but a great way to meet other moms.
  • My Gym Orlando: We have participated in a few parents night out events, birthday parties, and camp days at this location. And they remember my child. Every time. They see hundreds of kids a week, and we aren’t regulars, but I am super impressed with this staff and the variety of activities they offer the community.
  • The Southwest Orlando Public library branch does so much! We’ve done Baby Bash, Toddler crafts, Storytimes, and other themed events. The Windermere branch is wonderful as well, offering various kid-friendly events and different storytimes if the Southwest location doesn’t line up with your schedule. 
  • The YMCA in Dr Phillips is outstanding in cleanliness and offerings. We are members and enjoy swimming lessons, group exercise as well as their large childcare facility. They also have a lot of sport offerings like soccer and basketball.
  • The Rosen JCC has a seasonal calendar with classes, sports, and other offerings for toddlers, youth and adults. It’s another community center that does so much for the area with events like Taste of the J, Cultural Arts Festivals and more.

Lakes and Outdoor Life

Nestled among various lakes, the community has a few boat ramps, and some subdivisions do as well. In Windermere, we love checking out the Farmers’ Market every Friday morning in the quaint downtown. Occasional Food Truck Fridays also make an appearance in Windermere.

  • The Dr Phillips splash pad — one of our favorite locations to go to cool off! During the spring when it starts to get warm, and the big kids are still in school, it’s a great place to go with your toddler to cool down and meet other moms.
  • In the fall, check out the churches along Apopka Vineland Road for wonderful pumpkin patches, festivals and bazaars. We’ve ventured to other locations in the fall just to check things out, but we keep coming back to our community offerings — they really are that good!

Location, Location, Location

I love the area’s proximity to International Drive, Disney, and Universal. Just on the other side of I-4, you can enjoy all there is on International Drive with dining and entertainment, as well as any expos and conventions that come to the Orange County Convention Center. Universal Orlando Resort always has stuff going on and then on the edge of Windermere/Dr Phillips, Disney is right here in our backyards. I like to joke that we live somewhere between Hogwarts and Cinderella’s Castle, but it’s true! There truly is something magical going on around our town every weekend, and it’s all just minutes away.

Dr. Phillips and Windermere Florida

So, welcome Moms to the Dr. Phillips/Windermere area! Want to discover more about Orlando? You can plug into our Orlando Moms Blog Village Chat Group to meet more moms! You’ll quickly feel at home here.
I’ll see you around town!


  1. Thank you so much for writing this article! Moving to the area in May with a 15 month old and found this really helpful! I’m not familiar with this area but all of your recommendations are making me excited 🙂

    • I am so glad it helped you! For a 15-month old, again, I highly recommend Music With Mar with Ms Becky! You will meet lots of moms there 🙂 We go often!

  2. Moving to Windermere in June with three boys ages 10, 8, 4….my husband will have to travel between NY and FL for a few months. I am excited to meet new friends and hope my boys do as well! Thank you for this. I feel excited about our new journey!

  3. Hi Lauren your husband wouldn’t happen to be a pilot would he?
    My family and I are thinking of relocating as well. Recommend and communities?


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