Moving to Winter Garden / Windermere, Florida

Winter Garden / Windermere, Florida

Are you thinking of moving to the Winter Garden or Windermere, Florida area?

Being a mom and moving to a new area can be scary. It’s hard enough to get the kids shoes on, much less have time to explore and get out to meet other moms. I think we hit the jackpot in moving to the Winter Garden / Windermere side of town and I want to tell you why. My husband and I have moved a lot and I am pretty sure that I have never felt so welcomed into a community.

We recently relocated within the Orlando area for the community and commute. This area is a mix between new development, a good amount of history and culture and a whole lot of families with children. We have the fantastic benefit of being right next door to Walt Disney World, but there is so much more this area has to offer. 

So here is the deal, momming can be pretty lonely and it seems that the moms of this area are aware of that. They are outgoing, friendly and welcoming. I was able to build a small tribe before even moving here, and it is those moms and more who have welcomed me and my family with open arms. It is also those moms who helped me compile this list, because I needed their help, since I am still learning the area.  

So, this list is a collaborative effort from a good handful of moms in Winter Garden and Windermere. I hope you enjoy some of our recommendations and I know that if you choose to move here, there is a good chance that you too will feel welcomed. 

Enjoying the Outdoors

West Orange Trail – a runner, biker and walker’s dream. The West Orange Trail is a 22 mile converted railroad track. The trail even has stops with restrooms, some even have playgrounds.  

Winter Garden / Windermere, Florida

Winter Garden / Windermere, Florida

Tibet Butler Preserve – for those who love to be IN nature, this is the place for you. Tibet Butler Preserve offers miles of trails through natural Central Florida. Walk over boardwalks through marsh land and to lakes. See Florida as it used to be. The park also has an exhibit center featuring animals from the area and even offers educational classes for all ages.

Winter Garden / Windermere, Florida

Winter Garden / Windermere, Florida

Winter Garden Splash Pad – Right in the heart of quaint Winter Garden, this splash pad is open to the public year round and best of all, it is free!

Winter Garden / Windermere, Florida

Southern Hills Blueberry Farm – Blueberry picking! This is a local mommy favorite. Parking and admission are free and it is stroller accessible. Southern Hills is open seasonally, so check their website. They also open for a short time in the fall for pumpkin picking.  

Winter Garden / Windermere, Florida

Winter Garden / Windermere, Florida


With all of the new communities, many or most in this area offer playgrounds. In our community alone we have 5 within walking distance. However, for variety, I thought I would include some public playgrounds that are noteworthy.

George Bailey Park – this park has everything from ball fields to a covered playground (important in the summer sun).

R.D. Keene Park – there is a boat ramp here to one of our many local lakes. There is also a great playground for all ages. Good news, the county is also in the works on adding a sunshade.

Summerport Park – located in the heart of one of Windermere’s largest communities, this is a public park. It offers a gated and shaded playground for toddlers, one for older children and even a dog park.

Winter Garden / Windermere, Florida

Winter Garden / Windermere, Florida 

Craving Sweets?

Frozen Cow Ice Cream– a local favorite. Frozen Cow is a family owned business that uses milk from only ree Range Cows. They also offer a choice 21+ ice creams for some extra excitement in ice cream. Doesn’t “Cappuccino Kahlua” and “Grand Marnier Chocolate Truffle” sound amazing?!

Local History

Central Florida Railroad Museum – A great stop for the train lovers in your family, small and big.  There is a 30 min tour of the museum and talk about the history of trains in Winter Garden. You will find many historical artifacts with a very knowledgeable curator (whose daughter happens to make lactation bars).

Winter Garden Heritage Foundation – A great local history museum which also offers educational opportunities for adults and children.  

Date Nights

The Attic Door – Do you like wine? I do! Then this super comfy, laid-back wine bar is for you. They even have trivia nights on Tuesdays and Monday Date Nights where you get $10 off a bottle of wine when you also have a “sofa snack.”

Garden Theatre – The Garden Theatre is a fantastic venue featuring plays, concerts and movies. Check out their schedule for a great date night. 

Most Important – Places to Hang Out With Kids, That You Will Enjoy:

The Breakroom – An awesome find! A donation based coffee shop WITH free wifi, a children’s corner and a gated outdoor play area for kids full of toys, wagons, slides and tricycles.  All of the proceeds go to help the community. Truly a comfortable coffee shop with a great heart and mission.  

Winter Garden / Windermere, Florida

Winter Garden / Windermere, Florida

Winter Garden / Windermere, Florida

The Crooked Can – A unique brewery attached to the fantastic Plant Street Market. They have a great outdoor seating area, including a mostly gated grassy area that kids can play while you enjoy a cold brew, glass of wine and some pizza or sushi from the market.

    Winter Garden / Windermere, Florida

 Meeting Other Moms:

I have met many of my local mom friends on Facebook. Yup, that’s true! We have super supportive and helpful mom groups here. These mom groups set up playdates and mom get-togethers. There are also many groups in the area like Mom Life at the YMCA, bible studies, MOPS (seriously an amazing group of mamas), book groups, photography groups and exercise groups, like Baby Boot Camp. I could keep going. Want to discover more about Orlando? You can plug into our Orlando Moms Blog Village Chat Group to meet more moms!

Winter Garden / Windermere, Florida

Baby Boot Camp

If you head out to any of the above places, you will run into another Winter Garden / Windermere mom. Don’t be afraid to say hello. You will be greeted with a smile, especially if you and I get the opportunity to meet. 🙂 

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7 Responses to Moving to Winter Garden / Windermere, Florida

  1. Judith September 22, 2017 at 11:16 am #

    Wow! Great research! Providing ideas for extinguishing loneliness is a great gift to women in the area. Thank you, Jen

  2. Hayley December 27, 2017 at 12:02 pm #

    This looks great. We may be moving in the next year and was worried about this. I have older boys now. 10, 8 and 5. Do you know much about the mom culture for older kids? It changes so much after preschool.

    • Stacey January 10, 2018 at 1:52 pm #

      Hi Hayley…. I am moving there when school lets out in June. My kids are 11 & 10. Curious of the same.

  3. Stacey January 10, 2018 at 1:10 pm #

    Well, this was a good read! We are moving to the Windermere/Winter Garden area in June (not sure where yet… just starting the process). Is there a resource for a mom with an 11 and 10 year old? Best schools? Best community? Thanks in advance!

  4. Corie Dillard March 21, 2018 at 1:41 pm #

    Thank you so much for this. My family is moving to Winter Garden this summer!

  5. Christie March 23, 2018 at 9:56 pm #

    Thank you so much for writing this! My family has moved a few times these past couple of years and are now moving to Windermere/Winter Garden area in May. I always find friends using the local Facebook groups so thank you for the link 🙂 Can’t wait to meet some moms and friends for my one year old son 🙂

  6. C. Lopes April 24, 2018 at 11:35 am #

    Thank you so much for your help! I’m moving to Orlando next summer from Boston. Ee are thinking about areas like winter garden / Windermere or Lake Nona. My son is 11 years old. I’m a little bit afraid of pick up a retirement area without kids. Can you give me your opinion, please!!!!

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