One of the benefits of living in Southwest Orlando is the accessibility to other Central Florida neighborhoods. There is so much to see and do in the greater Orlando area, and we're exploring some of the other beloved downtowns that showcase just how much we love where we live. Located just about 30 minutes from Windermere, our first stop is in downtown Winter Park. It could be called the sister city to Windermere, with similar luxury lake living and a beautiful downtown scene, Winter Park truly has it all.
Winter Park Farmers Market & Central Park
Saturday mornings are a buzz in downtown, whether it be enjoying brunch at a local eatery on N. Park Avenue like the popular Briarpatch Restaurant, or heading over to Central Park for the Winter Park Farmers Market. Held from 8am - 1pm at the corner of New York Avenue and Morse Boulevard, the farmers market is home to nearly 60 vendors offering a variety of homemade goods, hand-made products, local produce, plants, gourmet food options, and so much more.
Central Park definitely feels like a smaller Forsyth Park, but has the same amount of charm. You'll find folks meandering along the sidewalks, spread out under shade trees, or around the Emily Fountain, all with great views of N. Park Avenue.
Supporting Small Local Shops
After the farmers' market, it's a must to stop by some of the local shops. There is so much variety with small, local shop owners to luxury brands; N. Park Avenue is the perfect place to explore. A picture-perfect downtown brick street with mature trees, flowers, and charming storefronts makes it such a cozy place to dip in and out of along the way. It's giving downtown Charleston or Savannah vibes. A visit is not complete without a stop at the Writer's Block Bookstore, where you can get lost in the selection of books, gift items, kids' toys and games, and even a Blind Date book section where you can select a book that is covered with brown paper and only a few hints as to the book category and highlights. If this shop feels familiar, as a southwest Orlando local, their sister store is located on Plant Street in downtown Winter Garden.
Around the corner at E Canton and N Center Street is the adorable shop, Gasp. You can't miss the storefront with its pink paint and signage, and inside you'll find the most cozy shop filled with curated gift items like stationery, stickers, candles, party supplies, and so much more.
Located to the west of downtown, south of W Fairbanks, and west of Orlando Ave is Cami Monet, the ultimate stop for hand-designed products, cards, party goods, accessories, wedding supplies, and more. Locally owned by watercolor artist Cami Monet, this cozy shop is definitely worth a visit on your way in or out of downtown.
Eating in downtown Winter Park
If you are in Winter Park on a Saturday and looking for a bite, you will likely see a crowd of happy diners at the popular Briarpatch, known for its popular breakfast and lunch menu items. Located off W. New England Ave in a unique circular lighthouse shaped eatery is the popular Jam Hot Chicken. Grab a seat at the picnic tables that dot the sidewalk and enjoy people watching as orders are called out from the pick up window. Hot tip (and we do mean hot)... the Jam Hot chicken is just that, a cayenne pepper-dusted fried chicken that ranges from (Plain to Jam Hot). We tried the mild, and on a summer day, it definitely had a kick. Our neighbors that we shared a picnic table with, however, didn't blink at the highest level of spice, so it's definitely a personal preference here! The fries were delicious, and the music was pumping, making it a great casual spot to check out while in town.
What to Know Before heading to Winter park
- There is street parking, but that fills up fast, especially on Saturdays. Located off W. Canton Ave, between N. New York Ave and N. Park Ave is a parking garage that was easy to access and in a great location near the hub of downtown.
- Dining reservations may not always be available, but when they are, book in advance. For those like Briarpatch, that is first-come, first served, plan on arriving early and expect a wait.
- Don't forget your reusable bags for the farmers' market and comfortable shoes.
- Check the events calendar first. Winter Park hosts plenty of events throughout the year, including the spring Sidewalk Art Festival and the Autumn Art Festival in October.
Orlando neighborhood Love
There is no shortage of things to do in and around greater Orlando and living in Southwest Orlando has so much in your own backyard, but great access to explore nearby gems like Winter Park. If you're thinking about making a move in Southwest Orlando (or beyond), connect with The Funk Collection. The team specializes in helping buyers and sellers with their hyper-local market knowledge and is ready to help you.
For more information on Winter Park homes for sale, check out the community page for market info, neighborhoods, and available homes.
Posted by Jeffrey G. Funk P.A. on
Newly announced! Jam Hot Chicken will be coming to Southwest Orlando in the Plant Street Market in historic Downtown Winter Garden.
Posted by Jeffrey G. Funk P.A. on Thursday, September 18th, 2025 at 12:14pmLeave A Comment