
Simmons Jewelry is thrilled to announce that we are back at our original location, where the late Robert Simmons, Sr. first established his beloved jewelry store—306 South Park Avenue, right next to Peterbrooke Chocolatier. This historic return marks a new chapter while honoring our rich legacy of exceptional craftsmanship and customer service. We continue to offer a stunning selection of engagement rings, wedding bands, watches, and unique jewelry pieces, along with special gifts for every occasion. Visit us to experience the timeless elegance and personalized service that have defined Simmons Jewelry for generations.












From engagement rings to luxury watches, we offer comprehensive jewelry services with the expertise and care that comes from three generations of experience.

Our expert jewelers meticulously assemble each piece to ensure durability, comfort, and flawless design — combining traditional techniques with modern precision.
We restore and enhance the brilliance of your jewelry through professional polishing that revives its original sparkle and shine.
Whether you’re resetting a diamond or adding a new gemstone, our stone and setting services guarantee security, symmetry, and timeless elegance.
Our appraisal service provides expert evaluations to determine accurate replacement values for insurance coverage and protection against loss, theft, or damage.
Bring your idea to life. Our designers work with you from concept to creation, crafting unique, one-of-a-kind jewelry tailored to your taste.
Our professional watch repair service specializes in restoring and maintaining luxury timepieces from major brands such as Rolex, Omega, Tag Heuer, Breitling, and Cartier.
Over 70 years of satisfied customers and counting. See why families trust Simmons Jewelers for their most precious moments.
Posted on Jaden L.Verified Honestly I called so many places and asked them if they would be able to resize my George watch which is a cheap watch and I did not find one place besides here, they took it in and did what they had to do they even helped me out with putting the battery in and make sure it was in good condition before it left they said anytime I need anything else with it just come back and they will help me out thank you guys!!Posted on Mariadanna Davis ..Verified Had my platinum wedding band and engagement ring, resized, a size bigger. The price was very reasonable compared to two other local jewelers in downtown Orlando. They had it done in 3 days, just in time for Christmas! I was very impressed with the friendly service, reasonable price, and quick turnaround. My rings were buffed and cleaned. Looked brand new! I will definitely make this my go to local jeweler.Posted on Lisa G.Verified Just left Simmons! By far, it's my favorite store to visit when I'm in Winter Park. They have been my go-to jeweler for purchases AND repairs for over 20 YEARS!! They always have an amazing selection of unique estate pieces that you cannot find anywhere else. Bobby the owner, even resized my ring for me while I waited since I was only in town for the day! Robin is the sweetest and I love hanging out with her and her pups while I shop. In a world where customer service is barely alive, it is so refreshing to have a store like this to shop. They truly make you feel like family.Posted on Luciano O.Verified 10/10 experience coming here! The owner of the store, I believe his name is Bobby, was amazing! Multiple other jewelry stores turned me down when I asked to get my ring sized down based on the complexity design of my ring. The owner laughed and said they're just inexperienced, and he'd have no issue getting it done, how right he was! The ring looks flawless! He also got the ring done in 3 days, which was AMAZING fast compared to what other store quoted me. Price was also unbeatable compared to any other jewelry store. He was also able to get my watch working when other stores weren't. Fair to say I WILL BE COMING BACK! Extremely friendly and helpful, not to mention the adorable dogs at the shop!Posted on Denise Z.Verified By far, Bobby & Robin are two of the NICEST & most KNOWLEDGEABLE jewelers and people you'll ever meet. They have helped us on several occasion and we have been extremely impressed with their customer service & commitment to exceeding expectations. We truly can't recommend Simmons Jewlers on Park Ave. enough. They are GOOD People. A special thank-you to them for helping my husband design a beautiful piece to commemorate our 30th wedding anniversary. It is stunning
We’re thrilled to be back at our original location where Robert Simmons Sr. first established his beloved jewelry store in 1953.
306 South Park Avenue
Winter Park, FL 32789
(Next to Peterbrooke Chocolatier)
(407) 644-3829
Street parking available on Park Avenue