We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
New! Find and book your ideal hotel on TripAdvisor — and get the lowest prices

Dexter's in Winter Park

Certificate of Excellence
$$ - $$$
American, Bar
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Get directions
558 W New England Ave, Winter Park, FL 32789-4256
+1 407-629-1150
11:00 - 22:00
Open now
All hours
Sun 10:00 - 22:00
Mon - Thu 11:00 - 22:00
Fri 11:00 - 00:00
Sat 10:00 - 00:00
More Info
Add Photo Write a Review

189 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Showing 182: English reviews
Orlando, Florida
Level Contributor
35 reviews
22 restaurant reviews
common_n_restaurant_reviews_1bd8 7 helpful votes
4 of 5 bubbles Reviewed 5 days ago NEW

Food, service, great. But it is not a place to go for dinner and expect to hear the person across from you. The building is not suited for live music, and it is deafening. Even the side away from the music. However, you could sit outside. I don't know why the musicians think they are better when they are louder.

Thank dcberndt
Ft Collins
Level Contributor
92 reviews
67 restaurant reviews
common_n_restaurant_reviews_1bd8 47 helpful votes
5 of 5 bubbles Reviewed 3 weeks ago via mobile

While in the Orlando area I had some spare time to meet with some old friends. A friend recommended the winter park area for the night life. Not really knowing where to go I picked Dexters purely because it was the name of the person dog I was going to meet. WHAT A GREAT CHOICE! Upon arrival the place is... More 

Thank Wehrli
Glasgow, United Kingdom
Level Contributor
5 reviews
5 restaurant reviews
5 of 5 bubbles Reviewed 21 October 2016

Visited at happy hour,fun local crowd,welcoming staff,place was2/3 full,was still early ..,band played early giving a little taste what was on later ,,main set on at 8.30,sorry we couldn't,t stay..had great sandwich and beer,family,s with kids ,some dancing,great vibe.great find 5 min from park drive..will return for meal and a great nights entertainment..

Thank alexkelly19
Alajuela, Costa Rica
Level Contributor
11 reviews
9 restaurant reviews
common_n_restaurant_reviews_1bd8 1 helpful vote
4 of 5 bubbles Reviewed 20 October 2016

This time was a "going away" girlfriends night at Dexter's. Art, margaritas, music and great food, and personalized attention. Making Dexter's one of my regular stops.

Thank TMurillo
Maitland, Florida
Level Contributor
32 reviews
17 restaurant reviews
common_n_restaurant_reviews_1bd8 5 helpful votes
4 of 5 bubbles Reviewed 20 October 2016

Dexter's offers music on the weekends. We have been a couple of times, but it is always sooo loud. It is difficult to order drinks and food. The music would be so much more enjoyable if it was a lot quieter. You can hear the music, down the block and all doors and windows are closed. Even the waiters seem... More 

Thank TerriF12_13
Level Contributor
27 reviews
19 restaurant reviews
common_n_restaurant_reviews_1bd8 10 helpful votes
3 of 5 bubbles Reviewed 17 October 2016

The view is fantastic the service was not that good...The food was served warm not hot as we got steak sandwich and eggs. They offer a brunch wish I would have had that instead.

Thank Mystie1959
Sydney, Australia
Level Contributor
63 reviews
46 restaurant reviews
common_n_restaurant_reviews_1bd8 11 helpful votes
4 of 5 bubbles Reviewed 8 October 2016 via mobile

Dexter's has been around in Winter Park for at leas 15 years. Their "new" location at Hannibal Square is spacious and well laid out. Nice bar area as well as outdoor seating. They usually have a band on Saturday nights. They've been so popular there are at least two or three more around central Florida. My favorite sandwich isn't on... More 

Thank Ken A
Atlanta, Georgia
Level Contributor
113 reviews
66 restaurant reviews
common_n_restaurant_reviews_1bd8 28 helpful votes
4 of 5 bubbles Reviewed 26 September 2016

We usually come to Dexter's in Winter Park a few times a year with friends. The menu is delicious and the drinks (double mimosa for just under $6) cannot be beat. Definitely get reservations as you approach the late morning/early afternoon brunch hours on weekends.

Thank AbsolutWallStreet
Winter Park, Florida
Level Contributor
440 reviews
242 restaurant reviews
common_n_restaurant_reviews_1bd8 120 helpful votes
3 of 5 bubbles Reviewed 24 September 2016 via mobile

In my opinion this is a better place for brunch or lunch, rather than dinner. The food was a little bland. Service was prompt & friendly. Try the vodka w/ pineapple juice & coconut water, yum

Thank Stephen K
London, United Kingdom
Level Contributor
144 reviews
112 restaurant reviews
common_n_restaurant_reviews_1bd8 137 helpful votes
4 of 5 bubbles Reviewed 23 September 2016

Having just arrived in the US and looking for some dinner at a pretty late hour on Saturday night we had Dexter's recommended to us by our hotel. Arriving at 10pm we found it totally heaving with people, with live music and a lot of fun being had. Despite it being very hot the only place we could sit was... More 

Thank Pechster71

Travellers who viewed Dexter's in Winter Park also viewed

Winter Park, Central Florida
Winter Park, Central Florida
Winter Park, Central Florida
Winter Park, Central Florida

Been to Dexter's in Winter Park? Share your experiences!

Write a Review Add Photos & Videos

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing
Improve this listing

Restaurant Details

Rating summary
  • Food
    4 of 5 bubbles
    4 of 5 bubbles
  • Value
    4 of 5 bubbles
    3.5 of 5 bubbles
Average prices
USD 20
American, Bar
Drinks, Brunch, Lunch, Dinner, After-hours
Restaurant features
Takeout, Seating, Waitstaff, Parking Available, Highchairs Available, Wheelchair Accessible, Serves Alcohol, Accepts American Express, Accepts Mastercard, Accepts Visa, Accepts Discover, Reservations, Television, Full Bar, Free Wifi
Good for
Business meetings, Child-friendly, Kids, Groups, Bar Scene
Open Hours
10:00 - 22:00
11:00 - 22:00
11:00 - 22:00
11:00 - 22:00
11:00 - 22:00
11:00 - 00:00
10:00 - 00:00
Location and Contact Information
  • Address: 558 W New England Ave, Winter Park, FL 32789-4256
  • Location: United States  >  Florida (FL)  >  Central Florida  >  Winter Park
  • Phone Number: +1 407-629-1150
With four locations in the Central Florida area, Dexter's is a favorite for wine and food enthusiasts. Dexter's offers signature dishes with a seasonally changing Café Menu. Our menu items are unique and inspired by our Chefs at all of our locations. Having started out as a wine bar, Dexter's is known for having an extensive wine list that is always reasonably priced. Each Dexter's location has it's own personality and there is something for everyone that visits our stores. From live music and wine pairing dinners to happy hours and a brunch that was voted best in Central Florida, Dexter's is the place to enjoy great food, drinks and atmosphere.

Questions & Answers

Here's what previous visitors have asked, with answers from representatives of Dexter's in Winter Park and other visitors
1 question
Ask a question
Questions? Get answers from Dexter's in Winter Park staff and past visitors.
Posting guidelines
Typical questions asked:
  • Do you have gluten-free options?
  • Is there a dress code?
  • Do you allow dogs on the outdoor patio?