Best Historic Restaurants in Winter Park

7 restaurants available nearby

A photo of The Tap Room at Dubsdread restaurant

1. The Tap Room at Dubsdread

4.9

Exceptional(3127)

Price: Expensive

• American • Downtown Orlando

Booked 49 times today

Our spectacular setting and award-winning food have made us a favorite in Central Florida. Join us for lunch, dinner or happy hour inside or out on the verandah. We proudly offer fresh fish, hand-cut prime steaks, homemade desserts and Orlando’s best burger!

2. KRES CHOPHOUSE

4.8

Exceptional(4925)

Price: Expensive

• Steak • Downtown Orlando

Booked 54 times today

The present and past pair beautifully at Kres Chophouse, a classic, top tier Steakhouse with a modern eclectic flair. This premier Steakhouse embodies the heart of Orlando's historic district, featuring chic and elegant décor within the striking architecture of a 1930's landmark. A thoughtful layout with luxurious banquettes and private dining options create an intimate dining atmosphere.Kres Chophouse specializes in house aged, hand cut prime steaks and the freshest seafood, sourcing quality ingredients that emphasize authenticity over pretension. The full bar boasts a diversified and well-curated wine list as original as the art on the walls, with a weeknight happy hour featuring half priced appetizers at the bar.Easy valet parking and the bustling nightlife of Orlando's legendary Church Street create an extraordinary dining experience for a night on the town!

A photo of Russell's on Lake Ivanhoe restaurant

3. Russell's on Lake Ivanhoe

4.7

Exceptional(1239)

Price: Expensive

• Contemporary American • Downtown Orlando

Booked 23 times today

Located on the historic Lake Ivanhoe, Russell's offers an upscale casual dining restaurant and bar featuring an innovative and fresh menu, all with an amazing view and atmosphere.Chef Emmanual Clement has created a varied and exciting menu based on his international experience.Some of our favorite suggestions include:Artisan Charcuterie Board, Roasted Beets & Burrata Napoleon & Octopus Escabeche (we cure our own meats)Entrees: Grilled Swordfish with Sorrel Sauce, Crispy Duck Confit & Tenderloin Au Poivre (all sauces made fresh in house)Desserts: White Chocolate Bread Pudding with Whiskey Sauce & Cranberry Crème Brulée (all our desserts are made in house)Awards:Top Tables 2020Best Burger 2021 Orlando Sentinel Foodie AwardBest Ambiance; Editor's Choice Orlando, The City's MagazineBest Brunch: Readers' Choice Orlando, The City's MagazineIf you any dietary requirements just let us know ahead of time and we will try and accommodate you.See you soon!

A photo of The District Gastrobar restaurant

4. The District Gastrobar

3.9

Excellent(157)

Price: Moderate

• American • Downtown Orlando

Booked 2 times today

The District GastroBar has an innovative design that starts in the restaurant's entrance, a well curated modern speak easy with a nostalgic vintage ambiance and an eclectic array of "one off" pieces of Prohibition and 1940 era inspired artwork. Walk past the restaurants front door, guests encounter a antique bronze tin ceiling wrapped around historic 1900 brick, custom vintage lighting, but only the adventurous will discover all that The District GastroBar has to offer. With a distinct dining room, grandiose bar layout, an open air patio and a women’s bathroom complete with a salon inspired feel and antique perfume bottles. The cuisine, much like the design, is intended to set a new course. Chef Lamond Cooper and menu creator Andre Walton have adapted to the new shared plate dining trend that has swept the nation, and with The District GastroBar menu, they have created waves on the food scene better known as GASTRONOMY!

A photo of The Great Southern Box Company Food Hall and Bar restaurant

5. The Great Southern Box Company Food Hall and Bar

new

(0)

Price: Moderate

• Global, International • College Park

Booked 1 time today

The Great Southern Box Company food hall and bar is the highly anticipated culinary collective located in the heart of the Packing District in Orlando. Located on North Orange Blossom Trail, this historic project transforms the original citrus warehouse from Dr. Phillips' into a bustling culinary hub focused on international cuisine that ensures there is something delicious for all guests to enjoy. The 13,000-square-foot food and beverage destination offers a curated selection of options from locally owned and nationally acclaimed concepts as well as a large event space to fill all your needs.Please note that full table service is not offered, but we do provide ample seating and QR code ordering from the bar and many of our tables.

6. Pine & Oak Tavern

4.6

Exceptional(38)

Price: Moderate

• American • Waterford Lakes

Booked 5 times today

Welcome to Pine and Oak Tavern, where golf and gastronomy unite to create a distinctive dining experience. Nestled within the historic Rio Pinar clubhouse, our restaurant emerges as the perfect fusion of culinary excellence and scenic beauty.Enjoy modern American cuisine in the elegant yet comfortable atmosphere at Pine & Oak!Created by the founders of Delaney's Tavern, Pine & Oak offers a new twist on our Chef Anthony award-winning dishes, touching all corners of the globe. With amazing views and a spectacular setting, it's the perfect place to bring that special someone or the entire family. We're more than confident that the flavors and offerings at Pine & Oak will leave you craving for more.We look forward to becoming a cherished part of your dining traditions, making every visit a celebration of great food, friendship, and the beauty of Rio Pinar Golf Course.

A photo of Oviedo Brewing Company restaurant

7. Oviedo Brewing Company

4.2

Awesome(26)

Price: Moderate

• Contemporary American • Oviedo

Booked 2 times today

Oviedo Brewing Co. is the only brewery in Oviedo, Florida! We are located right down the road from historic downtown Oviedo and newly built Oviedo on the Park. Outside seating includes a dog-friendly lawn and covered patio. Once inside, you will be greeted with our spacious 8,000 sq. ft. tap room, brewhouse, and full kitchen. We are a full-service family friendly environment with indoor and outdoor games, kid's menu, and happy hour! Whether you're looking for a casual bite or planning a large private event, we look forward to hosting you soon. Oviedo’s only Craft Brewery / GastropubEvent Space + Full KitchenEst. 2019

See what locals rave about

From verified diners like you

M
Madelinevip
Washington, D.C. Area •13 reviews
5.0
Dined 1 day ago
Had a great time! Went right at 10 am for brunch and was seated immediately The lavender lemonade and the cinnamon roll pancake was amazing!
More info
Russell's on Lake IvanhoePrice: Expensive• Contemporary American• Downtown Orlando
•
4.7
B
Bill
Greater Boston •11 reviews
5.0
Dined 2 days ago
My wife and I along with Our good friend had an amazing dinner last night at Kres. We all had different meals that included Elk, Pork Chop and a Porterhouse along with side, which were all excellent. Our server Brandon was spot on and we exchanged a few good stories, which added to our great dinner experience. He even told us about Happy Hour, so we’ll definitely try it out too. Kres has always been our go to place for a great meal and experience.
More info
KRES CHOPHOUSEPrice: Expensive• Steak• Downtown Orlando
•
4.8
K
Kevin
Orlando / Central Florida East •38 reviews
5.0
Dined 4 days ago
A great neighborhood “go to”. Food is top notch and everybody that works at the Taproom is friendly and professional.
More info
The Tap Room at DubsdreadPrice: Expensive• American• Downtown Orlando
•
4.9
J
Jean
Orlando / Central Florida East •11 reviews
4.0
Dined on Sep 25, 2024
Good food, close to the KIA center. I would have preferred a real plate instead of a piece of slate for a plate. Pimento burger was good but way messy.
More info
The District GastrobarPrice: Moderate• American• Downtown Orlando
•
3.9

Best Historic Restaurants in Winter Park

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7 restaurants available nearby

1. The Tap Room at Dubsdread

2. KRES CHOPHOUSE

3. Russell's on Lake Ivanhoe

4. The District Gastrobar

5. The Great Southern Box Company Food Hall and Bar

6. Pine & Oak Tavern

7. Oviedo Brewing Company

See what locals rave about

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