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Best Historic Restaurants in Longwood, Orlando / Central Florida East

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19 restaurants available nearby

How are Featured results ranked

A photo of The Old Jailhouse restaurant
1. The Old Jailhouse
4.7
Exceptional(724)
$$$$
• American • Sanford
Booked 14 times today
Coming Soon!
A photo of KRES CHOPHOUSE restaurant
2. KRES CHOPHOUSE
4.9
Exceptional(5691)
$$$$
• Steak • Downtown Orlando
Booked 64 times today
The present and past pair beautifully at Kres Chophouse, a classic, top tier Steakhouse with a modern eclectic flair. This premier Steakhouse embodies the heart of Orlando's historic district, featuring chic and elegant décor within the striking architecture of a 1930's landmark. A thoughtful layout with luxurious banquettes and private dining options create an intimate dining atmosphere.Kres Chophouse specializes in house aged, hand cut prime steaks and the freshest seafood, sourcing quality ingredients that emphasize authenticity over pretension. The full bar boasts a diversified and well-curated wine list as original as the art on the walls, with a weeknight happy hour featuring half priced appetizers at the bar.Easy valet parking and the bustling nightlife of Orlando's legendary Church Street create an extraordinary dining experience for a night on the town!
A photo of The Chapman restaurant
3. The Chapman
4.8
Exceptional(761)
$$$$
• Contemporary American • Winter Park
Booked 51 times today
Nestled in the heart of Winter Park, The Chapman enjoys a prime location on the charming and vibrant Park Avenue, surrounded by the city’s rich history, upscale boutiques, and picturesque lakes. The Chapman brings a fresh perspective to fine drinking and dining, where discovery meets comfort and indulgence. Warm, stylish, and artful with a distinctive Winter Park Florida look and feel, we invite you to celebrate the best of Florida while our hospitable team strives to pamper you and make every gathering truly memorable.
A photo of Russell's on Lake Ivanhoe restaurant
4. Russell's on Lake Ivanhoe
4.4
Awesome(1432)
$$$$
• Contemporary American • Downtown Orlando
Booked 17 times today
Located on the historic Lake Ivanhoe, Russell's offers an upscale casual dining restaurant and bar featuring an innovative and fresh menu, all with an amazing view and atmosphere.Chef Emmanual Clement has created a varied and exciting menu based on his international experience.Some of our favorite suggestions include:Artisan Charcuterie Board, Roasted Beets & Burrata Napoleon & Octopus Escabeche (we cure our own meats)Entrees: Grilled Swordfish with Sorrel Sauce, Crispy Duck Confit & Tenderloin Au Poivre (all sauces made fresh in house)Desserts: White Chocolate Bread Pudding with Whiskey Sauce & Cranberry Crème Brulée (all our desserts are made in house)Awards:Top Tables 2020Best Burger 2021 Orlando Sentinel Foodie AwardBest Ambiance; Editor's Choice Orlando, The City's MagazineBest Brunch: Readers' Choice Orlando, The City's MagazineIf you any dietary requirements just let us know ahead of time and we will try and accommodate you.See you soon!
A photo of Charley’s Steak House-Orlando, FL restaurant
5. Charley’s Steak House-Orlando, FL
4.8
Exceptional(6790)
$$$$
• Steakhouse • I Drive / Sand Lake
Booked 46 times today
Charley’s Steak House on Orlando’s iconic International Drive has been a Florida favorite since 1992, proudly owned by the Woodsby family. Specializing in USDA Prime and Choice Angus beef from three-year-old steers, each steak is aged 4–6 weeks, hand-cut daily by the management team, and flame-grilled over a 1,200º Florida citrus and oak wood fire for unmatched flavor. The ambiance is upscale yet inviting, with rich wood accents and a lively energy. Guests can also enjoy outdoor dining on the spacious patio, perfect for soaking in the Florida breeze. Charley’s boasts a world-class wine list with nearly 1,000 selections and has earned accolades including Wine Spectator’s “Best of Award of Excellence,” DiRōNA, and Orlando Magazine’s “Best Steak House.” Charley’s Steak House delivers top-notch service and exceptional dining experiences—come taste the difference and discover why it's considered the #1 steakhouse in America.
A photo of VINIA Wine & Kitchen restaurant
6. VINIA Wine & Kitchen
4.6
Exceptional(112)
$$$$
• Italian • Winter Park
Booked 5 times today
Recognized as one of the Most Romantic Restaurants in Orlando, VINIA Wine & Kitchen is a locally owned, family-run wine bar and restaurant in Historic Winter Park. Steps away from Park Avenue and Hannibal Square parking lot. Perfect for date night, girls' night, and private events, enjoy a complete wine-pairing dinner experience with a boutique wine list and European-style menu, accommodating all dietary preferences, including creative plant-based and gluten-free options.Embrace The VINIA Way of Life! Relax at the bar, outdoor seating, or cozy table. Enjoy small plates for Happy Hour, Live Music Thursdays, and 3-course dinner including wines, for $59!On select Spring, Fall, & Holiday dates, join THE VINIA TABLE, an elevated 5-course wine dinner experience offering both traditional and vegan menus.Founded in 2018, now proudly owned by Rafael and Marina Lima, carrying on the legacy, beloved recipes, and commitment to great wine, and food. Reservations recommended. Walk-ins welcome.
A photo of The District Gastrobar restaurant
7. The District Gastrobar
3.3
Good(248)
$$$$
• American • Downtown Orlando
Booked 4 times today
The District GastroBar has an innovative design that starts in the restaurant's entrance, a well ­curated modern speak easy with a nostalgic vintage ambiance and an eclectic array of "one ­off" pieces of Prohibition and 1940 era inspired artwork. Walk past the restaurants front door, guests encounter a antique bronze tin ceiling wrapped around historic 1900 brick, custom vintage lighting, but only the adventurous will discover all that The District GastroBar has to offer. With a distinct dining room, grandiose bar layout, an open air patio and a women’s bathroom complete with a salon inspired feel and antique perfume bottles. The cuisine, much like the design, is intended to set a new course. Chef Lamond Cooper and menu creator Andre Walton have adapted to the new shared plate dining trend that has swept the nation, and with The District GastroBar menu, they have created waves on the food scene better known as GASTRONOMY!
A photo of Chef's Table at the Edgewater restaurant
8. Chef's Table at the Edgewater
4.9
Exceptional(2784)
$$$$
• American • Winter Garden
Booked 12 times today
In historic downtown Winter Garden, a few miles from Orlando’s theme parks, an intimate gourmet dining experience awaits you. Local residents rave about it, and foodies come from all over to sample the superb cuisine and intimate service of The Chef's Table at the Edgewater. Our 3 Course Prix Fixe Dinner is priced at $74.99 per person, consists of 4 choices/course. Pricing may vary on holidays. Guests must be over the age of 8 to dine at the Chef's Table, which generally takes 2 hours.Brunch is now served on Sat & Sun at our Tasting Room. Recent awards include the Florida Trend Golden Spoon, Orlando Magazine Dining Awards, winning Best Restaurant, Best Kept Secret, Best Wine Pairing Dinner, Most Romantic Rendezvous, & Best Chef's Table. For diners wanting a more casual evening, our Tasting Room serves brunch, small plates, large plates & craft cocktails, and does not require a reservation.Group dining features dining areas for group sizes 10-60.
A photo of Il Mulino New York Trattoria - Orlando at the Walt Disney World Swan Resort restaurant
9. Il Mulino New York Trattoria - Orlando at the Walt Disney World Swan Resort
4.4
Awesome(3595)
$$$$
• Italian • Lake Buena Vista
Booked 56 times today
The acclaimed Il Mulino New York Trattoria offers its superior signature dining experience in a relaxed and vibrant setting. Guests can enjoy fragrant wood-fired pizzas, fresh fish, chicken, pastas and meats, all bursting with hearty blends of seasonal ingredients drawn from the Abruzzi region of Italy. Join us at Trattoria Il Mulino for an exquisite culinary experience where each bite evokes the skill, dedication and passion that has made Il Mulino New York an international icon for over 35 years. This restaurant is one of our Signature Dining experiences. Guests are expected to dress accordingly in attire that respects the restaurant's sophisticated and upscale aesthetic. Clothing should be clean, neat and in good condition, free from offensive language and/or graphics. Please no swimwear.
A photo of Chart House Restaurant - Daytona Beach restaurant
10. Chart House Restaurant - Daytona Beach
4.5
Awesome(5072)
$$$$
• Seafood • Daytona Beach
Booked 41 times today
Chart House is a fine dining restaurant serving seafood & steak and famous for their spectacular views. For more than 50 years, Chart House has redefined the ideal dining experience. With 26 waterfront and showcase locations ranging from the historic to the unforgettable, Chart House restaurants specialize in dazzling views, unique cuisine and exceptional service. From fresh fish specialties and seasonal seafood to slow-roasted prime rib and craft cocktails, the renowned chefs of Chart House have tailored a menu that adds a unique touch to local flavors. And the Chart House happy hour is a guest favorite, where guest favor our signature cocktails and delicious bites you are sure to enjoy. Our original Hot Chocolate Lava Cake is the perfect end to a memorable dining experience at Chart House. Chart House offers the ideal setting for your next event. We would be happy to assist you with all the details of your special occasion.

See what locals rave about

From verified diners like you
From verified diners like you
  • Lauren
    Orlando / Central Florida East •7 reviews
    5.0
    Dined on Jul 3, 2026
    I took my 6 year old daughter here to have a special mommy-daughter fancy dinner night and everything was amazing! Everybody was so sweet to her and helped to make it a very special evening. From the hostesses to the server and manager and even the chef……they all made her feel like a princess. Chef Mary made her a special dinner and dessert that was delicious and of the very best quality. Kres remains the best restaurant in Orlando, capable of handling business dinner and date nights and diners with the most distinguished of tastes……..children :) 5 stars across the board as usual!
    More info
    KRES CHOPHOUSE$$$$• Steak• Downtown Orlando
    •
    4.9
  • IXCHELGold
    Orlando / Central Florida East •9 reviews
    5.0
    Dined on Jul 3, 2026
    Great aesthetics, service exceptional, drinks amazing, decor-Florida glam. Can’t wait to return for brunch and dinner to taste what else is on the menu!
    More info
    The Chapman$$$$• Contemporary American• Winter Park
    •
    4.8
  • CarolynGold
    Chicago / Illinois •65 reviews
    5.0
    Dined on Jul 2, 2026
    Wonderful food, great hospitality, fun music on Thursdays
    More info
    VINIA Wine & Kitchen$$$$• Italian• Winter Park
    •
    4.6
  • Patti
    San Francisco Bay Area •6 reviews
    5.0
    Dined on Jun 30, 2026
    Hidden gem. Christian was a delight. Can’t wait to go back!
    More info
    Russell's on Lake Ivanhoe$$$$• Contemporary American• Downtown Orlando
    •
    4.4
  • Joel
    Orlando / Central Florida East •14 reviews
    4.0
    Dined on Jun 20, 2026
    Food was nice and hot, tasted good and was plentiful.
    More info
    The Old Jailhouse$$$$• American• Sanford
    •
    4.7

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