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Best Historic Restaurants in Longwood

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5 restaurants available nearby

A photo of The Chapman restaurant
4.7
Exceptional(93)
Price: Expensive
• Contemporary American • Winter Park
Booked 78 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
4.6
Exceptional(1272)
Price: Expensive
• Contemporary American • Downtown Orlando
Booked 8 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 Old Jailhouse restaurant
4.5
Awesome(589)
Price: Moderate
• American • Sanford
Booked 15 times today
Coming Soon!
A photo of Oviedo Brewing Company restaurant
4.2
Awesome(26)
Price: Moderate
• Contemporary American • Oviedo
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
A photo of The Great Southern Box Company Food Hall and Bar restaurant
Price: Moderate
• Global, International • College Park
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.

See what locals rave about

From verified diners like you
From verified diners like you
  • Phillip
    Orlando / Central Florida East •1 review
    4.0
    Dined 1 day ago
    empanadas, croquettes, and salmon were amazing - apple pie not so much
    More info
    The Old JailhousePrice: Moderate• American• Sanford
    4.5
  • Bill
    Orlando / Central Florida East •10 reviews
    5.0
    Dined 3 days ago
    Excellent service by very cheerful and professional waitress. Terrific food.
    More info
    Russell's on Lake IvanhoePrice: Expensive• Contemporary American• Downtown Orlando
    4.6
  • pamelaVIP
    San Francisco Bay Area •1 review
    5.0
    Dined 7 days ago
    I can’t stop telling people about The Chapman — the fabulous food, over the top flavor, the dishes (familiar with a delightful and delicious up twist!) From the Bang Bang Lion’s Mane to the jumbo lump crab cake to the citrus spiced whipped feta with roasted carrots — these are unique craveable starters unlike anything I’ve seen or tasted — flavors like this can only be experienced at The Chapman. The salads are all so compelling and flavor forward, I want to have them all every time! I’ve never had a more delicious Wedge (the Blue Cheese Vinaigrette is amazing!) or the Caesar (the croutons!)! Hard to pick my favorite entree — the shrimp bucatini? The pork tenderloin with the best polenta and oyster mushrooms? Can’t do those standouts at home — and wouldn’t try! Our table also had the chili lime salmon, and agreed it’s the best we’ve ever had! And the Fresh Florida fish has a sensational spicing. With all that, still had to have the sky high citrus meringue pie - so good there are no words to describe it — even Citrus zest in the delicious meringue! Thank you Chapman — can’t wait to come back — the table next to us had the 333 Grazing Board and the Waygu… I will do the same next time! Great Food, Great Service, Great Ambiance! A Wow all around!
    More info
    The ChapmanPrice: Expensive• Contemporary American• Winter Park
    4.7
  • EllenVIP
    Baltimore / Maryland •32 reviews
    5.0
    Dined on Dec 29, 2023
    Wonderful place to connect with a group of friends. Service was terrific. We had 20 people and everyone had a good time. Pizza was my favorite in addition to the beer.
    More info
    Oviedo Brewing CompanyPrice: Moderate• Contemporary American• Oviedo
    4.2
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