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Best Historic Restaurants in Longwood

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4 restaurants available nearby

A photo of Enzo's on the Lake restaurant
4.7
Exceptional(3127)
Price: Expensive
• Italian • Longwood
Booked 26 times today
Enzo's on the Lake is the perfect place for an evening of cocktails, fine food and wine, delicious desserts and very special hospitality. In 1980, Enzo's on the Lake opened as a lovely secluded lakefront restaurant, built in the style of an Italian villa. The restaurant is dedicated to the idea of simple yet sophisticated cuisine: family owned, crafted with love. The freshest fish, meats, fruits and vegetables that can be obtained are woven into a menu that emphasizes a unique culinary heritage. An antipasto bar welcomes you to the excitement of the dining room overlooking the lake. There is a full service european style bar, private dining areas for meetings and parties, and lakeside gardens and dock. We look forward to serving you!
A photo of Russell's on Lake Ivanhoe restaurant
4.6
Exceptional(1289)
Price: Expensive
• Contemporary American • Downtown Orlando
Booked 12 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(602)
Price: Moderate
• American • Sanford
Booked 20 times today
Coming Soon!
A photo of The Great Southern Box Company Food Hall and Bar restaurant
5.0
Exceptional(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.

See what locals rave about

From verified diners like you
From verified diners like you
  • Matt
    Orlando / Central Florida East •1 review
    5.0
    Dined 3 days ago
    The Old Jailhouse was highly recommended by a co-worker and the experience lived up to the recommendation. Very helpful and attentive staff, great service and food. Drinks were outstanding! Our group of friends were getting together for the first time in a couple of years and the staff was very accommodating, allowing us to stay long after we would have worn out our welcome in a less friendly and enjoyable establishment.
    More info
    The Old JailhousePrice: Moderate• American• Sanford
    4.5
  • PhilipE
    Orlando / Central Florida East •6 reviews
    5.0
    Dined 3 days ago
    If you are looking for o restaurant that offers amazing Italian food with great ambience and wait staff this is the place for you? I went with the wife for our anniversary and we were very pleased with everything. I was surprised at how busy they were on a Tuesday night, but it was packed. At the end of our dinner they provided us a free dessert for our anniversary. We will return in the near future. Thank you for a wonderful dining experience.
    More info
    Enzo's on the LakePrice: Expensive• Italian• Longwood
    4.7
  • AdrienneVIP
    Orlando / Central Florida East •89 reviews
    5.0
    Dined 3 days ago
    Food was delicious and ambiance was wonderful. Watching sunset on a beautiful evening -priceless
    More info
    Russell's on Lake IvanhoePrice: Expensive• Contemporary American• Downtown Orlando
    4.6
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