The ambiance, service, and food were outstanding! Kyle was our server, and couldn't have been more attentive, and pleasant. It was the beginning of dinner time, and a little slow, but the wait staff was very responsive to all the diners in the restaurant. We started with the focaccia w/ leftover oil, and it was quite good. For dinner, my wife had the chicken pot pie w/ grilled chicken, and I had the shrimp and grits... delicious. I highly recommend The Old Jailhouse! read more

The Old Jailhouse - This is the area referred to as the Cell Block - New American Near Me - Sanford, Florida

We had a good experience here with a group of 7 of us . Our server was nice but a bit aloof and mundane . I wish he would have told us about the tip already included on the bill but our friend pointed it out to us to make sure we didn't double tip. It was extremely hot in the restaurant for whatever reason and they played murder she wrote on the tv. They had a good selection of drafts and it was pretty busy as there was a festival happening in downtown Sanford . The food was the star of the night . We got the deconstructed bruschetta which was divine and then a pasta and mushroom dish . Mushroom gnocchi. Wow ! It was soooo yummy ! Really good flavors . Rich and I love mushrooms so it was a win win. I'm not rushing to come back, but the food was good! read more

The Old Jailhouse - Deconstructed bruschetta - New American Near Me - Sanford, Florida

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Such a great vibe! Our bartender was very knowledgeable and the huckleberry vodka was on point!! Great place for a date and just to look at history. Still has some original features from when it was first built. You appreciate these type of restaurants that keep a certain vibe. So many different things to try so we will be back. read more

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I am surprised that no one had never mentioned this place to me. My hubby found it for date night. The whole design of the restaurant was unique and interesting. The food is also amazing. I had the gnocchi with veggies and a grilled chicken. The flavor was perfect with the juicy grilled chicken. Highly recommend this location if you have not given it a try. The only thing is the peach "cobbler " on the menu is a peach crumble. I was a bit confused when it came out. Btw the staff was sooo kind. I appreciate all the positive energy even with all the questions I had. Lol read more

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Great ambience. Great staff. Liked the menu. The cocktail I ordered was... looked kiddie sized. But the bubble was cute

I wanted to love this place. The concept is unique and the decor is fun but the food and cocktails are mediocre. We had pork belly to start, then the steak Mac and buttermilk chicken and pork tenderloin. All were OK but nothing stood out as great. My cocktail looked cool but was cloyingly sweet, this is after I asked the server and he assured me it was balanced and not too sweet. I will probably give it another try when in the area. read more

The Old Jailhouse - Honey gin drink with smoke bubble - New American Near Me - Sanford, Florida

We came to Jailhouse to celebrate my husband's birthday with my in-laws. This wasn't our first visit, and as always, we had a great time. Overall, everything was good. The only issue was that our food wasn't very warm, it seemed like it may have been sitting in the back for a bit before being brought out. Other than that, all of our dishes were delicious. I ordered the spicy bbq honey shrimp skewers with Brussels sprouts and rice, my husband had the buttermilk chicken, and my in-laws ordered the New York strip and the steak mac. For dessert, we shared the cinnamon rolls, which were really good. The ambiance of the restaurant is nice, and the jail-themed details are great. Our server was great too! read more

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This place was really good. I've lived in Sanford for many years and this was the first time coming here. My girlfriend and I are trying new places this year and this was our first choice. I did make a reservation just in case, since reading some of the reviews it does get very busy. Walking in, it does remind you of an old jailhouse. It's small and very cozy. We got seated at a small table for two right next to the kitchen. The kitchen is open so you can see inside. Even being that close to it it was quiet and we could still have a conversation. That was nice. Some of the tables are set up in cells which was cool and they have big chandelier in them for lighting. She got the steak Mac, it was so good too. Packed full of flavor. It tasted amazing. I got the pork tenderloin, that too was very good. They slice the pork into thinner slices and grill it. The potatoes were seasoned perfectly. They have some other good looking items on the menu too. Will definitely be back to try again read more

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This is just a review on the Smokey Old Fashioned I had at the Old Jailhouse last weekend! I took a new local to check out the Old Jailhouse- I love converted spaces like this. I love the ambiance with the old brick and steel bar doors. We sat at the bar just to grab a drink. The atmosphere was very chill in there. Something about it was very serene and relaxing. The lighting is very pleasant. Our bartender was extremely nice. My buddy ordered a sour cider that he enjoyed, and I ordered the Smokey Old Fashioned. My drink came with a bit of a show! Since I got it Smokey, she pulled out a torch and started torching the wood above the drink. Very fun. And perfectly topped with a cherry. I enjoyed the smokiness of the drink. It was very well-made. I can't steak to the food, since we didn't order anything... but the Brussels sprouts smelled AMAZING. I will most definitely come back to try those. Overall, a great spot to have a quiet and relaxing drink. I'd definitely go back and check it out again! read more

I went on a date to the Old jailhouse over the weekend. The service was friendly, warm, and attentive. The pork belly was the highlight of my meal as it was the right temperature and texture. I ordered the grilled shrimp skewers which is supposed to have spicy honey orange glaze. The shrimp itself was great, but the glaze was not spicy at all and I found it to be overly sweet. My brussel sprouts were good they were just cold. The ambiance was quite bright which took me by surprise since it's a "jailhouse" restaurant I expected it to be a little dim. I thought my experience was ok. read more

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Thank you Sage for making our evening and meal selection less stressful, with my food allergies it can be overwhelming with meal selection. Your knowledge of the menu made that easy and the substitutes you suggested were fab! I had the pork tenderloin with the avocado aïoli. The only negative of the evening - the drinks. Not sure what your bartender does to the old fashioned but that wasn't it for sure. Sage you are an excellent server! read more

The Old Jailhouse in Sanford never disappoints! It's one of our favorite go-to spots -- we've tried almost everything on the menu, and every dish has been a hit. Never had bad experience or service My personal favorite is the shrimp skewers with crawfish étouffée -- the flavors are incredible, and that jasmine rice it's served over tastes like a sweet coconut rice? Out of this world. My husband swears by the salmon and rice, and it's perfectly cooked every time. The drinks are always on point -- creative, balanced, and full of flavor. The vibe is unique too, with that cool historic charm mixed with modern energy. If you're looking for consistently amazing food, great cocktails, and a spot that feels special every time you visit -- The Old Jailhouse is it! read more

The Old Jailhouse - Shrimp skewers with the creamy étouffée ! My go to every time - New American Near Me - Sanford, Florida

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Amazing cocktails and a large beer list. Appetizers are on point. Will revisit again and again. Knowledge and friendly staff. It was quiet on a weeknight. Very cool interior. Heavy bar chairs! read more

The Old Jailhouse - Deconstructed bruschetta, pork belly - New American Near Me - Sanford, Florida

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This was such a cool restaurant! Great vibes, kind and helpful servers, creative cocktails and delicious food! The cocktails were very reasonably priced. We also tried the focaccia (not pictured) and it was a hit. We will definitely come back to try their other options. read more

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My party of 4 arrived at The Old Jailhouse for our 6 pm reservation and were sat immediately. We liked the ambiance and were discussing how authentic the old brick looked. When we mentioned it to the waitress, Sage, she explained the whole history of the venue to include that it was actually the local Jail and other interesting historical facts. Sage was one of the best servers I've ever had and was so knowledgeable and passionate when explaining the Menu. I had the burger which was perfectly cooked to temperature and very flavorful and juicy. My wife had the shrimp skewers which were flavorful and perfectly cooked and served over a bed of rice. Our friends had the chicken which they loved. For dessert we had the Brownie with vanilla ice cream. They served it with Walnuts which I recently was discussing with my wife that it is rare now to find walnuts with brownies. The Brownie was a little too cake like but very tasty nonetheless. Overall, it was a great experience with our waitress Sage leading the charge. Do yourself a favor and check out the Old Jailhouse. You won't be sorry! read more

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This is a great spot in Sanford! Food and drinks were tasty, service was great, and the ambiance is cool and unique! The former jailhouse setting provides for a cool piece of history. We didn't have reservations and managed to snag someone's last minute cancellation, otherwise they said it would be about 3 hours. There is a first come, first serve bar, but only about 8 seats, so I'd recommend having a reservation here. read more

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The Old Jailhouse is a renovated jail which now is a restaurant located in downtown Sanford. I have never been here as I never visit Sanford but we recently went for a friend's birthday. We had 10 in our group so we made a reservation. Parking is a little bit of challenge as you need to find street parking or go to one of the few lots they have and walk. There were a handful of parking spots right in front of the restaurant but the restaurant itself did not have private parking. I first noticed it was a little missed, if you were not looking for it. It blends really well with the other building. I also noticed they had tables outside but I would never want to sit there, its on the street and people are always walking by. Once we checked in, we were seated in our own private room right off the main entrance. This was a small room, which we were told was the check in area, it had large table which held our entire group of 10. This room was very private and really nice that we got this for no additional charge. I would ask for this room if you had a large group for a more private experience. Our server was very nice, came over immediately, wanting to take our drink orders. Most of us had never been there so we needed a few minutes but it was kind of awkward since she sort of just stood there until we said come back. I personally did not care for any of the cocktails, they did not have fresh espresso so I didn't want an espresso martini (my favorite) so I went with wine. You cant go wrong with wine. My husband ended up ordering two different cocktails. I'm not sure if the server was not familiar with liquor but both my husband and a friend had issues ordering drinks with a specific liquor. They were not even ordering specialty booze. They wanted booze any restaurant should have. She kept telling us they did not have that at the same time telling us their bar is fully stocked. It was weird and I didn't understand. We finally asked for a liquor menu and even though both liquors were listed, she tried to tell us they didn't have it. It was strange. But my husband ended up ordering a dirty martini and then a Manhattan. He enjoyed both cocktails. Their menu is actually really small. I didn't really know what to expect, like what type of food, but it was fine. They had a decent variety with fish options, chicken, steak, a burger and more. My husband and I decided to share a couple of items so we could try more. We started with the Caesar salad (romaine lettuce, shaved parmesan and house croutons served with Caesar dressing). This was fine, it was your typical Caesar salad, I always love when they put a spin on it, like fresh in house made croutons, but it really was not that it was fine. I did enjoy the dressing but we needed more, the dressing was very scarce. We also ordered the crispy Brussel Sprouts (these were really good, and had crispy bacon mixed in) and then the Belly up Burger ( 1/2 lb. grilled chuck/short rib/brisket blend burger, topped with mustard bbq, pork belly, smoked gouda cheese, bibb lettuce, pickles and pepper jam). This was a great burger, really great flavor. Our only issue was the cooking of the burger. We asked for medium well and one half was cooked fine, but my half was actually rare. So much so, the bun was red and it really turned me off. I know some people like this but not with a burger. I was very shocked how half the burger could be more well and half rare, that takes talent in my book! If we had not been with a large group, I would have sent it back but I didn't want to make a big deal out of it. However, the flavor and taste was there, the fries were super crispy and really good as well. Overall this was fine. I honestly do not know if I would run back here but if I was in the area, this would be a good place to grab dinner. One of our friends said she had been there for brunch which was excellent. I would try that and give it a shot. The portions were kind of small, a couple of the guys were actually hungry and looking to their partners to finish their food. No one actually really seemed to love their dish to be honest. I would say give it a shot, you might like it better. read more

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We had a great experience at the old jailhouse and started out with some very good crafted cocktails I would say that they're smoked old fashioned was fantastic. We then went on to have some Croquettes calamari and our entrees included brussel sprouts and the steak and Mac dinner. I will say that the cocktail menu is very deep but the entrees are lacking some depth. Would be nice to see more than one steak option more than one pasta option and some imagery would be very good. Outside of any challenges of that, we will definitely be back. read more

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We went on a Friday night, spare at the moment and was set within 25 minutes. Was like the history of the place, the food was just ok. We had the salmon and rice and stake. It's a classy place good for dates or a one off experience Service was a little hit and miss as it seemed they our services was very busy with a bigger table. read more

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Lots of fun facts to learn about the establishment. The food is wonderful. Mushroom gnocchi has tons of flavor. Served piping hot. Server was very knowledgeable of the menu and the history of the building! So fun. Eating inside an old jail and hearing stories of the ghost, Percy were highlights of our trip! read more

The Old Jailhouse - Mushroom gnocchi - New American Near Me - Sanford, Florida

The food is a little pricey for the portions you get but, none the less tasty. Our waiter Kyle was super attentive and even put up with my husband's bad jokes. Ambiance is nice. Drinks were tasty . read more

Had dinner here to celebrate a friend's retirement. Very cool place ... an old converted jail house. Had bruschetta app that was great, also really enjoyed the Brussels sprouts. For an entree I got the NY strip which was great a cooked to my liking. The shrimp skewer was also a hit. The service was outstanding. If you're in Sanford ... this is THE place ! read more

The Old Jailhouse - NY strip ... - New American Near Me - Sanford, Florida

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The food was fabulous. The service was exceptional, and the ambience was perfect! We will be back!

Went last year for my birthday with a large party. Everyone was really impressed with the layout and being able to dine in an old jailhouse. Super cool concept, but the fun doesn't stop there. The food and drinks were amazing I had their scallop pasta special and was really happy with the portion size. Staff was very attentive and accommodating to our party of 12 guests. Super walkable area, plenty of spots to barhop or people watch. Can't wait to go back! read more

We brought out dogs and were seated at their court yard. The server was nice and he told us the history of the jail house. The menu was small but good came out really good. We will go back ! read more

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Met some friends on some chill stuff and it was a cool afternoon. Vibes were nice and liked the dark aesthetic. We went light and ordered the Brussels sprouts, empanadas , pork belly and croquettes. I probably could've done without the pork belly, it was okay. My faves were the Brussels and empanadas. Friend said the steak entrees and salmon entrees were good though read more

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The Old Jailhouse is a renovated restaurant in downtown Sanford. This actually use to be a jail back in the day. It is not a restaurant that we visited recently for a friend's birthday. She knew she wanted to go here and since it is not extremely large, we made a reservation. It is located around some other things in downtown Sanford. Parking is a little bit of challenge as you need to find street parking or go to one of the few lots they have and walk. There were a handful of spots right in front but they were already taken. I noticed they did have tables outside but honestly so many people were walking by, I would never want to sit out there. We were seated in our own private room right off the main entrance. It had a table large enough for our group of 10. It was very private and really nice that we got this. Our server was very nice, she came over immediately and wanted to take drink orders. Most of us had never been there so we needed a few minutes. I ended up getting a couple of different cocktails but I had a really hard time ordering. I asked for a specific liquor and she said they didn't have it. One of our friends asked for a specific bourbon and she said they didn't have it. All the while telling us they have a very stocked bar. It was very strange to us as we were just ordering normal gins and bourbons. We did finally ask for a liquor menu, which both liquors we wanted were listed. I'm honestly not sure if she didn't know or was confused. The drinks were good though. My wife stuck with wine, very easy and a couple others in the group got similar cocktails, beer or wine. Their menu is actually really small. I didn't really know what to expect from here. My wife and I decided to get a couple of things and then share and I'm actually really glad we did. I think we made good decisions. We started with the Caesar salad (romaine lettuce, shaved parmesan and house croutons served with Caesar dressing- nothing to write home about, but it was good, just nothing unique to it), the crispy Brussel Sprouts (these were really good, and had crispy bacon mixed in) and then the Belly up Burger ( 1/2 lb grilled chuck/short rib/brisket blend burger, topped with mustard bbq, pork belly, smoked gouda cheese, bibb lettuce, pickles and pepper jam). This was a great burger, really great flavor. Our only issue was the cooking. We asked for medium well and one half was cooked fine, but my wife's half was rare, it was actually bleeding on the bun. She was very turned off from it. Not sure how half the burger could be cooked and not the other half, it was very strange. If we had not been with a large group, I would have sent it back. But the flavor and taste was there, the fries were super crispy and really good as well. Overall the food was 3.5 out of 5. Overall this was fine. I honestly do not know if I would run back here but if I was in the area, this would be a good place to grab dinner. I heard their brunch was really great so we might check that out in the future. I would say give it a try, your experience might be totally different than mine. But the food was decent, we definitely left full. read more

Fun vibe, old jailhouse converted into a restaurant. We sat in "solitary confinement". Service was friendly and good, all our food was good, loved the salmon meatloaf! The skillet apple crumble was more like pie but was very tasty and big enough to share. Would return when in the area, fun place! read more

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Second time here forgot to write a review on the first visit. This was an actual Jail back in the day, they kept thy concept in the decor, from what I remember some of the structure is still the same. Their Cocktails are delicious, I've tried the Old Fashioned and the one in my photos, the waitress recommended it, it's on the sweet side so be warned. The Pork Belly Appetizer is really good, Crispy and tender at the same time, the slaw gives a little kick. The Gnocci and Chicken is really good, my friend and I shared it and was just enough, lots of flavor, great choice. read more

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Cute pricey little unique resturant with many impressive tasty dishes Call for reservations Service was exceptional History is dark Food was very good read more

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I visited the Old Jailhouse in August and have been itching to go back ever since! Unfortunately while looking at their menu to remember the names of the items we tried I found out they no longer have any vegetarian entrées on the menu, so I had to bump one star off the review for that. The mushroom gnocchi was phenomenal, so I can't believe it was removed! The star of the meal for us was the potato croquettes, which are stuffed with goat cheese and truffle aioli. As long as those are still on the menu, I'll probably come back and grab a seat at the bar just to have them again! The creme brulee was also great, as were the drinks. The only thing that I probably wouldn't get again were the mashed potatoes. There was nothing wrong with them, but everything else was so packed with flavor that they faded to the background. When we visited, we sat at a table out front of the restaurant (on the sidewalk) because we had our dog with us. The staff was very friendly and attentive despite us sitting out front (sometimes I find "out of sight, out of mind" to be too true). When I went inside to use the restroom, I thought the ambience inside was great, and the place was packed -- shocking because I barely saw anyone coming or going! If we go back, we'll definitely leave the pup at home to sit inside. I just hope they add at least one yummy vegetarian option to the menu so we can have a full dinner again! read more

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The Old Jailhouse is located in the heart of downtown Sanford, just steps away from the river, as well as other shops and restaurants. My boyfriend and I reserved a spot for 6pm and were seated right away. For starters, we had the pork belly as well as pretzels and beer cheese. Both were delicious! For entrees, we chose the chicken gnocchi (10/10 amazing) and the salmon, which was good but lacked in flavor. You can see in the photo that the sauce was minimum. I'm not sure I would order that dish again. But the chicken gnocchi was top notch. The interior of the restaurant was obviously amazing as it was converted from an old jailhouse. They did a great job of incorporating parts of the old jail house, as well as modern decor. Now, let's focus on the service. Our waitress Catina was very kind and great at her job. The food came fast. My only complaint about the service is that we were seated right next to the computer where servers put in orders. If I had scooted back, we would have been rubbing arms. This was awkward as it felt like every time we started talking, they were listening in, even though they weren't and were just doing their job. Tons of other seats were open during our time there so I'm unsure why we had to be seated there. Make sure to make a reservation as this is a busy place and local favorite. read more

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Yes, it is off season, but since I had a special request, and didn't want to make a plan B last minute I made one for here anyway. My first surprise was walking across the street and being greeted outside for the reservation. Well, that's never happened before. Coming inside, the second surprise happened: we were seated in the small private room to the left when you enter. Things were certainly off to a great start! The food continued the amazing experience. The SIDE SALAD - mixed greens, cucumber and pickled red onion dressed in a citrus poppy seed vinaigrette (gf) for my main was actually pretty amazing all on its own. Someone had a CAESAR SALAD - romaine lettuce, shaved parmesan and house croutons served with caesar dressing at the table that I tasted and that was great. It was huge! For my main event I had the SALMON AND RICE - pan sauteed chilean salmon served with buttered jasmine rice, green beans and lemon beurre blanc (gf). Yes, a simple dish, but sometimes the simple things are the hardest to make interesting, and somehow the chef managed to do that here. Speaking of the chef... that person that greeting our party outside for the reservation came around to ask us all how the meal went. It was then I saw "Ryan" and "Head Chef" on his uniform, and we got a chance to talk to him a little bit about the food. Yes, definitely coming back here! read more

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The chef does an outstanding job complimenting flavors! The bar tender makes some very delicious drinks, and the waiters are very nice.

Love the decor here. The hostess was a little short but our server was super friendly and helpful. We split the beet salad which was so good and light and flavorful. Got the chicken with beans base. It was so delicious. I can't resist a butternut squash and the one here is perfect. This is my third time here and the food is always a hit. Will be back for sure. read more

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Amazing ambiance, and the food was great. They had framed old records of inmates and had them hanging on the wall. The best part of it is they kept as much of the old jail as they could when doing this remodel. read more

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Been a long while. Went with friends. Snuck in before Happy Hour ended which was nice. Our friends all got burgers. I wrote a review 5 years ago griping about them being $17. They're $25 now lol. My wife and I tried the gnocchi and the Mac. Both were really good. It seemed better than years ago and our server Jade was just great. So it's a little pricey but good and we'll go back. The setting of course is fun with the whole jail vibe! read more

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Went there for a birthday dinner yesterday. Excellent service and food. We were greeted right away and taken to our table (had reservations). Ordered: Appetizers: Beet Salad and Deconstructed Bruschetta. Dinner: Mushroom Gnocchi, and side order of Garlic Mashed potatoes and Crispy Brussels Sprouts. Everything was so good but the Bruschetta and Gnocchi were exceptional. The service was very very good as well. Will definitely be back. read more

Not what I expected. Really like the vibe. The fish and chips were excellent. The burger was okay. Our waitress was awesome although I missed hearing all of the specials. She was very attentive and made great drink recommendations. Will definitely go back! read more

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I have been to this place a few times. I love downtown Sanford area. And this place has great food and drinks and ambiance. The service was good as well. read more

The Old Jailhouse - Delicious drinks! - New American Near Me - Sanford, Florida