Pros and Cons of Living in Chesapeake, VA

Pros and Cons of Moving to Chesapeake Virginia | That Fit Team

Are you thinking about making a move to Chesapeake, Virginia? Well, if so, stay tuned because we’re going to give you our six pros and two cons as it relates to Chesapeake, as well as an in-depth look what the future holds for Chesapeake real estate market. And it starts now. Hey, I’m Rachel, and this is my handsome stud, Jonathan Beasley. Welcome back to our channel. We are genuine natives to the Hampton Roads area and thoroughly enjoy educating folks all about Hampton Roads Community has to offer, as well as discussing real estate here. If you enjoyed this video, would you take a second and hit the Subscribe button below? Hit the like button That would mean a ton to us

Hey, I’m Rachel, and this is my handsome stud, Jonathan Beasley. Welcome back to our channel. We are genuine natives to the Hampton Roads area and thoroughly enjoy educating folks all about Hampton Roads Community has to offer, as well as discussing real estate here. If you enjoyed this video, would you take a second and hit the Subscribe button below? Hit the like button That would mean a ton to us. Feel free to leave comments or ask questions below, and each and every week we are going to roll out a different video because we are eager to connect with you and serve you in any way we can.


All right now, let’s get into it. So Chesapeake, while, it’s really one city. It can be divided up into like four distinct segments, so we’re going to take a very brief sort of micro look at each of those four segments, and they are Western Branch, Deep Creek, South Norfolk or Sono and South Chesapeake. And then we’ll zoom back out and sort of give you the broader pros and cons of our perspective on Chesapeake, and we’ll see what you think about what we have to say.

So just know that Chesapeake is a rather large city and the vibe and feel can vary greatly depending on what area you’re actually dialing in your focus and concentrating on. So let’s start with Western branch. It’s called Western branch for obvious reasons.

It’s in the westernmost portion of Chesapeake and it borders Suffolk on the west side. And I think on the north side and to the east is Portsmouth or Churchland and actually one of the nicer areas in Portsmouth.

Western Branch and other Segments

Western branch is sort of like a small town feel, and there are a lot of people that live there that grew up there. So that says a lot about the community itself, that people like it so much. They don’t move. But it definitely has sort of like a small town community feel. And a lot of the people know a lot of the people there, which is depending on what your perspective is, can be a really cool thing. Then there’s deep creek deep creeks, located about 20 minutes from Norfolk and Virginia Beach, and it has more of like an industrial feel. And I don’t say that is necessarily a bad thing. It’s just there’s a lot of industrial buildings. It’s an older area. It just has an old feel to it. A lot of the area was developed in like the sixties, seventies and eighties. You don’t see a lot of new development or new construction neighborhoods going up. You’ll see a lot of homes built in the seventies and eighties like that 14 to 18 hundred square foot ranch type of deal. So the cool thing is Deep Creek is pretty fair and reasonable in terms of real estate affordability. So especially depending on what your budget is if you’re looking for an entry point into owning your home. Deep Creek could present a good option for you.

South Norfolk

Then there’s South Norfolk or Sono. Oh, Sono it has some great areas and has some not great areas. I’ll just shoot it straight. It’s it has both an urban feel and sort of a historic feel. You’ll see a lot of older, you know, 120 to 150 year old Victorian homes and the area is seeing some development and gentrification. But it’s also worth noting that the high crime there is like the highest in Chesapeake. So not the whole area is riddled with crime, but Sono does have a bit of a reputation for the locals here. So the pockets of South Norfolk can vary greatly, even from street to street.

So for people that are interested in purchasing there, we just always recommend that they spend a good bit of time driving and getting a feel for what they’re comfortable with. Then there’s South Chesapeake and this is Greenbrier Great Bridge and the hickory area now. Grass field. It’s oh yes, grass field.

Think I could call my back basically one of the most in-demand areas, not only in Chesapeake, it is the most high demand area for Chesapeake and probably the first or second in the main area in all of Hampton Roads.

People just love it. It’s low crime. There’s a ton of parks, a ton of sporting facilities. The high school, actually the school’s in general rank really well because a lot of restaurants and it’s generally known as the most family friendly portion of all of Chesapeake.

Location, Location, Location

So by default, the three keys the real estate, location, location, location, this is the most in-demand location in Chesapeake, so by default it is the priciest to live there. Also boasts a lot of like sprawling land. And so if you’re looking to build, there’s a ton of options out there as well one of the reasons that we absolutely love South Chesapeake. So let’s get back to the macro view and the pros and cons. And mom always taught me when I was a boy. If you couldn’t say something nice, be vague.

You vague, don’t say anything at all. Yeah. So in this case, why don’t we start with the positives? And then we’ll loop back around to the couple of things that we may want to challenge our viewers to consider. So number one pro about Chesapeake is the quality of school districts.

Chesapeake is served by the Chesapeake Public School System, which offers education to more than 39,000 students at 45 schools, each with its own active parent teacher association and two educational centers. Students from kindergarten through 12th grade can receive a respectable education at the Chesapeake schools, which include Western Branch High School, Greenbrier Primary School, Grass Field, Middle High. Hickory Great Bridge that you just keep naming on the schools are they have a really good reputation. The district also supports its own radio station and TV station. How cool is that? And has a distinct educational facilities such as the Chesapeake Planetarium.

Beautiful Nature

Cool, right? Absolutely. Number two for me, and this was the one that I picked out with, so I’m glad I get to talk about it. It’s just beautiful, natural surroundings. Chesapeake is nestled in the heart of coastal Virginia along the intercoastal waterway, so that means you have access to roughly 22 miles of fresh and salt waterways, including the Dismal Swamp Canal, Oak Grove, Lake Drummond, which is really cool because it’s only one of two freshwater lakes and all of Virginia. And it’s I think it’s like 3000 acres. So it’s just huge is also the Elizabeth River.

So if you’re into like fishing, kayaking, paddling, canoeing, anything like that on the water. Chesapeake is for you or at least for you to consider because there is plentiful outdoor recreational opportunities. Additionally, the Great Dismal Swamp National Wildlife Refuge and Northwest River Park and Campground are great spots for walking scenic trails and catching sightings of really rare bird species. Which Why has your dad hit us up yet? Not sure. Her dad’s a total bird nerd. I hope he’s not watching. I love you. Love you too dad! We’ll get out there soon bud. The city also maintains a number of parks, including the Chesapeake City Park, home of a well known fun forest playground, which our kids have hit us up many times over the years, as well as Deep Creek Park. The Elizabeth River Park and Western Branch Park. So there’s just a ton to do outdoors in Chesapeake. Number three year round


Celebrations and festivals living in Chesapeake, Virginia is made all the richer by the city’s diverse offerings of family friendly events and festivals, which are held all throughout the year. During the summer, residents can purchase fresh, locally sourced fruits, vegetables, herbs, eggs, honey and meat from the Chesapeake Farmer’s markets. Looks like meats back on the menu boy! All the freshness there.

Chesapeake also hosts and participates in several festivals, including the Chesapeake Wine Festival. We like to enjoy Virginia Arts Festival Chesapeake Jubilee, which is a lot of fun if you like music. The Dismal Swamp Stomp Running Festival keeps us that dismal swamp stomp. It’s fun to say actually, try it. And The Great Dismal Swamp National Wildlife Refuge Bird Festival. There’s birds again

. I bet my dad goes to that, you’re not kidding haha. Why are we busted on pops. Foods man. You don’t have to be a foodie to love Chesapeake because there’s just so much to love if you’re not a foodie.

That doesn’t make any sense, but just stick in there with me. Every October, the city celebrates Chesapeake Restaurant Week, and that’s because there’s a lot to celebrate. Chesapeake dining options include more than chain restaurants and fast food. There’s a lot of local favorites, including Lock Sign, A Taste of Home Indiana Pizza, which is awesome.

I’m a sucker for Tikichi Japanese Bistro, The Courthouse Cafe, the cutting edge Cafe City Deli, and we’ll give you our three favorite places actually at the end of this video. Just know that you are not going to be disappointed with the food options in Chesapeake and number five attractions galore.

You guys, you don’t have to be an an outdoors enthusiast or a foodie to enjoy living in Chesapeake, Virginia. The city offers a number of other attractions to include two of the largest bowling alleys in the state. Kind of cool, right? The chilled ponds ice sports complex. So you can go like ice skating. They have like hockey for the kids and things like that. Chesapeake Arboretum Cloud nine Trampoline Park, which that is so much fun. I mean, you don’t have to have kids to have fun there.

I’m just saying watch the knees should be careful. Knees and ankles and toes. Greenbrier Family Skating Center and lots of other attractions. Chesapeake is known for its rich history as well and is home to top notch vintage stores. In addition to plenty other retail established and then lastly, central location. Generally speaking, Chesapeake has easy access to all the other areas at Hampton Roads.


     There is one caveat If you’re a big beachgoer and you like the oceanfront or you want to get close to the oceanfront, western branch in particular is like 35 to 40 minute drive, but everywhere else. If you’re wanting to avoid having to drive through the tunnels on a regular basis, Chesapeake is a great option because it offers a lot of pathways to avoid tunnels and the tunnel traffic. It’s also worth noting we have a huge military presence here the Hampton Roads area, and there are a variety of different military bases spread out all over the place. So if you’re active duty military and you’re PCSing to Hampton Roads, you’re definitely going to want to check out Chesapeake as an option for you. Let’s say if you’re working at the Naval Hospital or even the Coast Guard station, for example, Chesapeake is great option because you won’t have to deal with any tunnels whatsoever. However, with everything else in life, there is a give and take. So with that being said, maybe we’ll come to the first con and all of the locals are going to give us a resounding assurance that this is true.

Yeah, exactly. Con number one or one con is definitely traffic, so you have less to contend with in the way of tunnels. But depending on where you are and where you work, and particularly if you’re in the military going to those bases, you’re going to have a commute probably up about average of 30 minutes.

And that’s not for everybody. As locals, you’re going to know that we get used to it here. And personally, I actually really enjoy a little bit of a commute. I listen to podcasts, I listen to books while I’m driving. So, you know, I kind of I don’t mind it. Con number two is going to be the nightlife. Or should I say the lack thereof? There’s just not you’re never going to hear someone come up to you and be like, Dude, you got to come to Chesapeake it rocks.

Lack of Night Life

The parties are amazing, like, that’s not, you’re not going to hear that. Chesapeake Yeah, we love you. But that ain’t the gig. So if you’re super into the nightlife, just know that you’re going to be going to either Norfolk or Virginia Beach to scratch that itch. It just doesn’t have a ton to offer in that regard, but as we’ve mentioned before, has a ton of other stuff. So now how about we get into the cool part in our area of expertize, which is real estate?

Real Estate

Let’s do that one for the median list price of homes in Chesapeake. As of now, it’s $324,000, so trending up about 10.2% year over year. Yeah, the current median listing price per square foot is $167 a foot. So think about it this way. There are 27 neighborhoods in Chesapeake, Edinburgh, which is the most expensive area. It has a listing average of $1.3 million, makes it the most expensive neighborhood in Chesapeake Stonebridge Landing, which is close to Chesapeake Square Mall in the Western branch area.

It’s the most affordable neighborhood, with a median list price of $195,000, so you see sort of a broad spectrum in a wide range of price range and really options in Chesapeake. Everything from small ranch houses to is, you know, 25 acres, 7000 square foot of all that you want. Median days on market is still under 30 days, and as of this video, demand has not slowed down and even appears to still be pushing appreciation and prices higher. More than 50% of the homes listed that actively list go to contract above asking price.

So as long as demand continues to outweigh supply in this regard and short of global or national economic disaster, we are extremely bullish on Chesapeake because supply simply cannot keep up with demand and the reputation overall is really good.

Favorite Restaurants

The residents absolutely enjoy living there. So now let’s get into our favorite eateries, and I’m kind of excited because you have a unique one to suggest, Oh yes, you’ve got to try out Ang’s Sushi Bistro.

When you’re in the Chesapeake Bay Area, it stands to reason you’re going to want some seafood, right? And when you’re eating fish or sushi, particularly raw, it better be the freshest around. And that’s what you get when you head over to Ang’s sushi bistro, where you’ll find various sushi rolls and all of their cuts of fish are fresh and offer traditional Asian salads and amazing noodle dishes.

You can’t miss out with this place and you’ve got to check it out. That’s pretty good commercial. I should pay you for that. They really should. Number two is Burrito Perdido Rachel and I are always obsessed with Mexican. So it’s like, expect the Mexican recommendation for any local video. The whole thing with burrito Perdido is that they don’t own a can opener, and you will find a sign on the wall that reminds you of this fact. Everything there is homemade, fresh every day with the most local and organic ingredients available when you order from this Mexican hotspot. You know what you’re getting was made just for you. The tacos here are super amazing, which is why people drive from all over the area, all over Virginia Beach and Norfolk.

They come here to dine on the Mexican food. Highly recommend four and a half on Yelp as well. Go there. All right, number three. Last, but not least, is the Egg Bistro. So we love this place, and I have to say I really like brunch foods and they have amazing breakfast foods there.

They have a full bar. So, you know, if you want a day drink and have a good time, you could do that too. But they also serve lunch and they serve dinner as well. It’s a really amazing restaurant. Their food is like always on point. Their waist staff is also super sweet all the time. So like if you want to see good people, just go there. I’m Jonathan Beasley. This is Rachel. We hope you enjoyed this video.

We are That Fit Team professionals in real estate and passionate about people. We’ll see you next week.

Connect With Us!

If you're looking to buy or sell a property connect with us today!

How Can We Help You?

We would love to hear from you! Please fill out this form and we will get in touch with you shortly.
    (check all that apply)
  • This field is for validation purposes and should be left unchanged.

Leave a Reply

Your email address will not be published. Required fields are marked *