A natural harbor makes for one of the best ports on the East Coast, and shipping and shipbuilding activity along with fishing and seaport-related commerce. With this level of access to all types of water (ocean, bays, Inter-coastal, rivers, swamp), it could turn any landlubber into a water-lover overnight. The military plays a huge part in life here – It is the number 2 destination in the county for military retiree’s. Many places claim to be “a family,” but Chesapeake might win the prize. Because of its maritime and military background – and location, generations run very deep in the area.

Being coastal is both amazing and, at times, frustrating – navigating the streets, roads, and highways in and around the area requires crossing several bridges and tunnels, and without a metro rail and limited mass transit, this makes for very unpredictable travel times. As the military decommission bases, the installations and surrounding neighborhoods in some situations have become neglected. Business opportunities are tilted heavily toward government and related business. This could also be seen as a good thing if you work for the government. 

We highly recommend visiting Chesapeake and staying in the community in a [**VRBO**](vrbo.com/affiliate/p4JS4ZC) rather than a hotel to get a feel for what it's like to live among the locals. You can receive discounted fares on travel via our [**partnership with Expedia**](expedia.com/affiliate/9NZ8LBQ) as well. 


Beach and coastal paradise.

LookyLOO Review of Chesapeake

Chesapeake is roughly divided into 4 area’s – in 3 of the four, Western Branch, Deep Creek and  Greenbrier, single family homes, of varying lot sizes, dominate. Most have front and backyards which play a big part of living here.  

The South Norfolk neighborhood (officially part of the city of Chesapeake) has been undergoing a transformation and is emerging as a more urban area featuring a mix of revitalized loft spaces, row houses and a few eclectic shops and cafés. This area is unique compared to other neighborhoods, which tend to have a feel of the suburbs.  Most of the city retail zones are mall-like/big box. The restaurants are a mix of fast-casual, national or regional chains. With entertainment and dining options somewhat limited you may need to be prepared to make your own fun and dinner.


Lifestyle of Chesapeake

Compared to many East Coast seaside cities Chesapeake remains relatively undiscovered. It is easily possible to find great real estate value pockets on classic southern homes. The sense of community is apparent in every nook and cranny of the area. People here are very friendly. And if you strike up a conversation about boating or the Navy you may be in for a nice long chat.  The pace is not brisk which suits the local’s just fine. 


Discovery

Why You Should Move Here Now?

**Vert354**
10mo ago
🦉🦉🦉🦉

Can't go wrong with Chesapeake Schools, (VB's are alright too I guess ;)

As for where you choose to live in Chesapeake a lot depends on your appetite for commuting and what you're looking for in a property.

If you want lots of land you'll need to look at the southern part of the city (Hickory, Ballahack, Fentress). However if you live south of the intercoastal waterway, you (and everyone else) will need to cross it to get to the major employment centers. There's a finite number of crossings so when one goes out the whole system can't grind to a halt (happened this last summer when some jag-off hit one of the bridges with a barge)

Western Branch, Deep Creek, and Great Bridge are pretty much pure suburban and will stay that way for the foreseeable future. (Not that there won't be development, but it will stay suburban) So look there for that lifestyle

South Norfolk and Indian River are built on urban street grids but are suburban density. South Norfolk is the historic center of the city (a large part of it is on the historic register, so if you own one of those homes you've got to get special permits to make changes) The presence of industry along the river and railroads peppered throughout can make it less desirable, but the city has been pushing for urban renewal, especially around Poindexter St.

For more reviews of what living in Chesapeake is like from locals, check out [The Reviews](https://lookyloomove.com/locations/chesapeake/reviews).

Reviews of Chesapeake from Locals

**The Best Thing About Chesapeake?**  Beach and coastal paradise.  

A natural harbor makes for one of the best ports on the East Coast, and shipping and shipbuilding activity along with fishing and seaport-related commerce. With this level of access to all types of water (ocean, bays, Inter-coastal, rivers, swamp) it could turn any landlubber into a water-lover overnight. The military plays a huge part in life here – It is the number 2 destination in the county for military retiree’s. Many places claim to be “a family” but Chesapeake might actually win the prize. Because of its maritime and military background – and location, generations run very deep in the area. 


**The Worst Thing About Chesapeake?**

Being coastal is both amazing and at times frustrating – navigating the streets, roads and highway in and around the area requires crossing several bridges and tunnels and without a metro rail and limited mass transit this makes for very unpredictable travel times. As the military decommissions base’s the former installations and surrounding neighborhoods in some situation have become neglected. 
Business opportunities are tilted heavily to government and related business. This could also be seen as a good thing if you like working for the government.  
Not much of a concert scene and limited nightlife. 


**How You Living?**

Chesapeake is broadly divided into 4 area’s – in 3 of the four, Western Branch, Deep Creek and  Greenbrier, single family homes, of varying lots sizes, dominate. Most have front and backyards which play a big part of living here.  The South Norfolk neighborhood (officially part of the city of Chesapeake) has been undergoing a transformation and is emerging as a more urban area featuring a mix of revitalized loft spaces, row houses and a few eclectic shops and cafés. This area is unique compared to other neighborhoods, which tend to have a feel of the suburbs.  Most of the city retail zones are mall-like/big box. The restaurants are a mix of fast-casual, national or regional chains. With entertainment and dining options somewhat limited you may need to be prepared to make your own fun and dinner.


**Why You Should Move Here Now?**  Discovery

Compared to many East Coast seaside cities Chesapeake remains relatively undiscovered. It is easily possible to find great real estate value pockets on classic southern homes. The sense of community is apparent in every nook and cranny of the area. People here are very friendly. And if you strike up a conversation about boating or the Navy you may be in for a nice long chat.  The pace is not brisk which suits the local’s just fine. 


Historic South Norfolk is the closest thing to a young professional in Chesapeake. Redevelopment projects, those in the past and those planned make it an increasingly cool spot for youngsters as a result of newer loft apartments and condos, office and retail space, and planned commercial district. Chesapeake is largely suburban so this is your best bet if are looking for on area on the rise for youngsters. 
- Historic South Norfolk 


Young Professionals

Dock Landing is a riverfront neighborhood with beautiful old trees, great homes and yards,  and an enclosed safe feeling due to the single entrance to the streets. Most of the homes have pools for relieving the heat in summer and giving the kiddos a cool place to play. Good schools and again, plenty of yards and greenery to outdoor activities. Western Branch is another great choice. Home to some of the most highly-ranked schools in the state and beautiful homes near the water. The area also has access to great shopping, making it easy for families to stay stocked up on a daily basis. 
Dock Landing
- Western Branch
- Greenbrier
- Forest Lakes
- Summer Park 


Families

Chesapeake is a great spot for retiring as long as you don’t mind your primary commercial and social activities coming from neighboring Norfolk and Virginia Beach. Chesapeake is really a suburban city but one with beautiful green spaces, neighborhoods, and retirement communities. The planned communities that rise to the top include: Lighthouse Pointe and The Reserve at Greenbrier and a great neighborhood option in South Norfolk. In addition to luxury living options it also is home to an amazing medical complex in Sentara Norfolk General Hospital. 
- South Norfolk
- Lighthouse Pointe
- The Reserve


Retirees

Chesapeake

**Vert354**
10mo ago
🦉🦉🦉🦉

Can't go wrong with Chesapeake Schools, (VB's are alright too I guess ;)

As for where you choose to live in Chesapeake a lot depends on your appetite for commuting and what you're looking for in a property.

If you want lots of land you'll need to look at the southern part of the city (Hickory, Ballahack, Fentress). However if you live south of the intercoastal waterway, you (and everyone else) will need to cross it to get to the major employment centers. There's a finite number of crossings so when one goes out the whole system can't grind to a halt (happened this last summer when some jag-off hit one of the bridges with a barge)

Western Branch, Deep Creek, and Great Bridge are pretty much pure suburban and will stay that way for the foreseeable future. (Not that there won't be development, but it will stay suburban) So look there for that lifestyle

South Norfolk and Indian River are built on urban street grids but are suburban density. South Norfolk is the historic center of the city (a large part of it is on the historic register, so if you own one of those homes you've got to get special permits to make changes) The presence of industry along the river and railroads peppered throughout can make it less desirable, but the city has been pushing for urban renewal, especially around Pointexter St.

**jamieboy05**
2y ago
🦉🦉🦉🦉

My husband accepted a job in Chesapeake in Oct 2020 and his company relocated us to VB in Nov 2020. We relocated from the Midwest. It was single handedly the hardest decision we have ever made in our lives. His family is from Chicago and and mine is from the just north of Houston. We both grew up in the Midwest all our lives and it was difficult leaving them behind.

That being said… DO IT! TAKE THE PLUNGE!!!! It was the best decision we ever made. No Hampton Roads is not as big as DFW area. But we have everything Dallas has here in Virginia Beach, just a smaller footprint. The beach’s are clean and there is so much history in your back yard. Virginia Beach schools are good as well. One thing that’s unique about VB is they have an Out of Zone process that allows children to remain in the same school if they happen to move zones There is some paperwork to fill out, but that stood out to me when looking into schools.

There are tons of family oriented things to do. Busch Gardens is about 50 minutes away in Williamsburg and there’s tons of things going on at Oceanfront during the on season. There’s a small aquarium. If your wanting a quieter beach to go than Ocean Front, I recommend checking out other local beaches like ocean view. Much quieter more locals. People are friendly here as a whole, and tend to keep to themselves. The job market, especially for middle class incomes is competitive and there are plenty of openings.

**Significant-Plenty51**
7mo ago
🦉🦉

Ok here is a history lesson, Chesapeake, Va Beach, and Suffolk only exist to tame Norfolk & Portsmouth growth. Norfolk & Portsmouth both have downtowns and traditional built neighborhoods. Yes Portsmouth has a downtown the 2nd best in Hampton Roads by a long shot. I digress, during the 1960s, the counties of South Hampton Roads didn't want to be annexed by Norfolk and Portsmouth. So the state basically passed laws that wouldn't allow any city to annex another city initially, so the beach town of Virginia Beach merged with Princess Anne County making the city of VA Beach. Chesapeake is in the same situation, the city of South Norfolk merging with Norfolk County. The funny thing is Chesapeake had a downtown in South Norfolk, but Chesapeake also didn't invest into South Norfolk because it was a majority black area. All in all a lot of racist things happened that even allowed these cities to come into being. The real eff up thing about Hampton Roads is our suburban cities have done nothing to drive culture, or help the region economically. As you've mentioned Chesapeake has nothing that helps the area economy it's just an area where tax money is held hostage behind city lines,same as Virginia Beach, and Suffolk. Can you believe Hampton Roads had 200,000 less people than NoVa in 1990. Hampton Roads was bigger than Raleigh, Charlotte, and Nashville. Within the last 30 years our area has barely grown. NoVa now has close to 4 million, and all those other metros are as big or bigger than ours. That should put into perspective how eff up Hampton Roads and its cities are.

**Obizzle9**
7mo ago
🦉🦉

Chesapeake has a large city planning meeting scheduled for the 22nd. I personally believe they are going to address some of the issues/ comments mentioned here. I feel that if Chesapeake wants to make a plan to move forward in building “up” it starts with Greenbrier. There is so much wasted space that the city has self imposed over the years. The major plans I’d recommend:

Walking/ bike access: Wholeheartedly I despise bike lanes, and that is not my suggestion (just to get that out of the way). However Chesapeake does have a number of great ways to make the city more accessible for pedestrians and for cyclists. An extended greenway from S Battlefield to the convention center could be a great start. A natural path already exists near the railway and additional trails would not be conceivably difficult to build. One example of an extension could be to Stumpy Lake. Utilizing the City Park as the “hub” would make for a happier and enticing environment, imho.

Greenbrier Mall: We need not say more, the Mall is failing and presumably close to shuttering its doors in the next two to five years, if not sooner. My suggestion is to capitalize on not only the land here but the situation found in Norfolk. The Scope is also failing with the city spending far more than it’s worth to keep the place afloat. If Chesapeake was smart they would build an entertainment district complete with stadium. Capacity would depend on anticipated venues, however hockey seems to be constant so no less than 7500 likely 10k to target. If they wanted to drive Scope entirely out of business they could build a small theater to accommodate the theater crowd as well. Plenty of bars, restaurants, and spit use property, similar to what is on Volvo. While I think this would be a huge win for Chesapeake I don’t think it will ever happen.

Infrastructure: Yikes, where to begin. While not necessarily every major artery is bad, most seem to have their problems. When I drive through Chesapeake I notice that the planning is almost nonexistent or comically bad. I mean is it possible that everything was an afterthought? At a certain point someone had to realize this city wasn’t getting any smaller, in fact it’s still growing despite 7% interest rates. A major traffic survey needs to be completed and identify the areas where the problem is worst. In some areas I doubt much, if anything, can be done but it’s worth analyzing the data and coming up with a solution.

Chesapeake, Virginia

One Increasing Purpose

Looklyloo Score: 89