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.

Beach and coastal paradise.

The Best 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 bases the installations and surrounding neighborhoods in some situations 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.  


The Worst Thing About 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?

**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

**What are the downsides of living in Chesapeake, VA?**

Chesapeake is a thriving city. But it is such a large area that most people don’t realize it borders 4 other great cities. We are surrounded by many waterways that require bridges or tunnels to connect the cities. On one side of Chesapeake borders Virginia Beach andNorfolk, on the far side it borders Suffolk and Portsmouth . The economy grows because of the influx of Military, shipping commerce, shipyards and tourism. The housing market is reasonable and jobs are abundant. I live here in Chesapeake and I am always amazed at council men and women that share a similar view of growth and quality of life for the residents.

**What are the downsides of living in Chesapeake, VA?**

I wonder about the phrasing of the question. Every locality has good points and bad points, good neighborhoods and bad neighborhoods. So why ask just for a town’s downsides? I am qualified to respond because I grew up in Norfolk County, which joined the city of South Norfolk to become Chesapeake in 1963. I have lived there 1944–1967, 1985-2000 and 2005–2017.

Chesapeake has excellent schools, well-maintained local streets (albeit carrying more traffic every day), competent fire and police departments. City utilities such as water, refuse collection, sewers, parks/recreation run smoothly.

Downside #1. Chesapeake is a bedroom suburb with little specific, memorable, remarkable sites.

Downside #2. Despite Chesapeake being blessed with a portion of the Intracoastal Waterway, the city is just realizing its potential. Boaters traveling between New York and Florida get to experience much of the city. We can take down the ‘downside’ when Chesapeake finishes a boating welcoming facility.

Downside #3. Tourists traveling to Norfolk or Virginia Beach or to the Outer Banks of North Carolina barely notice the place.

Downside #4. City fathers have hiked the tolls on the Chesapeake Expressway so high that Nags Head rental agents publish maps for their customers to dodge the toll road.

Downside #5. Police with radar patrol the highway 24/7. One morbidly obese cop issues so many tickets, he has his own judge to hear his cases.

Downside #6. Chesapeake is just one of half-dozen cities who have never learned how to work or play together. Petty jealousy and competition for new industry pits one city against the other. The Chesapeake region is notable for its seafood, especially its crabs. Yet, like a crab struggling to climb out of its basket, the other crabs drag him back down. So it goes with Chesapeake’s mortal enemies: Suffolk, Norfolk, Virginia Beach and a plethora of towns across the James River doing the same.

**What advice would you give to someone who is moving to Chesapeake, VA?**

Chesapeake is one of several cities in the southern section of what is called Hampton Roads and includes the neighboring cities of Virginia Beach, Norfolk, Portsmouth & Suffolk. This area was previously known as “Tidewater” but regional leaders decided it needed a better identity about 15-20 years ago. Many old-timers still refer to it as “Tidewater”. A new push is on by some to identify the area as “Coastal Virginia/COVA”. Chesapeake is currently the 3rd most populous city in Virginia but is projected to be #2 in less than 5 years (Virginia Beach is #1 and Norfolk is #2). Chesapeake is essentially a bedroom community and it is best to think of the region rather than the individual cities, although each city has it similarities & differences as well as good and bad parts. Virginia Beach seems to have the edge in the recreational area and of course has the beach-front with an active restaurant scene, large outdoor amphitheater (that attracts big-name entertainment), Sandler Arena/Concert Hall, Marine Aquarium, Military Aviation Museum and a lot of businesses & shopping. Norfolk also has a lot of businesses, a downtown restaurant scene with a newly renovated waterfront area called Waterside, a trendy area called Ghent, the Wells Theater (plays), the Norva theater (touring bands), Scope Arena (pro hockey, sports, music), the Chrysler Art Museum, the Virginia Zoo, Old Dominion University (with Division 1 football & basketball and an arena for sports & concerts), Norfolk State University, Harbor Park (AAA baseball), airport, and the largest naval base in the world. Portsmouth also has an outdoor concert pavilion and a quaint area called Old Town. Several cities have little theaters and touring Broadway shows come to the larger venues. The area also has opera and a symphony.

It would be helpful to know why you are coming here and what your interests are. Chesapeake is known for excellent schools (for the most part), quiet & safe neighborhoods, youth sports, affordable housing, low crime and is generally considered a good place for families. Although it has its share of restaurants and some recreational facilities, that is not what it is known for. Recreation/dining in neighboring cities is close and usually easy to get to, but because we have lots of water, we have lots of bridges & tunnels that are often congested and unpredictable and some charge tolls (a growing trend in this area). Traffic can sometimes be an issue, especially at “rush hours”. Like any other city, Chesapeake has good & bad areas so you need to do your homework, but in general, it is a good place to live. There is a reason why it is a fast growing city. If you are commuting to a job, location is especially important and being on the “right” side of a bridge and/or tunnel makes a lot of sense.

**Life in Chesapeake
I've been offered a job here. Could you give me some idea about what it's like to live in this area?**

Chesapeake is a big city. And by big I mean land mass. What area of Chesapeake are you working in and where are you thinking about living? I'd recommend avoiding any bridges in your commute (we've had three get stuck while opening recently & the High Rise I64 Bridge starts construction this year).

You should be able to find a decent apartment in the $1000-$1200 range pretty much anywhere.

Chesapeake is considered to be a bedroom community so if you're looking for nightlife you'll likely head to Virginia Beach (Town Center & the Oceanfront) or Norfolk (Downtown & Ghent). Dollar Tree is expanding their HQ & developing a mixed use area called Summit Pointe but that is still very early in the construction process. There are plenty of parks with trails & kayaking/canoeing.

If you haven't already, check out r/Norfolk. It's a substantially more active sub.

Chesapeake, Virginia

One Increasing Purpose

Looklyloo Score: 74

Young Professionals

Families

Retirees