Chesapeake

VA
Average Sales Price
$522,022
Median Sales Price
$488,312
Population
225,813
Total Listings
1,170
Discover Life in Chesapeake with Serenity McCoy
Local Perspective
If I were walking a client through Chesapeake, I’d point out how this city truly captures the best of Hampton Roads living—balancing easy suburban comfort with meaningful connections to nature and community. Chesapeake often appeals to those who want a little more breathing room compared to Norfolk or Virginia Beach, but still want to stay close to the action. In my experience, Chesapeake’s neighborhoods offer a sense of stability and pride of ownership that’s hard to miss. Whether you’re looking for a family-friendly enclave, a peaceful retreat, or a spot that’s convenient for commuting, I often recommend Chesapeake because it delivers a lifestyle that feels both grounded and welcoming.
Neighborhood Highlights
Chesapeake has a distinctive, relaxed atmosphere—think tree-lined streets, well-kept parks, and a real sense of community. The area is known for its blend of established neighborhoods and newer developments, each with its own unique charm. You’ll find pockets that are lively and social, especially near shopping and dining hubs, while other corners are quiet and tucked away, perfect for those who value privacy. What sets Chesapeake apart is how it combines natural beauty—like the Great Dismal Swamp and scenic waterways—with the conveniences of modern suburban life. It’s a place where neighbors wave hello, kids play outside, and local events bring people together.
Homes & Architecture
Most homes in Chesapeake are single-family properties, ranging from classic brick colonials and traditional ranches to more contemporary craftsman and transitional styles. You’ll also spot some well-designed townhomes and the occasional condo, especially closer to the city’s commercial centers. Many neighborhoods feature spacious lots, mature landscaping, and thoughtful layouts—open-concept living spaces, inviting porches, and plenty of natural light are common. The age of homes varies, with established communities dating back several decades and newer subdivisions offering modern amenities and energy-efficient designs.

Demographics

Data provided by Attom Data
Population
Employment
Population
225.8K
225.8K in 2020
Density
633.2
per square mile
Households
80.7K
38 With Children
Gender
49% / 51%
Men Vs Women
Occupancy
73% / 27%
Owned Vs Rented
Age Median: -- Years
No Data
Education Level
No Data

Educational Environment

Elementary Schools (59)Middle Schools (20)High Schools (14)
Name
Category
Grades
Library
Ratio
9/10
Butts Road Intermediate School
1571 Mount Pleasant Rd, Chesapeake, VA 23322
Public
3 - 5
No
17:1 STUDENTS/TEACHERS
8/10
Great Bridge Intermediate School
253 Hanbury Rd W, Chesapeake, VA 23322
Public
3 - 5
No
20:1 STUDENTS/TEACHERS
8/10
Southeastern Elementary School
1853 Battlefield Blvd S, Chesapeake, VA 23322
Public
PK - 5
No
19:1 STUDENTS/TEACHERS
8/10
Grassfield Elementary School
2248 Averill Dr, Chesapeake, VA 23323
Public
PK - 5
No
23:1 STUDENTS/TEACHERS
7/10
Cedar Road Elementary School
1605 Cedar Rd, Chesapeake, VA 23322
Public
PK - 5
No
20:1 STUDENTS/TEACHERS
Name
Category
Grades
Library
Ratio
9/10
Hickory Middle School
1997 Hawk Blvd, Chesapeake, VA 23322
Public
6 - 8
No
14:1 STUDENTS/TEACHERS
8/10
Great Bridge Middle School
441 Battlefield Blvd S, Chesapeake, VA 23322
Public
6 - 8
No
17:1 STUDENTS/TEACHERS
7/10
Jolliff Middle School
1021 Jolliff Rd, Chesapeake, VA 23321
Public
6 - 8
No
14:1 STUDENTS/TEACHERS
7/10
Hugo A. Owens Middle School
1997 Horseback Run, Chesapeake, VA 23323
Public
6 - 8
No
14:1 STUDENTS/TEACHERS
6/10
Crestwood Middle School
1420 Great Bridge Blvd, Chesapeake, VA 23320
Public
6 - 8
No
13:1 STUDENTS/TEACHERS
Name
Category
Grades
Library
Ratio
9/10
Grassfield High School
2007 Grizzly Trl, Chesapeake, VA 23323
Public
9 - 12
No
16:1 STUDENTS/TEACHERS
8/10
Great Bridge High School
301 Hanbury Rd W, Chesapeake, VA 23322
Public
9 - 12
No
15:1 STUDENTS/TEACHERS
8/10
Hickory High School
1996 Hawk Blvd, Chesapeake, VA 23322
Public
9 - 12
No
15:1 STUDENTS/TEACHERS
7/10
Western Branch High School
1968 Bruin Pl, Chesapeake, VA 23321
Public
9 - 12
No
17:1 STUDENTS/TEACHERS
6/10
Indian River High School
1969 Braves Trl, Chesapeake, VA 23325
Public
9 - 12
No
16:1 STUDENTS/TEACHERS
Show More

Amenities & Attractions

Restaurants
Home Services
Health & Medical
Local Services
Shopping
Recreation
Arts & Entertainment
Food
Beauty
Nightlife
Event Planning & Services
Automotive
Religious Organizations
Financial Services
Professional Services
Travel
Education
Pets
  • Maxwell’s Tavern

    401 Cedar Commons Dr, Chesapeake, VA 23322

    American (Traditional) Phone: 757-436-5554

  • Chick-fil-A

    4204 Portsmouth Blvd, Chesapeake, VA 23321

    Fast Food Phone: 757-465-8138

  • Chen’s Garden Restaurant

    1800 Liberty St Ste 102, Chesapeake, VA 23324

    Phone: 757-543-4948

  • KFC

    139 Battlefield Blvd. S, Chesapeake, VA 23322

    Chicken Wings Phone: 757-482-2088

  • Pizza Hut

    1620 Cedar Rd, Chesapeake, VA 23322

    Pizza Phone: 757-382-4886

  • Burger King

    2100 Starmount Pkwy, Chesapeake, VA 23321

    Burgers Phone: 757-488-3745

  • Waffle World

    3254 Western Branch Blvd, Chesapeake, VA 23321

    American (New) Phone: 757-484-1984

  • Sonic Drive-In

    1600 Cedar Rd, Chesapeake, VA 23322

    Fast Food Phone: 757-410-2947

  • MIkado Japanese & Thai Restaurant

    1249 Cedar Rd, Chesapeake, VA 23322

    Thai Phone: 757-842-6488

  • Pro-Restaurant Greenbrier

    1220 Greenbrier Pkwy, Chesapeake, VA 23320

    Phone: 757-436-0460

  • Pizza Hut

    801 Volvo Pkwy Ste 102, Chesapeake, VA 23320

    Chicken Wings Phone: 757-548-7777

  • Crazy Buffet & Grill

    1745 Parkview Dr, Chesapeake, VA 23320

    Chinese Phone: 757-233-6838

  • Wendy’s

    1410 Kempsville Road, Chesapeake, VA 23320

    Fast Food Phone: 757-436-5413

  • Plaza Azteca

    1249 Cedar Road, Chesapeake, VA 23322

    Beer, Wine & Spirits Phone: 757-549-8008

  • Chuck E Cheeses

    4445 Portsmouth Blvd, Chesapeake, VA 23321

    Pizza Phone: 757-405-9488

  • La Parrilla Mexican Grill

    1501 Cedar Rd, Chesapeake, VA 23322

    Mexican Phone: 757-548-5222

  • Great Wall Chinese Food

    1400 Kempsville Rd Ste 104, Chesapeake, VA 23320

    Chinese Phone: 757-436-3357

  • Waffle House

    4800 Portsmouth Blvd, Chesapeake, VA 23321

    Breakfast & Brunch

Featured Listings

For Sale (565)
For Sold (5049)
More

Chesapeake Living: Your Local Questions Answered

To help you make informed decisions, we've compiled answers to some of the most commonly asked questions.

What types of homes are common in Chesapeake?
Chesapeake offers a mix of single-family homes, townhouses, and some condos. You’ll find neighborhoods with newer construction as well as established communities, so there’s a variety of styles and lot sizes to fit different preferences.
How convenient is commuting from Chesapeake?
What’s the lifestyle like in Chesapeake?
How fast do homes sell in Chesapeake?
What should I know about Chesapeake schools?
Are there HOAs or extra fees in Chesapeake neighborhoods?

Get In Touch