5 bedroom homes for sale in Chesapeake, VA

1 day on Rocket

$8,194 Closing Credit¹

$690,000

5 beds • 3.5 baths • 2,763 sqft

637 Middleton Way, Chesapeake, VA 23322

#10587695, Allen Harris, Listing office: Own Real Estate LLC

1 day on Rocket

$7,361 Closing Credit¹

$619,900

5 beds • 3 baths • 2,620 sqft

1212 Madeline Ryan Way, Chesapeake, VA 23322

#10587427, Ryan MacFarland, Listing office: Atlantic Sothebys Int'l Realty

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1 day on Rocket

$9,797 Closing Credit¹

$825,000

5 beds • 3.5 baths • 3,220 sqft

903 Aberdeen Ln, Chesapeake, VA 23322

#10587535, Laura Rowe, Listing office: EXP Realty LLC

2 days on Rocket

$7,719 Closing Credit¹

$650,000

5 beds • 3 baths • 2,972 sqft

517 Taryn Ct, Chesapeake, VA 23320

#10587536, Casey Preston, Listing office: KW Coastal Virginia Chesapeake

2 days on Rocket

$10,000 Closing Credit¹

$1,779,000

5 beds • 3.5 baths • 3,727 sqft

2801 Ballahack Rd, Chesapeake, VA 23322

#10587355, Donna Johnson, Listing office: Long & Foster Real Estate Inc.

2 days on Rocket

$10,000 Closing Credit¹

$924,900

5 beds • 3.5 baths • 3,730 sqft

1616 Sanderson Rd, Chesapeake, VA 23322

#10587325, Deana Renn, Listing office: AtCoastal Realty

5 days on Rocket

$7,125 Closing Credit¹

$600,000

5 beds • 3.5 baths • 3,070 sqft

624 Mill Creek Pkwy, Chesapeake, VA 23323

#10587264, Natalie Barrera, Listing office: Iron Valley Real Est Norfolk

Room to negotiate?

Median Sold Price

$338.5K

Avg. Sale Time

27 Days

Based on our May 2025 Market Report.

5 days on Rocket

$10,000 Closing Credit¹

$910,000

5 beds • 4 baths • 4,266 sqft

1208 Masters Row, Chesapeake, VA 23320

#10587205, Fred Helm, Listing office: BHHS RW Towne Realty

5 days on Rocket

$7,244 Closing Credit¹

$610,000

5 beds • 2.5 baths • 2,748 sqft

605 Robert Frost Rd, Chesapeake, VA 23323

#10587214, Johnna Hughes, Listing office: ONYX Realty Professionals LLC

5 days on Rocket

$6,411 Closing Credit¹

$539,900

5 beds • 3 baths • 2,505 sqft

729 Remington Dr, Chesapeake, VA 23322

#10586382, Rachael Turner, Listing office: GreenTree Realty Inc

5 days on Rocket

$7,006 Closing Credit¹

$590,000

5 beds • 3.5 baths • 3,309 sqft

2820 Crossings Dr, Chesapeake, VA 23321

#10587113, Christine Burgdorf, Listing office: Creed Realty

5 days on Rocket

$6,769 Closing Credit¹

$569,999

5 beds • 2.5 baths • 2,496 sqft

2519 Deals Creek Ct, Chesapeake, VA 23323

#10587079, Michael Daugherty, Listing office: Own Real Estate LLC

6 days on Rocket

$6,650 Closing Credit¹

$560,000

5 beds • 2.5 baths • 2,958 sqft

405 Bartell Dr, Chesapeake, VA 23322

#10586894, Rhonda Rockefeller, Listing office: The Real Estate Group

6 days on Rocket

$7,719 Closing Credit¹

$650,000

5 beds • 2.5 baths • 2,851 sqft

805 Lakeside Ct, Chesapeake, VA 23322

#10586835, Betsy Thompson, Listing office: The Agency

6 days on Rocket

$9,084 Closing Credit¹

$765,000

5 beds • 3 baths • 4,100 sqft

1001 Fairway Ct, Chesapeake, VA 23320

#10586551, Sheri Pynn, Listing office: Creed Realty

7 days on Rocket

$8,253 Closing Credit¹

$695,000

5 beds • 2.5 baths • 3,134 sqft

2209 Beeblossom Ln, Chesapeake, VA 23323

#10586457, Dani Brinson, Listing office: KW Coastal Virginia Chesapeake

7 days on Rocket

$8,301 Closing Credit¹

$699,000

5 beds • 4.5 baths • 4,100 sqft

4208 Mckenna Close Close, Chesapeake, VA 23321

#10586700, Heather Bass, Listing office: BHHS RW Towne Realty

7 days on RocketTour

$9,144 Closing Credit¹

$769,990

5 beds • 4 baths • 3,524 sqft

1236 Kidbrooke St, Chesapeake, VA 23322

#10586613, Victoria Clark, Listing office: D R Horton Realty of Virginia

7 days on RocketTour

$8,871 Closing Credit¹

$746,990

5 beds • 3.5 baths • 3,071 sqft

1228 Kidbrooke St, Chesapeake, VA 23322

#10586607, Victoria Clark, Listing office: D R Horton Realty of Virginia

7 days on Rocket

$7,303 Closing Credit¹

$614,990

5 beds • 3 baths • 2,718 sqft

1512 Bogue St, Chesapeake, VA 23322

#10586581, Jenny Lovell, Listing office: BHHS RW Towne Realty

7 days on Rocket

$8,194 Closing Credit¹

$689,990

5 beds • 3 baths • 3,606 sqft

1512 Charlie St, Chesapeake, VA 23322

#10586574, Jenny Lovell, Listing office: BHHS RW Towne Realty

$6,650 Closing Credit¹

$560,000

5 beds • 2.5 baths • 2,550 sqft

709 Creekwood Dr, Chesapeake, VA 23323

#10586514, Frankie Johnson, Listing office: KW Coastal Virginia Chesapeake

$8,776 Closing Credit¹

$739,000

5 beds • 3.5 baths • 2,850 sqft

813 Dawson Cir, Chesapeake, VA 23322

#10586451, Christopher Kostyrka, Listing office: RE/MAX Connect

$5,807 Closing Credit¹

$489,000

5 beds • 3 baths • 2,541 sqft

4901 Lake Shore Dr, Chesapeake, VA 23321

#10586417, Maria Smoot, Listing office: The Real Estate Group

$7,719 Closing Credit¹

$650,000

5 beds • 2.5 baths • 3,287 sqft

901 Mustoe Ct, Chesapeake, VA 23322

#10585868, Kathy Fink, Listing office: BHHS RW Towne Realty

$7,838 Closing Credit¹

$660,000

5 beds • 3 baths • 2,924 sqft

1025 Sullivan Ln, Chesapeake, VA 23322

#10585730, Stormy Grover, Listing office: BHHS RW Towne Realty

$10,000 Closing Credit¹

$1,270,000

5 beds • 3.5 baths • 4,110 sqft

3527 Glencoe Ct, Chesapeake, VA 23322

#10585600, Tyler Shelton, Listing office: RE/MAX Allegiance

$8,430 Closing Credit¹

$709,900

5 beds • 3.5 baths • 2,763 sqft

1922 Briton Ln, Chesapeake, VA 23322

#10585593, Daniel Whalen, Listing office: EXP Realty LLC

$7,956 Closing Credit¹

$670,000

5 beds • 2.5 baths • 2,705 sqft

921 Justin Lee Way, Chesapeake, VA 23322

#10585419, Natalie Stamey, Listing office: The Real Estate Group

$7,897 Closing Credit¹

$664,990

5 beds • 3 baths • 3,010 sqft

1505 Bogue St, Chesapeake, VA 23322

#10585478, Jenny Lovell, Listing office: BHHS RW Towne Realty

$8,312 Closing Credit¹

$699,990

5 beds • 4 baths • 3,656 sqft

1501 Bogue St, Chesapeake, VA 23322

#10585481, Jenny Lovell, Listing office: BHHS RW Towne Realty

Tour

$8,716 Closing Credit¹

$733,990

5 beds • 4 baths • 3,165 sqft

1227 Kidbrooke St, Chesapeake, VA 23322

#10585517, Victoria Clark, Listing office: D R Horton Realty of Virginia

$8,182 Closing Credit¹

$689,000

5 beds • 3 baths • 2,734 sqft

1809 Tristan Rd, Chesapeake, VA 23320

#10585126, Bessie Ostrander, Listing office: Fathom Realty

$7,422 Closing Credit¹

$625,000

5 beds • 4 baths • 3,901 sqft

2130 Rock Creek Dr, Chesapeake, VA 23323

#10585074, James Davis, Listing office: North End Realty Group

$8,906 Closing Credit¹

$750,000

5 beds • 3 baths • 2,416 sqft

3124 Douglas Rd, Chesapeake, VA 23322

#10585078, Traci Lewis VanCamp, Listing office: RE/MAX Alliance

$4,869 Closing Credit¹

$410,000

5 beds • 2.5 baths • 2,100 sqft

1504 Debbs Ln, Chesapeake, VA 23320

#10584605, Dani Brinson, Listing office: KW Coastal Virginia Chesapeake

$7,541 Closing Credit¹

$635,000

5 beds • 2.5 baths • 2,600 sqft

529 Graphite Trl, Chesapeake, VA 23320

#10584706, Diane Keeley, Listing office: BHHS RW Towne Realty

$10,000 Closing Credit¹

$1,050,000

5 beds • 3.5 baths • 3,600 sqft

1653 Shipyard Rd, Chesapeake, VA 23323

#10584839, Shanique Morris, Listing office: Opulent Realty LLC

$10,000 Closing Credit¹

$925,000

5 beds • 4 baths • 3,900 sqft

501 Peaceful Rd, Chesapeake, VA 23322

#10584233, Brian Wurst, Listing office: A Better Way Realty Inc.

$7,719 Closing Credit¹

$650,000

5 beds • 3 baths • 2,886 sqft

3304 Dodd Dr, Chesapeake, VA 23323

#10584614, Lee Halyard, Listing office: Lee S Halyard & Assoc Realtor

Chesapeake, VA Real Estate Market Overview

There are 97 5-bedroom homes for sale in Chesapeake, VA. The following market insights reflect all property types in the Chesapeake, VA real estate market. The number of homes in Chesapeake, VA increased by 15.4% between April 2025 and May 2025. The median list price of listings available in May 2025 was $338,500, while the average time on the real estate market was 27 days. Over 0 listings were sold over their listed price in May 2025 in Chesapeake, VA. In the same period over 0 listings were sold below the listed price and 1 listings were sold for the listed price.

From Rocket Homes Real Estate and based on county public records data

What is it like to live in Chesapeake, VA

Overview

Chesapeake is located in Virginia. There are roughly 226,078 residents, living in 80,829 households. The average temperature for Chesapeake this time of the year is low of 64F and high of 85F. On average, Chesapeake gets about 3.87 inches of precipitation in June. Most residents are home owners (73%), have a post secondary degree (56%) and are single, no kids (32%).

Data provided by Home Junction

Housing types

The housing landscape in Chesapeake, Virginia, is characterized by a mix of single-family homes, apartments, and townhouses, with single-family homes being the most prevalent. The architectural styles in the area are diverse, with a blend of modern, colonial, and ranch-style homes. A significant portion of the housing stock was developed from the 1980s to the early 2000s, reflecting a period of growth for the city. The homeownership rate in Chesapeake is robust, with a majority of residents owning their homes.

Advantages

Chesapeake prides itself on its serene suburban feel, offering residents a blend of urban amenities and rural charm. The community is celebrated for its well-maintained parks and annual events that showcase the local culture and foster a sense of togetherness. The city's green spaces and waterways provide a scenic backdrop for outdoor activities, contributing to the area's tranquil character.

Convenience

Chesapeake is served by a comprehensive educational system, including numerous public schools at the elementary, middle, and high school levels, as well as private institutions that cater to a range of educational needs. The city is home to several healthcare facilities, offering services from primary care to specialized medical treatments. The public library system in Chesapeake is extensive, supporting the community's educational and informational needs. Retail and dining options are plentiful, reflecting the local culture and providing residents with a variety of choices.

Transportation

Transportation options in Chesapeake include a network of roads and highways that facilitate travel and commuting within the city and to neighboring areas. Public transit services are available, with bus routes connecting key locations throughout the city. While specific schedules vary, the frequency of these services is designed to accommodate the needs of residents. The city also supports ride-sharing options, enhancing mobility for those without private vehicles. Chesapeake's layout offers varying degrees of walkability and bikeability, with certain areas being more pedestrian-friendly than others.

Schools near Chesapeake, VA

Elementary Schools

King's Grant Elementary School
612 N Lynnhaven Rd
Public District PK-5
St. Helena Elementary School
903 S Main St
Public District PK-5
Thalia Elementary School
421 Thalia Rd
Public District PK-5

Middle Schools

Plaza Middle School
3080 S Lynnhaven Rd
Public District 6-8
Jolliff Middle School
1021 Jolliff Rd
Public District 6-8
Ghent School
200 Shirley Ave
Public District KG-8

High Schools

Western Branch High School
1968 Bruin Pl
Public District 9-12
Tallwood High School
1668 Kempsville Rd
Public District 9-12
Green Run Collegiate
1700 Dahlia Dr Attn Riannepatricio
Public Charter 9-12

Data provided by Great Schools

5 bedroom homes for sale in Chesapeake, VA

Chesapeake, VA Real Estate Market Overview

What is it like to live in Chesapeake, VA

Overview

Housing types

Advantages

Convenience

Transportation

Explore popular home types in Chesapeake, VA

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Schools near Chesapeake, VA

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