5 bedroom homes for sale in Chesapeake, VA

view of front of home featuring a shingled roof and a front yard

exterior space with concrete driveway, roof with shingles, and fence

entryway featuring stairs, high vaulted ceiling, visible vents, and light wood-style flooring

New - 1 hour on Rocket

$10,000 Closing Credit¹

$1,700,000

5 beds • 4.5 baths • 5,480 sqft

1041 Taft Rd, Chesapeake VA 23322

#10570896, Matthew Monaco, Listing Office: BHHS RW Towne Realty

craftsman-style house with a front lawn and a garage

craftsman inspired home featuring a front lawn and a garage

craftsman house featuring covered porch, a front yard, and a garage

New - 10 hours on Rocket

$8,134 Closing Credit¹

$685,000

5 beds • 3 baths • 2,962 sqft

1000 Loutro Ct, Chesapeake VA 23322

#10570484, Cheri Bass-Wozniak, Listing Office: BHHS RW Towne Realty

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craftsman house with a garage, a front lawn, and covered porch

view of front of property featuring a garage, a porch, and a front lawn

New - 3 days on Rocket

$8,795 Closing Credit¹

$740,600

5 beds • 3.5 baths • 3,100 sqft

500 Kitson Ct, Chesapeake VA 23320

#10570556, Tonya Warren, Listing Office: ONYX Realty Professionals

view of front of home featuring a front yard

view of front of home with a garage, an outdoor structure, and a front yard

view of front of property with a front lawn

New - 3 days on Rocket

$10,000 Closing Credit¹

$1,200,000

5 beds • 5 baths • 4,450 sqft

226 Avonlea Pt, Chesapeake VA 23322

#10570309, Cheryl Walker, Listing Office: 757 Realty

view of front of property with a porch and a front lawn

kitchen with white cabinetry, appliances with stainless steel finishes, a kitchen island with sink, and decorative light fixtures

New - 3 days on Rocket

$8,491 Closing Credit¹

$715,000

5 beds • 3 baths • 2,867 sqft

1117 Edinburgh Pkwy, Chesapeake VA 23322

#10570480, David Allison, Listing Office: Atlantic Sothebys Int'l Realty

view of property featuring a garage, a front lawn, and covered porch

New - 6 days on Rocket

$5,926 Closing Credit¹

$499,000

5 beds • 2.5 baths • 3,080 sqft

3556 Calverton Way, Chesapeake VA 23321

#10570026, Ryan Benton, Listing Office: BHHS RW Towne Realty

New - 7 days on Rocket

$7,422 Closing Credit¹

$625,000

5 beds • 3.5 baths • 3,015 sqft

905 Porte Crayon St, Chesapeake VA 23323

#10570099, Riya Thorson, Listing Office: Liz Moore & Associates LLC

Room to negotiate?

Median List Price

$438.5K

Avg. Sale Time

89 Days

Based on our January 2025 Market Report.

view of front of property with a porch, a garage, and a front lawn

view of front of property featuring a garage and a front yard

view of front facade featuring a garage and a front lawn

New - 7 days on Rocket

$7,422 Closing Credit¹

$625,000

5 beds • 3 baths • 3,500 sqft

1608 Pinedale Ln, Chesapeake VA 23322

#10570129, Cheyenne Penn, Listing Office: Keller Williams Elite 757

ranch-style house featuring a front lawn

$4,988 Closing Credit¹

$420,000

5 beds • 3 baths • 3,901 sqft

2130 Rock Creek Dr, Chesapeake VA 23323

#10569831, James Davis, Listing Office: North End Realty Group

view of exterior entry featuring covered porch

$6,827 Closing Credit¹

$574,900

5 beds • 2.5 baths • 2,661 sqft

2204 Sanibel Ln, Chesapeake VA 23321

#10569826, Kathy Nelms, Listing Office: Corinth Realty LLC

ranch-style house featuring a front yard

rear view of house featuring a sunroom and a lawn

unfurnished living room with light hardwood / wood-style flooring

$4,749 Closing Credit¹

$399,900

5 beds • 4 baths • 3,005 sqft

4008 Cedar Grove Cres, Chesapeake VA 23321

#10569727, Lisa Martin, Listing Office: Judy Boone Realty Inc.

colonial inspired home with a front lawn

birds eye view of property with a water view

$8,894 Closing Credit¹

$749,000

5 beds • 3 baths • 2,980 sqft

3720 Farnsworth Dr, Chesapeake VA 23321

#10569419, Jonathan Dahl, Listing Office: BHHS RW Towne Realty

view of front of house with a garage and a front lawn

entryway featuring dark wood-type flooring

3D tour

$9,025 Closing Credit¹

$760,000

5 beds • 3.5 baths • 3,059 sqft

1909 Ferguson Loop, Chesapeake VA 23322

#10569387, Maria Hernandez, Listing Office: Better Homes & Gdns Ntv Am Grp

kitchen featuring wine cooler, high end fridge, a center island, gray cabinets, and pendant lighting

bar with gray cabinets, wood-type flooring, sink, backsplash, and light stone countertops

view of front facade featuring a front lawn and covered porch

$7,707 Closing Credit¹

$649,000

5 beds • 3.5 baths • 3,337 sqft

219 Marina Reach Reach, Chesapeake VA 23320

#10569316, Jackie Feagin, Listing Office: BHHS RW Towne Realty

view of front of house featuring a porch and a front lawn

exterior space with a porch and a front yard

view of front of house featuring a front lawn and covered porch

$4,749 Closing Credit¹

$399,900

5 beds • 2 baths • 2,380 sqft

3113 Mistletoe Ct, Chesapeake VA 23323

#10569389, Thomas Milan, Listing Office: LPT Realty LLC

craftsman-style house with a garage, covered porch, and a lawn

kitchen featuring dark wood-type flooring, white cabinetry, stainless steel appliances, tasteful backsplash, and wall chimney exhaust hood

$8,016 Closing Credit¹

$675,000

5 beds • 3 baths • 2,440 sqft

508 Rosegate St, Chesapeake VA 23320

#10569039, Jodi Linney, Listing Office: Atlantic Sothebys Int'l Realty

view of front facade with a front yard and a porch

rear view of house with a wooden deck, a yard, and central AC unit

$5,344 Closing Credit¹

$450,000

5 beds • 2 baths • 3,333 sqft

3861 Ahoy Dr, Chesapeake VA 23321

#10568930, Patrick Olds, Listing Office: Long & Foster Real Estate Inc.

MM Rosewood 2, Chesapeake VA, 23321, 5 bedrooms, 3.5 baths house for sale

Listing photo 2 for MM Rosewood 2, Chesapeake VA 23321

Listing photo 3 for MM Rosewood 2, Chesapeake VA 23321

$8,276 Closing Credit¹

$696,900

5 beds • 3.5 baths • 4,005 sqft

MM Rosewood 2, Chesapeake VA 23321

#10568776, Steve Freeman, Listing Office: RHOAD & CO.

view of front facade featuring a garage, a front lawn, and a porch

view of property featuring a garage, a front yard, and a porch

$7,897 Closing Credit¹

$665,000

5 beds • 3 baths • 3,272 sqft

1501 Clearwater Ln, Chesapeake VA 23322

#10568663, Desiree Ladyman, Listing Office: Howard Hanna Real Estate Svcs.

view of front of home featuring a garage, covered porch, and a front lawn

view of front of house with a porch, a garage, and a front yard

$7,244 Closing Credit¹

$610,000

5 beds • 3 baths • 3,000 sqft

404 Clara Dr, Chesapeake VA 23320

#10568747, Kelvin Reed, Listing Office: Your Home Sold Guaranteed

craftsman house featuring a garage and covered porch

craftsman-style house featuring a garage, a front lawn, and covered porch

$10,000 Closing Credit¹

$949,000

5 beds • 3.5 baths • 3,220 sqft

903 Aberdeen Ln, Chesapeake VA 23322

#10569056, Laura Rowe, Listing Office: EXP Realty LLC

view of front of house with a front yard

drone / aerial view featuring a water view

$8,014 Closing Credit¹

$674,900

5 beds • 3.5 baths • 4,326 sqft

3017 Voyager Ct, Chesapeake VA 23321

#10569048, Evelyn Thomas, Listing Office: CENTURY 21 Nachman Realty

entrance foyer featuring lofted ceiling, a chandelier, and light hardwood / wood-style floors

$9,441 Closing Credit¹

$795,000

5 beds • 4 baths • 2,700 sqft

1916 Mccoy Rd, Chesapeake VA 23323

#10568970, Monique Darling, Listing Office: Howard Hanna Real Estate Svcs.

view of front of home featuring a garage, a front yard, and covered porch

corridor with ornamental molding, dark hardwood / wood-style floors, and french doors

$6,055 Closing Credit¹

$509,900

5 beds • 2.5 baths • 2,244 sqft

1311 Wilrose Trce, Chesapeake VA 23322

#10568760, Cheryl Talbot, Listing Office: BHHS RW Towne Realty

view of front of property featuring a front lawn

$8,905 Closing Credit¹

$749,900

5 beds • 4 baths • 3,790 sqft

1801 Burson Dr, Chesapeake VA 23323

#10568791, Andre Jones, Listing Office: Keller Williams Elite 757

view of front facade featuring a porch and a front lawn

view of front facade with a front yard and covered porch

$8,134 Closing Credit¹

$685,000

5 beds • 3.5 baths • 3,628 sqft

1120 Walnut Neck Ave, Chesapeake VA 23320

#10568730, Dee Chaparro, Listing Office: Wainwright Real Estate

view of front of home featuring a garage

view of front of property featuring a garage and a front lawn

view of front of property featuring a garage and a storage shed

$5,284 Closing Credit¹

$445,000

5 beds • 2.5 baths • 1,835 sqft

3201 Grey Fox Ct, Chesapeake VA 23323

#10568296, Spencer Bass, Listing Office: Greenbrier Real Estate & Appr.

view of front property with a front yard

view of front facade with a garage and a front lawn

Video tour

$10,000 Closing Credit¹

$889,900

5 beds • 3.5 baths • 4,126 sqft

591 Dove Dr, Chesapeake VA 23322

#10567364, Colleen Kovach, Listing Office: Own Real Estate LLC

$6,887 Closing Credit¹

$579,999

5 beds • 3 baths • 2,522 sqft

2515 Deals Creek Ct, Chesapeake VA 23323

#10568026, Crista Mishler, Listing Office: Swell Realty Co

view of front of property featuring a porch

view of front of home featuring a front yard and covered porch

cape cod-style house with a porch and a front yard

$10,000 Closing Credit¹

$875,000

5 beds • 3 baths • 3,851 sqft

237 Cedar Rd, Chesapeake VA 23322

#10568060, Paul Tatum, Listing Office: Atlantic Sothebys Int'l Realty

$7,541 Closing Credit¹

$635,000

5 beds • 3 baths • 2,819 sqft

2084 Millville Rd, Chesapeake VA 23323

#10568084, Jai Johnson, Listing Office: EXIT Realty Central

view of front facade with a garage and covered porch

$6,905 Closing Credit¹

$581,499

5 beds • 2.5 baths • 2,378 sqft

2508 Deals Creek Ct, Chesapeake VA 23323

#10568015, Michael Daugherty, Listing Office: Own Real Estate LLC

view of front of home with a garage and covered porch

$7,618 Closing Credit¹

$641,499

5 beds • 2.5 baths • 2,378 sqft

2500 Deals Creek Ct, Chesapeake VA 23323

#10568007, Michael Daugherty, Listing Office: Own Real Estate LLC

MM Dogwood 2, Chesapeake VA, 23321, 5 bedrooms, 3 baths house for sale

Listing photo 2 for MM Dogwood 2, Chesapeake VA 23321

Listing photo 3 for MM Dogwood 2, Chesapeake VA 23321

$6,851 Closing Credit¹

$576,900

5 beds • 3 baths • 2,755 sqft

MM Dogwood 2, Chesapeake VA 23321

#10567621, Christian Ramirez, Listing Office: RHOAD & CO.

view of front of house featuring a garage and a front yard

$6,769 Closing Credit¹

$569,999

5 beds • 2.5 baths • 2,496 sqft

2519 Deals Creek Ct, Chesapeake VA 23323

#10567973, Michael Daugherty, Listing Office: Own Real Estate LLC

view of front property featuring a garage, covered porch, and solar panels

front of property with a porch, a garage, and solar panels

$7,836 Closing Credit¹

$659,900

5 beds • 3 baths • 3,140 sqft

1608 Banff Ct, Chesapeake VA 23320

#10567840, Vanessa Sawyer, Listing Office: BHHS RW Towne Realty

view of front of home featuring a garage and a front yard

$10,000 Closing Credit¹

$1,785,000

5 beds • 5 baths • 7,000 sqft

828 Oaklette Ave, Chesapeake VA 23325

#10567841, Kristen Randolph, Listing Office: BHHS RW Towne Realty

view of front of house featuring a garage

Video tour

$5,938 Closing Credit¹

$500,000

5 beds • 2.5 baths • 2,738 sqft

1416 Waterside Dr S, Chesapeake VA 23320

#10567681, Elizabeth Abrams, Listing Office: Abrams Realty

view of front of house featuring covered porch and a front yard

view of front facade featuring covered porch and a front lawn

kitchen with crown molding, dark brown cabinets, pendant lighting, and light wood-type flooring

$7,836 Closing Credit¹

$659,900

5 beds • 3.5 baths • 3,570 sqft

MM Willow, Chesapeake VA 23321

#10567593, Christian Ramirez, Listing Office: RHOAD & CO.

view of front facade with a garage and a front yard

view of front of home with a garage and a front yard

view of front of property with a garage and a front yard

$6,958 Closing Credit¹

$585,900

5 beds • 3.5 baths • 2,745 sqft

MM Bradford 2, Chesapeake VA 23321

#10567600, Christian Ramirez, Listing Office: RHOAD & CO.

Chesapeake, VA Real Estate Market Overview

Browse 79 5 bedroom homes for sale in Chesapeake, VA. View properties, photos, nearby real estate with school and housing market information. The number of homes for sale in Chesapeake, VA increased by 10.1% between December 2024 and January 2025. While the average time on the market in January 2025 was 89 days, the median list price was $438,547.

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

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

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