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Homes for sale in Chesapeake Career Center District

Chesapeake, Virginia

Browse 215 active homes for sale zoned to Chesapeake Career Center in Chesapeake, Virginia. School zone boundaries can change between school years — verify your child's assigned school directly with Chesapeake Public Schools before relying on zoning for housing decisions.

Listings & market data updated September 2026 · Live REIN MLS data

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Lots Moses Grandy ( Par.B,C,D) Trail, Chesapeake VA 23323

$3,537,900

Deep Creek

Lots Moses Grandy ( Par.B,C,D) Trail, Chesapeake VA 23323

Chesapeake, Virginia 23323

$1,750,000

Hunters Ridge

2505 Sylvia CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd4 ba5,707 sqft

$1,519,000

Great Bridge

641 Ravenwoods DR, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd4.1 ba6,848 sqft

$1,100,000

Hickory

1741 Taft RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd2.1 ba3,700 sqft

$1,089,000

2624 Ballahack RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd3.1 ba3,370 sqft

$1,000,000

Grassfield Meadows

3132 Benefit RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

6 bd3 ba3,600 sqft

$999,900

MM Carley (THE GRASSFIELD) CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd3.1 ba3,300 sqft

$998,895

Shillelagh Farms

1910 Hallmark WAY, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

5 bd3.1 ba3,988 sqft

$989,900

Hickory

4020 Tucker LN, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba3,000 sqft

1928 Moses Grandy Trail, Chesapeake VA 23323

$982,800

Deep Creek

1928 Moses Grandy Trail, Chesapeake VA 23323

Chesapeake, Virginia 23323

$979,307

1361 Jury RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba3,102 sqft

$935,000

Hickory

1908 Benefit RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd3 ba3,252 sqft

1421 Saint Brides Road West NONE, CHESAPEAKE VA 23322

$899,900

Hickory

1421 Saint Brides Road West NONE, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba2,720 sqft

$899,900

MM Carley (THE BALLAHACK) CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3 ba2,800 sqft

$869,000

Sentry Estates

2517 Number Ten LN, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

4 bd3.1 ba2,941 sqft

$859,900

MM Carley (The Albemarle) CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba2,700 sqft

$849,900

Shillelagh Farms

1833 Shillelagh RD, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

5 bd4.1 ba2,754 sqft

MM Taft (Holden 2-A) RD, CHESAPEAKE VA 23322

$849,900

The Fields At Taft

MM Taft (Holden 2-A) RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba3,424 sqft

$849,900

3722 Carley CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba2,650 sqft

$849,800

Sentry Estates

2537 Number Ten LN, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

6 bd4.1 ba3,251 sqft

MM Taft (Davidson Homesite A-2) RD, CHESAPEAKE VA 23322

$844,900

The Fields At Taft

MM Taft (Davidson Homesite A-2) RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba3,124 sqft

$840,000

Creekwood

2602 Cecilia TER, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

6 bd4 ba3,500 sqft

$825,000

Pleasant Grove

2239 Benefit RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba3,000 sqft

$825,000

Hickory

1837 Benefit RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd4 ba2,769 sqft

2907 Seven Eleven RD, CHESAPEAKE VA 23322

$799,900

Pleasant Grove

2907 Seven Eleven RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd2.1 ba2,400 sqft

$785,000

Hillcrest

633 Ambrose ST, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd3 ba3,300 sqft

$775,000

Riverwood

3708 Riverwood CRES, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd2.1 ba2,978 sqft

MM Taft (Engle B-1) RD, CHESAPEAKE VA 23322

$771,900

The Fields At Taft

MM Taft (Engle B-1) RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba2,766 sqft

MM Taft (Kentland B-1) RD, CHESAPEAKE VA 23322

$769,900

The Fields At Taft

MM Taft (Kentland B-1) RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

3 bd2.1 ba2,630 sqft

$759,900

3710 Carley CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3 ba2,400 sqft

MM Taft (Lee A-5) RD, CHESAPEAKE VA 23322

$753,647

The Fields At Taft

MM Taft (Lee A-5) RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba2,984 sqft

$750,000

Inland Colony

1148 Sunlight DR, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

$750,000

Pleasant Grove

28 Johnstown CRES, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

7.4 AC Moses Grandy TRL, CHESAPEAKE VA 23322

$750,000

Grassfield Meadows

7.4 AC Moses Grandy TRL, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

$749,000

Great Bridge

905 Washington DR, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd2.1 ba3,600 sqft

$735,000

Shillelagh Farms

1629 Shillelagh RD, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

5 bd2.1 ba2,490 sqft

$726,960

Parkview

1906 McCoy Rd NONE, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

4 bd4 ba2,500 sqft

$699,000

Forest Lakes

816 Forest Lakes CIR, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3 ba3,200 sqft

$699,000

Hickory

1833 Benefit RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.2 ba3,583 sqft

MM Fields At Taft (Squire A-5) RD, CHESAPEAKE VA 23322

$695,351

The Fields At Taft

MM Fields At Taft (Squire A-5) RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

3 bd2 ba2,134 sqft

$695,000

Dominion Meadows

2209 Beeblossom LN, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

5 bd2.1 ba3,200 sqft

$693,000

Hickory

2430 Ballahack RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba2,600 sqft

MM Taft (Derring A-5) RD, CHESAPEAKE VA 23322

$692,950

The Fields At Taft

MM Taft (Derring A-5) RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd2.1 ba2,287 sqft

952 Checkerspot WAY, CHESAPEAKE VA 23323

$685,000

Dominion Meadows

952 Checkerspot WAY, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

5 bd2.1 ba2,954 sqft

$675,000

42.4 Acres Benefit RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

$669,900

Great Bridge Crossings

806 Falls Creek DR, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd3 ba3,383 sqft

$669,900

Pleasant Grove

2237 Shillelagh RD, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

$667,000

Las Gaviotas

504 Aguila CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd3 ba3,084 sqft

$650,000

Deep Creek

2100 Millville RD, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

5 bd2.1 ba2,714 sqft

$647,499

Deep Creek

2116 Cedar RD, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

5 bd3 ba2,500 sqft

$645,000

Parkview

1928 Rockwood DR, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

4 bd2.1 ba3,146 sqft

$639,900

Parkview

2065 Shipyard RD, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

4 bd2.1 ba2,652 sqft

$639,900

Pleasant Grove

732 Washington DR, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd2 ba2,863 sqft

$639,000

Great Bridge

568 Waters RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

6 bd2.1 ba3,369 sqft

$635,000

Cedarwood

808 Bay Laurel CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba3,169 sqft

$635,000

Parkview

1826 Hazelwood RD, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

4 bd2.1 ba2,463 sqft

$635,000

Oak Ridge

1345 Oak Ridge DR, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd2 ba1,839 sqft

Coming Soon

$629,000

1703 Cheslie ARCH, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

4 bd2.1 ba2,506 sqft

$625,000

Marsh Creek

803 Gresham WAY, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

5 bd3.1 ba3,670 sqft

$625,000

Hillcrest

622 Ambrose ST, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd3 ba2,600 sqft

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