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Homes for sale in Grassfield High School District

Chesapeake, Virginia

Browse 223 active homes for sale zoned to Grassfield High School in Chesapeake, Virginia. Grassfield High School is rated 8/10 by GreatSchools. 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 August 2026 · Live REIN MLS data

About Grassfield High School — ratings, test scores, GreatSchools data, and other schools in Chesapeake →

223 homes

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

$3,537,900

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

Chesapeake, Virginia 23323

118Ac West RD, CHESAPEAKE VA 23323

$2,200,000

118Ac West RD, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

168 AC St Brides RD W, CHESAPEAKE VA 23322

$2,000,000

168 AC St Brides RD W, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

86.15A Taft Road, Chesapeake VA 23322

$1,800,000

86.15A Taft Road, Chesapeake VA 23322

Chesapeake, Virginia 23322

2505 Sylvia CT, CHESAPEAKE VA 23322

$1,750,000

2505 Sylvia CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd4 ba5,707 sqft

135ac St. Brides Road, Chesapeake VA 23322

$1,600,000

135ac St. Brides Road, Chesapeake VA 23322

Chesapeake, Virginia 23322

641 Ravenwoods DR, CHESAPEAKE VA 23322

$1,550,000

641 Ravenwoods DR, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd4.1 ba6,848 sqft

1741 Taft RD, CHESAPEAKE VA 23322

$1,269,997

1741 Taft RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd2.1 ba4,356 sqft

704 Washington DR, CHESAPEAKE VA 23322

$1,257,023

704 Washington DR, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

6 bd4 ba4,063 sqft

2700 Ballahack RD, CHESAPEAKE VA 23322

$1,250,000

2700 Ballahack RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

6 bd5 ba4,726 sqft

4030 Tucker LN, CHESAPEAKE VA 23322

$1,195,795

4030 Tucker LN, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd4 ba3,982 sqft

1452 Taft RD, CHESAPEAKE VA 23322

$1,150,000

1452 Taft RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd4 ba3,973 sqft

2624 Ballahack RD, CHESAPEAKE VA 23322

$1,089,000

2624 Ballahack RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd3.1 ba3,370 sqft

1425 TAFT RD, CHESAPEAKE VA 23322

$1,070,872

1425 TAFT RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba4,473 sqft

MM Carley (THE GRASSFIELD) CT, CHESAPEAKE VA 23322

$999,900

MM Carley (THE GRASSFIELD) CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd3.1 ba3,300 sqft

1630 Taft RD, CHESAPEAKE VA 23322

$995,000

1630 Taft RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba2,957 sqft

1429 Taft RD, CHESAPEAKE VA 23322

$985,769

1429 Taft RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba3,423 sqft

1928 Moses Grandy Trail, Chesapeake VA 23323

$982,800

1928 Moses Grandy Trail, Chesapeake VA 23323

Chesapeake, Virginia 23323

1361 Jury RD, CHESAPEAKE VA 23322

$979,307

1361 Jury RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba3,102 sqft

4020 Tucker LN, CHESAPEAKE VA 23322

$974,500

4020 Tucker LN, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba3,000 sqft

1908 Benefit RD, CHESAPEAKE VA 23322

$950,000

1908 Benefit RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd3 ba3,252 sqft

821 Spruce Forest CT, CHESAPEAKE VA 23322

$950,000

821 Spruce Forest CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

6 bd5 ba3,839 sqft

1421 Saint Brides Road West NONE, CHESAPEAKE VA 23322

$939,800

1421 Saint Brides Road West NONE, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba2,720 sqft

1432 Taft RD, CHESAPEAKE VA 23322

$938,197

1432 Taft RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba3,484 sqft

MM Carley (THE BALLAHACK) CT, CHESAPEAKE VA 23322

$899,900

MM Carley (THE BALLAHACK) CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3 ba2,800 sqft

1433 TAFT RD, CHESAPEAKE VA 23322

$880,384

1433 TAFT RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba2,730 sqft

1440 TAFT RD, CHESAPEAKE VA 23322

$880,265

1440 TAFT RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd2.1 ba3,407 sqft

2536 Seven Eleven RD, CHESAPEAKE VA 23322

$875,000

2536 Seven Eleven RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

6 bd3.1 ba4,536 sqft

No photo provided

$875,000

2532 Wild Horse RDG, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd2.1 ba2,280 sqft

2025 Hallmark WAY, CHESAPEAKE VA 23323

$875,000

2025 Hallmark WAY, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

4 bd3.1 ba3,200 sqft

MM Carley (The Albemarle) CT, CHESAPEAKE VA 23322

$859,900

MM Carley (The Albemarle) CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba2,700 sqft

1428 TAFT RD, CHESAPEAKE VA 23322

$855,821

1428 TAFT RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd2.1 ba3,057 sqft

1833 Shillelagh RD, CHESAPEAKE VA 23323

$849,900

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

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

Chesapeake, Virginia 23322

4 bd3.1 ba3,424 sqft

3722 Carley CT, CHESAPEAKE VA 23322

$849,900

3722 Carley CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba2,650 sqft

2537 Number Ten LN, CHESAPEAKE VA 23323

$849,900

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

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

Chesapeake, Virginia 23322

4 bd3.1 ba3,124 sqft

4500 Backwoods RD, CHESAPEAKE VA 23322

$840,000

4500 Backwoods RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

7 AC Shillelagh RD, CHESAPEAKE VA 23323

$834,900

7 AC Shillelagh RD, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

4 bd2.1 ba2,400 sqft

3700 Riverwood CRES, CHESAPEAKE VA 23322

$825,000

3700 Riverwood CRES, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd2.1 ba3,923 sqft

2239 Benefit RD, CHESAPEAKE VA 23322

$825,000

2239 Benefit RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba3,000 sqft

1837 Benefit RD, CHESAPEAKE VA 23322

$825,000

1837 Benefit RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd4 ba2,769 sqft

1932 Foxwood DR, CHESAPEAKE VA 23323

$820,000

1932 Foxwood DR, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

5 bd3 ba3,018 sqft

2504 Calabria Dr DR, CHESAPEAKE VA 23323

$815,000

2504 Calabria Dr DR, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

5 bd4 ba3,331 sqft

633 Ambrose ST, CHESAPEAKE VA 23322

$815,000

633 Ambrose ST, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd3 ba3,300 sqft

2907 Seven Eleven RD, CHESAPEAKE VA 23322

$799,900

2907 Seven Eleven RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd2.1 ba2,400 sqft

1909 McCoy Rd NONE, CHESAPEAKE VA 23323

$788,390

1909 McCoy Rd NONE, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

3 bd3.1 ba2,700 sqft

1916 McCoy RD, CHESAPEAKE VA 23323

$775,995

1916 McCoy RD, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

4 bd4 ba2,500 sqft

1124 Saint Brides RD W, CHESAPEAKE VA 23322

$774,900

1124 Saint Brides RD W, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3.1 ba2,800 sqft

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

$771,900

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

Chesapeake, Virginia 23322

4 bd3.1 ba2,766 sqft

1908 McCoy Road, Chesapeake VA 23323

$769,900

1908 McCoy Road, Chesapeake VA 23323

Chesapeake, Virginia 23323

4 bd4 ba2,500 sqft

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

$769,900

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

Chesapeake, Virginia 23322

3 bd2.1 ba2,630 sqft

3710 Carley CT, CHESAPEAKE VA 23322

$759,900

3710 Carley CT, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

4 bd3 ba2,400 sqft

1833 Benefit RD, CHESAPEAKE VA 23322

$755,000

1833 Benefit RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

5 bd3.2 ba3,583 sqft

2650 Benefit RD, CHESAPEAKE VA 23322

$750,000

2650 Benefit RD, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

1148 Sunlight DR, CHESAPEAKE VA 23322

$750,000

1148 Sunlight DR, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

7.4 AC Moses Grandy TRL, CHESAPEAKE VA 23322

$750,000

7.4 AC Moses Grandy TRL, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

28 Johnstown CRES, CHESAPEAKE VA 23322

$750,000

28 Johnstown CRES, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

1629 Shillelagh RD, CHESAPEAKE VA 23323

$750,000

1629 Shillelagh RD, CHESAPEAKE VA 23323

Chesapeake, Virginia 23323

5 bd2.1 ba2,490 sqft

3536 Riverwood CRES, CHESAPEAKE VA 23322

$744,900

3536 Riverwood CRES, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

3 bd3 ba2,464 sqft

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