Greenbrier Homes for Sale in Chesapeake, VA

Greenbrier is a residential neighborhood located in Chesapeake, Virginia, offering a suburban setting with tree-lined streets and well-maintained homes. The area features a mix of single-family residences and established properties that reflect the character of the region. The neighborhood benefits from its proximity to local amenities while maintaining a quiet, residential atmosphere.

18 homes for sale in Greenbrier right now.

18

Active Listings

$311,500

Median List Price

$173

Avg. $ / Sq. Ft.

21

Avg. Days on Market

1d ago

Newest Listing

Live from the REIN MLS, refreshed continuously. Stats reflect active for-sale inventory in Greenbrier.

1303 Fulton LN, CHESAPEAKE VA 23320

$719,000

1303 Fulton LN, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

5 bd3.1 ba3,107 sqft
800 Broad Reach RD, CHESAPEAKE VA 23320

$505,000

800 Broad Reach RD, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

3 bd2.1 ba2,383 sqft
527 Windward DR, CHESAPEAKE VA 23320

$504,500

527 Windward DR, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

4 bd2.1 ba2,100 sqft
1431 Thistlewood LN, CHESAPEAKE VA 23320

$496,500

1431 Thistlewood LN, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

3 bd2 ba2,248 sqft
1001 S Scarlet Oak CT, CHESAPEAKE VA 23320

$400,000

1001 S Scarlet Oak CT, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

3 bd2.1 ba1,722 sqft
1523 Pucknall DR, CHESAPEAKE VA 23320

$349,900

1523 Pucknall DR, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

3 bd2.1 ba1,870 sqft
1016 Winged Foot CT #B, CHESAPEAKE VA 23320

$349,500

1016 Winged Foot CT #B, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

3 bd2.1 ba1,472 sqft
1513 Pucknall DR, CHESAPEAKE VA 23320

$339,900

1513 Pucknall DR, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

2 bd2.1 ba1,870 sqft
1428 Leckford DR, CHESAPEAKE VA 23320

$338,000

1428 Leckford DR, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

3 bd2.1 ba1,870 sqft
1507 Hambledon LOOP, CHESAPEAKE VA 23320

$285,000

1507 Hambledon LOOP, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

2 bd2.1 ba1,350 sqft
500 Judah WAY #123, CHESAPEAKE VA 23320

$264,900

500 Judah WAY #123, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

2 bd2 ba1,215 sqft
918 Seabreeze CT, CHESAPEAKE VA 23320

$254,900

918 Seabreeze CT, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

2 bd1.1 ba950 sqft
917 Spinnaker CT, CHESAPEAKE VA 23320

$254,900

917 Spinnaker CT, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

2 bd1.1 ba1,026 sqft
952 Saint Andrews RCH #B, CHESAPEAKE VA 23320

$209,900

952 Saint Andrews RCH #B, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

1 bd1 ba900 sqft
912 Saint Andrews RCH #A, CHESAPEAKE VA 23320

$2,450

912 Saint Andrews RCH #A, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

3 bd2 ba1,300 sqft
1301 Cypress PL, CHESAPEAKE VA 23320

$2,400

1301 Cypress PL, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

3 bd2 ba1,204 sqft
1533 rollesby WAY, CHESAPEAKE VA 23320

$2,395

1533 rollesby WAY, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

3 bd2.1 ba1,870 sqft
935 Still Harbor CIR, CHESAPEAKE VA 23320

$1,995

935 Still Harbor CIR, CHESAPEAKE VA 23320

Chesapeake, Virginia 23320

2 bd1.1 ba1,064 sqft

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Living in Greenbrier

Residents enjoy access to parks, recreational facilities, and shopping areas within a reasonable distance. The community supports outdoor activities and family-oriented living with nearby green spaces and community gathering spots. Daily life in Greenbrier offers a balance between suburban convenience and neighborhood connectivity.

Greenbrier appeals to families and individuals seeking an established neighborhood with stable residential character in Chesapeake. The area's location and housing options make it accessible to those looking for suburban living with community infrastructure nearby. Buyers considering the neighborhood typically value its residential setting and established community presence.

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

Greenbrier real estate FAQ

Where is Greenbrier located in Chesapeake, VA?+

Greenbrier is a central Chesapeake area built around Greenbrier Mall and the Greenbrier Parkway corridor, just off Interstate 64 on the city's north side. It lies near the I-64/I-464 interchange, with Route 168 (Battlefield Boulevard) and US-17 among the major routes nearby. The area combines established residential streets with shopping centers, office parks, lakes, and golf courses.

What kinds of homes are in Greenbrier?+

Greenbrier has a varied mix of housing, including single-family homes, townhomes, condominiums, quadravillas, and duplexes. Architectural styles range from brick ranch homes to two-story houses, with communities such as The Retreat at Greenbrier, the Villas at Greenbrier (Cedar Glen), and Lakes of Greenbrier. Many subdivisions were developed from the 1970s through the early 2000s, so much of the housing stock is established rather than new construction.

What schools serve the Greenbrier area?+

Greenbrier is served by Chesapeake Public Schools, with Greenbrier Primary and Greenbrier Intermediate handling the earlier grades and Greenbrier Middle School serving grades 6-8. Depending on the specific address, the assigned high school is typically Indian River High School or Oscar Smith High School. Attendance zones depend on a home's exact location, so buyers should confirm the assigned schools and current GreatSchools ratings before purchasing.

How far is Greenbrier from the interstates and the naval bases?+

Greenbrier has direct access to Interstate 64 via the Greenbrier Parkway interchange, with Interstate 464 and Route 168 also nearby for north-south travel. Naval Station Norfolk is roughly 16 to 19 miles away, typically a 25 to 35 minute drive depending on traffic. The location also provides connections toward downtown Norfolk, Portsmouth, and Virginia Beach.

What lakes and golf options are around Greenbrier?+

Greenbrier includes several lakes, and a number of residential communities are built around these waters. Greenbrier Country Club, on Volvo Parkway, offers a private 18-hole course (designed by Rees Jones, opened 1987) and clubhouse. To the southeast, along the Chesapeake-Virginia Beach boundary, the Stumpy Lake Natural Area in Virginia Beach features a 278-acre lake, an 18-hole public golf course originally designed by Robert Trent Jones, plus surrounding greenspace, trails, and a canoe and kayak launch.

What shopping, dining, and offices are in Greenbrier?+

Greenbrier is one of Chesapeake's main commercial hubs, anchored by Greenbrier Mall and surrounded by retail centers, restaurants, hotels, and the Greenbrier Circle and Greenbrier Towne Center office and business parks. Medical offices and major employers cluster along the corridor, placing day-to-day shopping and services within a short drive of most homes.

About Chesapeake

Homes for sale in Chesapeake, VA appeal to buyers who want suburban space, top-rated schools, and easy access to Virginia Beach and Norfolk. The city's geography splits roughly into five corridors: Greenbrier (23320) with newer construction and shopping near the mall; Great Bridge (23320, 23322) with the historic Battlefield district and excellent schools; Hickory (23322) with large-lot family homes and Hickory High; Western Branch (23321) near the Portsmouth border with mature trees and starter homes; and Deep Creek / South Norfolk (23323, 23324) with affordable inventory and waterfront access. Buyer demand is anchored by Chesapeake Public Schools — among the highest-rated in Hampton Roads — including Hickory High, Grassfield High, Great Bridge High, and Western Branch High. Median home prices range from $300K starter homes in Deep Creek to $600K+ Great Bridge family homes and $1M+ luxury estates in Hickory's gated communities. Chesapeake's commute is excellent for buyers working in Virginia Beach, Norfolk Naval Shipyard, or Newport News Shipbuilding via the I-664 and I-64 corridors. Below you'll find every active Chesapeake MLS listing pulled every 5 minutes from the REIN feed.

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Schools serving Chesapeake

Browse Chesapeake homes by CPS attendance zone. Zoning is assigned by address and can change — always confirm a specific home’s zoned schools with the school division.

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