Crestwood Homes for Sale in Chesapeake, VA
Crestwood is an established residential neighborhood in Chesapeake, Virginia, set along Great Bridge Boulevard near the South Norfolk and Greenbrier areas. The neighborhood is composed mainly of detached single-family homes, with a housing stock that spans mid-century construction through more recently built residences. Crestwood Intermediate and Crestwood Middle schools sit along Great Bridge Boulevard, alongside Crestwood Park, and the area offers convenient access toward Greenbrier and nearby Chesapeake corridors.
2 homes for sale in Crestwood right now.
2
Active Listings
$339,950
Median List Price
$245
Avg. $ / Sq. Ft.
64
Avg. Days on Market
7d ago
Newest Listing
Live from the REIN MLS, refreshed continuously. Stats reflect active for-sale inventory in Crestwood.
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Crestwood real estate FAQ
Where is Crestwood located in Chesapeake?+
Crestwood is an inland residential neighborhood in Chesapeake, Virginia, set along Great Bridge Boulevard near the South Norfolk and Greenbrier areas. It offers convenient access to nearby Chesapeake commercial corridors.
What kind of homes are in Crestwood?+
Crestwood is made up primarily of detached single-family homes. The housing stock reflects a range of construction eras, from mid-century-built residences to homes built in more recent decades.
What schools serve the Crestwood neighborhood?+
The neighborhood is associated with Crestwood Intermediate School and Crestwood Middle School, both located on Great Bridge Boulevard and part of Chesapeake Public Schools. Buyers should confirm current zoning with the school division and review ratings on GreatSchools before relying on assignments.
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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What residents say about Crestwood
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