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.
1 home for sale in Crestwood right now.
1
Active Listings
$349,000
Median List Price
$253
Avg. $ / Sq. Ft.
—
Avg. Days on Market
3d ago
Newest Listing
Live from the REIN MLS, refreshed continuously. Stats reflect active for-sale inventory in Crestwood.
Neighborhood23
Sold · last 12 mo
$375,000
Median sale price
$205
Median sold $/sq ft
14
Median days on market
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What Crestwood homes actually sell for
Computed from REIN MLS closed sales over the trailing 12 months — updates with every MLS sync, not a third-party monthly aggregate.
$375,000
Median sale price · 12 mo
23 closed sales
$205
Median sold $ / sq ft
closed sales with recorded sq ft
14 days
Median days on market
for homes that closed
$349K–$349K
Active listing range
1 on the market today
| Property type | Sold · 12 mo | Median sale price |
|---|---|---|
| Detached homes | 23 | $375,000 |
Source: REIN MLS closed sales, trailing 12 months, computed by VaHome.
What buyers should know
Neutral counts from the 33 Crestwood homes VaHome has mapped against federal and state hazard layers — shown the same way for every neighborhood.
61%
of mapped homes sit in FEMA high-risk flood zones
AE · 20 · X · 13 — lenders require flood insurance in AE/VE
0 of 36
mapped homes inside a Navy jet-noise (AICUZ) contour
Every VaHome listing shows its exact noise zone and Accident Potential Zone.
Varies
hurricane evacuation zone (differs across the neighborhood)
Va. Dept. of Emergency Management — Know Your Zone.
Sources: FEMA National Flood Hazard Layer · U.S. Navy AICUZ via city GIS · Virginia Dept. of Emergency Management.
Census profile of the Crestwood area
$63,121
Median household income
37
Median age
76.4%
Owner-occupied households
36.3%
Bachelor's degree or higher
Source: U.S. Census Bureau, American Community Survey 2024 5-Year Estimates (2020–2024), census-tract level for the Crestwood area. Shown identically for every neighborhood.
Bases & commutes
Straight-line distances from the center of Crestwood. Every listing page shows live drive times with traffic.
Listings & market data updated July 2026 · Live REIN MLS data
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 2 minutes from the REIN feed.
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.
Explore more Chesapeake real estate
What residents say about Crestwood
Honest, moderated reviews from people who’ve lived in Crestwood. Share your own experience to help future neighbors decide.
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