Crestwood Homes for Sale in Chesapeake, VA
Crestwood is a settled neighborhood in Chesapeake, Virginia. It sits along Great Bridge Boulevard near the South Norfolk and Greenbrier areas. Most homes here are detached houses. Some date to the mid-century years, and some are much newer. Crestwood Intermediate and Crestwood Middle schools are on that same road, next to Crestwood Park. Greenbrier and other nearby corridors are an easy drive.
3 homes for sale in Crestwood right now.
3
Active Listings
$325,000
Median List Price
$158
Avg. $ / Sq. Ft.
20
Avg. Days on Market
9d ago
Newest Listing
Live from the REIN MLS, refreshed continuously. Stats reflect active for-sale inventory in Crestwood.
Neighborhood26
Sold · last 12 mo
$372,500
Median sale price
$209
Median sold $/sq ft
13
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.
$372,500
Median sale price · 12 mo
26 closed sales
$209
Median sold $ / sq ft
closed sales with recorded sq ft
13 days
Median days on market
for homes that closed
$3K–$420K
Active listing range
3 on the market today
| Property type | Sold · 12 mo | Median sale price |
|---|---|---|
| Detached homes | 26 | $372,500 |
Source: REIN MLS closed sales, trailing 12 months, computed by VaHome.
Recently sold in Crestwood
The latest 10 closings from the REIN MLS. Each opens the home's full sold record.
1245 Great Bridge BLVD, CHESAPEAKE VA 23320
3 bd · 1 ba · 917 sqft
$240,000
Sold Aug 2026
504 Tuskegee AVE, CHESAPEAKE VA 23320
3 bd · 2.1 ba · 1,700 sqft
$386,000
Sold Aug 2026
1620 Great Bridge BLVD, CHESAPEAKE VA 23320
5 bd · 3 ba · 2,363 sqft
$370,000
Sold Jul 2026
1618 Great Bridge BLVD, CHESAPEAKE VA 23320
5 bd · 2 ba · 2,122 sqft
$415,000
Sold Jul 2026
718 Marcus ST, CHESAPEAKE VA 23320
2 bd · 2 ba · 1,265 sqft
$339,900
Sold Jul 2026
612 Tuskegee AVE, CHESAPEAKE VA 23320
3 bd · 2.1 ba · 1,672 sqft
$375,000
Sold Jun 2026
1349 Great Bridge BLVD, CHESAPEAKE VA 23320
3 bd · 2 ba · 1,360 sqft
$315,000
Sold Jun 2026
614 Ray AVE, CHESAPEAKE VA 23320
4 bd · 2.1 ba · 2,076 sqft
$417,000
Sold Jun 2026
218 Gregg ST, CHESAPEAKE VA 23320
3 bd · 2.1 ba · 1,871 sqft
$367,000
Sold Jun 2026
5023 Booker ST, CHESAPEAKE VA 23320
3 bd · 2 ba · 1,013 sqft
$299,000
Sold Jun 2026
What buyers should know
Neutral counts from the 41 Crestwood homes VaHome has mapped against federal and state hazard layers — shown the same way for every neighborhood.
63%
of mapped homes sit in FEMA high-risk flood zones
AE · 26 · X · 15 — lenders require flood insurance in AE/VE
0 of 43
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 September 2026 · Live REIN MLS data
Crestwood real estate FAQ
Where is Crestwood located in Chesapeake?+
Crestwood is an inland neighborhood in Chesapeake, Virginia. It is not on the water. Homes sit along Great Bridge Boulevard near the South Norfolk and Greenbrier areas. Shops and business strips nearby are an easy drive.
What kind of homes are in Crestwood?+
Crestwood is mostly detached houses. The housing stock spans a range of building eras, from mid-century homes to houses built in more recent decades.
What schools serve the Crestwood neighborhood?+
The neighborhood is tied to Crestwood Intermediate School and Crestwood Middle School. Both sit on Great Bridge Boulevard and are part of Chesapeake Public Schools. Buyers should confirm current zoning with the school division. Check ratings on GreatSchools before relying on zones.
About Chesapeake
Homes for sale in Chesapeake, VA offer suburban space, top-rated schools, and easy access to Virginia Beach and Norfolk. The city splits roughly into five corridors. Greenbrier, ZIP 23320, has newer construction and shopping near the mall. Great Bridge, in 23320 and 23322, has the historic Battlefield district and excellent schools. Hickory, in 23322, has large-lot homes and Hickory High. Western Branch, in 23321, sits near the Portsmouth border. It has mature trees and starter homes. Deep Creek and South Norfolk, in 23323 and 23324, have lower-priced homes and waterfront access. Chesapeake Public Schools anchor buyer demand. They rank among the highest-rated in Hampton Roads. Hickory High, Grassfield High, Great Bridge High, and Western Branch High are all here. Median home prices range from $300K starter homes in Deep Creek to $600K+ homes in Great Bridge. Luxury estates in Hickory's gated neighborhoods run $1M+. The commute to Virginia Beach, Norfolk Naval Shipyard, or Newport News Shipbuilding is easy via I-664 and I-64. Below you'll find every active Chesapeake MLS listing. It is 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.
Looking for a realtor for Crestwood?
Looking for a realtor for Crestwood? Tom & Dariya Milan, Realtors know Crestwood street by street. Brokered by LPT Realty. As Chesapeake real estate agents, they track every Crestwood sale. 26 homes have sold here in the last 12 months, at a median of $372,500. Right now 3 homes are on the market. They also know what Crestwood buyers and sellers should expect next.
Need a Crestwood buyer’s agent to find the right home? Or a listing agent to sell your Crestwood house? The first conversation is free. There is never any pressure, just straight local answers. Thinking of selling? Start with a free home value estimate for Crestwood. It is instant, built from REIN closed sales. A hand-built report follows within 24 hours.
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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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