Greenbrier Homes for Sale in Chesapeake, VA
Greenbrier is a neighborhood in Chesapeake, Virginia. It has a suburban setting with streets lined with trees and well-kept homes. The area mixes single-family homes with settled properties. Together they reflect the feel of the region. What you need is close by, yet the streets stay quiet.
16 homes for sale in Greenbrier right now.
“Greenbrier is central Chesapeake convenience — established streets minutes from the region's biggest retail corridor and the interstate. Homes here move on practicality more than drama, which makes it one of the easier places in the city to buy well if you're patient about condition.”
16
Active Listings
$330,000
Median List Price
$226
Avg. $ / Sq. Ft.
21
Avg. Days on Market
3d ago
Newest Listing
Live from the REIN MLS, refreshed continuously. Stats reflect active for-sale inventory in Greenbrier.
Neighborhood118
Sold · last 12 mo
$318,500
Median sale price
$226
Median sold $/sq ft
15
Median days on market
$699,900
1421 Gemstone LN, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$498,000
527 Windward DR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$450,000
621 Windward DR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$385,000
925 N Scarlet Oak CT, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$345,000
1509 Waitsel DR #206, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$335,000
1561 Rollesby WAY, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$335,000
1005 Winged Foot CT #B, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$335,000
1440 Rollesby WAY, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$325,000
1439 Rollesby WAY, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$320,000
948 Shoal Creek TRL #A, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$317,000
1505 Waitsel DR #304, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$300,000
1528 Hambledon LOOP, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$279,900
1346 River Birch RN, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$270,000
500 Judah WAY #123, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$269,500
1063 Still Harbor CIR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$264,700
923 Ketch CT, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
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Living in Greenbrier
Parks, recreation spots, and shopping areas are all a short trip away. Nearby green spaces and meeting spots make it easy to get outside and connect. Daily life in Greenbrier balances suburban ease with a close, neighborly feel.
Greenbrier is a good fit if you want a settled Chesapeake neighborhood with a stable, homey feel. Its location and range of homes make suburban living easy to find here. The area's core services are close at hand. Buyers who look here tend to value its neighborhood setting and its settled community.
What Greenbrier 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.
$318,500
Median sale price · 12 mo
118 closed sales
$226
Median sold $ / sq ft
closed sales with recorded sq ft
15 days
Median days on market
for homes that closed
$265K–$700K
Active listing range
16 on the market today
| Property type | Sold · 12 mo | Median sale price |
|---|---|---|
| Detached homes | 33 | $416,250 |
| Townhomes & condos | 85 | $295,000 |
Source: REIN MLS closed sales, trailing 12 months, computed by VaHome.
How Greenbrier compares
The 3 closest Chesapeake neighborhoods VaHome profiles, measured from map center to map center. Same 12-month REIN closed-sales math for every row.
| Neighborhood | Median sale | $ / sq ft | Days on mkt | Sold · 12 mo | For sale |
|---|---|---|---|---|---|
| Greenbrier | $318,500 | $226 | 15 | 118 | 16 |
| Plantation Lakes · 1.3 mi | $389,900 | $235 | 7 | 5 | 1 |
| Butts Station · 1.6 mi | $325,813 | $216 | 18 | 6 | 1 |
| Knells Ridge · 1.6 mi | $345,000 | $211 | 17 | 16 | 7 |
Source: REIN MLS closed sales, trailing 12 months, refreshed every 10 minutes. Neighborhoods with fewer than 5 closed sales are left out so no row rests on one or two homes.
What the homes in Greenbrier are like
Age, size, lot and price band of the 118 Greenbrier homes that closed since Oct 11, 2025, as recorded in the REIN MLS.
1988
Median year built
most homes sold were built 1979–2013
1,419 sq ft
Median living area
3-bedroom is the most common layout
6,534 sq ft (0.15 ac)
Median lot · detached
14 detached sales with a recorded lot
| Price range by type | Sold · 12 mo | Lower quarter | Median | Upper quarter |
|---|---|---|---|---|
| Detached homes | 33 | $377,000 | $416,250 | $455,000 |
| Townhomes & condos | 85 | $254,900 | $295,000 | $334,000 |
Lower and upper quarter are the 25th and 75th percentile sale prices. Half of all sales fell between them.
HOA reality
87%
Sales with an HOA
103 of 118 closed sales where REIN recorded an association
$31/mo
Typical HOA fee
median of 66 sales that reported a fee
$345/mo
Typical condo fee
median of 56 condo sales that reported a fee
Fees are what the listing agent entered at the time of sale. Confirm the current amount and what it covers with the association before you write an offer.
Source: REIN MLS closed sales since Oct 11, 2025, computed by VaHome. Any figure with fewer than 5 recorded homes is left out.
Recently sold in Greenbrier
The latest 10 closings from the REIN MLS. Each opens the home's full sold record.
1555 Rollesby WAY #5, CHESAPEAKE VA 23320
3 bd · 2.1 ba · 1,870 sqft
$315,000
Sold Oct 2026
1535 Hambledon LOOP, CHESAPEAKE VA 23320
2 bd · 2.1 ba · 1,340 sqft
$286,000
Sold Oct 2026
1537 Hambledon LOOP, CHESAPEAKE VA 23320
2 bd · 2.1 ba · 1,340 sqft
$280,000
Sold Oct 2026
602 Windward DR, CHESAPEAKE VA 23320
4 bd · 2.1 ba · 2,100 sqft
$455,000
Sold Oct 2026
1001 Saint Andrews WAY #A, CHESAPEAKE VA 23320
2 bd · 2 ba · 1,224 sqft
$225,000
Sold Sep 2026
1016 Winged Foot CT #B, CHESAPEAKE VA 23320
3 bd · 2.1 ba · 1,472 sqft
$339,000
Sold Sep 2026
928 Saint Andrews RCH #A, CHESAPEAKE VA 23320
3 bd · 2 ba · 1,272 sqft
$236,680
Sold Sep 2026
1523 Pucknall DR, CHESAPEAKE VA 23320
3 bd · 2.1 ba · 1,870 sqft
$335,000
Sold Sep 2026
1718 Rock Bridge MEWS #B, CHESAPEAKE VA 23320
2 bd · 2 ba · 978 sqft
$220,000
Sold Sep 2026
1417 Blairwood LN, CHESAPEAKE VA 23320
3 bd · 2 ba · 2,106 sqft
$515,000
Sold Sep 2026
What buyers should know
Neutral counts from the 208 Greenbrier homes VaHome has mapped against federal and state hazard layers — shown the same way for every neighborhood.
0%
of mapped homes sit in FEMA high-risk flood zones
X · 208
0 of 213
mapped homes inside a Navy jet-noise (AICUZ) contour
Every VaHome listing shows its exact noise zone and Accident Potential Zone.
Zone NONE
hurricane evacuation zone
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 Greenbrier area
$87,794
Median household income
41.4
Median age
76.1%
Owner-occupied households
41.3%
Bachelor's degree or higher
Source: U.S. Census Bureau, American Community Survey 2024 5-Year Estimates (2020–2024), census-tract level for the Greenbrier area. Shown identically for every neighborhood.
Bases & commutes
Straight-line distances from the center of Greenbrier. Every listing page shows live drive times with traffic.
Listings & market data updated October 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. It sits just off Interstate 64 on the city's north side. The area lies near the I-64/I-464 interchange. Route 168, which is Battlefield Boulevard, and US-17 are among the major routes nearby. The area mixes settled home streets with shopping centers, office parks, lakes, and golf courses.
What kinds of homes are in Greenbrier?+
Greenbrier has a varied mix of housing. It includes houses, townhomes, condos, quadravillas, and duplexes. Architectural styles range from brick ranch homes to two-story houses. Communities include The Retreat at Greenbrier, the Villas at Greenbrier, also called Cedar Glen, and Lakes of Greenbrier. Many sections were built from the 1970s through the early 2000s. So much of the housing stock is settled rather than new builds.
What schools serve the Greenbrier area?+
Chesapeake Public Schools serves Greenbrier. Greenbrier Primary and Greenbrier Intermediate handle the early grades. Then Greenbrier Middle School serves grades 6-8. Depending on the address, the high school is usually Indian River High School or Oscar Smith High School. Attendance zones depend on a home's exact spot. So buyers should confirm the zoned schools and current GreatSchools ratings before they buy.
How far is Greenbrier from the interstates and the naval bases?+
Greenbrier has direct access to Interstate 64 at the Greenbrier Parkway interchange. I-464 and Route 168 are also close for north-south trips. Naval Station Norfolk is roughly 16 to 19 miles away. That drive usually takes 25 to 35 minutes, based on traffic. The spot also links to downtown Norfolk, Portsmouth, and Virginia Beach.
What lakes and golf options are around Greenbrier?+
Greenbrier has several lakes, and a number of home communities are built around them. On Volvo Parkway, Greenbrier Country Club has a private 18-hole course and a clubhouse. Rees Jones designed the course, and it opened in 1987. To the southeast, along the Chesapeake-Virginia Beach boundary, is the Stumpy Lake Natural Area in Virginia Beach. It has a 278-acre lake and an 18-hole public golf course first designed by Robert Trent Jones. There is also green space, trails, and a canoe and kayak launch.
What shopping, dining, and offices are in Greenbrier?+
Greenbrier is one of Chesapeake's main business hubs. Its anchor is Greenbrier Mall. Around it are retail centers, places to eat, and hotels. The Greenbrier Circle and Greenbrier Towne Center office and business parks are here too. Medical offices and big employers cluster along it. That puts day-to-day shopping and services within a short drive of most homes.
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 Greenbrier?
Looking for a realtor for Greenbrier? Tom & Dariya Milan, Realtors know Greenbrier street by street. Brokered by LPT Realty. As Chesapeake real estate agents, they track every Greenbrier sale. 118 homes have sold here in the last 12 months, at a median of $318,500. Right now 16 homes are on the market. They also know what Greenbrier buyers and sellers should expect next.
Need a Greenbrier buyer’s agent to find the right home? Or a listing agent to sell your Greenbrier 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 Greenbrier. It is instant, built from REIN closed sales. A hand-built report follows within 24 hours.
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What residents say about Greenbrier
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