Rollingwood Homes for Sale in Virginia Beach, VA
Rollingwood is a settled neighborhood in south-central Virginia Beach. It sits off the Holland Road corridor in the 23453 ZIP code. Princess Anne Road, Nimmo Parkway, and Dam Neck Road are near by. The community is mostly houses, including two-story homes, along streets such as Prodan Lane. Its spot puts it within reach of the Princess Anne and Holland Road shops, dining, and commuter routes.
2 homes for sale in Rollingwood right now.
2
Active Listings
$902,000
Median List Price
$220
Avg. $ / Sq. Ft.
37
Avg. Days on Market
38d ago
Newest Listing
Live from the REIN MLS, refreshed continuously. Stats reflect active for-sale inventory in Rollingwood.
Neighborhood10
Sold · last 12 mo
$259,450
Median sale price
$234
Median sold $/sq ft
19
Median days on market
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What Rollingwood 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.
$259,450
Median sale price · 12 mo
10 closed sales
$234
Median sold $ / sq ft
closed sales with recorded sq ft
19 days
Median days on market
for homes that closed
$839K–$965K
Active listing range
2 on the market today
| Property type | Sold · 12 mo | Median sale price |
|---|---|---|
| Detached homes | 10 | $259,450 |
Source: REIN MLS closed sales, trailing 12 months, computed by VaHome.
Recently sold in Rollingwood
The latest 10 closings from the REIN MLS. Each opens the home's full sold record.
4 Mohawk DR, PORTSMOUTH VA 23701
2 bd · 1 ba · 854 sqft
$236,000
Sold Sep 2026
20 Chippewa TRL, PORTSMOUTH VA 23701
2 bd · 1 ba · 860 sqft
$170,000
Sold Aug 2026
837 Greenfield LN, CHESAPEAKE VA 23322
4 bd · 4 ba · 2,660 sqft
$720,000
Sold Aug 2026
16 Chowan DR, PORTSMOUTH VA 23701
4 bd · 2 ba · 1,381 sqft
$160,000
Sold Aug 2026
852 Dawson CIR, CHESAPEAKE VA 23322
5 bd · 4 ba · 3,741 sqft
$780,000
Sold Jul 2026
15 Chowan DR, PORTSMOUTH VA 23701
3 bd · 1 ba · 986 sqft
$230,000
Sold May 2026
9 Croatan TRL, PORTSMOUTH VA 23701
3 bd · 2 ba · 1,200 sqft
$259,900
Sold May 2026
808 Greenfield LN, CHESAPEAKE VA 23322
6 bd · 3.1 ba · 3,593 sqft
$950,000
Sold Apr 2026
4601 Portsmouth BLVD, PORTSMOUTH VA 23701
2 bd · 2 ba · 1,000 sqft
$259,000
Sold Mar 2026
2404 Belle CT, VIRGINIA BEACH VA 23453
4 bd · 3 ba · 2,836 sqft
$664,900
Sold Mar 2026
What buyers should know
Neutral counts from the 14 Rollingwood 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 · 14
4 of 20
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 Rollingwood area
$89,040
Median household income
41.1
Median age
64.9%
Owner-occupied households
32%
Bachelor's degree or higher
Source: U.S. Census Bureau, American Community Survey 2024 5-Year Estimates (2020–2024), census-tract level for the Rollingwood area. Shown identically for every neighborhood.
Bases & commutes
Straight-line distances from the center of Rollingwood. Every listing page shows live drive times with traffic.
Listings & market data updated September 2026 · Live REIN MLS data
Rollingwood real estate FAQ
Where is Rollingwood located in Virginia Beach?+
Rollingwood sits in south-central Virginia Beach within the 23453 ZIP code. It is just off the Holland Road corridor. Princess Anne Road, Nimmo Parkway, and Dam Neck Road are close. Streets in the neighborhood include Prodan Lane.
What kinds of homes are in Rollingwood?+
Rollingwood is a settled neighborhood of houses, including two-story homes with three or more bedrooms. Use the live listings and stats above to see current homes for sale. They show square footage and other details in the community.
What is nearby Rollingwood for shopping and commuting?+
Rollingwood's spot along the Holland Road and Princess Anne Road corridors gives access to area shops and dining. Nimmo Parkway and Dam Neck Road add more routes across this part of Virginia Beach.
About Virginia Beach
Homes for sale in Virginia Beach, VA span every price point and lifestyle. Options run from oceanfront condos along the famous Boardwalk to large waterfront estates. Those estates sit on the Lynnhaven River and Linkhorn Bay. Virginia Beach is the largest city in Hampton Roads. Its real estate market is more varied than most. Great Neck in ZIP 23454 has established neighborhoods. Kempsville in 23464 has golf-course neighborhoods. Town Center in 23462 has modern townhomes close by. Sandbridge in 23456 has beach-cottage living. You might want a starter home under $300K. You might want a home in a top-rated school district. Or you might want a luxury home north of $2 million. The active MLS inventory here covers all three. It syncs from REIN every 2 minutes. Buyer demand stays strong year-round. The mild coastal climate helps. So do the Virginia Beach City Public Schools, top-ranked year after year. Kempsville High, Floyd E. Kellam High, Princess Anne High, and Cox High are among them. Naval Air Station Oceana is here too. It is the largest master jet base in the country. VA loan financing is widely used here. First-time buyers tend toward the inland ZIPs 23464, 23456, and 23452. Second-home and luxury buyers tend toward 23451, the Oceanfront and North End, and 23454, Great Neck and Bay Colony. Below you'll find every active Virginia Beach home for sale. It is pulled live from the REIN MLS and refreshed every 2 minutes.
Schools serving Virginia Beach
Browse Virginia Beach homes by VBCPS 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 Rollingwood?
Looking for a realtor for Rollingwood? Tom & Dariya Milan, Realtors know Rollingwood street by street. Brokered by LPT Realty. As Virginia Beach real estate agents, they track every Rollingwood sale. 10 homes have sold here in the last 12 months, at a median of $259,450. Right now 2 homes are on the market. They also know what Rollingwood buyers and sellers should expect next.
Need a Rollingwood buyer’s agent to find the right home? Or a listing agent to sell your Rollingwood 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 Rollingwood. It is instant, built from REIN closed sales. A hand-built report follows within 24 hours.
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What residents say about Rollingwood
Honest, moderated reviews from people who’ve lived in Rollingwood. Share your own experience to help future neighbors decide.
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