Grassfield Homes for Sale in Chesapeake, VA

Grassfield is a residential neighborhood in Chesapeake, Virginia, known for its planned community layout and tree-lined streets. The area features a mix of single-family homes with modern construction and established landscaping. Residents appreciate the quiet, suburban setting that maintains proximity to local amenities and services.

9 homes for sale in Grassfield right now.

9

Active Listings

$449,500

Median List Price

$142

Avg. $ / Sq. Ft.

32

Avg. Days on Market

18d ago

Newest Listing

Live from the REIN MLS, refreshed continuously. Stats reflect active for-sale inventory in Grassfield.

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Living in Grassfield

Daily life in Grassfield centers around a family-oriented community with parks, walking paths, and recreational spaces. The neighborhood supports outdoor activities and neighborhood gatherings throughout the year. Shopping, dining, and services are conveniently accessible without requiring lengthy travel.

Grassfield appeals to families and professionals seeking stable residential neighborhoods within Chesapeake. Homes in the area offer good value for those prioritizing community character and suburban comfort. The neighborhood attracts buyers looking for an established community with room for growth and stability.

Listings & market data updated July 2026 · Live REIN MLS data

Grassfield real estate FAQ

What kinds of homes are in Grassfield?+

Grassfield is one of Chesapeake's newer-construction areas, so the housing stock leans heavily toward homes built within the last two decades. You'll find planned subdivisions such as Dominion Meadows, Summerwood at Grassfield, The Landing at Grassfield, Grassfield Meadows, and Culpepper Landing, with single-family floor plans, some townhomes, and ongoing development like the approved Scenic Heights project off Dominion Boulevard. Many neighborhoods include amenities such as parks, ponds, and water features.

What schools serve the Grassfield area?+

Most of Grassfield is zoned to Grassfield High School on Grizzly Trail, which operates as a Governor's STEM Academy and offers Advanced Placement (AP) courses and Project Lead The Way curriculum. Grassfield Elementary School serves grades PK-5, and Hugo A. Owens Middle School is among the zoned feeders for the high school. Chesapeake City Public Schools sets attendance boundaries and can adjust them, so confirm the exact zoning and current GreatSchools ratings for any specific address.

Where is Grassfield located within Chesapeake?+

Grassfield sits in the central-to-southern part of Chesapeake along the Dominion Boulevard (US-17) corridor, near Grassfield Parkway. The city identifies it as one of its newest and fastest-growing planning areas. It is positioned between the Great Bridge area to the east and the more rural southern Chesapeake to the south.

How far is Grassfield from the interstates and Hampton Roads bases?+

Grassfield offers quick access to I-64, typically reachable in around 10 minutes via Dominion Boulevard, which connects north toward the I-64/I-464 interchange. Naval Station Norfolk is roughly 18 miles north, generally about a 30-minute drive in light traffic and longer at peak times. The corridor also provides routes toward the Norfolk Naval Shipyard, Joint Expeditionary Base Little Creek-Fort Story, and the Peninsula.

Is the Dominion Boulevard Veterans Bridge tolled?+

Yes. Dominion Boulevard (US-17) crosses the Southern Branch of the Elizabeth River on the Veterans Bridge, a fixed high-rise span that replaced the older drawbridge and carries four lanes of traffic toward the I-64/I-464 area. It uses open-road, fully electronic tolling via E-ZPass or toll-by-plate, with rates set by the City of Chesapeake and adjusted periodically. Many buyers commuting north factor the toll into their planning.

What shopping and amenities are near Grassfield?+

Everyday shopping centers around the Dominion Boulevard and Grassfield Parkway area, where the Cahoon Commons retail center is anchored by a Walmart Supercenter and includes grocery, pharmacy, dining, and other services. Because it is a growing corridor, additional retail and commercial development continues along Dominion Boulevard. The area is also a short drive from the Great Bridge shopping district and the Greenbrier area for larger retail and restaurants.

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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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.

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What residents say about Grassfield

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