Cheshire Forest Homes for Sale in Chesapeake, VA
Cheshire Forest is an established single-family neighborhood in the Great Bridge area of Chesapeake, VA, set along tree-lined streets in the 23322 ZIP code. The community was established in 1987 and was featured as the Tidewater Builders Association Homearama neighborhood in 1989, and its roughly 500 homes reflect that late-1980s-through-1990s era of construction. Homes here tend to be larger traditional single-family residences with varied architecture and generous yards, surrounded by mature landscaping and several ponds. With a homeowners association maintaining shared amenities and an easy reach to the Battlefield Boulevard corridor, Cheshire Forest is a well-rooted address in southern Chesapeake.
2 homes for sale in Cheshire Forest right now.
2
Active Listings
$597,500
Median List Price
$246
Avg. $ / Sq. Ft.
11
Avg. Days on Market
11d ago
Newest Listing
Live from the REIN MLS, refreshed continuously. Stats reflect active for-sale inventory in Cheshire Forest.
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Living in Cheshire Forest
Day-to-day life in Cheshire Forest centers on its amenities and walkable layout: the neighborhood offers a lifeguard-staffed community pool open from Memorial Day weekend through the weekend after Labor Day, a rentable clubhouse, two night-lit tennis and pickleball courts, a sand volleyball court, and two playgrounds. Cheshire Forest Park, north of Parker Road, adds a pond, playground, playing field, and picnic areas, while three ponds throughout the community draw ducks, geese, herons, and other wildlife, and wide streets with sidewalks make for pleasant dog walks and strolls. The neighborhood sits near the Battlefield Boulevard corridor, putting everyday shopping, dining, and grocery stores in the Great Bridge area within a short drive, with Greenbrier's larger retail centers a bit farther north. For commuters, the location offers access across Hampton Roads via Battlefield Boulevard and connections toward I-64, the Chesapeake Expressway, and the military installations in Norfolk and Virginia Beach.
Cheshire Forest is a mature, built-out community rather than a new-construction area, so its housing stock is dominated by established single-family homes from the late 1980s and 1990s, many on sizable lots with grown-in landscaping. Inventory is typically limited, with often only a small handful of homes active at any given time, reflecting modest turnover in the neighborhood. Demand is supported by the community's amenity package, its Great Bridge location, and commuting access across Hampton Roads, so well-maintained or updated homes tend to attract interest when they come to market. Because turnover is modest, buyers interested in Cheshire Forest often benefit from monitoring new listings closely.
Cheshire Forest real estate FAQ
Where is Cheshire Forest located in Chesapeake, VA?+
Cheshire Forest is in the Great Bridge area of southern Chesapeake, within the 23322 ZIP code and near the Battlefield Boulevard corridor. Its streets are organized around several ponds, with Cheshire Forest Park located north of Parker Road. The location offers access to shopping in the Great Bridge and Greenbrier areas, plus commuting routes across Hampton Roads.
What kinds of homes are in Cheshire Forest?+
Cheshire Forest is made up of roughly 500 single-family homes, most built from the late 1980s through the 1990s after the community was established in 1987. Homes tend to be larger traditional residences with varied architecture and generous yards, set among mature landscaping. The neighborhood was featured as the Tidewater Builders Association Homearama neighborhood in 1989.
What amenities does Cheshire Forest offer?+
The community's homeowners association maintains a lifeguard-staffed swimming pool (open Memorial Day weekend through the weekend after Labor Day), a rentable clubhouse, two night-lit tennis and pickleball courts, a sand volleyball court, and two playgrounds. Cheshire Forest Park adds a pond, playground, playing field, and picnic areas, and three ponds throughout the neighborhood attract local wildlife. Sidewalks and wide streets run through the community.
What schools serve Cheshire Forest?+
Cheshire Forest is part of Chesapeake Public Schools. Because attendance boundaries and GreatSchools ratings can change, buyers should confirm the current zoned elementary, middle, and high schools for a specific address directly with Chesapeake Public Schools.
How far is Cheshire Forest from the interstates and military bases?+
Cheshire Forest sits along the Battlefield Boulevard corridor, which links to I-64 and the Chesapeake Expressway for travel across Hampton Roads. From there, drivers can reach the Norfolk and Virginia Beach areas, including their military installations, though the southern Chesapeake location means commute times depend on traffic and destination.
What is the housing market like in Cheshire Forest?+
Cheshire Forest is an established, amenity-rich community where homes feature varied sizes, mature lots, and access to the neighborhood's recreational features. Inventory is usually limited, with only a small number of homes active at a time, so listings can move quickly when they appear. Touring in person and reviewing the HOA's amenities and dues is the best way to judge whether a home fits your needs.
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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What residents say about Cheshire Forest
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