Why this home stands out
Parcels of this scale are genuinely uncommon in the 23323 zip code, where most tracts have long been subdivided. At just under 98 acres, 2237 Shillelagh Road gives you the room to think in a completely different category — agricultural operation, timber management, a family compound with room to grow, or a conservation easement. The land speaks for itself, and the possibilities are wide open.
PLEASANT GROVE and the Chesapeake real estate market
Pleasant Grove sits in the western reaches of Chesapeake, one of the largest cities by land area on the entire East Coast. This corner of the city holds onto a rural character that has largely disappeared elsewhere in Hampton Roads — wide lots, working farms, and long sight lines that remind you how much open country still exists here. Chesapeake as a whole is known for its mix of suburban neighborhoods and genuine agricultural heritage, and Pleasant Grove leans firmly into that heritage. The city's infrastructure — maintained roads, reliable utilities, and strong public services — reaches out here without erasing the quiet. For buyers comparing Chesapeake homes for sale across the spectrum from suburban subdivisions to working farmland, this western corridor is a category of its own. The 23323 zip code covers a broad swath of this rural-meets-suburban transition zone, making it one of the more distinctive addresses in the region.
What's nearby
Everyday conveniences are more accessible than the acreage might suggest. The Chesapeake Square Mall area along Route 17 puts grocery stores, pharmacies, and a full range of retail within a reasonable drive. Restaurants and coffee shops cluster along the same corridor. Deeper into the city, the Greenbrier district adds more dining and shopping options. For outdoor recreation, Northwest River Park — one of Hampton Roads' most beloved natural areas — is practically a neighbor, offering paddling, camping, and miles of trails. Families comparing homes for sale in Chesapeake with serious land often point to this corridor as the sweet spot between rural privacy and urban access.
For different buyers
For military families relocating
The USCG Finance Center Chesapeake is an 18-minute drive, and Norfolk Naval Shipyard is reachable in about 26 minutes — making this land a realistic option for service members with a vision for building on their own terms. A VA loan can be used to purchase land when a construction loan is part of the plan, so the path from raw acreage to a custom home is more straightforward than many buyers realize.
For buyers drawn to character
If your version of the right property involves room to breathe — horses, a market garden, a private trail system, or simply a boundary line you can't see from the house — 2237 Shillelagh Road is worth a serious look. Nearly 98 acres in Chesapeake's rural west is the kind of holding that rarely surfaces, and when it does, it tends to attract buyers who know exactly what they want to build, grow, or protect.
More buyer questions
How far is 2237 Shillelagh Road from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is approximately 26 minutes from the property under normal traffic conditions, making it a workable commute for shipyard personnel who prioritize space and privacy over proximity.
What can the land at 2237 Shillelagh Road be used for?
The parcel's size and Pleasant Grove location make it well-suited for agricultural use, equestrian operations, timber management, a private family compound, or conservation — though buyers should verify current zoning with Chesapeake's Department of Development and Permits before finalizing any plans.
Is 2237 Shillelagh Road in a flood zone?
Flood zone status for this parcel is detailed in the FloodRisk tile on this page — given the acreage, portions of the tract may carry different designations, so reviewing the FEMA flood map for the full boundary is recommended.
Are there utilities available at 2237 Shillelagh Road?
Utility availability — including water, sewer, and electric service — should be confirmed directly with the City of Chesapeake and local utility providers, as rural parcels of this size often require well, septic, or extended service connections.
Where do students living at this address go to school?
Families researching homes for sale zoned for Grassfield High School and homes for sale zoned for Grassfield Elementary School will find that this address falls within that attendance zone — though school assignments should always be confirmed with Chesapeake Public Schools directly.
Ready to walk the land at 2237 Shillelagh Road? Tom and Dariya Milan know this corner of Chesapeake well — reach out and let's set up a site visit on your schedule.
