Why this home stands out
Land at this scale is a vanishing commodity in the Hampton Roads region. At just under 98 acres, 2237 Shillelagh Road offers the kind of canvas that lets you build entirely on your own terms — a custom estate, a working farm, a family compound, or simply wide-open space held for the future. Few parcels anywhere near Chesapeake come close to this footprint, and that alone sets this address apart.
PLEASANT GROVE and the Chesapeake real estate market
Pleasant Grove sits in the western reaches of Chesapeake, Virginia — a part of the city where the landscape still breathes. Large lots, mature tree lines, and a slower pace define the character here, a welcome contrast to the denser corridors closer to the interstate. This is the Chesapeake that long-time residents talk about when they describe why they stayed: room to spread out, genuine quiet, and a community that feels grounded. For anyone exploring chesapeake homes for sale with acreage in mind, Pleasant Grove consistently surfaces as one of the few areas where large-tract land still exists within city limits. Chesapeake itself is Virginia's second-largest city by land area, which means infrastructure, services, and connectivity are all within reasonable reach even when your address feels far removed from the bustle. The western side of the city leans rural without being remote — a balance that's increasingly rare.
What's nearby
Daily essentials are more accessible than the rural setting might suggest. The Chesapeake Square Mall corridor along Volvo Parkway puts grocery stores, pharmacies, and a range of dining options within a 15-to-20-minute drive. Deeper into the city, the Greenbrier area adds additional retail and restaurant depth. For outdoor recreation, Northwest River Park is a local favorite — over 700 acres of trails, camping, and paddling that pairs naturally with the lifestyle this property invites. Interstate 664 provides a direct link north toward Suffolk and the broader Hampton Roads metro, keeping the parcel genuinely connected despite its scale and seclusion.
For different buyers
For military families relocating
USCG Finance Center Chesapeake is roughly 18 minutes away, and Norfolk Naval Shipyard sits about 26 minutes out — both manageable commutes from this western Chesapeake location. If you're using a VA loan to finance a land purchase or future build, this parcel's size and location make it worth a detailed conversation with a VA-savvy lender familiar with construction and lot loans.
For buyers drawn to character
If your vision runs toward a working farm, an equestrian property, a private retreat, or simply land held on your own terms, 98 acres in Pleasant Grove is a rare starting point. Chesapeake VA homes for sale at this acreage are genuinely uncommon — and a parcel this size gives you the freedom to shape something that reflects exactly what you have in mind, without compromise.
More buyer questions
How far is 2237 Shillelagh Road from USCG Finance Center Chesapeake?
The drive runs approximately 18 minutes under normal traffic conditions, making it one of the closer large-acreage parcels to that installation in the region.
How far is 2237 Shillelagh Road from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is roughly 26 minutes away, a straightforward commute via the western Chesapeake road network connecting to the Portsmouth side of the shipyard.
What can land in Pleasant Grove be used for?
Chesapeake's zoning framework allows for a range of uses on large rural parcels, including residential construction, agricultural operations, and certain conservation uses — always verify current zoning and permitted uses with Chesapeake's Department of Development and Permits before making plans.
Is 2237 Shillelagh Road in a flood zone?
Flood zone status for this parcel should be confirmed through FEMA's current flood map service and verified with a licensed surveyor or lender, as large acreage parcels can include multiple flood designations across different sections of the property.
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's public utilities department and the relevant electric provider, as service to large rural parcels varies considerably by location.
Curious about what's possible on nearly 98 acres in Chesapeake? Tom and Dariya Milan at LPT Realty know this market well — reach out and let's talk through your vision for this property.
