131 days on market
$840,000
4500 Backwoods Rd
Chesapeake, Virginia 23322
MLS# 10614351 · PLEASANT GROVE · Chesapeake VA
Updated Jan 7, 2026 · Source: REIN MLS
Est. payment
$5,194/mo
Edit below
Price / sq ft
$0
0 sq ft
Days on market
131
HOA
None
Year built
N/A
Beds
0
Full Baths
0
Half Baths
0
Sq Ft
0
Garage
N/A
Schools
- ElementaryHickory Elementary School7/10
- MiddleHickory Middle School7/10
- 8/10
Info provided by GreatSchools
About this home
Property is priced to reflect the updates needed and is being sold as-is, including all buildings. The property features a pond, a dwelling and acreage. Ideal opportunity for investors or developers seeking future upside, potential tax advantages with the City of Chesapeake, or a private estate setting. Conveniently located just minutes from Grassfield High School, shopping, I-64, and easy access to Moyock, NC.
Listed by E Ashley McDougal · Howard Hanna Real Estate Svcs.
VaHome Team property overview
Meet 4500 Backwoods Road — 21 acres of open land in Chesapeake's Pleasant Grove area. Whether you're envisioning a private homestead, an agricultural operation, or a quiet rural retreat, this parcel offers the space and freedom that's genuinely hard to find this close to Hampton Roads.
Read full property overview ↓Show less ↑
Why this home stands out
Twenty-one acres is a rare find in a metro region as built-out as Hampton Roads. This Pleasant Grove parcel gives you room to design from scratch — whether that means a custom home with a long private driveway, outbuildings, livestock, crops, or simply land you can hold and enjoy. There are no existing structures dictating your vision, which means the possibilities are genuinely open.
PLEASANT GROVE and the Chesapeake real estate market
Chesapeake is one of Virginia's largest cities by land area, and if you've ever wondered what county is Chesapeake VA in — the answer is that Chesapeake is an independent city, meaning it operates outside any county jurisdiction entirely. That matters for land ownership: you deal directly with the City of Chesapeake for zoning, permits, and services. The Pleasant Grove corridor sits in the southern, more rural stretch of Chesapeake, where large lots and agricultural tracts are still the norm rather than the exception. Life out here moves at a different pace. Neighbors are spread out, tree lines are thick, and the road names tell you something about the land's history. You're still within reasonable reach of Virginia Beach, Norfolk, and the broader Hampton Roads metro — but this corner of Chesapeake feels genuinely removed from suburban density. It's the kind of place people move to when they want acreage without sacrificing regional access.
What's nearby
The Pleasant Grove area is rural by design, so daily errands require a short drive. The Chesapeake city center and its retail corridors along Battlefield Boulevard are roughly 20–25 minutes north. Grocery options, pharmacies, hardware stores, and dining are all accessible without a long haul. Outdoor recreation is a natural draw here — the Great Dismal Swamp National Wildlife Refuge is a short drive southwest, offering hiking, paddling, and wildlife observation across a vast protected landscape. Lake Drummond, at the heart of the refuge, is a local landmark worth knowing. For commuters, Interstate 64 and Route 17 provide the main corridors connecting this part of Chesapeake to the broader region.
For different buyers
For military families relocating
If you're stationed at USCG Finance Center Chesapeake or Norfolk Naval Shipyard, this parcel puts you within commuting range while keeping your family well outside the congestion of the urban core. A VA loan can be used to finance the purchase of land when paired with construction financing — worth exploring if you're ready to build your own place rather than settle for existing inventory. BAH rates in this region support meaningful purchasing power.
For buyers drawn to character
This is land for people who want to build something intentional — not just a house, but a property with a sense of place. Twenty-one acres in Pleasant Grove means you can plan a homestead, plant an orchard, keep horses, or simply create a private compound with room to breathe. If you've been browsing chesapeake homes for sale and finding that existing houses don't quite match your vision, raw acreage like this is where custom possibilities begin.
Frequently asked questions
What county is Chesapeake VA in?
Chesapeake is an independent city in Virginia, meaning it is not part of any county — it operates as its own separate jurisdiction. For land at 4500 Backwoods Road, all zoning, permitting, and tax matters are handled directly through the City of Chesapeake.
How far is 4500 Backwoods Road from USCG Finance Center Chesapeake?
The drive from 4500 Backwoods Road to USCG Finance Center Chesapeake is approximately 28 minutes under normal traffic conditions, making it a manageable commute for personnel stationed there.
How far is 4500 Backwoods Road from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is roughly 38 minutes from this address, accessible via the main road corridors connecting southern Chesapeake to Portsmouth.
Is 4500 Backwoods Road in a flood zone?
Flood zone status for this parcel is detailed in the FloodRisk tile on this page — we recommend reviewing that information and consulting with a local lender or surveyor before finalizing any land purchase.
Can a VA loan be used to purchase land in Chesapeake?
A VA loan on its own is not typically used for raw land purchases, but it can be combined with a VA construction loan to finance both the land and a new home build simultaneously — making it a viable path for eligible service members and veterans.
Curious about building on this land or want to understand zoning options in Chesapeake? Tom and Dariya Milan at LPT Realty know this market well — reach out and let's talk through what's possible.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Location & Street View
4500 Backwoods RD, Chesapeake
Map and Street View imagery © Google. Imagery may not be current.
Map data ©Google. Click and drag inside the map to explore the surrounding area.
Flood Risk
Property Details
Bedrooms
0
Full Baths
0
Half Baths
0
Approx Sq Ft
0
Stories
0
Fireplaces
0
Flooring
N/A
Heating
Cooling
Laundry
Interior Features
N/A
Sale & Tax History
List Price
$840,000
Price / Sq Ft
$0
Annual Taxes
$7,085
Monthly Tax
$590
HOA
None
Tax Rate (effective)
0.84%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Dec 29, 2025 | $840,000 | — |
| Currently listed | — | $840,000 | — |
Public-Records Assessment
Source: Chesapeake via Hampton Roads Regional Parcels. Fetched May 11, 2026.
Total Assessed
$733,500
Land
$365,600
Improvement
$367,900
Parcel ID: 1180000000065 · View on city GIS portal
Looking for multi-year tax assessments or prior sales? REIN MLS only ships data for the current listing. For full property history, check the city assessor record:
Tax data above from REIN public-records sync. Sale timeline tracked from this listing's first appearance in our feed forward; prior owner sales are not included.
Comparable Properties
Comps are selected by city, bed count, square footage and price proximity. Composite similarity score weights bed match, sqft variance, price variance, and straight-line distance.
About buying in Chesapeake
Chesapeake is Virginia's second-largest city by area and offers a mix of suburban subdivisions, rural acreage, and waterfront properties along the Intracoastal Waterway. Western Branch, Greenbrier, and Great Bridge are among the most sought-after neighborhoods, with top-rated public schools and easy access to I-64 and the Chesapeake Expressway. The city is known for lower property taxes and larger lot sizes compared to neighboring Virginia Beach and Norfolk, which makes it especially attractive to families looking for more space.
Military Commute
Drive times to nearest basesDrive times via Google Maps with current traffic patterns. Times are typical and may vary by time of day. Use the "Analyze" button up top to see live drive time to your saved base.
Estimate your monthly payment
$5,194/moPrincipal & interest
$4,359
Property tax
$590
Home insurance
$245
PMI
None
HOA
None
Estimate only. Insurance assumed at 0.35% of home value annually. Actual taxes, insurance, and rate will vary by lender, credit, and property. Contact a lender for a personalized quote.
Listed by Howard Hanna Real Estate Svcs. · MLS# 10614351
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$840,000
4500 Backwoods RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
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