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ChesapeakePLEASANT GROVE4500 Backwoods Rd✓ Source: REIN MLS #10614351 · record updated Aug 25, 2026 · synced every 2 min · your inquiry is never resold
4500 Backwoods RD, CHESAPEAKE VA 23322 - Main photo
4500 Backwoods RD, CHESAPEAKE VA 23322 - Photo 2
4500 Backwoods RD, CHESAPEAKE VA 23322 - Photo 3
4500 Backwoods RD, CHESAPEAKE VA 23322 - Photo 4
4500 Backwoods RD, CHESAPEAKE VA 23322 - Photo 5
$840,000
239days on market

4500 Backwoods Rd, Chesapeake, VA 23322

Under ContractLand and Farms · PLEASANT GROVE

Facts & features

Type

Land and Farms

HOA

None

Taxes

$7,085/yr

County

Chesapeake VA

MLS #

10614351

Construction & exterior

Fencing
Cross Fenced,Front Fenced

Utilities & systems

Utilities available
Septic, Well

Lot, parking & ownership

Lot size
21.0000
Road surface
Gravel
Subdivision
PLEASANT GROVE
Zoning
A1
Ownership
Fee Simple
Possession
CLOSING
Disclosures
Disclosure Statement

See more Chesapeake land & lots.

Sources: REIN MLS record · city assessor · null fields are suppressed, never faked

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.

Listing courtesy of E Ashley McDougal · RE/MAX Alliance · REIN MLS #10614351

VaHome team overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · LPT Realty

At a glance

4500 Backwoods Road is a land and farm parcel in Chesapeake, Virginia 23322 — a rare opportunity to own raw acreage in one of Hampton Roads' most sought-after rural corridors, where open space and Southern Virginia character are increasingly hard to find.

Read the full overview ↓

Why this home stands out

What sets 4500 Backwoods Road apart is the combination of genuine rural depth and surprising accessibility. Large tracts in this part of Chesapeake are becoming scarcer every year, and this address sits in a corridor where working farmland, wooded lots, and wide-open sky still define the landscape. Whether you're envisioning a custom homestead, an agricultural operation, or simply land to hold, the bones here are hard to replicate closer to the city.

PLEASANT GROVE and the Chesapeake real estate market

Chesapeake is the second-largest city by land area in Virginia, and the 23322 zip code captures some of its most rural, unhurried character. This part of the city — far from the commercial corridors along Battlefield Boulevard — feels more like the Virginia countryside than a suburb. Neighbors are measured in acres, not feet. Mature trees line the roads, and the pace of life slows considerably once you leave the main arteries. Still, Chesapeake's infrastructure is never far: city water connections, well-maintained roads, and emergency services all serve the area. Families comparing homes for sale in Chesapeake often discover that the 23322 zip code offers a lifestyle that's genuinely different from the rest of Hampton Roads — more land, more privacy, and more room to build something that's truly yours.

What's nearby

Daily logistics from 4500 Backwoods Road are more manageable than the rural setting might suggest. The Hickory area along Centerville Turnpike puts groceries, pharmacies, and dining within a reasonable drive. Chesapeake's Greenbrier district — home to a full range of retail, restaurants, and medical offices — is accessible via Western Branch or Centerville corridors. Outdoor recreation is woven into the fabric of this area, with the Northwest River Park offering paddling, camping, and hiking just a short drive south. The Great Dismal Swamp National Wildlife Refuge is also within reach for those who love birding and backcountry trails.

For different buyers

For military families relocating

USCG Finance Center Chesapeake is roughly 28 minutes away, and Norfolk Naval Shipyard is about 38 minutes — both workable commutes from this part of the city. Military families using a VA loan to finance a construction-to-permanent build on raw land should verify lender eligibility early, but the location puts you well within reach of Hampton Roads' major installations without the density of base-adjacent neighborhoods.

For buyers drawn to character

If your vision involves something you've designed from the ground up — a custom home, a small farm, a private retreat with room to breathe — 4500 Backwoods Road is the kind of canvas that's genuinely rare in Hampton Roads. Land with this kind of depth and rural character, still within Chesapeake city limits, is exactly what character-driven buyers search for and rarely find.

More buyer questions

How far is 4500 Backwoods Road from USCG Finance Center Chesapeake?

The USCG Finance Center Chesapeake is approximately 28 minutes from this address under typical driving conditions. Norfolk Naval Shipyard is roughly 38 minutes, making this parcel accessible to personnel at both installations.

What is the flood zone status for 4500 Backwoods Road?

Flood zone designation for this parcel is addressed in the dedicated FloodRisk tile on this page — review that section and consult FEMA's flood map service for the most current determination before making land-use decisions.

Is 4500 Backwoods Road in Chesapeake city limits or a county jurisdiction?

Yes — this address falls within the independent city of Chesapeake, Virginia, which operates its own city services, zoning authority, and school system rather than a county government.

What school zone does this address fall in?

Families evaluating homes for sale zoned for Grassfield High School and homes for sale zoned for Hickory Elementary School will want to confirm current zoning directly with Chesapeake Public Schools, as attendance boundaries can be updated by the district.

Can a VA loan be used to purchase raw land at 4500 Backwoods Road?

VA loans are generally structured for the purchase of a primary residence and typically require a home to be on the property; raw land purchases alone usually do not qualify, though construction-to-permanent loan options may be worth exploring with a VA-approved lender.

Curious about what's possible at 4500 Backwoods Road? Tom and Dariya Milan can walk you through land-use considerations, comparable parcels, and next steps — reach out to start the conversation.

Summary generated by AI from public records and publicly available information.

Homes like this one sell fast — see the next one first

Chesapeake$710K – $970K

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Schools

VaHome School Score

Our own 1–10 rating, scored from Virginia Department of Education data.

VaHome School Score — calculated by VaHome.com from Virginia Department of Education assessment, progress, and attendance data. Attendance zones come from the MLS listing record; confirm the current zone with the school division before making an offer.

Flood & environment

FEMA flood zone X · outside the high-risk area · FIRM 510034

Flood Risk

Looking up FEMA flood zone…

Hurricane Evacuation Zone

Evacuation Zone D

Source: Virginia Dept. of Emergency Management — Know Your Zone

Explore this neighborhood

Pleasant Grove

Pleasant Grove is one of southeastern Chesapeake's fastest-growing areas, set along the Mount Pleasant Road and Battlefield Boulevard corridor south of the Great Bridge area.

$569K

Median sale · 12 mo

$252

Sold $/sq ft

30d

Days on market

22

For sale now

$138K

HH income

84.7%

Owner-occupied

REIN MLS closed sales, trailing 12 mo · U.S. Census ACS 2024 5-year

Explore Pleasant Grove
Map of Pleasant Grove with neighborhood boundaryNeighborhood

see more Chesapeake homes

Location intelligence

Minutes to real places, not a score

Location & Neighborhood

Places within ~1 mile, ordered by distance from this property. Powered by Google Places.

Military Commute

Drive times to nearest bases

Drive 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.

The numbers

Run the real carrying cost

Estimates only — taxes come from the public record; confirm rates with your lender. VA-eligible buyers: $0-down financing may apply.

Estimate your monthly payment

$5,194/mo

Principal & interest

$4,359

Property tax

$590

Home insurance

$245

PMI

None

HOA/Condo (paid separately)

None

Estimate only. Association (HOA/condo) fees are paid separately and are not included in the payment above. 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.

Value & history

Judge value on real ground

Asking vs. assessment

115% of $733,500

City assessment record · taxes $7,085/yr

Land share of assessed value

50% — $365,600

Improvements $367,900 · assessor record ✓

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)

EventDatePriceDetail
ListedDec 29, 2025$840,000
Currently listed$840,000

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

15% above assessment

Total Assessed

$733,500

Land

$365,600

Improvement

$367,900

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:

Chesapeake Real Estate Assessor

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.

Questions buyers ask

Is 4500 Backwoods Rd in a good school zone?+
The assigned zones on the listing record are Hickory Elementary (VaHome School Score 8.2/10), Hickory Middle (VaHome School Score 9.2/10), Grassfield (VaHome School Score 8.8/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 4500 Backwoods Rd in a flood zone?+
FEMA maps this parcel in Zone X, outside the high-risk Special Flood Hazard Area. See the flood section on this page for details and sources.
Does 4500 Backwoods Rd have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.

Answers generated from the listing record, verified school zones, FEMA data, and cached nearby-places data — never invented.

The people

You'll talk to a person, not a lead queue

TD

Tom & Dariya Milan

LPT Realty · Hampton Roads · answer their own phone

✓ Your inquiry goes to Tom & Dariya — never sold to strangers

Listing courtesy of E Ashley McDougal · RE/MAX Alliance · REIN MLS #10614351

Call or text (757) 777-7577

Ask Dariya — instant answers

Schools, flood, drive times, what it really costs to own — answered from this page's data, by chat or voice.

Schedule a private tour

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4500 Backwoods Rd, Chesapeake — photo

See it in person — the record only says so much.

Call or text (757) 777-7577

4500 Backwoods Rd, Chesapeake, Virginia 23322 · MLS #10614351 · Source: REIN MLS + public record. Information deemed reliable but not guaranteed — verify independently. School zones subject to change; confirm with the local school division. All locations are described by neutral geographic fact. Equal Housing Opportunity.