CONTINGENT

Contingent

$840,000

Est. $5,236/mo —

Land

•

21.00

acres (lot)

4500 Backwoods Rd, Chesapeake, VA 23322

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.

Vacant landProperty Type

21 acresLot Size

$40,000Price/Acres

Listed by E Ashley McDougal • RE/MAX Alliance

Listing updated: Aug 25, 2026 at 05:59pm

Redfin checked: 2 minutes ago

•Source:REINMLS #10614351

Payment calculator

$5,236 per month

Principal and interest$4,415

Property taxes

$590

HOA dues

Home insurance

$231

Utilities

Add

Affordability tools

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN TODAY, 6PM TO 7PM3D WALKTHROUGH
$674,500
5 beds3 baths2,894 sq ft
1076 Scenic Blvd, Chesapeake, VA 23322
OPEN THU, 4PM TO 6PM3D WALKTHROUGH
$784,900
6 beds3 baths3,200 sq ft
1024 Loutro Ct, Chesapeake, VA 23322
OPEN FRI, 3PM TO 6PM
$695,000
5 beds3 baths3,337 sq ft
804 Catrina Ln, Chesapeake, VA 23322
REDFIN OPEN SAT, 11AM TO 1PM3D WALKTHROUGH
$630,000
4 beds2.5 baths2,681 sq ft
2101 Beeblossom Ln, Chesapeake, VA 23323
OPEN SAT, 11AM TO 2PM
$355,000
3 beds2.5 baths1,622 sq ft
207 Fost Blvd, Moyock, NC 27958
OPEN SAT, 1PM TO 4PM3D WALKTHROUGH
$545,900
3 beds3.5 baths2,200 sq ft
916 Jennings Ln, Chesapeake, VA 23322
OPEN SAT, 1PM TO 4PM3D WALKTHROUGH
$545,900
3 beds3.5 baths2,200 sq ft
908 Jennings Ln, Chesapeake, VA 23322
OPEN SAT, 1PM TO 4PM3D WALKTHROUGH
$525,900
4 beds3.5 baths2,200 sq ft
903 Bernard Ln, Chesapeake, VA 23322
OPEN SAT, 1PM TO 4PM3D WALKTHROUGH
$610,900
3 beds3.5 baths2,700 sq ft
900 Koonce Ln, Chesapeake, VA 23322
OPEN SAT, 2PM TO 4PM
$899,900
4 beds3.5 baths2,720 sq ft
1421 Saint Brides Road West, Chesapeake, VA 23322

Around this home

Schools

K - 12
Preschool & daycare

Hickory Elementary School

Public PreK-5 • Assigned • 5.3mi

10/10

Hickory Middle School

Public 6-8 • Assigned • 6.7mi

9/10

Grassfield High School

Public 9-12 • Assigned • 11.7mi

9/10

Provided by GreatSchools

About Pleasant

Grove

Pleasant Grove, located between Great Bridge and the North Carolina line, is a rural and residential Chesapeake neighborhood with working farmland and pine-wooded backroads. The neighborhood’s character concentrates around the Battlefield Blvd S and Pleasant Grove Rd crossroads, where feed stores, roadside produce stands, and small service shops set a practical, country cadence. Homes tend toward ranchers and newer builds on larger lots, with long driveways and wide skies. Two-lane roads and drainage canals trace the landscape, and evenings read quieter than the commercial corridors to the north. Outdoor time centers on nearby waterways and open fields rather than sidewalks.

Provided by Walk Score and Local Logic

Market insights

4500 Backwoods Rd · $840,000

DAYS ON MARKET

The average home goes pending in 27 days.

SALE-TO-LIST

Most homes are selling 0% above list price.

LIST PRICE

Median sale price in this area is $503,608. (40% lower than this home)

PRICE DROP

19% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior

Interior features
Barn and garage on the property
Habitable dwelling present
Suitable for agriculture and horses

Sale and tax history for 4500 Backwoods Rd

Sale History
Tax History

Date

Event

Price

REINMLS #10614351

May 31, 2026

Listing Removed

—

Dec 29, 2025

Listed

$840,000

REINMLS #10571897

Dec 12, 2025

Listing Removed

—

Apr 21, 2025

Price Changed

$840,000

Mar 3, 2025

Listed

$850,000

REINMLS #10537363

Jan 8, 2025

Listing Removed

—

Jun 7, 2024

Listed

$800,000

REINMLS #10519222

Apr 25, 2024

Listing Removed

—

Apr 24, 2024

Price Changed

$875,000

Mar 28, 2024

Price Changed

$899,000

Feb 29, 2024

Price Changed

$925,000

Feb 7, 2024

Listed

$975,000

REINMLS #10495573

Dec 15, 2023

Listing Removed

—

Jul 19, 2023

Listed

$995,000

Public Records

Dec 2, 1981

Sold

$60,000

Public record

Public record
Zoning
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

21.17 Acres

Year renovated

—

Finished Sq. Ft.

3,480

Unfinished Sq. Ft.

Total Sq. Ft.

3,480

Year built

1990

Style

Single Family Residential

County

Chesapeake

APN

1180000000065

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Apr 12, 2023.

A-1

Agricultural District

This district is created primarily for the protection of the agricultural industry and rural section of the city from the invasion of urban and suburban uses and to preserve agricultural lands, forest lands and open space in the interest of the health, safety and welfare of the community. This district is not intended for major residential development; therefore, residential development and subdivisions for residential purposes in the A-1 agricultural district are prohibited except for minor subdivisions, as that term is defined in section 3-403 of this ordinance, preservation divisions, as that term is defined in section 10-201 of this ordinance, and conditional cluster developments approved in accordance with section 6-2200 et seq. of this ordinance.

Permitted uses

Include but are not limited to:

Equestrian facility
Livestock production
Community / recreation center
Day care facility
Housing-Single unit
Fire house
Library
Police station
Communications tower
Agriculture-Cropland

Nov 11, 2015 • Final

Commercial gas

Install a gas line for a single-family home.

Gas

Nov 11, 2015 • Final

Residential plumbing

Renew a permit for a single-family home.

Plumbing

Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.62% chance of being in a wildfire in next 30 years

8/10 Heat Factor

7 days above 107° expected this year, 16 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

1/10 Air Factor

0 unhealthy days expected this year, 0 days in 30 years

Provided by First Street

Historical weather

Chesapeake, VA • 23322

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

95/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.6 hrs

6.1 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 4500 Backwoods Rd

$796,685

$43K under list price of $840K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $560K to $1.0M.

SOLD MAR 17, 2026
$685,000 Last sold price
3 beds3.5 baths2,981 sq ft
106 Fox Ln, Moyock, NC 27958
smaller lot
SOLD MAR 17, 2026
$685,000 Last sold price
3 beds4.5 baths3,520 sq ft
106 Fox Ln Lot 3, Moyock, NC 27958
smaller lot
SOLD AUG 3, 2026
$1,000,000 Last sold price
5 beds3 baths4,369 sq ft
1904 Ballahack Rd, Chesapeake, VA 23322
larger lot
SOLD AUG 21, 2026
$699,900 Last sold price
4 beds2.5 baths3,211 sq ft
161 Moyock Landing Dr, Moyock, NC 27958
smaller lot
SOLD JUL 24, 2026
$560,000 Last sold price
5 beds3 baths2,580 sq ft
107 Tyler Way, Moyock, NC 27958
smaller lot
SOLD OCT 21, 2025
$715,000 Last sold price
5 beds3 baths3,745 sq ft
3730 Battlefield Blvd, Chesapeake, VA 23322
smaller lot

This home may not be allowing tours right now

The seller has already accepted an offer. You can request a tour anyway or ask an agent about submitting a backup offer.

Ask a question

Start an offer

(757) 379-8786

Nearby similar homes

$525,000

Land— sq ft

1832 Munden Point Rd, Virginia Beach, VA 23457

$750,000

Land— sq ft

28 Johnstown Cres, Chesapeake, VA 23322

$2,200,000

Land— sq ft

118Ac West Rd, Chesapeake, VA 23323

$325,000

Land— sq ft

11.8 Acres Ballahack Rd, Chesapeake, VA 23322

$750,000

Land— sq ft

2650 Benefit Rd, Chesapeake, VA 23322

$16,700

Land— sq ft

1536 Tuck St, Chesapeake, VA 23322

New listings for sale in 23323

NEW 31 MINS AGO

$455,000

4 beds2.5 baths3,000 sq ft

1254 Winfall Dr, Chesapeake, VA 23323

COMING SOON

$769,000

5 beds3 baths3,712 sq ft

1204 Murray Dr, Chesapeake, VA 23322

NEW 19 HRS AGO

$550,000

4 beds3 baths2,485 sq ft

309 Barcelona Dr, Chesapeake, VA 23320

NEW 23 HRS AGO

$1,519,000

5 beds4.5 baths6,848 sq ft

641 Ravenwoods Dr, Chesapeake, VA 23322

$445,000

3 beds1.5 baths1,700 sq ft

656 Hillwell Rd, Chesapeake, VA 23322

$540,000

4 beds3.5 baths2,200 sq ft

917 Erie St, Chesapeake, VA 23322

$615,000

4 beds2.5 baths2,632 sq ft

1924 Bexley Ln, Chesapeake, VA 23322

$419,900

3 beds1.5 baths1,331 sq ft

229 Cedar Rd, Chesapeake, VA 23322

$450,000

4 beds2.5 baths3,081 sq ft

750 Beckley Ln, Chesapeake, VA 23322

Details provided by REINMLS and may not match the public record. Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

23320 homes for sale
23321 homes for sale
23322 homes for sale
23456 homes for sale
23435 homes for sale

Houses for rent in Chesapeake	Agents near me	Richmond, VA homes for sale	Chesapeake Housing Market
Houses for sale near me	Arlington, VA homes for sale	McLean, VA homes for sale
Land for sale near me	Alexandria, VA homes for sale	Chesapeake, VA homes for sale
Open Houses near me	Virginia Beach, VA homes for sale	Chesapeake Property Records
Condos for sale near me	Fairfax, VA homes for sale	VA New Listings

Virginia Beach homes for sale
Norfolk homes for sale
Suffolk homes for sale

Southern Chesapeake homes for sale
Pleasant Grove homes for sale

About this home

Payment calculator

Affordability tools

Open houses

Nearby open houses (10)

Around this home

Schools

Market insights

Property details

Sale and tax history for 4500 Backwoods Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 4500 Backwoods Rd

This home may not be allowing tours right now

Nearby similar homes

New listings for sale in 23323

More real estate resources