Welcome to 2244 Benefit Road in Chesapeake—a rare opportunity to own 6 private acres with the freedom of A-1 zoning and all the charm of country living, just minutes from city conveniences. This 2,300 sq ft home offers space, versatility, and major updates including a brand-new roof and new HVAC system for peace of mind. Bring your horses, cows, chickens and create the lifestyle you’ve been dreaming of—farmette, homestead, or private retreat. Bordered by a nature preserve, you’ll enjoy protected views and no future development behind you. The acreage, privacy, and agricultural zoning make this one stand out among Chesapeake homes for sale. Room to garden, ride, entertain, or simply enjoy wide open space under the stars. If you’ve been searching for homes with land in Chesapeake, horse property, or a unique rural escape with modern comfort, this is the one. Rarely does acreage, freedom, and location come together like this!
Single-familyProperty Type
1985Year Built
6 acresLot Size
$316Price/Sq.Ft.
2 car garageParking
Listed by Thomas Milan• LPT Realty LLC
Bought with Debbie Woolard• Howard Hanna Real Estate Svcs.
Est. $2,738 per month, based on comparable rentals
Sale and tax history for 2244 Benefit Rd
Sale History
Tax History
Date
Event
Price
Public Records
Jun 30, 2026
Sold
$730,000
$317/sq ft
REINMLS #10631960
Jul 1, 2026
Sold
$727,500
$316/sq ft
May 10, 2026
Price Changed
$730,000
$317/sq ft
Apr 28, 2026
Listed
$699,900
$304/sq ft
Public Records
Jun 9, 2022
Sold
$540,000
$235/sq ft
REINMLS #10433482
Apr 24, 2022
Listed
$525,000
$228/sq ft
Public Records
Dec 1, 2021
Sold
$500,000
$217/sq ft
REINMLS #10401805
Sep 18, 2021
Listed
$500,000
$217/sq ft
REINMLS #10386803
Jul 15, 2021
Listing Removed
—
Jun 25, 2021
Listed
$479,900
$209/sq ft
Public Records
Dec 20, 1982
Sold
$42,000
$18/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$6,217 (+4.6%)
$258,700 + $356,800
$615,500
2024
$5,943 (+9.1%)
$238,700 + $349,700
$588,400
2023
$5,445 (+11.2%)
$208,700 + $330,400
$539,100
2022
$4,894 (+20.9%)
$188,700 + $295,900
$484,600
2021
$4,049 (+0.3%)
$170,900 + $214,700
$385,600
2020
$4,037 (+13.0%)
$170,900 + $213,600
$384,500
2019
$3,573 (+2.7%)
$151,700 + $188,600
$340,300
2018
$3,478 (+0.8%)
$151,700 + $188,600
$340,300
2017
$3,449
$148,900 + $179,600
$328,500
2015
$3,449
$148,900 + $179,600
$328,500
2014
$3,449
$148,900 + $179,600
$328,500
2013
$3,449
$148,900 + $179,600
$328,500
2012
$3,449
$148,900 + $179,600
$328,500
Public record
Public record
Zoning
Permits
Beds
3
Baths
3
Stories
1
Lot width
—
Lot depth
—
Lot size
5.78 Acres
Year renovated
—
Sq. Ft.
2,298
Year built
1985
Style
Single Family Residential
County
Chesapeake
APN
0940000000400
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 26, 2026.
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
Residential addition
Convert an existing residential building into a barn.
Addition
Nov 11, 2015 • Final
Residential electrical
Install and update electrical circuits.
Electrical
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.