12 days on market
$730,000
2244 Benefit Rd
Chesapeake, Virginia 23322
MLS# 10631960 · PLEASANT GROVE · Chesapeake VA
Updated May 10, 2026 · Source: REIN MLS
Est. payment
$4,519/mo
Edit below
Price / sq ft
$317
2,300 sq ft
Days on market
12
New listing
HOA
None
Year built
1985
41 yrs old
Beds
4
Full Baths
2
Half Baths
1
Sq Ft
2,300
Garage
Yes
Schools
- ElementaryHickory Elementary School7/10
- MiddleHickory Middle School7/10
- 8/10
Info provided by GreatSchools
About this home
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, home…
Listed by Thomas Milan · LPT Realty LLC
VaHome Team property overview
Meet 2244 Benefit Road — a four-bedroom, 2.5-bath home on six private acres in Chesapeake's Pleasant Grove area. Built in 1985, this 2,300-square-foot property gives you serious elbow room, a rural feel, and surprisingly easy access to Hampton Roads' major corridors.
Read full property overview ↓Show less ↑
Why this home stands out
Six acres in Chesapeake is genuinely rare. Most residential lots in the region measure a fraction of that, so 2244 Benefit Road offers something you simply can't manufacture: space. Whether you're imagining a hobby farm, a sprawling backyard, a detached workshop, or just the quiet that comes with no neighbors crowding your windows, this lot delivers a lifestyle that compact subdivisions can't replicate.
PLEASANT GROVE and the Chesapeake real estate market
Pleasant Grove sits in the southern reaches of Chesapeake — one of Virginia's largest cities by land area and consistently ranked among the best places to live on the East Coast. This corner of the city leans rural and residential, with wide lots, mature trees, and a pace that feels a world away from the busier corridors up north, even though those corridors are never far. If you've been browsing houses for sale in Chesapeake and keep finding yourself drawn to properties with acreage and breathing room, Pleasant Grove tends to rise to the top of the list. The area attracts buyers who want a genuine sense of privacy without sacrificing proximity to jobs, shopping, or the water. Chesapeake's southern zip codes also benefit from relatively newer infrastructure investments and strong community character — the kind of place where neighbors wave and people put down long roots.
What's nearby
Daily life is well-supported from this address. Grocery runs, pharmacies, and big-box retail along Battlefield Boulevard are roughly 10–15 minutes north. The Chesapeake City Park complex and Northwest River Park — one of the region's best spots for hiking, kayaking, and camping — are both within easy reach. Moyock and the North Carolina border sit just south, opening up additional shopping and dining options. Interstate 168 and the Chesapeake Expressway provide quick connections to Virginia Beach, Norfolk, and the rest of Hampton Roads, making this rural setting far more connected than it might first appear.
For different buyers
For military families relocating
USCG Finance Center Chesapeake is about 20 minutes away, and Norfolk Naval Shipyard is a manageable 28-minute drive — making 2244 Benefit Road a practical base for service members assigned to either installation. Six acres gives military families the space to spread out between deployments, and a VA loan can make a property like this more accessible than many buyers expect.
For buyers drawn to character
If you've outgrown cookie-cutter subdivisions and want a property with genuine land, 2244 Benefit Road is worth a long look. The 1985 build sits on six acres in Pleasant Grove — the kind of setting where you can plant an orchard, keep chickens, park a boat, or simply enjoy a bonfire without a neighbor 15 feet away. Character here is measured in acreage, not architectural trim.
Frequently asked questions
How far is 2244 Benefit Road from USCG Finance Center Chesapeake?
The drive is approximately 20 minutes under normal conditions, heading north through Chesapeake's surface roads. It's a straightforward commute with no major highway bottlenecks.
How far is 2244 Benefit Road from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is roughly 28 minutes away, accessible via the Chesapeake Expressway and I-464. BAH rates for the Portsmouth/Norfolk area apply to personnel assigned there.
What is the lot size at 2244 Benefit Road?
The lot is six acres — a substantial parcel by Chesapeake standards that offers significant privacy, outdoor utility space, and potential for accessory structures depending on county zoning.
Is 2244 Benefit Road in a flood zone?
Flood zone status for this address should be confirmed through the FEMA Flood Map Service Center or the dedicated FloodRisk section on this page, as designations can change over time.
Does 2244 Benefit Road have an HOA?
Pleasant Grove is not a planned HOA community in the traditional sense, but buyers should verify any deed restrictions or community covenants with their title attorney during due diligence.
Want to walk six acres and see what this address feels like in person? Tom and Dariya Milan at LPT Realty know Pleasant Grove well — reach out and let's set something up.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Location & Street View
2244 benefit 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
4
Full Baths
2
Half Baths
1
Approx Sq Ft
2,300
Stories
2
Fireplaces
0
Flooring
Carpet, Ceramic, Laminate/LVP
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
220 V Elec, Dishwasher, Dryer Hookup, Microwave, Elec Range, Washer Hookup
Sale & Tax History
List Price
$730,000
Price / Sq Ft
$317
Annual Taxes
$6,217
Monthly Tax
$518
HOA
None
Tax Rate (effective)
0.85%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Apr 29, 2026 | $730,000 | — |
| Currently listed | — | $730,000 | — |
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
$4,519/moPrincipal & interest
$3,788
Property tax
$518
Home insurance
$213
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 LPT Realty LLC · MLS# 10631960
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$730,000
2244 benefit RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
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