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ChesapeakePLEASANT GROVE2244 Benefit Rd✓ Source: REIN MLS #10631960 · record updated Jul 9, 2026 · synced every 2 min · your inquiry is never resold
2244 benefit RD, CHESAPEAKE VA 23322 - Main photo
$727,500
$316 / sqft · est. $4,505/mo →
4beds
2.1baths
2,300sqft
63days on market

2244 Benefit Rd, Chesapeake, VA 23322

SoldResidential · built 1985 · PLEASANT GROVE

About this home

The listing, in the seller's words

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!

Listing courtesy of Thomas Milan · LPT Realty LLC · REIN MLS #10631960

VaHome team overview

Our read on this home

At a glance

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 the full overview ↓

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.

More buyer 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.

Schools

Info provided by GreatSchools

Facts & features

The record, sourced

Type

Residential

Year built

1985

Price / sqft

$316

HOA

None

Taxes

$6,217/yr

County

Chesapeake VA

Waterfront

Yes

MLS #

10631960

Interior

Bedrooms
4
Full baths
2
Half baths
1
Approx. sqft
2,300
Stories
2
Flooring
Carpet, Ceramic, Laminate/LVP
Ensuite bedrooms
1
First-floor bed & full bath
Yes
Total rooms
8
Appliances
220 V Elec, Dishwasher, Dryer Hookup, Microwave, Elec Range, Washer Hookup

Construction & exterior

Style
Transitional
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Vinyl
Pool
Above Ground Pool
Fencing
Back Fenced,Dog Run,Other
Waterfront
Not Waterfront

Utilities & systems

Heating
Forced Hot Air
Cooling
Central Air, Heat Pump
Water heater
Electric
Water
Well
Sewer
Septic

Lot, parking & ownership

Lot size
6.0000
Subdivision
PLEASANT GROVE
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 2 Car, Off Street, Driveway Spc
Possession
SETTLEMENT
Disclosures
Disclosure Statement

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

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 C

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.

$539K

Median sale · 12 mo

$258

Sold $/sq ft

23d

Days on market

17

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

Chesapeake houses for sale

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

$4,505/mo

Principal & interest

$3,775

Property tax

$518

Home insurance

$212

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.

Value & history

Judge value on real ground

Why we show no algorithmic estimate.

National AVMs misprice homes whose value drivers they can't see. Instead: the sourced assessment above, the carrying cost, real price history, and honest comparables below.

Price context — similar nearby homes

$419,900$670,000

The 6 most similar homes nearby (same city, within ~20% of this size, ~2.5 mi; 6 sold). Context for judging the asking price — not an appraisal or an estimate of this home's value.

2736 Benefit RD · 1 mi · 2,070 sqft$419,900 sold 2026-06
2841 Bunch Walnuts RD · 1.4 mi · 2,016 sqft$585,000 sold 2026-03
2820 Bunch Walnuts RD · 1.3 mi · 1,932 sqft$670,000 sold 2026-06

Sale & Tax History

List Price

$727,500

Price / Sq Ft

$316

Annual Taxes

$6,217

Monthly Tax

$518

HOA

None

Tax Rate (effective)

0.85%

Sale Timeline (this listing)

EventDatePriceDetail
ListedMay 7, 2026$727,500
Price reducedJul 9, 2026$727,500−$2,500
SoldJul 1, 2026$727,500

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

Real questions, answered from the record

Is 2244 Benefit Rd in a good school zone?+
The assigned zones on the listing record are Hickory Elementary (GreatSchools 9/10), Hickory Middle (GreatSchools 9/10), Grassfield (GreatSchools 8/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 2244 Benefit 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 2244 Benefit Rd have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 2244 Benefit Rd built?+
It was built in 1985, per the listing record.

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 Thomas Milan · LPT Realty LLC · REIN MLS #10631960

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.

This home has sold

Curious what it means for your own plans? Ask about similar homes nearby, or what your home might sell for in this market.

This one's sold — the next one doesn't have to be.

2244 Benefit Rd, Chesapeake, Virginia 23322 · MLS #10631960 · 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.