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✓ Source: REIN MLS #10647485 · record updated Sep 7, 2026 · synced every 2 min · your inquiry is never resold
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$825,000est. $5,041/mo all-in · adjust →
4beds
4baths
2,769sqft
$298per sqft
29days on market

1837 Benefit Rd, Chesapeake, VA 23322

ActiveResidential · built 1993 · 5 acres · HICKORY · MLS #10647485

Price per sqft$298compare with nearby salesSchools
GrassfieldHigh9.1
HickoryMiddle9
HickoryElementary9.1
VaHome School ScoreEst. payment$5,041/moall-in · 20% down · 6.75% · adjustPrice since listing…checking price historyFlood
Low / moderate riskZone X
flood insurance not requiredTaxes$6,237/yrasking is 134% of assessmentHOANoneno HOA fee on the MLS recordCondo feeNAnot a condo

OverviewAbout this home

Welcome to this custom-built retreat situated on 5 acres in a highly desirable Grassfield school district. Thoughtfully designed this exceptional property offers generous indoor and outdoor space with features ideal for multigenerational living, entertaining, hobbies, and storage. The private in-law suite includes a kitchenette and its own screened porch, creating a welcoming space for guests or extended family. Upstairs, you'll find two ensuite bedrooms, along with an additional bedroom that offers excellent potential as a theater room, home office, or flexible living space. Car enthusiasts, hobbyists, and those seeking extra workspace will appreciate the two-car attached garage, one-car detached garage with work area, and two storage sheds. From the inviting front porch—perfect for quiet mornings and scenic views—to the rear deck designed for gathering with family and friends, this one-of-a-kind property offers the space, privacy, and versatility today's buyers are looking for.

Listing courtesy of Tyler Shelton · RE/MAX Allegiance · REIN MLS #10647485

Facts & features

TypeResidential
Year built1993
Price / sqft$298
HOANone
Taxes$6,237/yr
CountyChesapeake VA
MLS #10647485

Interior

Bedrooms
4
Full baths
4
Approx. sqft
2,769
Stories
2
Flooring
Carpet, Vinyl
Ensuite bedrooms
3
First-floor bed & full bath
Yes
Total rooms
9
Other rooms
1st Floor Primary BR, Attic, Breakfast Area, In-Law Suite, PBR with Bath, Office/Study, Screened Porch, Utility Room, Workshop
Equipment
Cable Hookup, Ceiling Fan, Central Vac, Jetted Tub
Accessibility
Pocket Doors

Construction & exterior

Style
Farmhouse
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Brick,Vinyl
Pool
No Pool

Utilities & systems

Heating
Forced Hot Air, Propane Gas, Zoned
Cooling
Central Air, Zoned
Water heater
Electric
Water
Well
Sewer
Septic

Lot, parking & ownership

Lot size
5.0000
Subdivision
HICKORY
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 2 Car, Garage Det 1 Car, Driveway Spc
Possession
CLOSING
Miscellaneous
Fuel In Tank Conveys
Disclosures
Disclosure Statement

Sources: REIN MLS record · city assessor

Tom & Dariya's overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · Brokered by LPT Realty

At a glance

This four-bedroom, four-bath home sits on a quiet Benefit Road lot in Chesapeake, built in 1993 with 2,769 square feet of living space. You're about nine minutes from NSA Northwest Annex, making it convenient for base commuters. The layout offers room to spread out, and homes for sale in 23322 in this pocket tend to offer solid value.

Keep searching in Chesapeake

See all Chesapeake homes for sale, including homes for sale in 23322, homes for sale zoned for Grassfield High School, and homes for sale zoned for Hickory Elementary School. Nearby, look at Hickory homes for sale, Chesapeake waterfront homes for sale, Chesapeake condos and townhomes for sale, and new construction homes in Chesapeake.

Read the full overview ↓

Why this home stands out

Four full bathrooms mean less morning conflict and more flexibility for remote work or guests. The 1993 construction brings established neighborhood character without requiring a major renovation. A 2,769-square-foot footprint gives you genuine space to grow without oversized utility bills. The lot sits on a residential street away from main corridors, so you get quiet without isolation. If you're comparing Chesapeake homes for sale, this property's bath-to-bedroom ratio and square footage stand out in the mid-range market.

HICKORY and the Chesapeake real estate market

Benefit Road sits in a mature, tree-lined section of Chesapeake where homes have settled in over decades. The street itself is residential and calm—the kind of block that anchors homes for sale in Chesapeake with steady appeal. You'll find a mix of ranch and two-story homes, most built between the 1980s and 2000s, creating a neighborhood with consistent character. Chesapeake itself is Virginia's second-largest city by area, stretching across 430 square miles of suburban and rural landscape. Daily life centers on local shopping, parks, and schools rather than a downtown core. Getting around is straightforward: major routes like Battlefield Boulevard and Military Highway connect you to Hampton Roads' employment centers, shopping, and entertainment. The Naval Station Norfolk area is about 25 minutes south; Virginia Beach and the beach itself are roughly 30 minutes away.

What's nearby

The area is zoned for homes for sale zoned for Hickory Elementary School and homes for sale zoned for Grassfield High School. For shopping and dining, you're close to local convenience stores and family restaurants along nearby corridors. Battlefield Boulevard, about a mile away, carries most of the area's retail and service traffic. The Chesapeake City Parks system includes several neighborhood parks with playgrounds and walking trails within five to ten minutes' drive. Medical care is accessible through Chesapeake Regional Medical Center and urgent-care clinics scattered throughout the city.

For different buyers

Base commute and VA loan notes

NSA Northwest Annex is nine minutes away by car, making this address practical for active-duty and civilian personnel assigned there. VA loan financing is common in this area, and the home's 1993 construction and solid systems mean you can close and move in without major delays. The quiet street and established neighborhood appeal to those seeking stability near base.

Room to grow

Four bedrooms and four bathrooms give each household member their own space and bathroom access. The 2,769-square-foot layout spreads across a practical floor plan suited to remote work, hobbies, or a home office. A full lot provides room for outdoor projects, play, or future additions. Storage and garage space round out the flexibility that comes with an established home of this size.

More buyer questions

How far is 1837 Benefit Road from NSA Northwest Annex?

About nine minutes by car, depending on traffic. It's one of the closer residential areas to the base.

What are the zoning assignments for this address?

This address falls within the attendance zones for homes for sale zoned for Hickory Elementary School and homes for sale zoned for Grassfield High School.

Is there an HOA at this address?

The property is in an unincorporated section of Chesapeake; confirm HOA status with your agent or the county records.

How far is this home from Virginia Beach and the beach?

About 30 minutes to the Virginia Beach oceanfront, depending on which beach access you choose and traffic conditions.

What is the lot size at 1837 Benefit Road?

Lot dimensions are available through Chesapeake County property records; ask your agent for the exact survey or plat.

Ready to explore this four-bedroom Chesapeake home? Contact Tom & Dariya Milan to schedule a showing and ask about current market conditions in 23322.

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

Schools · VaHome School ScoreAssigned schools

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

HighGrassfield High School
9.1/10
Up 0.3 from 2024–25
MiddleHickory Middle School
9/10
Down 0.2 from 2024–25
ElementaryHickory Elementary School
9.1/10
Up 0.9 from 2024–25

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.

How Far Is?

Driving distance by road and typical drive time via Google Maps, to the nearest location of each.

Also nearby

Distances are straight-line (as the crow flies) from this property, not driving miles. Places within ~1 mile, nearest first. Powered by Google Places.

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

Chesapeake$700K – $950K4+ beds

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Military Commute

Drive times to nearest bases

NW Annex

Navy

11min·6.6mi

USCG Finance Ctr

Coast Guard

22min·10.9mi

NNSY

Navy

30min·19.2mi

USCG Portsmouth

Coast Guard

27min·17.7mi

NMCP

Navy

31min·19.6mi

Typical drive times from Google Maps, without live traffic. Rush hour and tunnel backups can add time.

Flood & environmentFlood risk (FEMA)

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

Flood Risk (FEMA)

Source: FEMA National Flood Hazard Layer · FIRM 510034

Low / Moderate Risk

FEMA flood zone

X (low to moderate risk)

Base flood elevation

Not applicable in low-risk zones

Zone X is outside the Special Flood Hazard Area; FEMA doesn’t define a BFE here.

Property elevation

15.5 ft above sea level

USGS 3DEP digital elevation model

Outside the high-risk Special Flood Hazard Area. Federal flood insurance is NOT required, though optional preferred-rate NFIP coverage is still worth considering in coastal Hampton Roads.

Data sources: Flood zone and base flood elevation come from FEMA’s National Flood Hazard Layer. Property elevation is sampled from a single point on the parcel using the USGS National Map elevation service — actual elevations across a single property can vary by several feet higher or lower than the figure shown. Use these numbers as a starting reference and do your own due diligence (a professional survey or elevation certificate) before relying on them for any financial, insurance, or construction decision.

Hurricane Evacuation Zone

Evacuation Zone A

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

Explore this neighborhoodHickory

Hickory is a place where country meets suburb. It sits in the far south of Chesapeake, Virginia. The area runs along the Battlefield Boulevard South corridor toward the North Carolina line.

$647KMedian sale · 12 mo
$246Sold $/sq ft
19dDays on market
42For sale now
$132KHH income
82.9%Owner-occupied

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

Explore Hickory →
Map of Hickory with neighborhood boundaryNeighborhood

Chesapeake homes for sale →

CostPayment calculator

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

$5,041/mo

Principal & interest

$4,281

Property tax

$520

Home insurance

$241

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 & historyComparables

Asking vs. assessment134% of $617,500City assessment record · taxes $6,237/yr
Land share of assessed value41% · $252,000Improvements $365,500 · assessor record ✓
Price context: similar nearby homes$600,000 – $794,540The 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.
1421 Taft RD · 1.8 mi · 2,766 sqft$794,540 sold 2026-07
2244 benefit RD · 0.9 mi · 2,300 sqft$727,500 sold 2026-07
941 Pleasant Ridge DR · 2.1 mi · 2,728 sqft$765,000 sold 2026-04

Own a home nearby? See what it is worth today: What's your Chesapeake home worth?

Sale & Tax History

List Price

$825,000

Price / Sq Ft

$298

Annual Taxes

$6,237

Monthly Tax

$520

HOA

None

Tax Rate (effective)

0.76%

Sale Timeline (this listing)

EventDatePriceDetail
ListedAug 9, 2026$825,000—
Currently listed—$825,000—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

34% above assessment

Total Assessed

$617,500

Land

$252,000

Improvement

$365,500

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.

29 days on market: read it in context

Days on market reflects pricing, season, and inventory. Compare it against similar nearby homes before reading anything into it.

CompareThis home next to what else is for sale nearby

HomePriceBedsBathsSqft$ / sqft
1837 Benefit Rdthis home$825,000442,769$298
Loading nearby homes for sale…

Active comparables from the REIN MLS, the same homes shown under Comparable Properties. Context for judging the asking price, not an appraisal.

Questions buyers ask

Is 1837 Benefit Rd in a good school zone?
The assigned zones on the listing record are Hickory Elementary (VaHome School Score 9.1/10), Hickory Middle (VaHome School Score 9/10), Grassfield (VaHome School Score 9.1/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 1837 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 1837 Benefit Rd have an HOA?
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 1837 Benefit Rd built?
It was built in 1993, per the listing record.

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

Tom and Dariya Milan

Tom & Dariya Milan | LPT Realty

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1837 Benefit Rd, Chesapeake, Virginia 23322 · MLS #10647485 · 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.

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