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✓ Source: REIN MLS #10657263 · record updated Oct 27, 2026 · synced every 2 min · your inquiry is never resold
3365 Benefit RD, CHESAPEAKE VA 23322 - Main photo
3365 Benefit RD, CHESAPEAKE VA 23322 - Photo 2
3365 Benefit RD, CHESAPEAKE VA 23322 - Photo 3
3365 Benefit RD, CHESAPEAKE VA 23322 - Photo 4
3365 Benefit RD, CHESAPEAKE VA 23322 - Photo 5
2beds
1baths
1,230sqft
14days on market

3365 Benefit Rd, Chesapeake, VA 23322

ActiveResidential · built 1953 · PLEASANT GROVE

About this home

This 3 acre lot is great for your dream home! It can not be subdivided. Lot is established and has privacy for you and your animals. It has a huge 2 story, detached, approx. 4 car garage that has its own well and electricity. It has over 530 feet of road frontage, facing a pristine, stunning horse farm. The home that is on the property is fully gutted and can be torn down or remodeled and added on, to make your perfect home. The property is being sold as-is, as well as the septic and well is as-is. Call today for your private showing, this one will not last long!

Listing courtesy of Jodi Bolling · Wainwright Real Estate · REIN MLS #10657263

Facts & features

Type

Residential

Year built

1953

Price / sqft

$264

HOA

None

Taxes

$3,252/yr

County

Chesapeake VA

MLS #

10657263

Interior

Bedrooms
2
Full baths
1
Approx. sqft
1,230
Stories
1
Flooring
Other
First-floor bed & full bath
Yes
Total rooms
5
Other rooms
1st Floor BR, Spare Room

Construction & exterior

Style
Ranch
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Vinyl
Pool
No Pool

Utilities & systems

Water heater
Other
Water
Well
Sewer
Septic

Lot, parking & ownership

Lot size
3.0000
Subdivision
PLEASANT GROVE
Zoning
MULTI
Ownership
Fee Simple
Garage
Yes
Parking
Garage Det 3+ Car
Possession
SETTLEMENT
Miscellaneous
Fixer Upper
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

3365 Benefit Road is a 1,230-square-foot, two-bedroom home built in 1953 in Chesapeake, Virginia 23322. The lot sits along a quiet stretch of Benefit Road in the 23322 zip code. It's a compact, manageable footprint with a full bath and decades of solid construction behind it. Chesapeake homes for sale at this price point and size are worth a close look.

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 Grassfield Elementary School. Nearby, look at Pleasant Grove 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

What sets 3365 Benefit Road apart is its age and address. Homes from the early 1950s in this part of Chesapeake carry a build quality that newer construction rarely matches. The floor plan is tight and efficient — nothing wasted, nothing extra. Benefit Road itself runs through a low-traffic corridor that feels removed from the busier parts of the city. That combination of quiet location and durable bones is harder to find than it sounds among homes for sale in 23322.

PLEASANT GROVE and the Chesapeake real estate market

Benefit Road sits in the western reaches of Chesapeake's 23322 zip code. This part of the city blends rural character with suburban convenience. The streets here are wide and low-traffic, with mature trees and generous lot spacing. Housing along this corridor tends toward single-family homes on larger parcels, many of them built mid-century. It's a grounded, unpretentious stretch of Chesapeake that has stayed relatively stable over the decades. Chesapeake itself is one of the largest cities by land area in Virginia. It spans from the North Carolina border up through the Great Dismal Swamp and into the heart of Hampton Roads. Getting around is straightforward — Indian River Road, Battlefield Boulevard, and Interstate 64 all connect this part of the city to the broader region. Downtown Norfolk is about 30 minutes northeast. Virginia Beach is a similar drive east. Anyone comparing homes for sale in Chesapeake will notice that the 23322 zip code consistently offers more space per dollar than the city's northern neighborhoods.

What's nearby

Daily errands are covered without a long drive. A Walmart Supercenter and a Food Lion are both within a few miles along the Battlefield Boulevard corridor. Several local diners and fast-casual spots cluster near the intersection of Battlefield and Elbow Road. Walgreens and CVS pharmacies are close by for routine needs. Chesapeake City Park, one of the largest municipal parks in Hampton Roads, is about 10 minutes north and offers trails, sports fields, and open green space. The Great Dismal Swamp National Wildlife Refuge is a short drive south for anyone who wants a longer walk in the woods.

For different buyers

Base commute and VA loan notes

NSA Northwest Annex is about 14 minutes from 3365 Benefit Road — a short, low-stress commute on local roads. The USCG Finance Center Chesapeake is roughly 20 minutes away. VA loan financing is well-established in this zip code, and the two-bedroom layout means a quick, uncomplicated purchase process. Buyers using a VA loan will find the property's age and size straightforward to work with.

For first-time buyers

A 1,230-square-foot home with two bedrooms and one bath is a manageable entry point into Chesapeake homeownership. The 1953 construction means the home has already weathered decades — the bones are proven. Benefit Road's low traffic and quiet setting make it easy to settle in. First-time buyers comparing homes for sale zoned for Grassfield High School and homes for sale zoned for Grassfield Elementary School will find this address falls within that attendance zone.

More buyer questions

How far is 3365 Benefit Road from NSA Northwest Annex?

The drive is about 14 minutes on local roads. It's one of the shorter base commutes available in the 23322 zip code.

What year was 3365 Benefit Road built?

The home was built in 1953. That makes it one of the older properties along this stretch of Benefit Road.

Is 3365 Benefit Road in a flood zone?

Flood zone information for this address is covered in the FloodRisk tile on this page. Check that section for the current FEMA designation.

What grocery stores are near 3365 Benefit Road?

Food Lion and a Walmart Supercenter are both within a few miles along the Battlefield Boulevard corridor. Either covers a full weekly shop without a long drive.

Does 3365 Benefit Road have a garage?

Garage details are confirmed in the property specs section of this page. Homes of this era in Chesapeake often include a carport or detached structure, so it's worth reviewing the full listing details.

Want to see 3365 Benefit Road in person? Tom and Dariya Milan can schedule a showing and answer your questions about this address and the surrounding area.

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

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$275K – $375K2+ beds

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Schools

VaHome School Score

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

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.

Flood & environment

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\u2019t define a BFE here.

Property elevation

17 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\u2019s National Flood Hazard Layer. Property elevation is sampled from a single point on the parcel using the USGS National Map elevation service \u2014 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 C

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

Explore this neighborhood

Pleasant Grove

Pleasant Grove is one of southeast Chesapeake's fastest-growing areas. It sits along Mount Pleasant Road and Battlefield Boulevard, south of the Great Bridge area.

$545K

Median sale · 12 mo

$247

Sold $/sq ft

28d

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 →

Military Commute

Drive times to nearest bases

NW Annex

Navy

13min·9mi

USCG Finance Ctr

Coast Guard

18min·14.6mi

NNSY

Navy

23min·18.8mi

USCG Portsmouth

Coast Guard

21min·17.3mi

NMCP

Navy

24min·19.2mi

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

Payment 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

$2,052/mo

Principal & interest

$1,686

Property tax

$271

Home insurance

$95

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 & history

Comparables

Asking vs. assessment

112% of $290,100

City assessment record · taxes $3,252/yr

Land share of assessed value

81% — $235,000

Improvements $55,100 · assessor record ✓

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

Sale & Tax History

List Price

$324,999

Price / Sq Ft

$264

Annual Taxes

$3,252

Monthly Tax

$271

HOA

None

Tax Rate (effective)

1.00%

Sale Timeline (this listing)

EventDatePriceDetail
ListedOct 13, 2026$324,999—
Price reducedOct 27, 2026$324,999−$24,001
Currently listed—$324,999—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

12% above assessment

Total Assessed

$290,100

Land

$235,000

Improvement

$55,100

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.

Market tempo

14 days on market — read it in context

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

Questions buyers ask

Is 3365 Benefit Rd in a good school zone?+
The assigned zones on the listing record are Grassfield 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 3365 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 3365 Benefit Rd have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 3365 Benefit Rd built?+
It was built in 1953, 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

Brokered by LPT Realty · Hampton Roads

Listing courtesy of Jodi Bolling · Wainwright Real Estate · REIN MLS #10657263

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.

Schedule a private tour

Free, no obligation — your inquiry goes to Tom & Dariya, never resold.

3365 Benefit Rd, Chesapeake — photo

See it in person — the record only says so much.

Call or text (757) 777-7577

3365 Benefit Rd, Chesapeake, Virginia 23322 · MLS #10657263 · 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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