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ChesapeakeCHURCHLAND PARK4416 Greendell Rd✓ Source: REIN MLS #10643180 · record updated Jul 17, 2026 · synced every 2 min · your inquiry is never resold
4416 Greendell RD, CHESAPEAKE VA 23321 - Main photo
4416 Greendell RD, CHESAPEAKE VA 23321 - Photo 2
4416 Greendell RD, CHESAPEAKE VA 23321 - Photo 3
4416 Greendell RD, CHESAPEAKE VA 23321 - Photo 4
4416 Greendell RD, CHESAPEAKE VA 23321 - Photo 5
$375,000
$258 / sqft · est. $2,339/mo →
4beds
2.1baths
1,456sqft
8days on market

4416 Greendell Rd, Chesapeake, VA 23321

ActiveResidential · built 1968 · CHURCHLAND PARK

About this home

The listing, in the seller's words

Welcome to 4416 Greendell Rd, where natural light pours into every corner of this beautifully updated home. This stunning ranch has it all 4 spacious bedrooms, a gorgeous updated kitchen with stainless steel appliances, and an awesome floor plan for everyday living and entertaining. Everything feels fresh and move in ready, with major updates already done for you, including an HVAC replaced in 2025 for added peace of mind. Tucked away on a quiet cul-de-sac in the sought-after Western Branch area, this home offers the perfect mix of comfort, charm, and location.

Listing courtesy of Cindy Sinclair · Iron Valley Real Estate Prestige · REIN MLS #10643180

VaHome team overview

Our read on this home

At a glance

4416 Greendell Road is a four-bedroom, two-and-a-half-bath home in Chesapeake, Virginia — built in 1968 and offering 1,456 square feet of living space on a residential lot, just minutes from major military installations and everyday conveniences.

Read the full overview ↓

Why this home stands out

What sets 4416 Greendell Road apart is its position in western Chesapeake, where commute times to multiple military installations are genuinely short. Eight minutes to NSA Northwest Annex and twelve minutes to Naval Medical Center Portsmouth puts two significant duty stations within easy reach — a combination that's harder to find than most people expect when they start their home search in Hampton Roads.

CHURCHLAND PARK and the Chesapeake real estate market

Greendell Road sits in the western reaches of Chesapeake, Virginia — one of the largest cities by land area on the East Coast and a place that consistently draws families looking for a quieter pace without giving up urban access. This part of Chesapeake has a settled, established feel: streets lined with mature trees, homes built across several decades, and neighbors who tend to stay. Western Chesapeake is connected to the rest of Hampton Roads through a network of major corridors, making it practical for commuters heading in almost any direction. The city itself offers a wide range of parks, waterways, and recreational options, and the western neighborhoods benefit from proximity to retail and dining along key commercial strips without sitting directly on top of them. It's the kind of area where daily life moves at a manageable speed — close enough to everything, far enough from the noise.

What's nearby

Day-to-day errands are straightforward from Greendell Road. Grocery options, pharmacies, and big-box retail are all within a short drive along the western Chesapeake corridors. For coffee and casual dining, you'll find familiar names and local spots clustered nearby. Outdoor enthusiasts have access to the parks and green spaces that western Chesapeake is known for, including trails and waterway access that make weekends easy to fill. The broader Hampton Roads region — with its waterfront dining, cultural venues, and coastline — is accessible without a long haul from this address.

For different buyers

For military families relocating

If your orders bring you to NSA Northwest Annex or Naval Medical Center Portsmouth, 4416 Greendell Road puts both installations within a twelve-minute drive. That kind of dual-base accessibility is genuinely useful for households where two people serve or where assignments change. A VA loan can make this four-bedroom home even more attainable — and western Chesapeake has a long history of welcoming military families.

For families upgrading

Four bedrooms and two and a half baths give a growing household real room to breathe. The 1968 build means solid construction on an established street, and western Chesapeake's community feel makes it a natural fit for families who want space, stability, and a neighborhood where kids can actually grow up. There's genuine room here — not just square footage on paper.

More buyer questions

How far is 4416 Greendell Road from NSA Northwest Annex?

The drive from 4416 Greendell Road to NSA Northwest Annex is approximately 8 minutes under normal traffic conditions, making it one of the closer residential options to that installation in the area.

How far is 4416 Greendell Road from Naval Medical Center Portsmouth?

Naval Medical Center Portsmouth is about 12 minutes from this address, a commute that holds up well even during peak morning hours given the route options available from western Chesapeake.

What is the lot and property type at 4416 Greendell Road?

4416 Greendell Road is a single-family residential property built in 1968, offering 1,456 square feet across four bedrooms and two and a half bathrooms on a residential lot in western Chesapeake.

Is 4416 Greendell Road in a flood zone?

Flood zone designation for this address is detailed in the FloodRisk tile on this page, which pulls current FEMA map data for the specific parcel.

What city and county does 4416 Greendell Road fall under?

This address is located in Chesapeake, Virginia — an independent city that serves as its own jurisdiction, meaning city services, permitting, and local governance all fall under the City of Chesapeake.

Want to know more about 4416 Greendell Road or western Chesapeake? Tom and Dariya Milan at LPT Realty are here to walk you through every detail — reach out anytime.

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

1968

Price / sqft

$258

HOA

None

Taxes

$3,400/yr

County

Chesapeake VA

Waterfront

Yes

MLS #

10643180

Interior

Bedrooms
4
Full baths
2
Half baths
1
Approx. sqft
1,456
Stories
1
Flooring
Laminate/LVP
First-floor bed & full bath
Yes
Total rooms
7
Other rooms
1st Floor Primary BR, Breakfast Area, Converted Gar, PBR with Bath, Utility Closet
Appliances
Dishwasher, Dryer Hookup, Microwave, Elec Range, Washer Hookup
Equipment
Ceiling Fan

Construction & exterior

Style
Ranch
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Brick
Pool
No Pool
Waterfront
Not Waterfront

Utilities & systems

Heating
Heat Pump
Cooling
Heat Pump
Water heater
Electric
Water
City/County
Sewer
City/County

Lot, parking & ownership

Subdivision
CHURCHLAND PARK
Zoning
R8S
Ownership
Fee Simple
Garage
No
Parking
4 Space, Off Street, Driveway Spc
Possession
SETTLE
Disclosures
Disclosure Statement

Sources: REIN MLS record · city assessor · 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 D

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

Explore this neighborhood

Churchland

Churchland is an established residential neighborhood in Portsmouth, Virginia, known for its tree-lined streets and collection of well-maintained homes spanning multiple decades.

$312K

Median sale · 12 mo

$205

Sold $/sq ft

17d

Days on market

5

For sale now

$66K

HH income

46%

Owner-occupied

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

Explore Churchland
Map of Churchland with neighborhood boundaryNeighborhood

houses for sale in Chesapeake

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

$2,339/mo

Principal & interest

$1,946

Property tax

$283

Home insurance

$109

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

Asking vs. assessment

115% of $326,400

City assessment record · taxes $3,400/yr

Land share of assessed value

44% — $145,000

Improvements $181,400 · assessor record ✓

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

$245,000$445,000

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.

3807 Whitechapel ARCH · 1.7 mi · 1,451 sqft$305,000 sold 2026-03
3711 Whitechapel ARCH · 1.7 mi · 1,456 sqft$306,000 sold 2026-04
2828 Meadow DR · 1.5 mi · 1,585 sqft$445,000 sold 2026-07

Sale & Tax History

List Price

$375,000

Price / Sq Ft

$258

Annual Taxes

$3,400

Monthly Tax

$283

HOA

None

Tax Rate (effective)

0.91%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJul 9, 2026$375,000
Currently listed$375,000

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

15% above assessment

Total Assessed

$326,400

Land

$145,000

Improvement

$181,400

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

8 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

Real questions, answered from the record

Is 4416 Greendell Rd in a good school zone?+
The assigned zones on the listing record are Western Branch Primary, Western Branch Middle, Western Branch. School attendance zones can change — always confirm enrollment with the local school division.
Is 4416 Greendell 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 4416 Greendell Rd have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 4416 Greendell Rd built?+
It was built in 1968, 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 Cindy Sinclair · Iron Valley Real Estate Prestige · REIN MLS #10643180

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.

4416 Greendell Rd, Chesapeake — photo

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

Call or text (757) 777-7577

4416 Greendell Rd, Chesapeake, Virginia 23321 · MLS #10643180 · 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.