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ChesapeakeJOLLIFF WOODS4936 Oriole Dr✓ Source: REIN MLS #10647434 · record updated Sep 8, 2026 · synced every 2 min · your inquiry is never resold
4936 Oriole DR, CHESAPEAKE VA 23321 - Main photo
4936 Oriole DR, CHESAPEAKE VA 23321 - Photo 2
4936 Oriole DR, CHESAPEAKE VA 23321 - Photo 3
4936 Oriole DR, CHESAPEAKE VA 23321 - Photo 4
4936 Oriole DR, CHESAPEAKE VA 23321 - Photo 5
4beds
2.1baths
2,378sqft
33days on market

4936 Oriole Dr, Chesapeake, VA 23321

ActiveResidential · built 2001 · JOLLIFF WOODS

Facts & features

Type

Residential

Year built

2001

Price / sqft

$219

HOA

None

Taxes

$4,906/yr

County

Chesapeake VA

MLS #

10647434

Interior

Bedrooms
4
Full baths
2
Half baths
1
Approx. sqft
2,378
Stories
2
Flooring
Carpet, Laminate/LVP
Total rooms
8
Other rooms
Attic, Breakfast Area, Fin. Rm Over Gar, Foyer, PBR with Bath, Utility Room
Appliances
Dishwasher, Dryer, Microwave, Elec Range, Refrigerator, Washer
Equipment
Cable Hookup, Ceiling Fan

Construction & exterior

Style
Traditional
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Vinyl
Pool
In Ground Pool
Fencing
Back Fenced

Utilities & systems

Heating
Nat Gas
Cooling
Central Air
Water heater
Gas
Water
City/County
Sewer
City/County

Lot, parking & ownership

Subdivision
JOLLIFF WOODS
Zoning
R15S
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 2 Car, Multi Car, Driveway Spc
Possession
SETTLE
Disclosures
Disclosure Statement

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

About this home

Welcome to this beautifully maintained home in Jolliff Woods! Offering approx 2,400 square feet of living space, this spacious 4-bedroom, 2.5-bath residence combines comfort, style, and functionality. Step inside to a beautiful two-story foyer filled with natural light, creating a bright and inviting first impression. The main level features engineered hardwood flooring, a well-appointed kitchen with stainless steel appliances, and a spacious family room highlighted by a cozy gas fireplace and custom built-in cabinetry—perfect for everyday living and entertaining. Situated on a generous 0.63-acre lot, the backyard is an entertainer's dream, featuring a large new deck with in-ground pool and expansive yard, providing the ideal setting for summer gatherings, outdoor dining, or simply relaxing in your own private retreat. Upstairs, you'll find four generously sized bedrooms with abundant closet space. The impressive primary suite offers a walk-in closet ,a spa-inspired ensuite bath with a jetted soaking tub, separate walk-in shower, and plenty of room to unwind. Additional features include ceiling fans throughout, elegant dining room light fixtures, and ample storage. Don't miss this incredible opportunity to make it yours!

Listing courtesy of Judy Reed · REIN MLS #10647434

Tom & Dariya's overview

Our read on this home

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

At a glance

4936 Oriole Drive is a four-bedroom, 2.1-bath single-family home in Chesapeake, Virginia, offering 2,378 square feet of living space built in 2001. It sits in the 23321 zip code, minutes from two military installations and the everyday conveniences of western Chesapeake.

Read the full overview ↓

Why this home stands out

What sets 4936 Oriole Drive apart is the combination of generous square footage — 2,378 feet across four bedrooms — and a location that puts two military installations within a 17-minute drive. The 2001 build year means you get a layout designed for modern living without the quirks of an older home, and the western Chesapeake corridor keeps daily errands genuinely close. There's a lot to like about this particular pocket of the city.

JOLLIFF WOODS and the Chesapeake real estate market

Chesapeake is one of the largest cities by land area on the East Coast, and the 23321 zip code sits in its western branch — a quieter, more suburban stretch where neighborhoods feel intentional rather than accidental. Streets here tend to be tree-lined, lots are generous, and neighbors tend to stay put. That stability gives the area a settled, comfortable character that's hard to manufacture. Western Chesapeake connects easily to the rest of Hampton Roads via the interstate system, so you're never truly isolated — but on a weekday morning, Oriole Drive itself is calm. Families comparing Chesapeake homes for sale often gravitate to this zip code specifically because it balances accessibility with a genuine sense of place. The city itself offers a mix of waterways, parks, and commercial corridors, and the western branch has its own grocery anchors, restaurants, and services that mean you rarely need to cross the bridge-tunnel for everyday life.

What's nearby

Day-to-day life runs smoothly from Oriole Drive. The western branch commercial corridor along Airline Boulevard and Taylor Road puts grocery stores, pharmacies, and casual dining within a short drive. Western Branch Lynnhaven Park and nearby green spaces give families and dog owners room to roam. For coffee, local spots and national chains alike are reachable in under ten minutes. Portsmouth's waterfront and downtown dining scene add a weekend dimension, and the broader Hampton Roads network of beaches, marinas, and regional parks is accessible without a long haul. Commuters heading toward Norfolk or Suffolk find the routing straightforward from this part of Chesapeake.

For different buyers

For military families relocating

Naval Medical Center Portsmouth and NSA Northwest Annex are each about 17 minutes from Oriole Drive — a commute that works whether you're on a rotating shift or a standard schedule. The VA loan is a natural fit for this property type and price band, and western Chesapeake has a strong track record of welcoming military households. Families weighing homes for sale in 23321 will find this address checks the proximity and space boxes at the same time.

For families upgrading

Four bedrooms and 2,378 square feet give a growing family genuine room to spread out — dedicated space for a home office, a guest room, or a playroom without anyone feeling crowded. Families comparing homes for sale zoned for Western Branch High School and homes for sale zoned for Edwin W. Chittum Elementary School will find Oriole Drive squarely in that attendance zone, making the school question straightforward. The 2001 build year means the bones are solid and the layout reflects how families actually live today.

More buyer questions

How far is 4936 Oriole Drive from Naval Medical Center Portsmouth?

Naval Medical Center Portsmouth is approximately 17 minutes from 4936 Oriole Drive under normal traffic conditions. The route via I-664 is consistent and avoids most of the downtown Norfolk congestion.

How far is 4936 Oriole Drive from NSA Northwest Annex?

NSA Northwest Annex is also about 17 minutes away, making Oriole Drive a practical base for personnel assigned to either installation. The two bases share a similar drive time from this address, which is useful for dual-military households.

What zip code is 4936 Oriole Drive in, and what does that mean for the neighborhood?

The property falls in the 23321 zip code, which covers the western branch of Chesapeake — a well-established suburban corridor known for its accessibility to both military installations and everyday services. It's one of the more consistently in-demand zip codes among families looking at homes for sale in Chesapeake.

Is 4936 Oriole Drive in a flood zone?

Flood zone status for this address is covered in the FloodRisk tile on this page, which pulls current FEMA map data. Western Chesapeake varies by parcel, so reviewing that tile directly is the most accurate approach.

Does 4936 Oriole Drive have a garage?

Garage details for this property are best confirmed through the current listing data or a direct walkthrough — the home's 2001 construction is consistent with attached garage configurations common in the neighborhood, but specifics should be verified.

Tom and Dariya Milan at LPT Realty know western Chesapeake well — reach out to get your questions answered and schedule a walkthrough of 4936 Oriole Drive on your timeline.

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

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

Chesapeake$440K – $600K4+ 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

Looking up FEMA flood zone…

Hurricane Evacuation Zone

Evacuation Zone C

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

Explore this neighborhood

Dock Landing

Dock Landing is a residential community in the Western Branch area of Chesapeake, Virginia, centered along Dock Landing Road in the 23321 ZIP code.

$536K

Median sale · 12 mo

$222

Sold $/sq ft

18d

Days on market

2

For sale now

$169K

HH income

95.3%

Owner-occupied

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

Explore Dock Landing
Map of Dock Landing 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

$3,259/mo

Principal & interest

$2,698

Property tax

$409

Home insurance

$152

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

Judge value on real ground

Asking vs. assessment

107% of $485,800

City assessment record · taxes $4,906/yr

Land share of assessed value

34% — $165,000

Improvements $320,800 · assessor record ✓

Price context — similar nearby homes

$485,000$600,000

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.

4737 Condor DR · 0.4 mi · 2,350 sqft$600,000 sold 2026-08
4827 Condor DR · 0.2 mi · 2,511 sqft$550,000 sold 2026-06
5521 White Swallow WAY · 0.5 mi · 2,238 sqft$555,000 sold 2026-07

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

Sale & Tax History

List Price

$520,000

Price / Sq Ft

$219

Annual Taxes

$4,906

Monthly Tax

$409

HOA

None

Tax Rate (effective)

0.94%

Sale Timeline (this listing)

EventDatePriceDetail
ListedAug 6, 2026$520,000
Price reducedSep 2, 2026$520,000−$20,000
Currently listed$520,000

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

7% above assessment

Total Assessed

$485,800

Land

$165,000

Improvement

$320,800

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

33 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 4936 Oriole Dr in a good school zone?+
The assigned zones on the listing record are Edwin W. Chittum Elementary (VaHome School Score 7.9/10), Jolliff Middle (VaHome School Score 8.2/10), Western Branch (VaHome School Score 6.2/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 4936 Oriole Dr 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 4936 Oriole Dr have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 4936 Oriole Dr built?+
It was built in 2001, 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 · answer their own phone

✓ Your inquiry goes to Tom & Dariya — never sold to strangers

Listing courtesy of Judy Reed · REIN MLS #10647434

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.

4936 Oriole Dr, Chesapeake — photo

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

Call or text (757) 777-7577

4936 Oriole Dr, Chesapeake, Virginia 23321 · MLS #10647434 · 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.