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Chesapeake › JOLLIFF WOODS › 4936 Oriole Dr✓ Source: REIN MLS #10647434 · record updated Aug 6, 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
$560,000
$235 / sqft · est. $3,478/mo →
4beds
2.1baths
2,378sqft
0days on market

4936 Oriole Dr, Chesapeake, VA 23321

New ListingResidential · built 2001 · JOLLIFF WOODS

About this home

The listing, in the seller's words

Welcome to this beautifully maintained home in Joliff 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

VaHome team overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · LPT Realty

At a glance

4936 Oriole Drive is a four-bedroom, 2.5-bath single-family home in Chesapeake, Virginia, offering 2,378 square feet of living space built in 2001. It sits in a quiet residential pocket of western Chesapeake with easy access to military installations, everyday shopping, and major commuter routes.

Read the full overview ↓

Why this home stands out

With four bedrooms spread across 2,378 square feet, this 2001-built home gives growing households real breathing room — not just extra square footage on paper. The half-bath on the main level keeps daily traffic flowing, and the layout separates living and sleeping areas in a way that actually works for busy families. Western Chesapeake delivers that balance of suburban calm and genuine accessibility that's hard to find at this size.

JOLLIFF WOODS and the Chesapeake real estate market

Chesapeake is one of the largest cities by land area on the East Coast, and the western reaches — where Oriole Drive sits — have a distinctly neighborhood feel that sets them apart from the city's more commercial corridors. Streets here tend to be quiet, lots are generously sized, and neighbors tend to put down roots. You're in the part of Chesapeake that draws people who want a real backyard, a manageable commute, and a sense of community without sacrificing access to everything the region offers. The broader Chesapeake area continues to attract families and professionals alike thanks to its mix of parks, waterways, and proximity to the Hampton Roads metro. Western Chesapeake in particular benefits from quick connections to Portsmouth, Suffolk, and Interstate 664, making it a practical base for navigating the region without the congestion of the urban core.

What's nearby

Daily errands are straightforward from Oriole Drive. Grocery options, pharmacies, and big-box retail are all within a short drive along the major corridors of western Chesapeake. For green space, Northwest River Park and the trails and open areas scattered through this part of the city offer genuine outdoor recreation close to home. Portsmouth's waterfront dining and historic district are roughly 20 minutes away for a change of pace. Commuters heading toward the Hampton Roads Bridge-Tunnel or downtown Norfolk will find Interstate 664 a reliable on-ramp to the wider region, and Naval Medical Center Portsmouth is just 17 minutes out.

For different buyers

For military families relocating

Naval Medical Center Portsmouth is 17 minutes from Oriole Drive, and NSA Northwest Annex matches that same drive time — making this address a practical fit for service members stationed at either installation. Four bedrooms handle deployments and homecomings with room to spare, and a VA loan can make the path to ownership here more straightforward than you might expect.

For families upgrading

If you've outgrown your current space, 2,378 square feet across four bedrooms gives everyone in the household their own corner. The 2001 construction means the bones are solid without the quirks of an older home, and western Chesapeake's quieter streets make it the kind of place where kids can actually be outside. There's real room to grow here.

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 typical traffic conditions. The route connects easily via western Chesapeake's main corridors into Portsmouth.

How far is 4936 Oriole Drive from NSA Northwest Annex?

NSA Northwest Annex is also about 17 minutes away, making Oriole Drive a convenient home base for personnel assigned to either installation in the area.

What is the square footage and layout of 4936 Oriole Drive?

The home offers 2,378 square feet with four bedrooms and 2.5 bathrooms. The half-bath is located on the main level, and the bedroom count gives households flexible options for offices, guest rooms, or dedicated kids' spaces.

Is 4936 Oriole Drive in a flood zone?

Flood zone information for this address is displayed in the FloodRisk tile on this page, which pulls current FEMA map data. We recommend reviewing that section and discussing it with your agent before making any decisions.

What are the closest grocery stores and everyday conveniences to Oriole Drive?

Western Chesapeake has solid retail coverage along its main commercial corridors, with grocery stores, pharmacies, and general retail all reachable within a short drive from Oriole Drive.

Want to know more about 4936 Oriole Drive or western Chesapeake? Tom and Dariya Milan at LPT Realty are happy to walk you through the details — 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

2001

Price / sqft

$235

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 · 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…

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

0

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

$3,478/mo

Principal & interest

$2,906

Property tax

$409

Home insurance

$163

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

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

$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

Sale & Tax History

List Price

$560,000

Price / Sq Ft

$235

Annual Taxes

$4,906

Monthly Tax

$409

HOA

None

Tax Rate (effective)

0.88%

Sale Timeline (this listing)

EventDatePriceDetail
ListedAug 6, 2026$560,000—
Currently listed—$560,000—

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

0 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 4936 Oriole Dr in a good school zone?+
The assigned zones on the listing record are Edwin W. Chittum Elementary (GreatSchools 6/10), Jolliff Middle (GreatSchools 7/10), Western Branch. 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

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.

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