Estate Sale Associate – Part-Time; Hybrid Online & In-Person

Location: Chesapeake / Virginia Beach / Hampton Roads
Company: Caring Transitions of Chesapeake & Virginia Beach West
Job Type: Part-Time (with opportunity for more hours)

Caring Transitions of Chesapeake & Virginia Beach West specializes in estate sales, online auctions, relocations, and clear-outs. We use a hybrid estate sale model
, combining online auctions through with traditional in-person estate sales
, allowing us to maximize value for our clients and create a better buying experience.

We’re looking for reliable, detail-oriented team members who enjoy hands‑on work, variety in their day, and being part of a supportive, fast-paced team.

As an Estate Sale Associate
, you’ll assist with both online auction preparation and on‑site estate sales
. This role is ideal for someone who enjoys organizing, working with unique items, helping customers, and being on their feet.

No two days are the same — one day you may be photographing collectibles for online bidding, and another day you’ll be assisting customers at an in‑person estate sale.

Sort, stage, and organize estate items for online auctions

Photograph items accurately and consistently

Assist with basic item descriptions and inventory tracking

Help prepare items for customer pickup or shipping

Set up estate sale spaces (tables, displays, signage)

Answer basic questions and help locate items

Handle transactions using point‑of‑sale systems

Assist with pricing adjustments and end‑of‑sale breakdown

General Duties

Maintain professionalism and compassion when working in client homes

Follow company procedures for handling estate property

Work as part of a team to meet deadlines and sale schedules

Light lifting and moving of household items as needed

Reliable transportation and punctuality are required

Able to lift up to 40 lbs with assistance

Strong attention to detail and organization

Friendly, professional demeanor with customers and clients

Comfortable using a smartphone (photos, basic apps) with unlimited data.

Estate sale, retail, or customer service experience is a plus — but not required

• Competitive hourly pay: Employees typically start between $14–$17 per hour
  , depending on experience, with opportunities to earn up to $20 per hour based on performance and skill development.
  
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• Additional compensation: Team members are eligible for performance‑based team bonuses when estate sales meet or exceed established targets.

Variety — no repetitive shifts or environments

Opportunity to learn estate sales, online auctions, and resale markets

Supportive team and clear expectations

While hours may vary slightly based on the size and scope of each estate, a typical work week generally looks like this:

Sunday and Monday: Off

Tuesday & Wednesday: Core hours 9:00 AM – 3:00 PM
(Occasionally may extend to 4:00 or 5:00 PM depending on workload)

Thursday:
Half day or off
, if prep work is complete

Organizing and staging

Unique items and collectibles

A mix of independent and team‑based tasks
this position is a great fit.

Have you ever been convicted of a felony?*

Do you work better independently or as part of a team?

Are you willing to work Tuesday - Saturdays*

This job involves early mornings on Fridays and Saturdays. Is that schedule something you can reliably commit to?*

Not all homes are the same. With proper PPE provided, are you comfortable working in environments that may be dusty, cluttered, or otherwise less than ideal?*

Can you comfortably use tools such as Google Lens and ChatGPT to assist with item identification, research, and writing accurate listings and descriptions.*

Some people thrive in team environments, others prefer working solo. Where do you do your best work, and how do you adapt when teamwork is required?*

Employment with our company is contingent upon passing a background check. Are you able to meet this requirement?*