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.
Online Estate Sale (CTBids) Support
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
Maintain clean, organized workspaces during prep days
In-Person Estate Sale Support
Set up estate sale spaces (tables, displays, signage)
Assist customers during sale hours
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
Comfortable working in private homes
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
Flexible scheduling (weekday prep + weekends)
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
Friday: 7:00 AM – 2:00 PM (In-person estate sale day)
Saturday: 7:00 AM – 2:00 PM (In-person estate sale day/Online Pickup Day)
If you enjoy:
Organizing and staging
Unique items and collectibles
A mix of independent and team-based tasks
this position is a great fit.
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