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.

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

• 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. - 
• Additional compensation: Team members are eligible for performance-based team bonuses when estate sales meet or exceed established targets

• 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:

• Hands-on work

• Organizing and staging

• Unique items and collectibles

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