Estate Sale Associate (Hybrid: Online & In-Person Sales)

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

About Us

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.

Position Overview

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.

Key Responsibilities

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

Qualifications

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

What We OfferCompetitive 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

Schedule 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)

Why This Role Works

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.