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Careers at Streetside

Build your real estate career streetside.

Streetside Realty is growing, and we're looking for agents who care about doing right by people. Join a hands-on, broker-led brokerage serving northern-central Connecticut and the Massachusetts line — where you're a name, not a number.

Led by
Chris Piccoli, Broker
Licensed
Connecticut & Massachusetts
Home base
Suffield, Connecticut
Why Streetside

A brokerage built around its agents

Everything we promise our clients — hands-on service, modern tools, real marketing — is exactly what we put behind our agents. Here's what joining actually gets you.

  1. Competitive compensation

    Competitive pay with a structure that rewards the work you put in. We keep the details for a real conversation — reach out and we'll walk you through exactly how it works.

  2. Broker-led mentorship

    Work directly with a broker licensed in both Connecticut and Massachusetts. No layers, no getting lost in a big office — real guidance on pricing, negotiation, and building your book.

  3. Marketing that wins listings

    Every Streetside listing comes with an AI-powered deluxe marketing package, free pre-listing inspections, and a curb-appeal program. You walk into listing appointments with something real to offer.

  4. Modern tools, ready on day one

    A full platform behind you from your first day — IDX listing search, instant home valuation, live market data, a mobile app, and a CRM that keeps your follow-ups on track.

  5. A two-state local footprint

    Rooted in Suffield with clients across northern-central Connecticut and into Massachusetts. Dual-state reach means more doors for you and the people you serve.

Is this you?

Licensed or just curious — let's talk

You don't need years of production to start the conversation. Wherever you are on the path, the first step looks the same.

  • Experienced agents

    You're licensed and producing, but you want more support and a better home for your business. Your conversation with us stays completely confidential.

  • Newly licensed agents

    You've passed the exam and want to launch the right way — with a broker who picks up the phone and shows you how deals actually get done.

  • Considering the leap

    You're exploring real estate as a career, maybe still in licensing school. Reach out — we're happy to talk through what the path really looks like.

How joining works

  1. 1

    Introduce yourself

    Fill out the short form below — it takes about two minutes. Tell us as much or as little as you like.

  2. 2

    Have a real conversation

    Chris will reach out personally to talk about your goals, our compensation, and whether we're a fit. Always private, never pushy.

  3. 3

    Make the move

    If it feels right on both sides, we handle the transition details and get you up and running.

Already with another brokerage? Every inquiry is handled personally and kept strictly confidential.

Optional
Where are you on the licensing path? *
Optional
Optional

Confidential — your details go only to Chris Piccoli and are never shared.

Apply

Introduce yourself — the rest is a conversation

Two minutes now, a personal call from Chris after. No recruiters, no pressure — just an honest conversation about your goals, our competitive compensation, and whether Streetside is the right home for your business.

Chris Piccoli, Broker · CT License REB.0795677 · MA License 9589317