HARBOUR & HILL ESTATES — PRIVATE ESTATE MANAGEMENTHARBOUR & HILL ESTATESFILE 2026–27 — NOW TAKING FOUNDING CLIENTSCOLLINGWOOD, ON

Who & where

FILE HH-CO

Two people, ten minutes away

Harbour & Hill is not a franchise and not a call centre. It is two Collingwood residents, the towns they cover, and the keys they hold — this page is who we are, where we work, and the questions owners ask before handing either over.

Section 01 — Who attends

We live here. That is the whole idea.

Harbour & Hill was started by two Collingwood residents who kept hearing the same thing from friends with places up here: everything is fine until it isn’t, and then you are three hours away with a contractor’s voicemail. The harbour is this town’s shipbuilding past. The hill is why most of our clients came here in the first place. We look after the places in between.

Tom Griggs, cofounder of Harbour & Hill Estates

PERSONNEL 01

Tom Griggs

Cofounder · Real Estate Lead

Has sold and managed property in this area for years, which means he knows which roofs hold snow, which lanes don’t get plowed, and which trades actually show up.

Knows which roofs hold snow and which trades show up.

Jonathan Simopoulos, cofounder of Harbour & Hill Estates

PERSONNEL 02

Jonathan Simopoulos

Cofounder · Operations

Builds the checklists and the reporting. If your property has a quirk, it gets written down once and then it is never forgotten again.

Builds the checklists, writes the reports, answers the phone.

Bonded
You are protected against theft or damage caused by us.
Insured
Commercial general liability.
Keys
Only the two of us ever hold your keys.
  • Background-checked
  • Keys coded, never labelled
  • Owner-operated
  • Now taking founding clients for the 2026–27 season.

Section 02 — Service area

From the harbour to the hills

We keep our area deliberately tight so we can be at your property quickly when it matters. Ten minutes away, not three hours.

  1. 01Collingwood
  2. 02The Blue Mountains
  3. 03Craigleith
  4. 04Thornbury
  5. 05Georgian Bay shoreline
  6. 06Wasaga Beach
  7. 07Osler Bluff
  8. 08Georgian Peaks
  9. 09Alpine
  10. 10Devil's Glen

Just outside the lines? Ask — we probably drive past you.

illustrativephoto — the escarpment across the bay

Section 03 — Queries on file

Questions about keys, coverage and scope

Anything else, call Tom at 705.444.4338. We reply within one business day.

Q.01

Do you hold keys and alarm codes?

Yes. Keys are coded rather than labelled with addresses and kept in a locked box; codes are stored in an encrypted record. Only background-checked Harbour & Hill staff ever enter your home.

Q.02

Are you insured?

We carry commercial general liability and are bonded. We are happy to send certificates to you or directly to your broker.

Q.03

Do you also clean, plow or do repairs?

We coordinate rather than compete with the people already doing good work here. We will manage your plow contractor, cleaner and trades, supervise access, and check the result.

Q.04

Are you a security company?

No. Alarms and cameras tell you something happened; our job is making sure nothing does. We check your systems — alarm status is on every visit’s checklist — but the work is prevention and documentation: water, heat, roof, and a record your insurer can read.

Section 04 — Free property assessment

Let’s walk your property together.

An hour on site, no cost and no obligation. Here is what happens after you press send:

  • Tom or Jon replies within one business day
  • We walk the property together — about an hour
  • You get a written recommendation: cadence, watch list, and what it would cost
  • We never share your address or that your home sits empty
Call Tom & Jon705.444.4338Professional oversight. Complete peace of mind.
Assessment requestFORM HH-ASSESS

Replies come from Tom or Jon within one business day. We never share your address — or that your home sits empty.

Prefer to talk? Call Tom & Jon at 705.444.4338.

Call Tom & Jon705.444.4338Free assessment