Island-rooted property & rental management for Chebeague.

Because Chebeague deserves to be cared for by its own.

Endorsements from Island Pillars

“It's a great service. I really do think so. This is something the island has needed for a long time — I thought about doing it myself years ago and never did.”

— Bev Johnson, founder of Chebeague.org

“You ask somebody if they can paint half the house next year, and it's a crapshoot whether it happens. That's how it ends up being for everybody out here.”

— Doug Ross, island builder

“You could do quite a lot with this. Nobody's really doing it on Chebeague — a few people doing little bits of it, but not to the extent it could be done.”

— Jon Rich, founder of Rich Plumbing

“A place where homeowners can find vetted contractors they can trust would be huge. When word got out that I was building again, I went from two projects to twenty in a month.”

— Mark Heels Construction, partner

Rental Properties — Coming Soon!

Sunset over Casco Bay with boats, silhouetted trees, and an umbrella in the foreground.

COMING SOON

3 bed, 2 bath. South Road
$300/night

Silhouettes of people standing and sitting along a coastline at sunset, with a sky filled with clouds and the last light of day.

COMING SOON

2 bed, 2 bath. Fire House Rd
$325/night

A nighttime scene by a calm body of water with boats floating and a person paddleboarding, silhouetted by trees, with a dark sky and faint light reflections on the water.

COMING SOON

4 bed, 2.5 bath. Cottage Road
$450/night

Four children exploring rocky shoreline by water with dense trees and cloudy sky in background.

COMING SOON

3 bed, 2 bath. Deer Point Road
$375/night

People sitting around a campfire, warming their hands by the flames, with rocks and logs surrounding the fire pit.

COMING SOON

Yurt & Campsite
$200/night

A house with wooden shingles, a large arched window, and a chimney on a coastal area. There is a wooden pier with an American flag and a small boat in the water. The sky is partly cloudy and the ground is rocky and sandy.

COMING SOON

6 bed, 4 bath. North Road
$5k/week

Questions about what renting your property would look like?

Schedule a call with us

Two things we do best —

01

Contractor Network
& Project Management

The roof you've been watching sag. The sills rotting away. The kitchen that you always dreamed of renovating. The garage that could be two more bedrooms for guests. We scope it, price it, build it with island trades, handle the barge, and send you progress photos until it's done.

Includes:

  • Scoped honestly. What the work actually needs, said plainly, before there's a price attached.

  • Island tradespeople first. Every job, every time, before anyone from the mainland gets a call.

  • Materials and freight handled. Sourcing, the mainland yard run, barge scheduling, landing, and somewhere dry to stage it.

  • Everybody scheduled around each other, and around the boat. Which is most of the job on an island.

  • Somebody on-site checking the work. Not a text asking how it's going.

  • Photos as it goes. Delays and change orders included, not just the good weeks.

02

Rental Readiness
& Property Management

Your house earns while you're away, and comes back to you in the condition you left it. We ready it, stage and photograph it, list it on our new Chebeague Rentals platform, market it to guests who love this island in every season, and handle every guest conversation ourselves.

Includes:

  • An honest read before you list. What the house can realistically earn, what it needs first, and what that costs.

  • Set up to rent well. Repairs, upgrades, and a deep clean handled by island trades before the first guest.

  • Listed and marketed. On hamiltonmgt.com and wherever else makes sense for your house.

  • Bookings handled. Inquiries, rates, calendar, guest questions at eleven at night. You're not the one answering.

  • The turn between guests. Cleaned, linens changed, restocked, reset, and inspected twice — once after the clean, once before the guest walks in.

  • Every booking reported, both directions. Including any you take yourself. You see the whole picture, and so do I.

Ready for some peace-of-mind?

15 minutes on the phone and you'll know whether your peace-of-mind is worth it.