Spacious 5BR Cottage w/Pool, Water & Resort Access

Ocean front home / private dock /winter rent avail

Direct Beach Access - Casual Luxury on the Ocean

Little Harbor Cottage

The Historic Captain York House

Beautiful Nezinscott Cottage on Bailey Island

With home theater, pool table and ocean views!

The Spruces: Summer Cottage

Oceanfront Cottage with Spectacular Views

Cricket Lodge

Orchid Harbor, Bailey Island 3BR

The Cribstone Cottage on Bailey Island

A multi-level home on the cliffs of Casco Bay!

The Hideaway, In Harpswell Maine

Fairwinds Home, Bailey Island, in Harpswell Maine

Homeport - Modern oceanfront cottage overlooking q

Renovated New Englander home on Orr's Island.

Oceanfront Escape: Deck & Granite Steps to Shore

Ocean Views Near Beach w/ AC • Dog Friendly

Brand new year-round oceanfront home with beach.

Coastal Home away from Home

2 Views Cottage

Ole Greeley Cottage - Classic oceanfront, pet-frie

Enjoy Stunning Ocean Views & Coastal Access!

Waterfront Maine cottage

Rudman's Retreat - Deep waterfront, AC with a view

Shore House, Leona Unit - Ocean Front Property

A beautiful 3 bedroom home overlooking Basin Cove.

Shore House, Posey Unit - Ocean Front Property

Sunset Saltbox on Basin Cove

Located at the Mouth of picturesque Mackerel Cove!

Cozy Orr's Island Bungalow

Newly renovated cottage with stunning ocean views

On Island Time Cottage

Sterling View Condo

The Bailey Island Condo - The perfect seaside retr

Sunset Hideaway on Bailey Island

Discover the possibilities with this unique property featuring two separate homes on one lot, each with its own private well and septic system. Whether you're looking for an investment property, multi-generational living, or the perfect coastal family compound, this exceptional Bailey Island offering provides endless potential.

#14, originally built around 1910, 1252 square feet of living space, offers 3 bedrooms, 2 bathrooms, water views, and a cozy fireplace that adds warmth and character. Previously used as a rental, this home has solid bones and is ready for your vision and a little TLC to restore its full coastal charm. 

#18, built in 1991, 1926 square feet of living space, features 3 bedrooms, 2 bathrooms, hardwood floors, carpeting, a beautiful double-sided fireplace, and scenic water views. Thoughtfully designed for comfortable year-round living or a relaxing coastal retreat, this home is move-in ready while still offering room to make it your own.

Ideally located in the heart of Bailey Island, you'll enjoy being within walking distance of the local store, nearby beaches, and everything this quintessential Maine island community has to offer.

Whether you're looking to continue renting one or both homes, establish a private family compound, or live in one while generating income from the other, the possibilities are endless. Properties offering two homes, separate utilities, water views, and an unbeatable Bailey Island location are exceptionally rare. Don't miss this incredible opportunity to own a truly special piece of the Maine coast.

Harpswell Community School

Mt Ararat Middle School

Mt Ararat High School

18 Steamboat Rd Harpswell, Maine

$72,337

Annual Revenue

Investment Value Over Time