Updated on Jul 20, 2026
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Type
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Private vacation home
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Bedrooms
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3
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Bathrooms
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2
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House Rules
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-
Pets allowed
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Children allowed: ages 0-17
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Smoking is not permitted
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No events allowed
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Max Occupancy
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6
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Host Language
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English
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Property Id
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3879670
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Welcome to Orr's Overlook!
Perched at the southern tip of Orr's Island, this classic New Englander blends coastal charm with thoughtful updates, creating a comfortable retreat in one of Harpswell's most beloved locations. Whether you're seeking peaceful ocean views, easy access to local cafés and restaurants, or sunset strolls with your four-legged companion, Orr's Overlook is pet friendly and ready to welcome the entire family.
The Space
Step inside to find a beautifully renovated kitchen featuring new appliances, fresh flooring, and plenty of natural light. Enjoy breakfast in the cozy nook, gather at the kitchen island, or head out to the new side deck to dine in the salty Maine breeze. The open dining and living area provide plenty of space to unwind after a day of exploring, while a half bath downstairs adds convenience for everyone.
Upstairs, three inviting bedrooms, two with queen beds and one with two twins, offer room for a family or small group to spread out comfortably. The full bathroom on this floor boasts a large walk-in shower, perfect for rinsing off after a day on the water or at the beach. New flooring runs throughout the home, giving Orr's Overlook a clean, refreshed feel, complemented by its wrap-around yard—ideal for lawn games, relaxing, or letting your pet explore.
Above-Garage Lookout Deck
One of the most unique highlights of this property is the elevated viewing deck above the detached garage. Just steps away from the main house, this quiet perch offers some of the best views on Orr's Island. Bring your morning coffee, settle in with a good book, or enjoy an evening cocktail as the sun sets over the water. From here, you can watch lobster boats work the coves, spot seabirds and local wildlife, and soak in panoramic views of nearby islands. It's also a picture-perfect place to take in sunrise, sunset, or Maine's incredible night sky.
The Location
Orr's Overlook is ideally positioned for walking, sightseeing, and adventure. Take a short stroll to the world-famous Cribstone Bridge or launch the provided kayaks just feet from it to explore the waterways up close. You're also within easy walking distance to:
Salt Cod Café & H2O Outfitters – 0.1 miles
Island Candy Company – 0.4 miles
Sundrenched – 0.4 miles
Cook's Lobster & Ale House – 1 mile
A local general store (BIGS on Bailey Island) is just over a mile away, and full grocery stores are a quick drive back into Brunswick.
Whether you're dreaming of quiet mornings by the water, afternoons spent kayaking, or evenings relaxing on your private lookout deck with your pet at your side, Orr's Overlook offers a quintessential Maine experience with comfort, charm, and unbeatable convenience.
BOOK YOUR ISLAND GETAWAY TODAY!
Please Note:
The fireplace is NOT available for tenant use.
Kayaks and bicycles are provided and used at tenants' own risk.
Located in Bailey Island, this vacation home is in a rural area and by the sea. Gulf of Maine and Brunswick Golf Course are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Brunswick Town Commons and Casco Bay. Paddleworks and Land's End Gift Shop are also worth visiting. Kayaking and snorkeling offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and mountain biking nearby.
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