Airport, Portland, ME (PWM-Portland Intl. Jetport)
59 min drive
Rooms & beds
3 bedrooms (sleeps 6)
Bedroom 2
1 Queen Bed
Bedroom 3
2 Twin Beds
Primary bedroom
1 Queen Bed
2 bathrooms
First floor
Toilet · Shower only
Second floor full bath
Bathtub or shower · Toilet
Spaces
Deck or patio
Kitchen
Balcony
Dining area
About this property
A newly renovated New Englander style home on the southern tip of Orr's Island.
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.
Our prices include all fees. No hidden fees.
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
About the neighborhood
Bailey Island
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/biking trails and cycling nearby.
beach near Merritt House Road - 3 min walk - 0.3 km
Bailey Island Bridge - 8 min walk - 0.7 km
beach near Channel View Lane - 10 min walk - 0.9 km
Cobwork Bridge - 11 min walk - 1.0 km
Paddleworks - 16 min walk - 1.4 km
Getting around
Brunswick Station - 23 min drive
Portland Intl. Jetport Airport (PWM) - 60 min drive
Restaurants
Cook's Lobster & Ale House - 2 min drive
Bailey Island General Store - 2 min drive
Anna's Water's Edge Restaurant - 49 min drive
Morse’s - 17 min drive
Dolphin Marina & Restaurant - 31 min drive
Frequently asked questions
Is A newly renovated New Englander style home on the southern tip of Orr's Island. pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at A newly renovated New Englander style home on the southern tip of Orr's Island.?
As of May 10, 2026, prices found for a 1-night stay for 2 adults at A newly renovated New Englander style home on the southern tip of Orr's Island. on Sep 4, 2026 start from $507, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking?
Onsite parking is available at the property.
What time is check-in at A newly renovated New Englander style home on the southern tip of Orr's Island.?
Check-in begins at 4:00 PM.
What time is check-out at A newly renovated New Englander style home on the southern tip of Orr's Island.?
Check-out is at 10:00 AM.
Where is A newly renovated New Englander style home on the southern tip of Orr's Island. located?
Situated by the sea, this vacation home is within 1 mi (2 km) of Casco Bay, Bailey Island Bridge, and Paddleworks. Cobwork Bridge and Ragged Island are also within 2 mi (3 km).