Entire home
A newly renovated New Englander style home on the southern tip of Orr's Island.
Holiday home in Bailey Island with kitchen and balcony
Photo gallery for A newly renovated New Englander style home on the southern tip of Orr's Island.





Reviews
10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6120.5 sq m
Popular amenities
Explore the area
Orrs Island, ME
- Place, Bailey Island Bridge8 min walk
- Place, Cobwork Bridge11 min walk
- Place, Paddleworks16 min walk
- Airport, Portland, ME (PWM-Portland Intl. Jetport)64 min drive
Rooms & beds
3 bedrooms (sleeps 6)
Bedroom 2
1 Queen Bed
Bedroom 3
2 Single 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.
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.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Outdoor space
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House Rules
Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that 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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Property # 3879670vb
About the area
Bailey Island
Located in Bailey Island, this holiday 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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Orrs Island, ME
What's nearby
- Bailey Island Bridge - 8 min walk - 0.7 km
- Cobwork Bridge - 11 min walk - 1.0 km
- Paddleworks - 16 min walk - 1.4 km
- Ragged Island - 3 min drive - 2.2 km
- LL Bean Flagship Store - 40 min drive - 48.8 km
Getting around
Restaurants
- Dolphin Marina & Restaurant - 31 min drive
- Cook's Lobster & Ale House - 2 min drive
- Erica's Seafood & Lobster Shop - 31 min drive
- Anna's Water's Edge Restaurant - 49 min drive
- Ledges Pub at Sebasco - 46 min drive
Frequently asked questions
About the host
Hosted by Your Island Connection, LLC
Languages:
English
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