Entire home
A newly renovated New Englander style home on the southern tip of Orr's Island.
Photo gallery for A newly renovated New Englander style home on the southern tip of Orr's Island.





Reviews
1010 out of 10
Exceptional
Popular amenities
- Garage parking available
- Pet-friendly
- Kitchen
- Washing machine
- Barbecue grill
- Balcony
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
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

Oceanfront Escape: Deck & Granite Steps to Shore
Harpswell
Oceanfront Escape: Deck & Granite Steps to Shore
Harpswell
- Kitchen
- Free Wi-Fi
- Parking available
- Barbecue grill
9.4 out of 10, Exceptional, (3 reviews)
9.4/10
Exceptional
(3 reviews)

Swim, Kayak & Relax in Coastal Comfort from this Charming, Pet-Friendly Home
Harpswell
Swim, Kayak & Relax in Coastal Comfort from this Charming, Pet-Friendly Home
Harpswell
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (3 reviews)
10/10
Exceptional
(3 reviews)

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Bailey Island
Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Bailey Island
- Ocean view
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (236 reviews)
10/10
Exceptional
(236 reviews)

Windward - Enjoy privacy, comfortable living spaces, and easy water access
Harpswell
Windward - Enjoy privacy, comfortable living spaces, and easy water access
Harpswell
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.8 out of 10, Exceptional, (23 reviews)
9.8/10
Exceptional
(23 reviews)

Beautifully landscaped, Spacious home, conveniently located in Harpswell
Bailey Island
Beautifully landscaped, Spacious home, conveniently located in Harpswell
Bailey Island
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.8 out of 10, Exceptional, (18 reviews)
9.8/10
Exceptional
(18 reviews)

Enjoy Stunning Ocean Views & Coastal Access at Sea Mist Overlook!
Harpswell
Enjoy Stunning Ocean Views & Coastal Access at Sea Mist Overlook!
Harpswell
- Ocean view
- Kitchen
- Free Wi-Fi
- Laundry room
10.0 out of 10, Exceptional, (5 reviews)
10/10
Exceptional
(5 reviews)

The Beach House Bailey Island Maine
Harpswell
The Beach House Bailey Island Maine
Harpswell
- Kitchen
- Free Wi-Fi
- Outdoor space
- Parking available
10.0 out of 10, Exceptional, (35 reviews)
10/10
Exceptional
(35 reviews)

On Top of the Sea North Harpswell House
Harpswell
On Top of the Sea North Harpswell House
Harpswell
- Ocean view
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (99 reviews)
10/10
Exceptional
(99 reviews)

Enjoy spectacular sunset and water views from the deck and balconies with water access.
Bailey Island
Enjoy spectacular sunset and water views from the deck and balconies with water access.
Bailey Island
- Ocean view
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (12 reviews)
10/10
Exceptional
(12 reviews)

Spacious 3 Bedroom, 2 bath, new home, ocean views, close to Maine seafood!
Orr's Island
Spacious 3 Bedroom, 2 bath, new home, ocean views, close to Maine seafood!
Orr's Island
- Ocean view
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (54 reviews)
10/10
Exceptional
(54 reviews)

Grace's Place, a Real Maine Cottage
West Harpswell
Grace's Place, a Real Maine Cottage
West Harpswell
- Ocean view
- Kitchen
- Washing machine
- Dryer
9.8 out of 10, Exceptional, (51 reviews)
9.8/10
Exceptional
(51 reviews)

Clean, Cozy, and Professional Waterfront Home- minutes to Portland
Falmouth
Clean, Cozy, and Professional Waterfront Home- minutes to Portland
Falmouth
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (57 reviews)
10/10
Exceptional
(57 reviews)

With an easy, scenic walk to the beach, you'll enjoy daily tides and sunsets.
Harpswell
With an easy, scenic walk to the beach, you'll enjoy daily tides and sunsets.
Harpswell
- Kitchen
- Pet-friendly
- Free Wi-Fi
- Parking available

Beautiful Oceanfront House- Stunning Water Views
Harpswell
Beautiful Oceanfront House- Stunning Water Views
Harpswell
- Washing machine
- Dryer
- Pet-friendly
- Air-conditioning
9.4 out of 10, Exceptional, (25 reviews)
9.4/10
Exceptional
(25 reviews)

Full sized home
Harpswell
Full sized home
Harpswell
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.8 out of 10, Exceptional, (51 reviews)
9.8/10
Exceptional
(51 reviews)

Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views!
Orr's Island
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views!
Orr's Island
- Kitchen
- Free Wi-Fi
- Outdoor space
- Parking available
9.8 out of 10, Exceptional, (37 reviews)
9.8/10
Exceptional
(37 reviews)

Shady Potts Point Cottage Cooled by Ocean Breezes
Harpswell
Shady Potts Point Cottage Cooled by Ocean Breezes
Harpswell
- Kitchen
- Pet-friendly
- Free Wi-Fi
- Laundry room
9.6 out of 10, Exceptional, (90 reviews)
9.6/10
Exceptional
(90 reviews)

Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Bailey Island
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Bailey Island
- Kitchen
- Washing machine
- Pet-friendly
- Free Wi-Fi
9.8 out of 10, Exceptional, (12 reviews)
9.8/10
Exceptional
(12 reviews)

In the heart of beautiful Bailey Island, this coastal retreat offers a blend of comfort and charm.
Bailey Island
In the heart of beautiful Bailey Island, this coastal retreat offers a blend of comfort and charm.
Bailey Island
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi

Sea Salt Cottage: 4 BR, 1 BA Cottage in Harpswell, Sleeps 7
Harpswell
Sea Salt Cottage: 4 BR, 1 BA Cottage in Harpswell, Sleeps 7
Harpswell
- Kitchen
- Pet-friendly
- Outdoor space
- Parking available

Spend a relaxing time on Orr's Island
Orr's Island
Spend a relaxing time on Orr's Island
Orr's Island
- Ocean view
- Kitchen
- Free Wi-Fi
- Laundry room
10.0 out of 10, Exceptional, (37 reviews)
10/10
Exceptional
(37 reviews)

Turn-of-the-Century Classic Maine Cottage with Sweeping Southeasterly Ocean Views
Bailey Island
Turn-of-the-Century Classic Maine Cottage with Sweeping Southeasterly Ocean Views
Bailey Island
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.2 out of 10, Wonderful, (10 reviews)
9.2/10
Wonderful
(10 reviews)

Maine Oceanfront Home
Orrs Island
Maine Oceanfront Home
Orrs Island
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (179 reviews)
10/10
Exceptional
(179 reviews)

The Cove Retreat is the perfect spot to walk the family or dog down to Stover's Point Beach.
Harpswell
The Cove Retreat is the perfect spot to walk the family or dog down to Stover's Point Beach.
Harpswell
- Kitchen
- Washing machine
- Dryer
- Pet-friendly

Classic 3 bedroom cape on the stunning coast of Maine, sleeps 8 people
Harpswell
Classic 3 bedroom cape on the stunning coast of Maine, sleeps 8 people
Harpswell
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.6 out of 10, Exceptional, (35 reviews)
9.6/10
Exceptional
(35 reviews)

Gorgeous ocean views with private beach access.
Bailey Island
Gorgeous ocean views with private beach access.
Bailey Island
- Ocean view
- Kitchen
- Washing machine
- Dryer

Recently updated cottage featuring beautiful easterly views of Casco Bay
Bailey Island
Recently updated cottage featuring beautiful easterly views of Casco Bay
Bailey Island
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.2 out of 10, Wonderful, (12 reviews)
9.2/10
Wonderful
(12 reviews)

Blue Lobster! 2-BR/1.5 BA with Heat, AC, Deck and Seasonal Dock in Harpswell
Harpswell
Blue Lobster! 2-BR/1.5 BA with Heat, AC, Deck and Seasonal Dock in Harpswell
Harpswell
- Ocean view
- Kitchen
- Washing machine
- Dryer
9.8 out of 10, Exceptional, (24 reviews)
9.8/10
Exceptional
(24 reviews)

Maine waterfront, walkable to historic downtown
Bath
Maine waterfront, walkable to historic downtown
Bath
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)

Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
Harpswell
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
Harpswell
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.8 out of 10, Exceptional, (42 reviews)
9.8/10
Exceptional
(42 reviews)
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. Kayaking and snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and cycling nearby.

Orrs Island, ME
What's nearby
- beach near Water Cove - 2 min walk - 0.2 km
- beach near Merritt House Road - 3 min walk - 0.3 km
- Bailey Island Bridge - 8 min walk - 0.7 km
- Cobwork Bridge - 11 min walk - 1.0 km
- Paddleworks - 16 min walk - 1.4 km
Getting around
- Brunswick Station - 23 min drive
- Portland, ME (PWM-Portland Intl. Jetport) - 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
Tell us how we can improve our siteShare feedback