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Light, airy and ocean!!

Bedrooms 3
Half Baths1
Space 2,400 sq. ft.
Property type house
Minimum Stay 7 nights


About the property

House, 3 Bedrooms + Den, 2.5 Baths, (Sleeps 8)

Spectacular ocean side location. Breathtaking views of ocean, light houses, nearby islands, ships and open ocean. This beautiful three level, 3 bed room, 2.5 bath Victorian Shingled Style home has all you’ll need for a wonderful and memorable vacation.

The 1st level has private accommodations for guests and family, that include kitchen, living area, bath, laundry & impressive ocean views from the 2 bedrooms. On this 1st level there's a queen bed, and 4 twin beds; 2 singles in one bedroom and a trundle bed in living area that makes out into 2 singles.

The 2nd level has an open living & dining area, a well outfitted kitchen, all with expansive ocean views.

The 3rd level is the master suite. It has a private bath, soaking tub, shower & laundry. The bedroom has a king bed, vaulted ceiling & an attached 8 sided turret sitting room; these spaces offer spectacular ocean views. From the king size bed you can lay and watch the moon glimmer on the ocean and the sound of surf will lull you to sleep.

For exterior spaces, there's an ocean side deck for dining & lounging; 2 covered porches.

The setting is arguably one of nicest on Peaks. Incredible ocean views all in front & in back, it's adjacent to and looks out over a freshwater pond, nature trails & natural seaside vegetation. There’s a spacious lawn for playing and gathering. Set above and looking out over the shore road; Peaks Island's “backshore,” offers one of the most beautiful places to walk, jog & bicycle along the New England coast.

The location: Private but not isolated, it's about 15 min walk to the ferry & village or 5 min bike ride. Eight min walk to closest swimming beach, Hadlock Cove. "Sandy Beach" is about a 10 min walk from the house. The beach next to the ferry dock and kayak rentals is about 15 min. Centennial Beach next to the public boat launch and Trefethen Beach next to our sailing and tennis club are easy bike rides away.

Surely one of the finest properties on the Island.

At $3,600.00 per week, you won’t be disappointed.

More Details

Jean Ashmore
Member since: 2007
Speaks: english, french
Response time:
Within a day
Response rate:
Calendar last updated:
November 6, 2017

About Jean Ashmore

'Oceanside Retreat' was built with a great deal of thought; taking advantage of the incredible views as well allowing it to fit the natural landscape & the historic shingled architecture of the island. My husband and I built this house with the intentions of renting it to you. We are so lucky to live here September to June that we'd like to share the beauty of this location, and pay our taxes more easily, with you. Ralph came to the island as a boy and spent summers on the island. Our family has been here for 4 generations. Our son and daughter-in-law and grandson Alistair return to the island from Austin, TX this Fall. Nate was brought up on the island,attended the Children's Workshop and elementary school. He'll introduce his 3 year to the island in 2013. We are very excited about another generation here. The island runs in folks blood!

Ralph and I are lucky to live and work on the island. I used to commute into Portland for years but as of late I joined him in our real estate office as the rental agent. I do enjoy getting off the rock often!

Ralph has been a broker on the island for 30 plus years. He gave up his office on Commercial Street a few years ago and now just concentrates on island property.

We both belong to Brackett Methodist Church and are active in the Church as well as island activities. I'm taking ukulele lessons this winter, yoga and a weight class. Ralph plays tennis on the island in summer and off the island several times a week.

We love walking into town for dinner, a movie or the museum.

We love Peaks Island.

Jean Ashmore purchased this house in 1996

Why Jean Ashmore chose Peaks Island

This property is private and has ample front, side and back yards. The ocean view is the front view. The back side has the pond, frogs, birds and trails. There's woods to the side and along the trails. The porches and the decks allow for enjoyment of all these views. The 3 level house offers separation and privacy for our guests. Multiple baths are a plus on every floor as are both sets of washer and dryer on the top level and lower levels. It's a comfortable,family home not a museum, with tile floors throughout. The peacefulness and solitude provided by this property is a sure winner for a great vacation!

Peaks is a 15-20 min. ferry ride from the city of Portland. The ferry schedule runs nearly on the hour till 11:30 pm at night in summer. Portland ranks as one of the top small cities in the US offering a full array of entertainment, dining, shopping and all within easy walking distance of the ferry terminal. Portland is just a two hour drive to downtown Boston and twenty min. ride to Freeport, home of LL Bean and other great shopping. Portland offers public transportation and an international airport.

What makes this house unique

Incredible natural ocean side beauty and private surroundings. The pond's stillness offers good birding and the peepers at night tell you stories before bedtime. EZ walk to town for an after dinner stroll to get an ice cream, or for the grocery store.

Guestbook comments from the owner

What a comfortable home! And the views!! The location is private, off the beaten path. Great bird watching from the back of the house where there's a pond. Put the grandkids on the first floor while we had the master on the top floor. Oh the soaking tub....

We had a great stay and recommend it.
Aug 2014
  • 1 of 2


Nearest Airport
3 Miles
Nearest Barpub
0.5 Miles
The Inn
Nearest Ferry
0.5 Miles
Casco Bay Lines
Nearest Golf
4 Miles
Portland Country Club
Nearest Train
2 Miles
Nearest Motorway
1 Miles
Nearest Restaurant
0.4 Miles
Peaks Island House
Nearest Ski
80 Miles
Sunday River
Nearest Beach
0.2 Miles
Hadlock Cove

Explore some of the old WWII military fortifications on the island or explore in-town Portland!


Peaks Island House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 2400 sq. ft.
House Rules:
  • Check-in: 4:00 PM / Check-out: 11:00 AM
  • Max. occupancy: 8
  • pets considered
  • children welcome ...
  • non smoking only ...
Location Type:
  • Lakefront ...
  • Ocean View ...
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Broadband Access
  • Clothes Dryer
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided ...
  • Parking Off Street ...
  • Towels Provided ...
  • Washing Machine
  • Wireless Internet
  • Coffee Maker
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator
  • Stove
  • Toaster
  • Dining ...
  • Dining Room
  • seating for 8 people
  • 2 Bathrooms
  • 1 Half Bath
  • Bathroom 1 -
    Bathroom 2 -
  • Master bath (3rd level) has 5 1/2' soaking tub, separate shower, double sink, marble topped custom made cabinets and washer/dryer. Second level has 1/2 bath w/ glass sink, tile and custom cabinet. First level: shower and single vanity, washer/dryer.
  • 3 Bedrooms, Sleeps 8
  • King size bed (1) located on the 3rd floor, Queen size Bed (1) located on the 1st floor, (4) Twin or Single Beds located on the 1st floor, Baby Cribs (1)
  • Books
  • CD Player
  • DVD Player
  • Music Library
  • Satellite / Cable
  • Television
  • Bicycles ...
  • Deck / Patio ...
  • Kayak / Canoe ...
  • Lawn / Garden
  • Outdoor Grill ...
  • Tennis ...
  • churches
  • cinemas
  • festivals
  • library
  • live theater
  • marina
  • museums
  • playground
  • restaurants
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • horseback riding
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • hiking
  • kayaking
  • mountain biking
  • pier fishing
  • roller blading
  • sailing
  • snorkeling/diving
  • sound/bay fishing
  • swimming
  • tennis
  • water skiing
  • wind-surfing
There's a freshwater pond out back along with acres of hiking trails through nearby conservation lands.


5/5 -
(4 traveler reviews)

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Light, airy and ocean!!
average rating of 5.0 based on 6 reviews

The beauty of Peaks

  • 5 of 5

My wife and I had been to Peaks Island for a day trip when our boys were younger and always said we would like to come back. Well the boys are grown now with significant others and one grandson and we spent a week on Peaks Island that was wonderful. The house and the owners only added to the great time we had. The house was all that the description and pictures said it was. The deck looking over the ocean will wake you up in the morning and put you to sleep at night. We really missed it when we left. The last night my wife and I were going to the Inn for dinner and the major decision we had to make was to either walk or ride our bikes.

  • Submitted: Aug 13, 2015
  • Stayed: July 2015
  • Source: VRBO, from HomeAway
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Absolutely Gorgeous!

  • 5 of 5

Seven of us stayed here for a week. The house is beautiful, the view is even more so. Deck on ocean side and a porch on the pond side. Both spots are great to hang out in in. The kids and adults both loved their rooms. You can't hear or see any neighbors, very private. The owners mentioned a lobster pot and burner which we couldn't find, they drove it over in 15 minutes. Every question about the house was answered immediately. These folks were awesome. The island is incredible for all, walking, biking, exploring, eating, reading... The day we left, my wife cried because we had to leave ;-)

  • Submitted: Jul 20, 2015
  • Stayed: July 2015
  • Source: VRBO, from HomeAway
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Boston, MA

Loved our time

  • 5 of 5

My husband and I have been returning every year to this beautiful home on Winding Way. SOme years we brought our children whom enjoyed exploring the property - the field and pond, also the short walk to the ocean to collect rocks and shells . For my husband and I we loved the peacefulness and privacy of the site - lounging on the deck to soak up the sun, view the lovely greenery and flower beds and of course all the extras the island has to offer from walking while viewing the spectacular ocean, bike riding, fishing etc. The hosts Jeanie and Ralph have always been available at a minutes notice if needed and have provided an exceptionally clean well maintained property. We can't wait to go back every summer. It is a piece of heaven - even on a cloudy day!! See you soon

  • Submitted: Mar 3, 2015
  • Stayed: June 2014
  • Source: VRBO, from HomeAway
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Newton, MA USA

A wonderful week on Winding Way

  • 5 of 5

My three generation family just returned from a wonderful week on Peaks Island at this beautiful, comfortable home. It's a private, quiet space that has room for some to sit and read quietly on the deck while bird watching and for some to kick a soccer ball around on the open grounds. We biked and walked everywhere from the beach to the tennis courts. Jean and Ralph are wonderful hosts who are helpful when needed. My grandchildren call it our summer stay house, and we can't wait to return.

  • Submitted: Aug 6, 2014
  • Stayed: July 2014
  • Source: VRBO, from HomeAway
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Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $1,000
Pet Fee $100
Tax Rate 9.0%

We are located on Peaks Island just off city of Portland. Travel to and from the island is by ferry service. Contact Casco Bay Lines (CBL), 207-774-7871 for details and their web site:

Refer to our Guest Agreement, as well as our cancellation policy, no refunds!

Owner's Cancellation Policy

  • 50% refund if canceled at least 7 days before arrival date.
  • 100% refund if canceled at least 14 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.