Anchor to Windward consists of a main house with 5 bedrooms and 5.5 baths and a boathouse directly on a private beach with 3 bedrooms and 2 baths. The property is located on West Bay in Osterville, MA and has a deep water dock, dock slide, outdoor 7 person hot tub/spa on elevated deck with sunset views. Boat House has its own kitchen/family room and a garage/room that can be used for small gatherings. ATW has a tennis court, bay swimming, perfect water for paddle boarding or kayaking. A/C throughout, updated high end kitchen with wet bar, ice machine and wine cooler. Full size billiard table in family room off main house kitchen. Short bike ride (1 mile) into Osterville for shopping, groceries, coffee shops and 15 minutes from Hyannis, the largest town on Cape Cod and where the island ferry service can take you to Nantucket or Martha's Vineyard. Nothing is missing from this gorgeous and perfectly located summer home!
Spectacular sunset and water views from this beach front, 8 bedroom, 2 house
- Calendar last updated:
- Jan 19, 2019
About Long Ellis
We are originally from CA, but are currently spread out all over the states. We have had family reunions at Anchor to Windward for many years and could not think of a better place to locate during the summers.
Long Ellis purchased this Estate in 1957
Why Long Ellis chose Osterville
Anchor to Windward is located in the town of Osterville, which is one of the most attractive towns on Cape Cod for both its natural beauty and the wonderful families that summer here.
What makes this Estate unique
We are blessed with an ideal location that has a private beach, a deep water dock, a main house and boat house. The set up offers a lot of flexibility in terms of handling different size families and guests. Our location has one of the best sunset views in Barstable County from a bluff overlooking the waters of West Bay. You can watch the sail boats race out of the Wianno Yacht Club or get out on the water yourself. Heaven for anyone who enjoys coastal living and wants both privacy and direct water access.
Pool / Spa
Check-in: 4:00 PM
Check-out: 11:00 AM
Canceled bookings will not receive a refund
Classic Cape Compound
Our party consisted of 6 couples in town for a wedding at a nearby club. The property exceeded our expectations with plenty of room, activities and character. This property is in a perfect and private setting with beautiful sunsets and plenty of space to spend outdoors. Our group gravitated to the main house for meals and wandered down to the boat house for a cocktail for the evenings. The guests stayed busy by playing tennis, beach volleyball, billiards, using the hot tub and of course going down the slide! This is a precious home that has been well cared for and is a classic cape experience.
Beautiful Home, Beautiful Setting
This house is huge and beautiful. We arrived with 16 members over three generations of our family. The house and property were immaculate. The 16 of us were accommodated comfortably between the house and boathouse. The house is beautifully furnished. There are 2 large eating areas, the formal dining room, and a nice sized breakfast room off a large modern, fully equipped kitchen. A large laundry room also houses an extra refrigerator. Off the comfortable living room is a less formal sunroom, ideal for morning coffee and evening cocktails, overlooking the outdoor terrace and the sailboats in the bay. The whole house is suffused with light and the gentle breeze off the water giving the place a cool comfort on the warmest of days. Upstairs, all bedrooms look out on the water. A casual and inviting boathouse is perfect for sunset cocktails while the kids play on the dock and beach. And most memorable are those sunsets over the bay.
There are numerous public golf courses, charter fishing, kayak and paddle board rentals. Whale watching trips out of Barstable Harbor.
Additional information about rental rates
Our payment schedules are different from the VRBO listing. The damage deposit is $550, but can be higher depending on whether there are pets/dogs. We require an initial, non-refundable deposit of $1,500 for 4 nights or less and $3,500 for 5 nights or more. This deposit is required within 7 days and is non-refundable. The remainder of the rental fees are due in two equal installments, with a separate check for the damage deposit included with the last payment. Refunds on all payments, excluding the initial deposit which is non-refundable, are only refundable 60 days before the check-in date.