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Unbeatable location, views and water access from this rare family compound

Bedrooms 8
Half Baths1
Space 8,000 sq ft
Property type estate


About the property

Spectacular sunset and water views from this beach front, 8 bedroom, 2 house

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!

Long Ellis
Member since: 2014
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
September 17, 2018

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.


Osterville Estate Accommodation and Amenities

Property Type:
  • estate
  • Guests provide their own meals
Floor Area:
  • 8000 sq ft
House Rules:
  • Max. occupancy: 20
  • Minimum Age Limit for Renters ...
  • pets considered
  • non smoking only
Location Type:
  • Beach View ...
  • Beachfront ...
  • Village ...
  • Water View ...
  • Waterfront ...
  • Air Conditioning ...
  • Clothes Dryer ...
  • Fireplace ...
  • Garage ...
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Telephone ...
  • Towels Provided
  • Washing Machine ...
  • Coffee Maker
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Microwave
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Room
  • seating for 10 people
  • 7 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - Main house master - toilet , tub , shower , Steam shower - double sinks - private toilet room
    Bathroom 2 - Main house - toilet , shower
    Bathroom 3 - Main house - toilet , shower
    Bathroom 4 - Main house - toilet , shower , Water view
    Bathroom 5 - Main house - toilet , shower , Third floor
    Bathroom 6 - Main house - toilet , First floor off kitchen/family room
    Bathroom 7 - Boat house master - toilet , shower , jetted tub , Double sinks, separate shower and tub, private toilet room
    Bathroom 8 - Boat house - toilet , combination tub/shower , Double sinks, private toilet room
    Bathroom 9 - Boat house - outdoor shower - outdoor shower , Outdoor shower on beach level
  • 8 Bedrooms, Sleeps 20
  • Bedroom 2 - Main House - 1 queen , Water views - Private bath
    Bedroom 1- Main house - 1 king , Water views with large private bathroom and dressing room
    Bedroom 3 - Main House - 2 twin/ single , Water views - private bath
    Bedroom 4 - Main House - 1 king , Water views - private bath
    Bedroom 5 - Main house - 1 queen , Third floor - private bath, separate landing with pull out
    Bedroom 6 - Boat House Master - 1 king , Water views - private bath
    Bedroom 7 - Boat house - 1 queen , 2 bunk bed , Water views, shares bathroom in hallway
    Bedroom 8 - Boat house - 1 queen , 2 bunk bed , Water view, shares bathroom in hallway
  • Books
  • DVD Player
  • Game Room ...
  • Games ...
  • Pool Table ...
  • Satellite / Cable ...
  • Stereo
  • Television ...
  • Toys
  • Deck / Patio ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Tennis ...
  • Long-term Renters Welcome
Pool / Spa:
  • Hot Tub ...
  • churches
  • cinemas
  • health/beauty spa
  • library
  • marina
  • museums
  • playground
  • restaurants
  • synagogues
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • horseback riding
  • miniature golf
  • paddle boating
  • photography
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • kayaking
  • pier fishing
  • racquetball
  • sailing
  • sound/bay fishing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing


5/5 -
(2 traveler reviews)

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Unbeatable location, views and water access from this rare family compound
average rating of 5.0 based on 2 reviews

Classic Cape Compound

  • 5 of 5

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.

  • Submitted: Sep 30, 2016
  • Stayed: September 2016
  • Source: VRBO, from HomeAway
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Beautiful Home, Beautiful Setting

  • 5 of 5

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.

  • Submitted: Mar 1, 2016
  • Stayed: September 2015
  • Source: VRBO, from HomeAway
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Nearest Airport
8 Miles
Barnstable Municipal Airport
Nearest Ferry
8 Miles
Hyannis, MA
Nearest Train
8 Miles
Hyannis. MA
Nearest Motorway
6 Miles
Route 6, mid Cape highway
Nearest Beach
House has own private beach
Car: necessary

There are numerous public golf courses, charter fishing, kayak and paddle board rentals. Whale watching trips out of Barstable Harbor.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Weekly cleaning fee $550
Pet Fee $100
Property Damage Protection $59
Refundable damage deposit $1,500

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.

Owner's Cancellation Policy

100% refund if canceled at least 30 days before arrival date.

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