House in Osterville, MA

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

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

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

Sunset view from main house patio. Perfect for outdoor dinners and entertaining
View of main residence from the south
Main residence from path down to boathouse and beach
Front lawn with tennis court in background
Thanksgiving hot tub!

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

Reviews
10 out of 10 Exceptional
8 bedrooms7+ bathroomsSleeps 20743 sq m

Popular amenities

  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly
  • Air conditioning

Check out the area

Osterville, MA
  • Popular LocationCraigville Beach12 min drive
  • Popular LocationCape Cod Melody Tent13 min drive
  • Popular LocationCape Codder Water Park13 min drive
  • AirportHyannis, MA (HYA-Barnstable Municipal)20 min drive

Rooms & beds

8 bedrooms (sleeps 20)

Bedroom 1- Main house

Bedroom 2 - Main House

Bedroom 3 - Main House

Bedroom 4 - Main House

Bedroom 5 - Main house

Bedroom 6 - Boathouse

Bedroom 7 - Boathouse

Bedroom 8 - Boathouse

7 bathrooms, 1 half bathroom

Bathroom 1 - Main house master

Bathtub · Toilet · Shower only

Bathroom 2 - Main house

Toilet · Shower only

Bathroom 3 - Main house

Toilet · Shower only

Bathroom 4 - Main house

Toilet · Shower only

Bathroom 5 - Main house

Toilet · Shower only

Bathroom 6 - Main house

Toilet

Bathroom 7 - Boathouse

Bathtub · Toilet · Shower only · Jetted bathtub

Bathroom 8 - Boathouse

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Garden

About this property

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

Anchor to Windward has 8 bedrooms and 7.5 baths: a main house with 5 bedrooms and 5.5 baths and a boathouse directly on a private beach with 3 bedrooms and 2 baths. (During Winter rental months, the boathouse is closed up). The property is located on West Bay in Osterville, MA and has a deep water dock, dock slide, outdoor 7 person, seasonally operated 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 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!

Property manager

Long Ellis

Amenities

Hot tub
Kitchen
Washer
Dryer
Pet-friendly
Air conditioning

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM

Children

Children allowed: ages 0-17

Events

No events allowed

Pets

Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total)

Smoking

Smoking is not permitted
No parties with outside people, no tents, no caterers, no bands, no bar tenders and no weddings

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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
Onsite parties or group events are strictly prohibited
Safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit

We should mention

A car is required for transportation to and from this property

About the area

Osterville

Located in Osterville, this vacation home is on the beach. Hyannis Harbor and Barnstable Superior Courthouse are local landmarks, and some of the area's activities can be experienced at Olde Barnstable Fairgrounds Golf Course and Twin Brooks Golf Course. Traveling with kids? Consider Stand Up & Paddle Cape Cod and Cape Codder Water Park. Be sure to check out the area's animals with activities such as game walks and birdwatching.

What's nearby

  • Stand Up & Paddle Cape Cod - 19 min walk
  • Craigville Beach - 12 min drive
  • Cape Cod Melody Tent - 13 min drive
  • Cape Codder Water Park - 13 min drive
  • Hyannis Harbor - 15 min drive

Getting around

  • Hyannis Transportation Center - 19 min drive
  • Hyannis, MA (HYA-Barnstable Municipal) - 20 min drive

Restaurants

  • Dunkin' - 8 min drive
  • Dunkin' - 11 min drive
  • Osterville Fish Market - 6 min drive
  • Honey Dew Donuts - 11 min drive
  • Lambert's Fruit Co. - 10 min drive

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 3 out of 3 reviews" "
Rating 8 - Good. 0 out of 3 reviews" "
Rating 6 - Okay. 0 out of 3 reviews" "
Rating 4 - Poor. 0 out of 3 reviews" "
Rating 2 - Terrible. 0 out of 3 reviews" "

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Conor L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great experience
Great
Stayed 3 nights in Nov 2021
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Mike M.

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.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

John C.

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.

About the host

Hosted by Long Ellis

Host profile image
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.

Why they chose this property

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 property 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.
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