


Beam Reach
Set at the quiet end of a winding road along Pleasant Bay, this rare waterfront compound unfolds as a private Cape Cod retreat with two distinct homes and uninterrupted views across the water. Windward and Leeward sit gracefully on either side of a heated pool, offering both togetherness and separation for groups of up to fourteen. Just steps from the shoreline, mornings begin with soft light over the bay and evenings settle into a calm, coastal stillness that defines this tucked away setting. Windward has been thoughtfully reimagined with a fresh, elevated feel, featuring a new kitchen, refined furnishings, and expansive windows that draw in the surrounding landscape. Three bedrooms offer a mix of comfort and flexibility, including two serene suites and a tucked away bunk room ideal for families. Across the pool, Leeward adds depth to the experience with its own inviting living spaces, screened porch, and three additional bedrooms, including an upper level suite designed for shared stays. A lower level media lounge with kitchenette creates an easy space for relaxed evenings indoors. Life here naturally moves outdoors, where the heated pool, water views, and open sky set the tone for long, unhurried days. Gather for alfresco meals, unwind beside the fire table, or launch a kayak directly into the bay for a quiet afternoon on the water. With paddle boards, an outdoor shower, and every modern convenience thoughtfully included, this dual home retreat offers a timeless coastal escape designed for connection, privacy, and lasting memories.
Our promise
We've reviewed thousands of homes and approve only the best. Each one is professionally managed and vetted for comfort and style, raising the bar for every stay.
Amenities
Elevate your stay with add-on services
Book a home, then customize your experience. From beach gear delivery to pre-arrival groceries and private chefs, we coordinate everything you need so you can make memories in the waves and stories at sunset.
Bedroom details
Location
Inside the destination
Neighborhood: East Orleans - The pool, which has a gate around the outside for safety, is heated, so it’s a great option even in June or September (pool is heated from Memorial Day – Columbus Day). - 3.9 Miles from downtown Orleans - 7.1 Miles from downtown Chatham
We're here to help
Whether you have questions on this home or want us to source other options, we're a message away!
Policies
Cancellation policy
Plans change, we get it.
Enjoy peace of mind when booking with KEY.co.
75% Refund: Receive a 75% refund when you cancel your reservation at least 120 days before check-in.
No Refund: Reservations canceled 119 days or less before check-in are not eligible for a refund.
Refunds subject to a 5% processing fee of the total.
Things you need to know
All towels and bedding washed in hot water that's at least 60ºC.
High-touch surfaces cleaned with disinfectant.
Restrictions
- Minimum night stay requirements vary by home and time of year.
- We cannot guarantee that upon your arrival, you will find the property exactly as represented in the photos and descriptions provided at the time of booking. We must be held harmless for any misinformation, typographical errors, or changes made by the owner of which we have no knowledge.
- No refund if non-essential appliances and equipment – such as air conditioning, dishwasher, TV/Internet, or washer/dryer are not functioning properly.
- Refunds are not provided for noise or other annoyances such as construction when the source is another property not owned by the owner of the property you have rented.
- During peak hours at town beaches, parking stickers are required. Of course, most of our properties are directly on or within easy walking distance of private, neighborhood association beaches, so no pass is required. For those properties that aren’t right on or within walking distance a pass is necessary. You can stop by the town offices to pick up a weekly pass or pay per visit. Beach passes are issued by vehicle so are not transferable.
- No more than the listed number of persons, including infants, children and overnight visitors listed on the lease shall occupy said premises and shall not permit more than the listed number of vehicles on the lease to be parked in the spaces assigned to the premises at any time.
- No smoking, nor animals, birds, or pets of any description shall be allowed on the leased premises (unless otherwise noted on the lease). Violation of any of these policies will result in a $5,000 penalty charged to the account on file.
- Avoid wasting of water, heating fuel, electricity or other utilities provided.
- The premises (which includes outdoor spaces accessible by guests) shall not be used for functions such as weddings, wedding receptions, family reunions, or any other gathering involving more than the number of occupants specified in this lease agreement unless permission is obtained.
- Use of illegal materials such as fireworks at the property is prohibited.
- The property may be protected with outside security cameras (e.g., Ring doorbell). These cameras are used to protect the property from potential break-ins and theft. Any attempt at disabling, redirecting, or obscuring the cameras is prohibited and may result in lease cancellation. There are NO cameras activated inside the house.
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