Enjoy spacious layout that give everyone more room to relax.
On the beach
A rare beachfront property in the area - enjoy direct access to the sand and sea.
Unmatched views, unforgettable moments
Guests like the location for the scenic views.
Discover nearby landmarks
Near Cape Cod Beaches
9 bedrooms5+ bathroomsSleeps 19
Popular amenities
On beach
Private pool
Onsite parking available
Kitchen
Washing machine
Air-conditioning
Explore the area
Orleans, MA
Cape Cod Beaches
Place, Cape Cod Beaches
6 min walk
Nauset Beach
Place, Nauset Beach
16 min drive
Mayflower Beach
Place, Mayflower Beach
38 min drive
Hyannis, MA (HYA-Barnstable Municipal)
Airport, Hyannis, MA (HYA-Barnstable Municipal)
38 min drive
Rooms & beds
9 bedrooms (sleeps 19)
Bedroom
1 Queen Bed
Bedroom
2 Single Beds
Bedroom
2 Single Beds
Bedroom
1 Queen Bed
Bedroom
2 Single Beds
Bedroom
1 King Bed
Bedroom
2 Single Beds
Bedroom
3 Single Beds
Bedroom
1 Queen Bed
5 bathrooms, 1 half bathroom
Bathroom
Bathtub or shower · Toilet
Bathroom
Toilet · Shower only
Bathroom
Bathtub or shower · Toilet
Bathroom
Toilet · Shower only
Bathroom
Toilet
Bathroom
Bathtub or shower · Toilet
Bathroom 7
Outdoor shower
Spaces
Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Garden
Dining area
About this property
Waterfront. Private beach. Pool. Estate has it all!!
Chosen by Cape Cod Life magazine as one of the Top Ten places to stay on Cape Cod. Our waterfront estate now has a gorgeous heated pool plus breathtaking views of over 180 ' plus of Pleasant Bay and 300' of your own PRIVATE waterfront. Plus you are directly on the water, not across the street or down the lane. This very special property is a landmark to the area and owned by the same family since it was built on the shores of Pleasant Bay 100 years ago. It had been lovingly cared for and maintained and matches the grandeur of times past with modern amenities. It is an ideal environment for multi generational family members to vacation together - or old or new friends with lots of room to spread out, enjoy each others company, yet find privacy and peace.
Down the end of an old cape cod road, then down the end of a private seashell driveway, there are no streets, traffic, or even pedestrians nearby. Pleasant Bay is reached by a pathway down the bluff in front of the house. Although the sandy beach disappears during a high tide, there is a deck to sit on until the beach reappears. The Bay has a gradual sandy bottom, warm water great for swimming, floating on rafts, paddle boarding, sailing, kayaking, and walking along the shore. The new heated pool and deck area are sun filled and full of fun for all ages. There is a gas barbecue grill, seating for your family group, lounge chairs - everything you need for fun. The pool is open and heated from mid June until Labor Day.
There are 3 acres of open lawn, 17 rms, 9 bedrms, 5 1/2 baths plus an enclosed outdoor showe. All of the bedrooms plus the dining room and family room are air conditioned. The kitchen features a 48' refrigerator, Corian counters, plus the estate includes a 2nd fully equipped kitchen. There is lots of room for everyone to spread out with three living rooms, game room with pool table, private deck on the beach and the pool and pool terrace. .The pool is 16.5' by 39'. . The nine bedrooms are really nine bedrooms - not common rooms that become bedrooms at night with pull out sofas. There are no sofa beds, futons, trundle beds, bunk beds or cots. Everyone has a personal and private space. All of the bedrooms have twin beds or queens. The master bedroom has a king bed. Each bedroom sleeps two guests except for one extra large bedroom that has three twin beds. The 2 lofts have privacy walls and doors are accessed by staircases - on the west end thru the triple bedrm and on the east end thru the primary bedrm. Beach, bed and bath linens are included for weekly rentals. Weekenders please plan to bring your own or use one of the local linen services. The cleaning fee is included for weekly rentals. Available by the week only from early June to late Sept. Please do not ask us about one or two night stays. The minimum is three nights and only occasionally in May or October. See a floor plan at our web site winslowestates.com.
Summer rentals are Friday to Friday so you can avoid all the headaches of the more typical Saturday with hours of backed up traffic. Great to include family and friends who otherwise could not enjoy a weekend with you.
Cancellation Policy - all payments returned upon ability to re-rent the same time period for the same amount.
Our prices include all fees. No hidden fees.
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All monies returned upon ability to re- rent the same time period for the same amount of rent
Check in and check out times may change in off season
Important information
You need to know
Property Registration Number C0059852240
Property # 105234
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
On-site parties or group events are strictly prohibited
Note from host: ask owner
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Orleans
Located in South Orleans, a neighbourhood in Orleans, this holiday home is near a water park and on the beach. The area's natural beauty can be seen at Cape Cod Beaches and Cape Cod National Seashore. Cape Escape Adventure Golf and Adventure Chatham are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with mountain biking and hiking/biking trails.
Cape Cod National Seashore - 21 min drive - 15.4 km
Mayflower Beach - 38 min drive - 35.2 km
Getting around
Hyannis Transportation Center - 31 min drive
Hyannis, MA (HYA-Barnstable Municipal) - 38 min drive
Restaurants
Cumberland Farms - 13 min drive
Hog Island Beer Co. - 11 min drive
Dunkin' - 10 min drive
Dunkin' - 14 min drive
Dunkin' - 11 min drive
Frequently asked questions
Does Waterfront. Private beach. Pool. Estate has it all!! have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at Waterfront. Private beach. Pool. Estate has it all!!?
As of 19 Aug 2026, prices found for a 1-night stay for 2 adults at Waterfront. Private beach. Pool. Estate has it all!! on 1 Nov 2026 start from £7,080, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Waterfront. Private beach. Pool. Estate has it all!! pet-friendly?
No, pets are not allowed at this property.
How much is parking at Waterfront. Private beach. Pool. Estate has it all!!?
On-site parking is available at the property.
What time is check-in at Waterfront. Private beach. Pool. Estate has it all!!?
Check-in begins at 3:00 PM.
What time is check-out at Waterfront. Private beach. Pool. Estate has it all!!?
Checkout is at 10:00 AM.
Where is Waterfront. Private beach. Pool. Estate has it all!! located?
Nestled on the beach, this South Orleans holiday home is within 3 mi (5 km) of Cape Cod Beaches, Captains Golf Course and Nickerson State Park. Pilgrim Lake is 2.7 mi (4.4 km) away.
About the host
Hosted by Ken Winslow
Why they chose this property
Cancellation Policy - all payments returned upon our ability to re-rent the property for the same time period for the same amount.
Rental period in the summer is Friday to Friday to allow you to have friends and family visit for a FULL weekend. It also skips all the terrible traffic tie ups on Saturday and Sunday.
Special family celebrations are allowed before mid June and after Labor Day for a one week rental. Special pricing applies.
This historic property has been in the same family since it was built 100 years ago. Lovingly updated throughout the years, you are sure to have a wonderful time.
What makes this property unique
Cancellation Policy - all payments returned upon our ability to re-rent the property for the same time period for the same amount.
Rental period in the summer is Friday to Friday to allow you to have friends and family visit for a FULL weekend. It also skips all the terrible traffic tie ups on Saturday and Sunday.
Special family celebrations are allowed before mid June and after Labor Day for a one week rental. Special pricing applies.