Entire home
Waterfront. Private beach. Pool. Estate has it all!!
Family-friendly holiday home on the beach, with water park
Photo gallery for Waterfront. Private beach. Pool. Estate has it all!!





Reviews
10 out of 10
Exceptional
9 bedrooms5+ bathroomsSleeps 19
Popular amenities
Explore the area

- Place, Chatham Fish Pier
- Place, Ocean Edge Golf Club
- Place, Chatham Lighthouse
- Airport, Hyannis, MA (HYA-Barnstable Municipal)
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.
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.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
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House Rules
Check in after 3:00 PM
Minimum age to rent: 30
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Ask owner
Pets
No pets allowed
Ask owner
Smoking
Smoking is not permitted
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
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
Property Registration Number C0059852240
About the area
Orleans
Located in Orleans, this holiday home is on the beach. Jonathan Young Windmill and Edward Penniman House and Barn are local landmarks, and some of the area's attractions include Orleans Bowling Center and Chatham Marconi Maritime Center. Travelling with kids? Consider Adventure Chatham, or check out an event or a game at Veterans Field. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with hiking/biking trails and horse riding.

Orleans, MA
What's nearby
- Chatham Fish Pier - 13 min drive - 13.4 km
- Skaket Beach - 13 min drive - 9.5 km
- Ocean Edge Golf Club - 14 min drive - 10.3 km
- Harwich Port - 15 min drive - 14.1 km
- Chatham Lighthouse - 15 min drive - 14.4 km
Getting around
Restaurants
- Dunkin' - 11 min drive
- Three Fins Coffee House & Cacao Factory - 12 min drive
- Hog Island Beer Co. - 11 min drive
- The Barley Neck Inn - 11 min drive
- Pain D'avignon - 12 min drive
Frequently asked questions
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.
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.
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.
Languages:
English
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