Entire home
Waterfront. Private beach. Pool. Estate has it all!!
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

Orleans, MA
- Place, Cape Cod Beaches6 min walk
- Place, Mayflower Beach28 min drive
- Place, Hyannis Harbor29 min drive
- Airport, Hyannis, MA (HYA-Barnstable Municipal)29 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.
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.
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9.8 out of 10, Exceptional, (40 reviews)
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 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. Orleans Bowling Center and Cape Escape Adventure Golf are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with cycling and mountain biking.

Orleans, MA
What's nearby
- Cape Cod Beaches - 6 min walk - 0.5 km
- Chatham Lighthouse - 15 min drive - 14.4 km
- Cape Cod National Seashore - 16 min drive - 14.7 km
- Mayflower Beach - 28 min drive - 31.1 km
- Hyannis Harbor - 29 min drive - 36.2 km
Getting around
Restaurants
- Dunkin' - 11 min drive
- Hog Island Beer Co. - 11 min drive
- Three Fins Coffee House & Cacao Factory - 12 min drive
- Corner Store - 11 min drive
- 400 East - 11 min drive
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window8.0/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
9.2/10
Listing accuracy
Reviews
11 July 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Jul 2022
10/10 Excellent
Korey R.
16 Aug 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Own Beach & Pool
Korey R.
Stayed 7 nights in Aug 2024
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Amy & Roger P.
31 Aug 2016
Gorgeous Views on the Water for peace on The Cape
Amy & Roger P.
6/10 Okay
Karen R.
4 Sept 2025
Liked: Check-in, communication, location
Disliked: Cleanliness
Karen R.
Stayed 7 nights in Aug 2025
10/10 Excellent
Laura K.
25 Aug 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect getaway in the year of Covid!
Laura K.
Stayed 7 nights in Aug 2020
10/10 Excellent
Jack C.
27 Aug 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
About as good as it gets for large families
Jack C.
Stayed 14 nights in Aug 2019
10/10 Excellent
Ayaz M.
7 Nov 2018
Fantastic Property!
Ayaz M.
Stayed 2 nights in Nov 2018
10/10 Excellent
Doug M.
9 Sept 2018
Incredible Location & Home!!
Doug M.
Stayed 6 nights in Aug 2018
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Christopher C., New York
28 Nov 2017
Outstanding property and owners
Christopher C.
Stayed 3 nights in Nov 2017
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Matthew C.
9 May 2017
An epic landscape bedecked by a unique jewel
Matthew C.
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Robert K.
20 Oct 2016
To call it spectacular doesn't even do it justice!
Robert K.
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Susan F.
19 Oct 2016
Perfect venue to have a personalized wedding
Susan F.
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Farrah r.
1 Sept 2016
Exquisite, Fascinating!!
Farrah r.
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Tobin S.
4 Aug 2016
Absolutely picturesque
Tobin S.
This review was submitted before 2018 and can't be verified.
10/10 Excellent
John H., Natick MA 01760
12 July 2016
A Beautiful Place!
John H.
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Kayla R.
21 June 2016
Breathtaking, one of a kind home
Kayla R.
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Kristina P., Santa Barbara
13 June 2016
Gorgeous views, spacious home, a MUST stay!
Kristina P.
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Kerry C.
31 Oct 2015
Unique, special and excellent wedding venue!!
Kerry C.
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Loet V.
8 Aug 2015
A wonderful family holiday at Gentle Heritage
Loet V.
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Anne S.
29 May 2015
The perfect spot for a group getaway or retreat!
Anne S.
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Denise G.
28 Oct 2014
The Winslow Estate was the perfect venue !
Denise G.
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10/10 Excellent
27 Oct 2014
Spectcular Property
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Laura O.
9 Oct 2014
Unforgettable Wedding Location!
Laura O.
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Kate M.
1 Oct 2014
Amazing week
Kate M.
This review was submitted before 2018 and can't be verified.
10/10 Excellent
Daria M.
8 Aug 2014
Absolutely BEAUTIFUL!!
Daria M.
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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