Entire home

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

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

Photo gallery for Waterfront. Private beach. Pool. Estate has it all!!

Aerial of the property. A point of land into Pleasant Bay. Water all around.
Twilight at Gentle Heritage from the driveway
twilight from the water side
17 rooms ready for your vacation. Lots of parking
the lawn looking south east. Lots of room for games.

Overview of Waterfront. Private beach. Pool. Estate has it all!!

Reviews
10 out of 10 Exceptional
9 bedrooms5+ bathroomsSleeps 19

Popular amenities

  • PoolPoolPool
  • FireplaceFireplaceFireplace
  • WasherWasherWasher
  • DryerDryerDryer
  • KitchenKitchenKitchen
  • Barbecue grillBarbecue grillBarbecue grill

Explore the area

Map
Orleans, MA
  • Popular LocationNickerson State Park13 min drive
  • Popular LocationSkaket Beach14 min drive
  • Popular LocationOcean Edge Golf Club16 min drive
  • AirportHyannis, MA (HYA-Barnstable Municipal)31 min drive

Rooms & beds

9 bedrooms (sleeps 19)

Bedroom

1 Queen Bed

Bedroom

2 Twin Beds

Bedroom

2 Twin Beds

Bedroom

1 Queen Bed

Bedroom

2 Twin Beds

Bedroom

1 King Bed

Bedroom

2 Twin Beds

Bedroom

3 Twin 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
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.

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.



Property manager

Ken Winslow

Amenities

Pool
Kitchen
Washer
Dryer
Air conditioning
Outdoor Space

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
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

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
Note from host: ask owner
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property

About the neighborhood

Orleans

Located in Orleans, this vacation home is on the beach. The area's natural beauty can be seen at Cape Cod National Seashore and Cape Cod Beaches. Traveling with kids? Consider Orleans Bowling Center and Adventure Chatham. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with cycling and horse riding.
Map
Orleans, MA

What's nearby

  • Nickerson State Park - 13 min drive
  • Chatham Fish Pier - 13 min drive
  • Skaket Beach - 14 min drive
  • Ocean Edge Golf Club - 16 min drive
  • Nauset Beach - 33 min drive

Getting around

  • Hyannis Transportation Center - 31 min drive
  • Hyannis, MA (HYA-Barnstable Municipal) - 32 min drive

Restaurants

  • Chatham Pier Fish Market - 13 min drive
  • Mac's Chatham Fish & Lobster - 14 min drive
  • Dunkin' - 10 min drive
  • Chatham Perk - 11 min drive
  • Corner Store- Chatham - 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.

Is Waterfront. Private beach. Pool. Estate has it all!! pet-friendly?

No, pets are not allowed at this 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!!?

Check-out is at 10:00 AM.

Where is Waterfront. Private beach. Pool. Estate has it all!! located?

Nestled on the beach, this Orleans vacation home is within 3 mi (5 km) of Cape Cod Beaches, Captain's Cove Golf Course, and Captains Golf Course. Nickerson State Park and Cape Cod National Seashore are also within 3 mi (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 33 out of 33 reviews" "
Rating 8 - Good. 0 out of 33 reviews" "
Rating 6 - Okay. 0 out of 33 reviews" "
Rating 4 - Poor. 0 out of 33 reviews" "
Rating 2 - Terrible. 0 out of 33 reviews" "

9.4/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Angelique C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect in every way!
The Winslow estate was the perfect spot for our family vacation. Three generations enjoyed every aspect of the property. Ken and Ginger were a pleasure to work with.
Stayed 7 nights in Jul 2022

10/10 Excellent

Laura K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect getaway in the year of Covid!
This property is just as stunning and beautiful as the pictures show. We were at maximum capacity with 19 people (4 families) and we never once felt crowded or that we didn’t have enough room. Amazing. Loved the historic nature of the house that’s over 100 years old but that also included modern updates where it mattered the most (bathrooms, beautiful new pool). With Covid we barely left the property but you didn’t have to!!! Such a fun and relaxing week. We felt like we were the Kennedys on the compound for a week! Ken and Ginger were very responsive to any questions or issues. Highly recommend.👍
Stayed 7 nights in Aug 2020

10/10 Excellent

Jack C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
About as good as it gets for large families
We were looking for a place that could accommodate our extended family and friend’s reunion on Cape Cod. Ken and Ginger’s historic home overlooking Pleasant Bay was exactly what we were looking for. The house absorbed the comings and goings of 25 guests over the two week stay. The location was breathtaking, the house met our needs and Ken and Ginger couldn’t have been more accommodating. Nothing is perfect. The house is a bit funky and looks more like a Bermuda cottage resort than Cape Cod, but it’s clean, well equipped, beautifully situated and everyone thoroughly enjoyed being there. If I could change anything it would be to add another bathroom or two. Nine bedrooms and 5 bathrooms require some flexibility, but we made it work. We recommend it highly to anyone planning an important family event.
Stayed 14 nights in Aug 2019

10/10 Excellent

Ayaz M.

Fantastic Property!
Our Bookclub of 6 couples stayed at Ken and Ginger's home this past weekend. We found the homeowners to be a pleasure to work with and each one of us had a great time. The home is well appointed with plenty of space and a fantastic water view with many areas to gather or find space if you need to. The kitchen and dining room easily held all of us. The pool table and dart board were a nice bonus!
Stayed 2 nights in Nov 2018

10/10 Excellent

Doug M.

Incredible Location & Home!!
We brought the entire extended family to celebrate our parents' 50th wedding anniversary and we could not have been happier with Gentle Heritage. The home is enormous, giving everyone the space they needed and also the common areas to all meet up for meals, chatting or just enjoying the incredible views of Pleasant Bay. The house is up to date, charming and we could not have asked for a better location. The Winslows were very attentive to our needs and made for very gracious hosts. We ranged in ages from 5 to 75 and the home worked for all of us. The private beach was so great for days we didn't want to leave the compound...and we found that we really didn't need to as we had everything we needed at the house. We were all very sad to leave, but plans to return are already in the works! Thanks again to the Winslows for sharing their amazing home with us. A trip to remember!
Stayed 6 nights in Aug 2018

About the host

Hosted by Ken Winslow

Host profile image

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.
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