Orleans, Massachusetts
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'.
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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.
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.
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.?
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.
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!
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!
Must concur with the rave reviews of others. Gentle Heritage estate is unique and magnificent. Gorgeous grounds in a prime Cape Cod location. Ginger and Ken could not have been any kinder in all of their communications and accommodations. Highly recommend this estate and you can rest assured that it will be a pleasant experience with the Winslows.
A superb venue; a persistent rain the first day couldn't dampen the great fun experienced by 6 couples while staying for a get-away at this magnificent property. The charming accommodations, fine food, many nearby leisure pursuits and breath taking vistas of the wild beauty of Cape Cod were only exceeded by the warmth & genuine hospitality of the Winslows.
I rented the Winslow Estate for my daughter's wedding. Renting from Wednesday to Wednesday gave us all time to get settled in and time to relax after the fact. As I stated above to call the estate spectacular is truly an understatement. Everything was as promised. Ken & Ginger were great to deal with. I would strongly recommend this property to anyone. A little piece of heaven on Cape Cod!
If you're looking for that special place to hold your wedding, look no further. Unlike a resort venue with packaged plans, at the Winslow Estate you can make your wedding your own. The owners, Ken and Ginger, are eager to help you pull the pieces together with suggestions and lists of auxiliary vendors. Don't be deterred by the idea of an afternoon wedding. Nothing was more romantic than the tent coming alive for dinner and dancing after enjoying mid afternoon cocktails and fantastic views of Pleasant Bay in the bright sunshine. Not to mention the brilliant sunset enjoyed by all the guests! There was plenty of room for the entire wedding party and spouses to stay at the estate and they enjoyed their own post-wedding hang time together in a very relaxed, fun space. The Winslow Estate is the perfect wedding venue!
My husband and I have stayed there for my birthday. We had a fantastic time! The owners ken and ginger are awesome and were very accommodating to our needs. We had a great time. We are planning on coming back here again next summer.
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Includes taxes and fees