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Waterfront Estate Private Beach

Orleans, MA, USA
  • Estate
  • Bedrooms9
  • Sleeps19
  • Bathrooms5
  • Half Baths1
  • Minimum Stay2 - 7 nights

9 bedrooms, 5 1/2 baths, sleeps 19,

Chosen by Cape Cod Life magazine as one of the Top Ten places to stay on Cape Cod, our waterfront estate has breathtaking views of over 180' 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 and features a deck to sit on.The Bay has a gradual sandy bottom, warm water great for swimming, floating on rafts, paddle boarding, sailing, kayaking, and walking along the shore. There are 3 acres of open lawn, 17 rms, 9 bedrms, 5 1/2 baths plus an enclosed outdoor shower with dressing room. All of the bedrooms plus the dining room and family room are air conditioned. The 2001 kitchen features a 48' Sub-zero refrigerator, Corian counters, plus the estate includes the former servants wing with a 2nd fully equipped kitchen. There is lots of room for everyone to spread out with three living rooms, game room with pool table and darts, private deck on the beach, and mooring for your boat.

The estate is on one of the highest points on Pleasant Bay offering magnificent views. You walk down a bluff to the waterfront below. There is a large crescent shaped beach at low tide. This gets covered as the tide comes in and a deck is on the waterfront to enjoy at high tide.

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 twins 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 included. No cleaning fee or taxes or hidden fees. Available by the week only from early June to late Sept. Weekends considered in April and May and October and November. June and Sept are popular for important family gatherings by the week. WIFI. See a floor plan at our web site winslowestates.com.


Ken Winslow

Member Since 2004
Response rate:
Response time:
within one day
Calendar last updated:
Dec 15, 2017


    • Internet
    • Air Conditioning
    • Accessible
    • Heater
    • Fireplace
    • Satellite or Cable
    • Kids Welcome
    • Washer & Dryer
    • TV
    • No Smoking


      • 9 Bedrooms, Sleeps 19
      • Bedroom
        2 twin/ single
      • Bedroom
        1 king
      • Bedroom
        1 queen
      • Bedroom
        1 queen
      • Bedroom
        2 twin/ single
      • Bedroom
        3 twin/ single
      • Bedroom
        2 twin/ single
      • Bedroom
        2 twin/ single
      • Bedroom
        1 queen
      • 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 twins beds or queens. The master bedroom has a king bed. Each bedroom sleeps two guests except for one extra large one that has a set of three twin beds. Two wings of the house plus the two second floor bedrooms have central air. All bedrms have A/C as well as the dining room and family room. Please see our web site for a floor plan and room sizes.


      • 5 Bathrooms, 1 Half Bath
      • Bathroom
        toilet, combination tub/shower
      • Bathroom
        toilet, combination tub/shower
      • Bathroom
        toilet, combination tub/shower
      • Bathroom
        toilet, shower
      • Bathroom
        toilet, shower
      • Bathroom
      • Bathroom 7
        outdoor shower, enclosed
      • There is a fully enclosed outdoor shower with hot and cold water plus a dressing room.

      Location Type

        • Beach
        • Waterfront


            • Family


                • Guests provide their own meals


                    • Laundry Soap
                    • Air Conditioning
                    • Basic Soaps
                    • Clothes Dryer
                    • Filtered Water
                    • Fireplace
                    • Hair Dryer
                    • Heating
                    • Internet
                    • Iron & Board
                    • Alarm Clock
                    • Linens Provided
                    • Local Activities Guide
                    • Local Maps
                    • Local Restaurant Guide
                    • Paper Towels
                    • Shampoo
                    • Telephone
                    • Toilet Paper
                    • Washing Machine
                    • Wireless Internet


                        • Lobster Pot
                        • Blender
                        • Cooking Utensils
                        • Dishwasher
                        • Freezer
                        • Ice Maker
                        • Coffee Maker
                        • Microwave
                        • Oven
                        • Pantry Items
                        • Refrigerator
                        • Stove
                        • Toaster


                            • Dining Area


                                • Music Library
                                • Audio Tape Player
                                • Books for Adults
                                • Books for Kids
                                • CD Player
                                • DVD Player
                                • Game Room
                                • Games
                                • Games for Kids
                                • Books
                                • Pool Table
                                • Radio
                                • Satellite / Cable
                                • Stereo
                                • Television
                                • Toys
                                • VCR
                                • Video Games
                                • Video Library


                                    • Barbecue
                                    • Beach Chairs
                                    • Beach Towels
                                    • Binoculars
                                    • Large Cooler
                                    • Outdoor Grill
                                    • Outdoor Grill Gas
                                    • Patio
                                    • Small Cooler
                                    • Terrace


                                        • suitable for elderly or infirm
                                        • wheelchair accessible


                                            • marina
                                            • autumn foliage
                                            • churches
                                            • cinemas
                                            • forests
                                            • library
                                            • live theater
                                            • bay/sound
                                            • museums
                                            • playground
                                            • pond
                                            • recreation center
                                            • restaurants
                                            • water parks

                                              Leisure Activities

                                                • antiquing
                                                • beachcombing
                                                • bird watching
                                                • horseback riding
                                                • scenic drives
                                                • sight seeing
                                                • walking
                                                • whale watching

                                                  Local Services & Businesses

                                                    • ATM/bank
                                                    • Babysitter
                                                    • fitness center
                                                    • groceries
                                                    • hospital
                                                    • laundromat
                                                    • massage therapist
                                                    • medical services

                                                      Sports & Adventure Activities

                                                        • pier fishing
                                                        • cycling
                                                        • equestrian events
                                                        • fishing
                                                        • fly fishing
                                                        • freshwater fishing
                                                        • golf
                                                        • golf privileges optional
                                                        • hiking
                                                        • jet skiing
                                                        • mountain biking
                                                        • paragliding
                                                        • deepsea fishing
                                                        • roller blading
                                                        • sailing
                                                        • scuba diving or snorkeling
                                                        • snorkeling
                                                        • sound/bay fishing
                                                        • surf fishing
                                                        • surfing
                                                        • swimming
                                                        • tennis
                                                        • water skiing
                                                        • water tubing
                                                        • wind-surfing


                                                            • 1 king, 3 queens, 11 twins, 5 1/2 bathrooms plus a fully enclosed outdoor shower with hot and cold water and a dressing room. Please see our web site for a floor plan with room sizes. All of the bedrooms have A/C and several of the common areas do as well.

                                                              30 Reviews


                                                              Latest reviews

                                                              Outstanding property and owners

                                                              Christopher C.New York

                                                              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.

                                                              An epic landscape bedecked by a unique jewel

                                                              Matthew C.

                                                              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.

                                                              To call it spectacular doesn't even do it justice!

                                                              Robert K.

                                                              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!

                                                              Perfect venue to have a personalized wedding

                                                              Susan F.

                                                              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!

                                                              Exquisite, Fascinating!!

                                                              Farrah r.

                                                              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.

                                                              Gorgeous Views on the Water for peace on The Cape

                                                              Amy & Roger-

                                                              Three generations of our family spent a lovely week at the Gentle Heritage in late August. The views are spectacular of the water and surrounding land, and has a nicely-manicured lawn on which to play games while surrounded by the beauty. We could walk down the hill to enjoy a little seating area just above a small beach to launch our kayak. The home is cool in its long extended layout which reminds us of its history, with 2 kitchens and a joined wing that has its own suite and glassed in porch, tv room and dining are. Favorite spots to hang out were in the billiard room, another large screened porch overlooking the water off the Master bedroom and the main living room with it's high ceiling and architectural beams. We also enjoyed an outdoor dining patio and lounge chairs on the lawn to gaze at the stars. The property has a good number of bedrooms and bathrooms to be used by the 12 in our group. The owners also provided information for a local chef who prepared a glorious meal at the home for us...highly recommended. Definitely worth a stay for relaxation and a great spot on The Cape!


                                                              Orleans, MA, USA

                                                              The estate is in South Orleans equal distance between Chatham and Orleans. Chatham's beatiful Main Sreet is noted for its quaint Cape Cod feeling and variety of shops including restaurants, antiques, clothing, and surf shops. Pleasant Bay is excellent for swimming, sailing, fishing, wind surfing, kayaking, motor boating (your own or rent one) water skiing, or just walking the shoreline. The estate comes with a mooring and a skiff and oars. Nauset Beach in Orleans has big waves for body surfing, boogie or skim boarding, surfboarding and surf casting for bluesfish and bass. Skaket Beach in Orleans is noted for the warm salt water flats, sand bars, clamming, and is always a favorite for children. You can walk seemingly forever into Cape Cod Bay when the tide is out or just swim sand bar to sand bar when it is in.

                                                              Rates & Availability

                                                              Additional information about rental rates

                                                              15000-21000 Linens - bath towel sets as well as beach towels - and cleaning fees are included in weekly rental rate. Group gatherings, family reunion, birthday parties, etc. constitute additional use of the property and there will be increased charges.Rental fees are for the stated occupancy of the house only. Our refund policy - we will return all payments upon our ability to rerent the property for the same time period for the same rate.

                                                              30 Reviews
                                                              Exceptional 5/5
                                                              Enter dates for accurate pricing
                                                              For booking assistance, call 888-640-7927

                                                              Property # 105234