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Stunning Waterfront Estate on Chesapeake with Private Guesthouse at end of Pier

Pasadena, MD, USA
  • Estate
  • Bedrooms4
  • Sleeps14
  • Bathrooms3
  • Half Baths2
  • Minimum Stay2 - 4 nights

Enjoy this spectacular one-of-a-kind property on the Chesapeake Bay. This secluded home offers the best of outdoor living as you experience large grassy yards, big trees, your own beach, outdoor hot tub, and stunning views. The home features a gourmet kitchen, stone fireplace, beautiful master suite, and an old fashioned covered porch. The property includes a one-of-a-kind guest house which sits at the end of one of the longest private piers on the Chesapeake Bay - fully equipped with kitchen, bathroom and living room with sleeping sofa. Bring your fishing gear or just a glass of wine-- views are magnificent! You can literally sleep on the bay with the wind and the water luring you to sleep. The waterfront estate property is situated amidst 85 acres of woods and horse farm, adjacent to a 245-acre park (Downs Park) with miles of paved bike paths and nature trails (we have for bikes to offer). We are located 25 minutes from Annapolis, Baltimore inner harbor and BWI airport - and just 45 minutes from Washington D.C.

FUN FACT: Historic records show that our property was owned in colonial times by Charles Carroll of Carrollton, who served as a delegate to the Continental Congress and was the longest-lived (and last surviving) signatory of the Declaration of Independence.


Elaine Little, owner

Member Since 2017
Premier Partner
This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.
Response rate:
Response time:
within two days
Calendar last updated:
Apr 09, 2018


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


      • 4 Bedrooms, Sleeps 14
      • Bedroom 1- Master Suite
        1 king
      • Bedroom 2
        1 queen
      • Bedroom 3
        1 king, 1 double, 1 twin/ single
      • Bedroom 4
        1 queen
      • Bedroom 5
        1 twin/ single
      • Bedroom 6
        1 sleep sofa /futon, Guesthouse at the end of the pier


        • 3 Bathrooms, 2 Half Baths
        • Bathroom 2
          toilet, combination tub/shower
        • Bathroom 3
          toilet, combination tub/shower, This bathroom is full of charm with original double sinks
        • Bathroom 4
        • Bathroom 5
          toilet, In the Guesthouse at end of pier
        • Bathroom 1 Master
          toilet, tub, shower, Large custom bath with huge shower and two sinks

          Location Type

            • Beachfront
            • Water View
            • Waterfront


                • Adventure
                • Away From It All
                • Family
                • Romantic
                • Sports & Activities
                • Tourist Attractions


                    • Guests provide their own meals


                        • Iron & Board
                        • Air Conditioning
                        • Fireplace
                        • Fitness Room / Equipment
                          Treadmill available
                        • Hair Dryer
                        • Heating
                        • Internet
                          Free Wifi throughout the home including the Guest House
                        • Clothes Dryer
                        • Linens Provided
                        • Living Room
                        • Parking
                          Plenty of parking in the oversized driveway, as well as along the street on both sides in the grass. We are at the end of the paved road and have great flexibility with parking.
                        • Towels Provided
                        • Washing Machine
                        • Free Wifi


                            • Coffee Maker
                              Keurig and French Press
                            • Dishes & Utensils
                              Everything you would need
                            • Dishwasher
                            • Kitchen
                              Fully stocked with dishes, silverware, toaster, Keurig, Microwave, etc.
                            • Microwave
                            • Oven
                            • Refrigerator
                            • Stove
                              Commercial grade Wolf Range including grill and griddle
                            • Toaster


                                • Dining
                                  Can seat 6-14. Please let us know so we can expand the table.
                                • Dining Area
                                • comfy seating for 12 people


                                    • Books
                                    • DVD Player
                                    • Game Room
                                      with ping pong table and wet bar
                                    • Games
                                      20+ Board Games
                                    • Ping Pong Table
                                    • Satellite / Cable
                                    • Television
                                      We have two flat-screened TV's. One in the main living area and one in the Master Suite.
                                    • Video Games


                                        • Balcony
                                          at the guest house
                                        • Bicycles
                                        • Deck / Patio
                                        • Lawn / Garden
                                        • Outdoor Grill
                                          Weber Grill


                                            • Long-term Renters Welcome
                                            • wheelchair inaccessible

                                              Pool / Spa

                                                • Hot Tub
                                                  5-6 person outdoor hot tub


                                                    • bay/sound
                                                    • churches
                                                    • cinemas
                                                    • forests
                                                    • library
                                                    • marina
                                                    • museums
                                                    • playground
                                                    • restaurants
                                                    • synagogues

                                                      Leisure Activities

                                                        • antiquing
                                                        • beachcombing
                                                        • bird watching
                                                        • gambling casinos
                                                        • horseback riding
                                                        • outlet shopping
                                                        • photography
                                                        • scenic drives
                                                        • sight seeing
                                                        • walking

                                                          Local Services & Businesses

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

                                                              Sports & Adventure Activities

                                                                • snorkeling
                                                                • cycling
                                                                • hiking
                                                                • mountain biking
                                                                • pier fishing
                                                                • roller blading
                                                                • sailing
                                                                • fishing
                                                                • sound/bay fishing
                                                                • swimming
                                                                • tennis
                                                                • water skiing
                                                                • water tubing
                                                                • wind-surfing

                                                                  House Rules

                                                                  Check-in: 2:00 PM

                                                                  Check-out: 12:00 PM

                                                                  Cancellation Policy

                                                                  100% refund if canceled at least 60 days before arrival date. 50% refund if canceled at least 30 days before arrival date. You must contact the owner directly to request cancellation.

                                                                  15 Reviews


                                                                  Latest reviews

                                                                  Wonderful. Fantastic. When can we come back?!

                                                                  Robert S.Philadelphia

                                                                  This is a wonderful house in an incredible location. Owners Elaine and Rick are the perfect hosts. I stayed 3 nights with 11 friends and we all loved it. There was ample room and beds for 12 adults. We all left saying that we needed to figure out a date we can come back. The guest house at the end of the pier is something you have to see to believe -- and is even better in real life than in the pictures. The only problem is that I didn't book a week or a month.

                                                                  Networking Retreat

                                                                  Alice C.

                                                                  We just returned from a networking retreat for clients and prospects that we held at this property. In the main house, the property was as described and there were lots of places for gathering, large and small spaces. The kitchen had everything we needed and the sleeping rooms were quiet and comfortable. This weekend is an annual event we host in advance of a larger national conference that moves to different cities. The next time this convention takes place in DC, we will rent this property again. We had 11 women total.

                                                                  Girls weekend away

                                                                  Beth L.

                                                                  From the beginning planning stages with Elaine to when we departed this wonderful home it was all so seamless, and let me just say there were 9 woman (dear friends) staying for 4 days and 3 nights...what a house!! it was clean, it was gorgeous, it was comfy..it had all the creature comforts of home and when 9 woman get together we like things just so---well there is nothing we would have changed from the towels to the bedding to the spices on hand, and all the wonderful cozy throw blankets---the kitchen was enormous we practically lived in the kitchen all of us cooking and laughing and eating, and then there was the magnificent view of the Chesapeake Bay from sunrise to moonrise it was spectacular, soothing, and relaxing. When we were not laughing or reading or playing games together we were napping out on the lawn listening to the water, or out at the one of a kind Boat house sitting on the back deck soaking up the sun and talking. My sister slept out there every night not because there was no room in the house but because it was so wonderful !! We saw a massive bald eagle scoop a fish out of the bay and fly directly in front of the house to the woods next door to eat his fish on a tree limb...we can't wait to come back. Thank you Elaine for sharing your amazing home and all the precious memories we made !!!

                                                                  Outstanding space, even better hosts

                                                                  Erick J.

                                                                  Our organization needed a space for our annual faculty retreat. We had our pick of several dozen places that fit the requirements. We chose this property for its proximity, space layout, reasonable price point, and unique features like the pier and boathouse.

                                                                  When I met Rick, I was overwhelmed by his friendliness and demeanor. Both he and Elaine are clearly people who understand what world-class hospitality looks and feels like. The process for both check in and check out was unobtrusive but thorough.

                                                                  The space itself was perfect for our needs. Every member of the faculty was in a bed (no need for sofas or floor sleeping) and we used six distinct areas for breakout sessions and workshops. Truly, it was the most productive we've been in years, and a big part of that, was the space.

                                                                  On a personal note, sitting on the deck at the end of the pier, on the bay side of the boathouse, I saw about half a dozen shooting stars in an hour. A great place to contemplate one's life's work.

                                                                  We'll be back if they'll have us.

                                                                  Wonderful property!

                                                                  Robert S.

                                                                  We had an amazing weekend. Check in and check out was easy and well organized. The property itself is hard to describe in a few words. It was stunning and comfortable. The property has so many areas to explore. We are already planning a return visit. Could not ask for more!

                                                                  Thank you for sharing your home!


                                                                  Peg S.

                                                                  This was the absolute perfect home to celebrate our 60th birthdays with 8 dear college friends. The property is gorgeous and the views are incredible. We took advantage of everything: wine and cheese on the front porch, meals and games on the screened porch, hikes to Downs Park next door, lounging in the hot tub, lunch in Annapolis, naps in the boathouse and just enjoying the million dollar views! The house itself was very well equipped, up to date, beautifully decorated and extremely comfortable.

                                                                  Elaine was very responsive and wonderful to work with. Thank you for providing us the perfect place celebrate and renew our special friendships.


                                                                  Pasadena, MD, USA

                                                                  Our property is located right on the Chesapeake Bay equal distance by water between Baltimore's beautiful inner harbor and the smaller quaint Annapolis harbor. Baltimore's many attractions include the National Aquarium, Maryland Science Center, Hard Rock Cafe, the Walters Art Museum, Port Discovery Children's Museum, the Baltimore Orioles and Ravens, and many excellent restaurants and events year round. Annapolis also has many year-round fun activities ranging from the famous Blue Angels performances, the Naval Academy, antique shops, historic tours, jazz clubs, coffee shops and much more. And it's about an hour's drive to Washington D.C. -- with so much to see and do -- from the Smithsonian on the National Mall to the National Zoo, and so much more.

                                                                  Rates & Availability

                                                                  Additional information about rental rates

                                                                  Cleaning Fee
                                                                  Damage Insurance
                                                                  Tax Rate
                                                                  15 Reviews
                                                                  Exceptional 5/5
                                                                  Premier Partner
                                                                  Enter dates for accurate pricing
                                                                  For booking assistance, call 888-640-7927

                                                                  Property # 4461077ha