Luxury Private Waterfront Compound on the Chesapeake Bay for 20+ Pool, Tennis...

Enjoy a private waterfront compound on the Chesapeake Bay designed for family reunions and large group gatherings. Set on 18 secluded acres with over 600 feet of shoreline, Bay Cliff includes a main house, guest house, and barn studio—perfect for multi-generational families, corporate retreats, and groups of 20–30 guests. With a pool, private pier, tennis/pickleball courts, and expansive indoor and outdoor gathering spaces, this is a rare place where everyone can be together and have room to spread out.

The space
Welcome to our home away from home. We hope this one-of-a-kind place will be the setting for wonderful memories that last a lifetime. Enjoy views and stunning sunsets of the Chesapeake Bay on a spectacular 18 acres: Bay Cliff has over 600 feet of waterfront. The magical main house, guest house, and barn studio have a total of 13 bedrooms, 7 full bathrooms, and 2 half bathrooms. As you will see, the property features a swimming pool, tennis court with two pickleball courts (and nets), a basketball hoop, two outdoor showers, a private beach, a fishing pier and large deck overlooking the water, a large screened porch, a waterfront patio, and a 5-minute stroll to the largest public beach in Kent County. Enjoy water activities, such as swimming, kayaking, fishing/crabbing, and even outdoor showering! Equally fun, take advantage of the land activities, such as tennis, pickleball, basketball, croquet, bocce, bald-eagle watching, hammock snoozing, and billiards. End your days of fun on the 11 Adirondack chairs taking in the breathtaking view and watching stunning sunsets over the Bay. Kent County and the Eastern Shore of the Chesapeake Bay offer a wealth of activities, adventures, and a rich history in their own right.

Amenities + Experience

Waterfront & Outdoor Living

* Private pier and platform for swimming, fishing, and crabbing
* Private beach at low tide + 5-minute walk to Kent County’s largest public beach
* Kayaking and other water activities
* Waterfront patio + large screened porch for group gatherings
* Hammocks and Ample Adirondack chairs for sunset views

Recreation & Group Activities

* Swimming pool (open mid-May through September)
* Tennis court lined for two pickleball courts
* Basketball hoop, croquet, bocce, billiards
* Bald eagle watching and wide-open green space

Designed for Large Groups

* Multiple homes on one private property (compound-style layout)
* Large shared spaces for meals and gatherings
* Plenty of room for both together time and quiet retreats
* Outdoor showers, expansive grounds, and flexible hangout areas

MAIN HOUSE
General: Central AC and radiator heating

First Floor:
– Sitting Room with gas fireplace, seating for four, and Bay view
– Gourmet Kitchen/Dining area: Newly renovated (2023) and fully equipped kitchen for serving large crowds. Custom cabinets, new six-burner gas range with griddle and double ovens, new GE Monogram refrigerator & freezer, new GE Monogram dishwasher, and new drawer microwave. A center island with seating for five people, in addition to an expandable dining table with leaves to seat 18 people. One kitchen door opens to the back of house and other large sliding French doors open to screened porch on the front of the house. Spectacular views of the Chesapeake Bay
– Pantry Room off of the kitchen features a second refrigerator, sink, second dishwasher, and a drip coffee maker with a window overlooking the side yard and pool area
– Laundry Room, connected to pantry room, contains washer, dryer, and utility sink
– Powder Room
– Bar Area with beverage drawers, ice maker and bar sink. Fully equipped with glassware and Nespresso Coffee Maker
– Den/Library with wall of built-in bookshelves, gas fireplace, and large wall-mounted flat screen TV
– Living Room with three sofas, club chairs, large flat screen TV, piano, gas fireplace, and bay window overlooking front lawn and Chesapeake Bay
– First Floor Bedroom (Bedroom #1): Located off the Den/Library. Entrance to back patio. Queen-size Bed
– Ensuite Full Bathroom with walk in shower.
– Front Screened Porch: Large porch (with tile flooring and ceiling fans) that opens off of the kitchen/dining room and hallway. Expansive views of front lawn and the Chesapeake Bay. At one end of the porch, there is table seating for 22, at the other end of the porch there is wicker seating for 12
– Front Patio: Large front patio with Polywood Adirondack chairs, tables, and love seats with seating for 12-14

Second Floor:
– Linen closet with additional linens and towels
– Primary Bedroom (Bedroom #2): Spacious with king-size bed, two closets, and windows facing the water and backyard
– Beautiful, newly renovated en-suite bathroom with soaking tub, separate shower, double sinks, a toilet and linen closet
– Yellow Bedroom #3: Sundrenched and with Bay views, queen-size bed, and closet. Double doors that connect to Bedroom #4
– Yellow Bedroom #4: One double bed and two twin beds, bay and side yard views, and two closets
– Blue Bedroom #5: Queen-size bed, large closet, and window facing backyard. Connects to Bedroom #6.
– Blue Bedroom #6: One double bed and two twin beds, a closet, and two windows
– Hall Bathroom: Gorgeous newly renovated full bathroom with large walk-in shower, vanity, and toilet

Third Floor:
– Red Bedroom #7: Queen-size bed, three twin beds, and a closet
– Dormer Bedroom #8: Double futon bed
– Half Bathroom: Small newly renovated half bathroom in hallway
– Green Bedroom #9: Queen-size bed and three twin beds with dormer closet and en-suite bathroom
– En-suite bathroom: Vanity, toilet and shower

Lower Level:
– Recreation Room/Playroom: Sitting area, table for games or cards, third refrigerator
– Full Bathroom
– Billiards Room: Pool table with love seat and pool chairs


GUEST HOUSE
General: Electric baseboard heating and AC units

First Floor:
– Living Room/Bedroom #10: large family room with non-functioning fireplace and beam ceilings. Double-size bed, exercise bicycle, sofa, and television. Wall of windows facing the Bay
– Laundry Room: washer and dryer
– Kitchen: fully equipped kitchen with small stove and oven, 3rd full-size refrigerator/freezerand bay window facing the water
– Full bathroom with bathtub and shower

Second Floor:
– Bedroom #11: Queen-size bed, full-size platform bed, and two twin beds
– Bedroom #12: Full-size bed and two twin beds


STUDIO ABOVE THE BARN
General: Electric baseboard heating and AC Unit

First Floor:
– Tile entry way with sitting area
– Full bathroom

Second Floor:
– Bedroom #13: cathedral ceilings, king-size bed, desk and kitchenette with sink, small refrigerator, and microwave


EXTERIOR
– Split rail fences line the entrance to the property along 1st Avenue, with a bucolic field to the right and red barns to the left
– Long tree-lined driveway with ample room to park on either side of the driveway or on gravel parking pad between two barns
– Beautifully landscaped, massive front yard with enormous tulip poplar trees, two hammocks, and 11 Adirondack chairs overlooking the Chesapeake Bay
– Fenced-in pool area with an electric pool cover and pool house with refrigerator. Ample supply of pool towels and pool toys, chaise lounges, tables, and chairs. The pool is open from mid-May through September. Two outdoor showers behind pool house
– Tennis court with two pickleball courts outlined on both sides of the tennis court net – includes pickleball net, pickleball paddles and balls, all housed in a charming playhouse shed, along with other sporting activities – bocce, croquet, spike ball, etc
– Basketball hoop
– Long Staircase down to large platform with ladder to the beach
– Large pier great for fishing or crabbing
– Ravine pathway with area to launch kayaks or paddle boards

Guest access
You will have access to the entire property - the main house, the guest house, the studio above the barn, the pool (open mid-May through September), tennis/pickleball courts, and--best of all--the Bay!

Other things to note
This fabulous family compound is ideal for a multi-generational gathering or reunion! The views, the Bay, tennis court, pool (open mid-May through September), pickleball, basketball and huge lawns make this place an amazing playground!