257 Prospect Bay Dr W, Grasonville, MD

Auction begins in



Tara McLean



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Saturday, May 1, 1-4 PM
Sunday, May 2, 1-4 PM

Saturday, May 8, 1-4 PM
Sunday, May 9, 1-4 PM

Saturday, May 15, 1-4 PM
Sunday, May 16, 1-4 PM


Friday, May 21, 1-4 PM


Saturday, May 22, 11 AM, On-Site
Registration begins at 9 AM
Remote bidding is available

Broker Participation

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Saturday, May 22, 2021 • 11 AM • On-Site


  • Gated entrance and driveway
  • Very private, 6.4-acre lot; 0.25 miles from the access road
  • 7,231 sq ft home
  • Levels: 2
  • Floor-to-ceiling Palladian windows
  • Four bedrooms with ensuites
  • Large recreation room with full bath
  • 6 full/2 half baths
  • Office with built-in library and fireplace
  • Gourmet kitchen with breakfast bar
  • Family room and dining space overlooking rear patio
  • Butler’s pantry/laundry room
  • Heated, in-ground, saltwater pool (20’ x 40’)
  • Brick pool house with equipment room and outdoor kitchen, full cabana bath, and spa
  • Automatic pool cover
  • Waterside gazebo
  • Private, sheltered boat basin boat lift, floating dock, boat ramp, rip-rap and bulkheaded shoreline
  • Private boardwalk and gazebo
  • Equipment storage sheds
  • Large yard with half-regulation-size baseball field or room to add a helipad
  • Lightning protection system on primary residence and pool house

Auction Without Reserve

– Remote Bidding Available –

Guarding Greenwood Creek’s approach, where it joins Prospect Bay like a colonial-era fortress, stands a modern, luxury estate that has no equal anywhere on the Eastern Shore.

257 Prospect Bay Dr W is a one-of-a-kind, 6.4-acre, palatial property at the southernmost tip of the Piney Neck peninsula that stuns with nearly 360-degree water views. The gated, winding, .25-mile drive brings you away from the primary road to reveal a private cove, a boat basin, and an exquisite, 7,231 square-foot home packed with luxury features and amenities.

Incredible floor-to-ceiling Palladian windows flank the main sitting room filling it with natural light. Enjoy your favorite music or audio from anywhere in the house with the built-in Sonos multi-room sound system. Come outside at dawn and take a stroll down to the waterside gazebo, private pier/boardwalk and take in the sunrise over the bay with your cup of coffee. Step outside in the afternoon and relax in the in-ground saltwater pool, complete with a pool house with an outdoor kitchen, full cabana bath and separate spa. Or, invite friends and family to join you down at the boat lift and floating dock in the private boat basin and spend the afternoon on the bay. 

A rip-rap and bulkheaded shoreline provide peace of mind against wind and waves when the weather kicks up. 

Offering four bedrooms — all with en-suite bathrooms — this luxury home also features a large recreation room with a full bathroom, two additional half baths, an office with a built-in library and fireplace, gourmet kitchen with breakfast bar, family room and eat-in area overlooking the rear patio, and a butler’s pantry/laundry room.

When you’re ready to venture out, explore Grasonville if you’re not familiar with it already. It’s the first town after coming off the Kent Narrows bridge, with a population of 3,495. Located directly on Prospect Bay, you’ll be treated to some of the best seafood restaurants anywhere on the famed Eastern Shore: Harris’ Crab House, The Jetty, The Narrows, Annie’s Paramount Steakhouse, Bridges, and Big Owl Tiki Bar – to name a few, are several worth checking out. All of these are right on the water and offer a fantastic view.

For recreation, direct access to the water makes it easy to enjoy a day of boating or fishing. Other nearby points of interest for taking in the outdoors include Grasonville Park, Long Point Park, and Ewing Pond Park.

The nearby Chesapeake Bay Environmental Center offers nature camps, kayaking, and hiking trails. And, the scenic Eastern Neck National Wildlife Refuge provides fishing, hunting, and hiking all year round.

Don’t miss your chance to bid and win this extraordinary property and the lifestyle that comes with it. Register to bid remote or live, in-person, by auction day, May 22, 2021.

257 Prospect Bay Dr W, Grasonville, MD

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This property is listed for sale by licensed real estate agent Chuck V Mangold Jr. (LIC # 527518) of Benson & Mangold (LIC # 271), PH: 410.822.6665. Elite Auctions is a marketing service provider for auctions and is not a licensed real estate broker. The auction services referred to herein are not available to residents of any state where prohibited by applicable state law. Elite Auctions, its agents and affiliates, broker partners, auctioneer, and sellers do not warrant or guarantee the accuracy or completeness of any information and shall have no liability for errors or omissions or inaccuracies under any circumstances in this or any other property listings or advertising, promotional or publicity statements and materials. This is not meant as a solicitation for listings. Brokers are protected and encouraged to participate. All bidders are required to pre-register for each property auction in accordance with the Terms and Conditions. Equal Housing Opportunity. In cooperation with licensed auctioneer John Nicholls.

To pre-register for bidding, please call 844-94-ELITE or email