4 Extraordinary Waterfront Estates and Historic Properties Across Maryland

Explore four extraordinary Maryland properties that redefine luxury living. From a LEED-certified estate along the Potomac River to a historic inn dating back to 1710, these homes offer unparalleled elegance, breathtaking waterfront views, and a harmonious blend of modern amenities and timeless charm. Discover prime locations, unique features, and the stories behind these one-of-a-kind estates.

Waterfront Estate | $6,500,000

41505 Knight Road, Leonardtown, MD 20650
Listing agents: Travis Gray And Katie Moore

Stunning waterfront estate on 18 acres along the Potomac River. This custom-built, four-level home features a spiral staircase, private elevator, floor-to-ceiling windows with panoramic water views, a gourmet kitchen, and seamless indoor-outdoor living.

 

Size: 12,113 sf

 

Price: $6,500,000

 

Listing details: The primary suite includes a spa-like bathroom, private terrace, and spacious walk-in closet. Additional highlights include a guest suite with a rooftop terrace, a lower level with a theater room and au pair suite, and a saltwater pool. Silver LEED certified, this estate offers luxury, privacy, and proximity to DC and local amenities.

 

Contact: Travis Gray And Katie Moore, Engel & Volkers Annapolis, +1 301.641.0809, 443.623.7887

Prime Waterfront Living | $4,495,000

6153 Long Point Rd, Neavitt, MD 21652
Listing agent: Juliet Wells

Discover a haven of exquisite living with this magnificent property set over 5 acres of prime waterfront, just 15 minutes from St. Michaels. Designed for multi- generational families, large families, or entertaining, the property includes a main residence and a recently renovated guest house, both featuring ground-floor primary suites.

 

Size: 11,700 sf

 

Price: $4,495,000

 

Listing details: The main residence offers breathtaking water vistas, spacious en-suite bedrooms, a versatile third-floor space, an extra-large pantry, and an extra-large laundry room. The guest house includes a modern kitchen, dining and lounging space, a ground- level master suite, a screened porch, and a separate laundry room. Six bathrooms are modern, tiled, and feature quartz finishes, adding to the home’s elegant and contemporary design. The property also boasts over 300 feet of pristine shoreline, beautiful views of the bay, a deep-water dock that can host multiple boats and jet skis with its own ramp, an outdoor saltwater pool with an inbuilt jacuzzi, and an indoor Endless Pool Swim/Spa with 3 hydromassage seats. Sustainable amenities include geothermal heating, cooling, and a solar energy system. The second floor of the main residence features an additional primary suite plus another bedroom, both with renovated bathrooms and large walk-in closets. A versatile third-floor space is ideal for a home office or creative studio. An interior corridor past the 3-car garage leads to a dedicated indoor pool zone, fitness area, and cozy family lounge with fireplace and media abilities. The guest house’s second floor has two bedrooms, a common area, and a renovated bathroom. With ample space to host family and friends for long periods of time, this property offers both comfort and sustainability in a picturesque setting near St. Michaels and Easton.

 

Contact: Juliet Wells, Coldwell Banker Chesapeake Real Estate Company, +1 917.375.8204

Waterfront Estate | $3,900,000

5841 Rockhold Creek Rd, Deale, MD 20751
Listing agents: Dawn Riley & Charlene Wilson

Nestled along the tranquil shores of Rockhold Creek in Deale, MD, this magnificent 10,000+ sq ft waterfront estate, affectionately known as “The Inn,” offers a rare blend of luxury, privacy, and versatility.

 

Size: 10,000  sf

 

Price: $3,900,000

 

Listing details: Spanning six acres of pristine land, this 8 Bedroom, 10 Bath property is designed not only as a personal residence and haven, but also as a thriving income-producing retreat, also included is a charming with an additional 3-bedrooms, 2.5-bath carriage guest house and a separate caretaker’s residence. Want a compound and a third house? The house next door is also for sale at 5875 Rockhold Creek Rd for 1.5M. As you approach, lighted paved walkways guide you through lush landscapes to the heart of this estate, where breathtaking water views and a deep connection to nature await.

 

Contact: Dawn Riley & Charlene Wilson, The Riley Team, RE/MAX One, +1 443.532.2430, 443.684.9586

314 N Morris Street | $3,200,000 (Sold)

314 N Morris Street, Oxford, MD 21654
Listing agents: Tom Williams & Monica Molloy

SOLD! Built as River View House in 1710 and an Inn since 1800, this is the oldest full-service Inn in America. Once owned by Founding Father Robert Morris Jnr, in his day the wealthiest man in the country and financier of the American Revolution, now the Eastern Shore’s most unique historic restaurant with rooms. This waterfront property is located across from the oldest privately owned Ferry operation in North America and in the charming and equally historic seaport of Oxford, which began life in 1666. This is a unique opportunity to own a part of our American History located in one of the most affluent Counties in Maryland, Talbot County.

 

Size: 12,447 sf

 

Price: $3,200,000 (Sold)

 

Listing details: An iconic property and strong business with a rare possibility to expand its waterfront location, with a bedroom extension and retail. Recent Updates include new Boiler for heat and hot water, Cosmetic repairs to ceiling tiles in many portions. New carpeting in 4 guest rooms. Freshened paint, addition of new furnishings in some public room and many other items. New price ……

 

Contact: Tom Williams & Monica Molloy, TTR Sotheby’s International Realty, +1 202.255.3650, 202.607.4843