Stunningly renovated home in Shorewood Estates. Your back yard is Swantown Creek. Professional pics and rest of the details are coming. Expected on market date is 9/25. ...

Waterfront Living at the Head of Still Pond Creek Well-maintained and beautifully situated, this 3-bedroom, 3-bath waterfront home offers a peaceful setting at the head ...

Discover the best of waterfront living in the sought-after community of Kinnairds Point. Set on 3.5 acres in a private, peaceful setting and thoughtfully designed for bot...

Set within a stately 1800s waterfront home, this beautifully renovated one-bedroom condominium offers an effortless life along the Chester River. Begin your mornings with...

Set on a moderate bluff along the upper Sassafras River, this inviting waterfront property offers pristine, natural down river views and exceptional access to the water. ...

Enjoy a long, secluded driveway to a 2,185 sq ft home sitting on 7.9 acres of mature, heavily-forested woods with waterfront views of Grey’s Inn Creek. The home features ...

Enjoy sweeping water views, a bulkheaded shoreline, and a lawn extending to the water's edge—an exceptional and hard-to-find combination. Boating enthusiasts will apprec...

Beautiful waterfront on nearly 7 acres. Spacious composite deck overlooking Still Pond Creek. Private dock with 3 ft MLW (buyer to verify). Large living room with glea...

Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natur...

Charming waterfront rancher on the Chester River! This move-in ready home features 3 bedrooms, 1.5 baths, and luxury viny plank flooring throughout. Recent upgrades inclu...

This over 5 acre waterfront estate on Churn Creek is a true Eastern Shore recreational property. Besides the home itself, the grounds include a board and batten cabin to...

Welcome to Rigbie Bluff, where coastal charm meets modern comfort. This rare furnished 2-bedroom, 2-bath end-unit top floor condominium offers panoramic views of the uppe...

PARADISE AWAITS * BIG BUCK FARM * GEESE * DUCKS AND GAGGLE OF TURKEYS Hidden away at the end of country lane Privacy awaits Surrounded by woods with a unique mix of fiel...

Welcome to Wymont Park, a sought-after waterfront community on picturesque Still Pond Creek, where every day feels like a vacation on Maryland's Eastern Shore. From sippi...

Cute cottage located on the upper Chester River! Entertain on the spacious rear deck. Watch the Chester River slowly meander to more wide open waters. Follow the gentl...

Luxury deep water retreat on the Sassafras River: an exceptional custom waterfront crafted residence Offering expansive river views, a private dep water pier, resort styl...

Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip.  3.55 acres, partly wooded, exceptionally landscap...

Located on the upper Chester River in Millington, River Bend Lane offers the perfect blend of convenience and waterfront lifestyle just seconds from Route 301 for easy co...

Unique opportunity offering two adjoining parcels with exceptional potential in Rock Hall. Parcel 1 consists of approximately 1.4 acres located on Geen Lane and is zoned ...

It is a rare opportunity for a private waterfront lot off the Sassafras River to come available. This 14 acre parcel of land is located above the bridge in a well estab...

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...

**Listing price is for FOUR units for sale as an investment package! 117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a ...

Experience riverfront living on the Sassafras River with this exceptional home on just over 13 acres. There’s room for everyone with 5/6 bedrooms, 3 full baths, and two ...

THE PRICE HAS CHANGED — THE WATERFRONT LIFESTYLE HASN'T. Newly reduced $10,000! Where else can you find Chester River waterfront with a private dock at this price? Welco...

Discover 18.62 acres of waterfront land on Tavern Creek, offering 1,086 feet of shoreline and stunning natural surroundings. Zoned Resource Conservation and currently til...

Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat s...

Located along Shipyard Creek just outside Rock Hall, this 113-acre farm offers a strong combination of productive soils, waterfront access, and long-term investment value...