Tulip Forest, a farm defined by scale, stewardship, and long-term value. Recognized as a premier sporting estate, this legacy holding property is the kind of asset that ...

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...

Discover 6324 Quaker Neck Road, an exceptional waterfront estate spanning over 5 acres along the East Fork of Langford Creek offering over 5 feet of water at low tide. Ov...

5307 Elburn Lane presents a compelling assisted living investment in Maryland’s Eastern Shore, offering immediate operational scale through approved bed expansion. The pr...

Versatile commercial property, featuring just over 23,000 sq ft of workshop and/or warehouse space on 6.71 acres. Conveniently located on 298, just over 30 minutes to Mid...

A rare turnkey, profitable, investment property in downtown Chestertown. Renovated to the studs in 2022, 200-202-204 High Street has 5 apartments and 3 storefronts and s...

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...

Versatile commercial property, featuring just over 23,000 sq ft of workshop and/or warehouse space on 6.71 acres. Conveniently located on 298, just over 30 minutes to Mid...

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 ...

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...

Impressive Masterpiece on Swantown Creek with 2 Boat Lifts! Exquisitely Crafted, the high quality upgrades have created an oasis for serenity, relaxation and entertainin...

Rare opportunity to acquire both the real estate and established business of Blue Heron Oyster House & Inn, a highly popular neighborhood restaurant in the heart of Rock ...

**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 ...

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...

FEELING LUCKY? HERE IS YOUR CHANCE! 106 Acre Recreational Farm surrounded by woods offers a unique lifestyle for Hunting, Fishing, Horses. 26 ac grain farm plus acres o...

FEELING LUCKY? WELL STEP UP, THIS IS YOUR CHANCE! BIG BUCK FARM * GEESE * DUCKS & GAGGLE OF TURKEYS Hidden away at the end of country lane Privacy awaits Surrounded by w...

Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the...

Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the...

**To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The h...

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...

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...

Mixed-use commercial property in charming historic Chestertown. 327 Cannon was newly constructed in 2006, yet is perfectly situated in bustling historic district. Offerin...

Step into your own private world, just 2.75 miles from Historic Downtown Chestertown. Tucked away at the rear of a mostly wooded 19+/- acre parcel, this exceptionally wel...

Lot 1 is +/- 86 acres of prime development land in Kent County's Rt. 301 Growth Corridor. With +2,500 ft along Rt. 301 and 1,295 ft along Carroll Clark Rd, this propert...

50 acres of mixed use development property within Rock Hall town limits. Great location with access via state highway/MD Rt. 20, and 3 town roads; almost 1000 ft of road ...

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, o...

Remarkable 1 acre downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesi...

Remarkable 1 acre downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homes...

Over half an acre of prime bayfront property! Build a beautiful home on popular Lawton Avenue, the Gratitude neighborhood in Rock Hall. Enjoy sunsets, spectacular views...

Unique opportunity to expand or start your business just minutes from the Eastern Shore thoroughfares of Routes 301 and 213 and also just outside of downtown Chestertown....