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$1,495,000 (USD)
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Chestertown Area Residential Home

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8796 Maryland Parkway Chestertown, MD 21620

9 Bed
7 Baths
4776 sqft
MLS# MDKE2006596
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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 National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates.The grounds unfold past champion and organic fruit trees, a generous herb garden, an original 18th-century smoke house, two private bridges over Stoneybrook Pond which are all framed by woods and rolling farm fields.Inside, nine bedrooms and six-and-a-half bathrooms reveal nearly two and a half centuries of craftsmanship: original wood floors, brick floors in the dining room and kitchen, signature Bulls Eye moldings, exposed hand hewn beams, eight fireplaces and soaring 11-foot ceilings.For more than 40 years the property has operated as a successful Bed & Breakfast. An optional furniture package is available for a seamless turnkey transition. Its origins as a single-family residence also make it an extraordinary private estate, full-time home or weekend retreat. A coveted sewer allotment is included with the sale which opens the door for a future carriage house, barn, additional dwelling, stable, studio or expanded hospitality use.A new roof, a complete exterior paint job, new hot water heater, new well pump and updated electrical service were completed in 2025–2026. This delivers the rare combination of historic character and modern peace of mind. Tolchester Marina and the Shanty Beach Bar are a mile away. Rock Hall is six miles down the road and the charming historic district of Chestertown is just ten miles away.After nearly four decades of careful stewardship, the current owners are ready to pass on the privilege and the story of The Mitchell House.
Listing Courtesy of BRIGHT IDX / Listed By: Tracy Stone, Coldwell Banker Chesapeake Real Estate Company
$1,350,000 (USD)
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Cambridge Area Residential Home

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5419 Ragged Point Road Cambridge, MD 21613

4 Bed
5 Baths
4512 sqft
MLS# MDDO2011562
Welcome to 5419 Ragged Point Road — Closer than you think to D.C., Baltimore, and Ocean City, a striking contemporary waterfront estate set on 11.88 private acres with an incredible 1,500 feet of frontage along serene Brooks Creek. Designed for those who appreciate the best of Eastern Shore living, this 4-bedroom, 2 full/3 half bath custom home, built in 2007, offers exceptional craftsmanship and luxury throughout with all the designer furnishings included.The gourmet kitchen is a chef’s dream, featuring marble countertops and top-tier appliances, including Wolf, Bosch, and Sub-Zero. The elegant primary suite offers a spa-like retreat with a soaking tub and separate shower. Expansive living spaces open to multiple balconies and decks, each perfectly positioned to capture breathtaking water views.Outdoor amenities include a private pier with approximately 3 feet MLW (mean low water), complete with water, electric, and a 12,000 lb boat lift — ideal for boating and fishing enthusiasts. For hunters, a duck blind on the property and abundant wildlife make this a rare hunting paradise.Whether you are savoring the sunrise over the creek, entertaining guests, or exploring the surrounding natural beauty, this extraordinary property delivers a lifestyle of unmatched tranquility and recreation.
Listing Courtesy of BRIGHT IDX / Listed By: Gwen Eskridge, Coldwell Banker Chesapeake Real Estate Company
$1,195,000 (USD)
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Chestertown Area Land

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302 S Mill Street Chestertown, MD 21620

Bed
0 Baths
sqft
MLS# MDKE2007020
Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 302 S Mill (.45 acres) and 300 S Mill (.55 acres) - totaling approximately 1 acre. 300 is unimproved and 302 has a 1960s brick home on it. R:6 Traditional Neighborhood Development Zoning permits a wide range of dense residential development opportunities. Maximum residential density is limited to 42 bedrooms which could be single family homes, multi-family, apartments, townhouses, rowhouses, condos, and others. Smaller commercial options available as well. Public water and sewer is on site and additional allocations are available. Entire site is usable. Property is partially wooded with several large mature Oak Trees. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Additional information available upon request. Buyer to perform own due diligence. Do not enter property without and appointment.
Listing Courtesy of BRIGHT IDX / Listed By: Joseph Ciganek, Coldwell Banker Chesapeake Real Estate Company
$1,195,000 (USD)
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Chestertown Area Residential Home

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302 S Mill Street Chestertown, MD 21620

2 Bed
1 Baths
806 sqft
MLS# MDKE2006850
Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 302 S Mill (.45 acres) and 300 S Mill (.55 acres) - totaling approximately 1 acre. 300 is unimproved and 302 has a 1960s brick home on it. R:6 Traditional Neighborhood Development Zoning permits a wide range of dense residential development opportunities. Maximum residential density is limited to 42 bedrooms which could be single family homes, multi-family, apartments, townhouses, rowhouses, condos, and others. Smaller commercial options available as well. Public water and sewer is on site and additional allocations are available. Entire site is usable. Property is partially wooded with several large mature Oak Trees. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Additional information available upon request. Buyer to perform own due diligence. Do not enter property without and appointment.
Listing Courtesy of BRIGHT IDX / Listed By: Joseph Ciganek, Coldwell Banker Chesapeake Real Estate Company