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UPDATED HOME, 1.66 ACRES, public water and sewer, and NO HOA - ALL FOR $299,500! Discover the value of this beautifully updated 3-bedroom, 1.5-bath home. Featuring a BRAND-NEW ROOF, NEW HVAC SYSTEM, and a ONE-YEAR HOME WARRANTY, this property offers major improvements already completed and the convenience of one-level living. In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs. Step inside to discover a bright, inviting interior featuring brand-new luxury vinyl plank flooring and carpet, fresh paint throughout, and a thoughtfully updated kitchen complete with new butcher block countertops, brand-new stainless-steel appliances, and cabinet space. Outside, the expansive lot offers endless opportunities for gardening, entertaining, recreation, or simply enjoying the tranquility of nature. A storage shed provides additional space for tools, lawn equipment, or outdoor hobbies. Whether you're a first-time homebuyer, someone looking for convenient one-level living, or looking for a vacation home, this property checks all the boxes! Conveniently located just minutes from historic downtown Chestertown, Rock Hall, nearby marinas, dining, shopping, and waterfront activities - with convenient access to major routes into Delaware and Pennsylvania - this property offers the ideal balance of peaceful rural living and easy travel. This is a rare combination of acreage, versatility, and affordability. Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape!

3 Beds ⋅ 2 Baths

UPDATED HOME, 1.66 ACRES, public water and sewer, and NO HOA - ALL FOR $299,500! Discover the value of this beautifully updated 3-bedroom, 1.5-bath home. Featuring a BRAND-NEW ROOF, NEW HVAC SYSTEM, and a ONE-YEAR HOME WARRANTY, this property offers major improvements already completed and the convenience of one-level living. In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs. Step inside to discover a bright, inviting interior featuring brand-new luxury vinyl plank flooring and carpet, fresh paint throughout, and a thoughtfully updated kitchen complete with new butcher block countertops, brand-new stainless-steel appliances, and cabinet space. Outside, the expansive lot offers endless opportunities for gardening, entertaining, recreation, or simply enjoying the tranquility of nature. A storage shed provides additional space for tools, lawn equipment, or outdoor hobbies. Whether you're a first-time homebuyer, someone looking for convenient one-level living, or looking for a vacation home, this property checks all the boxes! Conveniently located just minutes from historic downtown Chestertown, Rock Hall, nearby marinas, dining, shopping, and waterfront activities - with convenient access to major routes into Delaware and Pennsylvania - this property offers the ideal balance of peaceful rural living and easy travel. This is a rare combination of acreage, versatility, and affordability. Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape!

9126 Fairlee Rd, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$325,000

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

3 Beds ⋅ 1 Baths

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

896 Washington Ave, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$79,000

Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or restoration. Located near downtown Chestertown’s shops, restaurants, and waterfront, the location can’t be beat. Original architectural details, a cozy layout, and timeless curb appeal make this home a standout gem waiting to be polished. Don't miss your chance to invest in one of Maryland’s most beloved small towns. Sold as-is. Cash or renovation loans preferred.

2 Beds ⋅ 1 Baths

Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or restoration. Located near downtown Chestertown’s shops, restaurants, and waterfront, the location can’t be beat. Original architectural details, a cozy layout, and timeless curb appeal make this home a standout gem waiting to be polished. Don't miss your chance to invest in one of Maryland’s most beloved small towns. Sold as-is. Cash or renovation loans preferred.

234 N College Ave, Chestertown

Listing courtesy of Cummings & Co Realtors. Contact:

$1,495,000

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.

9 Beds ⋅ 7 Baths

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.

8796 Maryland Pkwy, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$799,900

Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic District The Bedingfield Hands House, circa 1750, is more than a home—it's a living piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make historic homes so special. History is woven into every corner of the property—from the prominence of past owners down to the foundation, which contains the mast of a ship. The only home downtown with such a generous private front courtyard framed by mature landscaping, vibrant seasonal gardens, brick herringbone paths that create a peaceful retreat just steps from town and the Chester River. Whether enjoying a quiet morning coffee, entertaining guests, or simply admiring the blooms, the outdoor spaces are truly a stand-out feature. Approaching the home, guests are welcomed by a wide red front door, a traditional symbol of hospitality in early America, inviting visitors inside just as it has for centuries. Inside, approximately 2,472 square feet of thoughtfully preserved living space blends historic character with modern comfort. Original wide-plank hardwood floors, period moldings and built-in cabinetry, reflect the home's 18th-century origins, while updated kitchens, baths, and central air/heat provide the conveniences expected today. To the right of the grand foyer, a cozy study lined with built-in bookshelves provides the perfect home office or library and could easily be converted into a first-floor bedroom for those seeking single-level living flexibility. A first floor full bathroom with walk in shower is located conveniently around the corner straight through the foyer. To the left of the foyer and at the forefront of the home, the stunningly preserved parlor, featuring 12x12 wavy glass windows, original panel walls and stunning gas fireplace with pine panel surround, offers an elegant setting for entertaining guests or enjoying quiet evenings at home. Just beyond, the large dining room serves as a memorable gathering space, complete with another fireplace, built-in cabinetry, and a charming pop-out window seat overlooking the side gardens. Just beyond that is a chef's kitchen featuring updated appliances, abundant storage cabinetry, generous island workspace, and a soaring tapered tray ceiling that creates an airy and inviting atmosphere. The kitchen breakfast nook is highlighted by panoramic bay window wall. Off the breakfast nook is a convenient half bath and steps to the side courtyard with pergola and a screened porch. The garage—another rarity in the Historic District—provides valuable storage and convenience. Upstairs, the spacious primary suite blends historic character with thoughtful updates, featuring a practical double closet and an en-suite bath highlighted by distinctive MacKenzie-Childs tile floors and decorative vanity hardware. Two additional generously sized bedrooms and a full bathroom provide comfortable accommodations for guests. Beyond its appeal as a private residence, it is ranked in the top 5% of Chestertown AirBnbs and a guest favorite. Whether you're seeking a full-time residence, weekend retreat, or income-producing investment, this property offers exceptional flexibility. Furniture is negotiable for a truly turnkey opportunity. Step outside and enjoy everything that makes Chestertown so beloved. Stroll to art galleries, Chestertown marina, quaint shops, restaurants, the farmers market, and waterfront park. Enjoy annual traditions such as the Tea Party Festival, Downrigging Weekend, and Dickens of a Christmas, all just moments from your front door. Become the steward of a treasured landmark while enjoying the comfort, beauty, and lifestyle that have made it one of Chestertown's most admired homes for generations.

3 Beds ⋅ 4 Baths

Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic District The Bedingfield Hands House, circa 1750, is more than a home—it's a living piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make historic homes so special. History is woven into every corner of the property—from the prominence of past owners down to the foundation, which contains the mast of a ship. The only home downtown with such a generous private front courtyard framed by mature landscaping, vibrant seasonal gardens, brick herringbone paths that create a peaceful retreat just steps from town and the Chester River. Whether enjoying a quiet morning coffee, entertaining guests, or simply admiring the blooms, the outdoor spaces are truly a stand-out feature. Approaching the home, guests are welcomed by a wide red front door, a traditional symbol of hospitality in early America, inviting visitors inside just as it has for centuries. Inside, approximately 2,472 square feet of thoughtfully preserved living space blends historic character with modern comfort. Original wide-plank hardwood floors, period moldings and built-in cabinetry, reflect the home's 18th-century origins, while updated kitchens, baths, and central air/heat provide the conveniences expected today. To the right of the grand foyer, a cozy study lined with built-in bookshelves provides the perfect home office or library and could easily be converted into a first-floor bedroom for those seeking single-level living flexibility. A first floor full bathroom with walk in shower is located conveniently around the corner straight through the foyer. To the left of the foyer and at the forefront of the home, the stunningly preserved parlor, featuring 12x12 wavy glass windows, original panel walls and stunning gas fireplace with pine panel surround, offers an elegant setting for entertaining guests or enjoying quiet evenings at home. Just beyond, the large dining room serves as a memorable gathering space, complete with another fireplace, built-in cabinetry, and a charming pop-out window seat overlooking the side gardens. Just beyond that is a chef's kitchen featuring updated appliances, abundant storage cabinetry, generous island workspace, and a soaring tapered tray ceiling that creates an airy and inviting atmosphere. The kitchen breakfast nook is highlighted by panoramic bay window wall. Off the breakfast nook is a convenient half bath and steps to the side courtyard with pergola and a screened porch. The garage—another rarity in the Historic District—provides valuable storage and convenience. Upstairs, the spacious primary suite blends historic character with thoughtful updates, featuring a practical double closet and an en-suite bath highlighted by distinctive MacKenzie-Childs tile floors and decorative vanity hardware. Two additional generously sized bedrooms and a full bathroom provide comfortable accommodations for guests. Beyond its appeal as a private residence, it is ranked in the top 5% of Chestertown AirBnbs and a guest favorite. Whether you're seeking a full-time residence, weekend retreat, or income-producing investment, this property offers exceptional flexibility. Furniture is negotiable for a truly turnkey opportunity. Step outside and enjoy everything that makes Chestertown so beloved. Stroll to art galleries, Chestertown marina, quaint shops, restaurants, the farmers market, and waterfront park. Enjoy annual traditions such as the Tea Party Festival, Downrigging Weekend, and Dickens of a Christmas, all just moments from your front door. Become the steward of a treasured landmark while enjoying the comfort, beauty, and lifestyle that have made it one of Chestertown's most admired homes for generations.

106 Queen St S, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$700,000

Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.

2 Baths

Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.

201 N Lynchburg St, Chestertown

Listing courtesy of RE/MAX Associates-Hockessin. Contact:

$1,195,000

Morning light pours through restored original windows. The river shimmers a block away, and a mansard roof that has watched over High Street since 1863 frames it all. Rebuilt after the fire of its day, the Tilley Residence has been brought back since 2022 by a top builder and his designer sister. A grand staircase, refinished by hand over many months, rises past glimpses of the water. The new custom kitchen is made for gathering. Upstairs, the primary suite has its own fireplace, and there are 4.5 brand-new baths. Below, a bright lower level holds a wine cellar. Everything unseen is new, too: HVAC, electrical, plumbing, roof and insulation. Outside, there’s a private fenced yard, a remodeled garage, and the historic Custom House next door. Shops, galleries, dining and the marina are all a short stroll away. There is no better chance to drop your keys and create your legacy in Chestertown's Historic District.

5 Beds ⋅ 5 Baths

Morning light pours through restored original windows. The river shimmers a block away, and a mansard roof that has watched over High Street since 1863 frames it all. Rebuilt after the fire of its day, the Tilley Residence has been brought back since 2022 by a top builder and his designer sister. A grand staircase, refinished by hand over many months, rises past glimpses of the water. The new custom kitchen is made for gathering. Upstairs, the primary suite has its own fireplace, and there are 4.5 brand-new baths. Below, a bright lower level holds a wine cellar. Everything unseen is new, too: HVAC, electrical, plumbing, roof and insulation. Outside, there’s a private fenced yard, a remodeled garage, and the historic Custom House next door. Shops, galleries, dining and the marina are all a short stroll away. There is no better chance to drop your keys and create your legacy in Chestertown's Historic District.

105 High St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$298,000

Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

3 Beds ⋅ 2 Baths

Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

222 Dutchess Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$385,000

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.

4 Beds ⋅ 3 Baths

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.

23043 Bay Shore Spur, Chestertown

Listing courtesy of Rock Hall Properties Real Estate. Contact:

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How much is your home worth?