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Nestled in a serene enclave, this exceptional 0.55-acre lot offers a rare opportunity to create your dream retreat, perfectly positioned just a block away from the tranquil waters of Swan Creek and The Chesapeake Bay. and just across the street from The Haven on Swan Creek. The property boasts a level, cleared landscape, with water-views of The Haven. Perfect for a permanent residence or a seasonal escape. Keep your boat at any one of several marinas nearby, just a stroll or bike ride away. Town water and sewer both available on Hynson Road. The lot is flagged. A survey plat is available upon request.

Hynson Rd., Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$1,195,000

Remarkable 1 acre 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 - 300 S Mill (.55 acres) and 302 S Mill (.45 acres) - totaling 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 an appointment.

2 Beds ⋅ 1 Baths

Remarkable 1 acre 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 - 300 S Mill (.55 acres) and 302 S Mill (.45 acres) - totaling 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 an appointment.

300 And 302 S Mill St, Chestertown

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

$1,495,000

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 both everyday comfort and effortless entertaining, this home provides generous space for guests while maintaining inviting living areas that feel equally welcoming when it is just a few people, approximate square footage is close to 3,000. It is the best of both worlds: room to gather, comfortable spaces to unwind, and an exceptional waterfront setting. This home provides five bedrooms with an additional enclosed sleeping loft attached to one of the bedrooms, three and a half bathrooms, renovated kitchen and bathrooms, fireplace, a deck overlooking the water, easy access to a private dock with a boatlift, protected shoreline and the Bay is just around the corner. The outdoor spaces offer additional spots to take in the water views, watch the wildlife, entertain guests, or simply relax and enjoy the tranquility of Churn Creek. Mature trees, landscaping and hardscaping surround this waterfront oasis. In addition to your own private dock and waterfront, Kinnairds Point offers two waterfront community areas with a beach, pavilion, kayak rack and a boat ramp. Located just outside of Chestertown and within easy reach of points north and south.

5 Beds ⋅ 4 Baths

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 both everyday comfort and effortless entertaining, this home provides generous space for guests while maintaining inviting living areas that feel equally welcoming when it is just a few people, approximate square footage is close to 3,000. It is the best of both worlds: room to gather, comfortable spaces to unwind, and an exceptional waterfront setting. This home provides five bedrooms with an additional enclosed sleeping loft attached to one of the bedrooms, three and a half bathrooms, renovated kitchen and bathrooms, fireplace, a deck overlooking the water, easy access to a private dock with a boatlift, protected shoreline and the Bay is just around the corner. The outdoor spaces offer additional spots to take in the water views, watch the wildlife, entertain guests, or simply relax and enjoy the tranquility of Churn Creek. Mature trees, landscaping and hardscaping surround this waterfront oasis. In addition to your own private dock and waterfront, Kinnairds Point offers two waterfront community areas with a beach, pavilion, kayak rack and a boat ramp. Located just outside of Chestertown and within easy reach of points north and south.

23911 Kinnards Point Dr, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

$299,000

The house number is now 11037. Nestled among the farmland and waterways in Kent County is a cul-de-sac of new homes on Bottom Road just outside of Chestertown. The new 3 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5" baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 2 additional bedrooms add options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck. Chestertown is a quaint, historic district on the Eastern Shore with an active art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front-foot fee of $15,000 that can be paid off with installments, annually over 15-20 years. The driveway of 10971 is an easement. The property line of 11037 goes beyond the driveway of 10971. See photos and site plan. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE

3 Beds ⋅ 2 Baths

The house number is now 11037. Nestled among the farmland and waterways in Kent County is a cul-de-sac of new homes on Bottom Road just outside of Chestertown. The new 3 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5" baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 2 additional bedrooms add options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck. Chestertown is a quaint, historic district on the Eastern Shore with an active art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front-foot fee of $15,000 that can be paid off with installments, annually over 15-20 years. The driveway of 10971 is an easement. The property line of 11037 goes beyond the driveway of 10971. See photos and site plan. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE

11037 Bottom Rd, Worton

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

$565,000

Waterfront condo in Rigbie Bluff with elevated, unobstructed waterfront views! This second-floor unit offers two levels of comfortable living with beautiful Chesapeake Bay views from multiple rooms. The main level features an updated kitchen with cherry cabinets and granite countertops, dining area, and living room overlooking the Bay. A flexible bedroom/sitting room with wet bar and water view, Jack-and-Jill bath with tub and laundry, and second bedroom complete this level. Upstairs, the spacious loft offers additional living space, skylights, and another great Bay view. The primary suite features a generous closet, en-suite bath with walk-in shower, and private deck - just the spot to enjoy your morning coffee or watch the sunrise over the Bay. Enjoy the community pool, private dock, deeded boat slip with an 8,000-lb boat lift, and a private basement with exterior access for plenty of storage. The condo association has completed numerous improvements in recent years, including new siding, decking, and stairs where needed. Located in Betterton, “The Jewel of the Chesapeake,” with the beach, pier, boardwalk, and park nearby. A wonderful opportunity to enjoy elevated, unobstructed waterfront living, boating, and all that this charming Chesapeake Bay town has to offer!

3 Beds ⋅ 2 Baths

Waterfront condo in Rigbie Bluff with elevated, unobstructed waterfront views! This second-floor unit offers two levels of comfortable living with beautiful Chesapeake Bay views from multiple rooms. The main level features an updated kitchen with cherry cabinets and granite countertops, dining area, and living room overlooking the Bay. A flexible bedroom/sitting room with wet bar and water view, Jack-and-Jill bath with tub and laundry, and second bedroom complete this level. Upstairs, the spacious loft offers additional living space, skylights, and another great Bay view. The primary suite features a generous closet, en-suite bath with walk-in shower, and private deck - just the spot to enjoy your morning coffee or watch the sunrise over the Bay. Enjoy the community pool, private dock, deeded boat slip with an 8,000-lb boat lift, and a private basement with exterior access for plenty of storage. The condo association has completed numerous improvements in recent years, including new siding, decking, and stairs where needed. Located in Betterton, “The Jewel of the Chesapeake,” with the beach, pier, boardwalk, and park nearby. A wonderful opportunity to enjoy elevated, unobstructed waterfront living, boating, and all that this charming Chesapeake Bay town has to offer!

1 Bayview Rd Unit 12B, Betterton

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

$559,500

There's a joyful feeling here that takes you straight back to childhood summers on the water. The Kinnairds Point community and property itself delivers this on just over two private acres at the end of a quiet cul-de-sac in Worton. Fully remodeled in 2020, the home opens into a vaulted great room with an exposed beam ceiling and a brick fireplace, flowing into a gorgeous, move-in-ready kitchen finished in crisp white cabinetry and a farmhouse sink. The owner's suite offers a spacious walk-in closet and an amazing renovated bath, while a screened porch and picnic lawn keep everyday living just as easy outdoors. The screened porch is designed for sharing beautiful moments and taking in nature. The full basement allows you to keep all of your "toys" tucked away while still keeping your cars in the garage. Best of all, Kinnairds Point offers access to two private Chesapeake waterfronts each with its own beach, pavilion, and kayak storage, one with a boat ramp just a walk or golf cart ride from your door. Crab pots, boat cruises, and sunset chairs are all in your future. Come life the Eastern Shore lifestyle in a polished setting just minutes from Historic Chestertown.

3 Beds ⋅ 2 Baths

There's a joyful feeling here that takes you straight back to childhood summers on the water. The Kinnairds Point community and property itself delivers this on just over two private acres at the end of a quiet cul-de-sac in Worton. Fully remodeled in 2020, the home opens into a vaulted great room with an exposed beam ceiling and a brick fireplace, flowing into a gorgeous, move-in-ready kitchen finished in crisp white cabinetry and a farmhouse sink. The owner's suite offers a spacious walk-in closet and an amazing renovated bath, while a screened porch and picnic lawn keep everyday living just as easy outdoors. The screened porch is designed for sharing beautiful moments and taking in nature. The full basement allows you to keep all of your "toys" tucked away while still keeping your cars in the garage. Best of all, Kinnairds Point offers access to two private Chesapeake waterfronts each with its own beach, pavilion, and kayak storage, one with a boat ramp just a walk or golf cart ride from your door. Crab pots, boat cruises, and sunset chairs are all in your future. Come life the Eastern Shore lifestyle in a polished setting just minutes from Historic Chestertown.

12613 Walnut Valley Ct, Worton

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

$599,999

Welcome to 21191 West Sharp Street - conveniently located just a few steps from downtown Main Street and the Rock Hall Marinas, this 1920s craftsman has recently undergone a remarkable renovation from top to bottom. Taken down to the framing and expanding upon the existing square footage, it was completely rebuilt by a reputable local builder. No surface was left untouched! Several interior walls were removed for a new modern open-floor layout with elevated ceilings. The exceptional construction quality, a main floor primary suite and practical indoor / outdoor living spaces make this the perfect home for everyday living or a weekend retreat. A few of the outstanding features include: coffered ceilings, thick crown moldings and railings, dark hardwood floors, plantation shutters, double wine bar, a Wolf kitchen range, a conditioned two-car garage, screened-in porch, a copper water line, the list goes on. The home was also fitted with dual mini-split systems and a large Rinnai instant hot water heater: both energy efficient and budget friendly! As you enter you are greeted by a spacious living room and dining room combination which naturally flow into the modern kitchen. Finished with granite countertops, ceramic tile backsplash, and Wolf and GE appliances, The first floor primary bedroom with large ensuite bath enables one to enjoy all one floor living should they desire. A double chilled wine bar and powder room behind the kitchen complete the first floor living area. Moving upstairs, there is a generously sized living space in the front and two full bedrooms behind in the newly added dormers. A new full bath with ceramic tile flooring and shower, and stone vanity further complements the upstairs living space. Moving to the back of the house; the screened-in porch is perfect for summertime crabs feasts and the propane fire pit is great for summer evenings with friends and family. Plenty of parking in the back driveway or in the two-car garage which is heated, air conditioned and spray-foam insulated. A quick walk to Java Rock for a morning coffee or an easy stroll to the Marina’s or the beach. Rock Hall is a vibrant town with many great restaurants, a brewery, and many festivals like Pirates and Wenches and Fall Fest. You dont want to miss this remarkable home.

3 Beds ⋅ 3 Baths

Welcome to 21191 West Sharp Street - conveniently located just a few steps from downtown Main Street and the Rock Hall Marinas, this 1920s craftsman has recently undergone a remarkable renovation from top to bottom. Taken down to the framing and expanding upon the existing square footage, it was completely rebuilt by a reputable local builder. No surface was left untouched! Several interior walls were removed for a new modern open-floor layout with elevated ceilings. The exceptional construction quality, a main floor primary suite and practical indoor / outdoor living spaces make this the perfect home for everyday living or a weekend retreat. A few of the outstanding features include: coffered ceilings, thick crown moldings and railings, dark hardwood floors, plantation shutters, double wine bar, a Wolf kitchen range, a conditioned two-car garage, screened-in porch, a copper water line, the list goes on. The home was also fitted with dual mini-split systems and a large Rinnai instant hot water heater: both energy efficient and budget friendly! As you enter you are greeted by a spacious living room and dining room combination which naturally flow into the modern kitchen. Finished with granite countertops, ceramic tile backsplash, and Wolf and GE appliances, The first floor primary bedroom with large ensuite bath enables one to enjoy all one floor living should they desire. A double chilled wine bar and powder room behind the kitchen complete the first floor living area. Moving upstairs, there is a generously sized living space in the front and two full bedrooms behind in the newly added dormers. A new full bath with ceramic tile flooring and shower, and stone vanity further complements the upstairs living space. Moving to the back of the house; the screened-in porch is perfect for summertime crabs feasts and the propane fire pit is great for summer evenings with friends and family. Plenty of parking in the back driveway or in the two-car garage which is heated, air conditioned and spray-foam insulated. A quick walk to Java Rock for a morning coffee or an easy stroll to the Marina’s or the beach. Rock Hall is a vibrant town with many great restaurants, a brewery, and many festivals like Pirates and Wenches and Fall Fest. You dont want to miss this remarkable home.

21191 W Sharp St, Rock Hall

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

$370,000

Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience. The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and en suite bath with dual vanities. Need even more space? The mostly finished basement adds approximately 600 sq. ft. of flexible living space. Plus the attached two car garage with plenty of room to park your vehicle and still have storage space. Outside, enjoy a stamped-concrete patio and fenced backyard—perfect for relaxing and entertaining. Recent updates include HVAC replaced in 2021, upgraded bathrooms, and additional cabinets and counter space in the kitchen. Just under 2 miles from historic downtown Chestertown, you’ll be close to restaurants, shopping, festivals, walking trail, the waterfront park, and everything town has to offer.

4 Beds ⋅ 3 Baths

Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience. The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and en suite bath with dual vanities. Need even more space? The mostly finished basement adds approximately 600 sq. ft. of flexible living space. Plus the attached two car garage with plenty of room to park your vehicle and still have storage space. Outside, enjoy a stamped-concrete patio and fenced backyard—perfect for relaxing and entertaining. Recent updates include HVAC replaced in 2021, upgraded bathrooms, and additional cabinets and counter space in the kitchen. Just under 2 miles from historic downtown Chestertown, you’ll be close to restaurants, shopping, festivals, walking trail, the waterfront park, and everything town has to offer.

123 Trafford Dr, Chestertown

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

$369,900

Welcome to this beautifully updated country farmhouse, where classic charm meets modern comfort in a serene rural setting. Thoughtfully renovated throughout, this inviting home offers a spacious first-floor primary suite, two additional bedrooms, and generous walk-in attic space—perfect for storage. The main level has been freshly painted and features new flooring, creating a bright, move-in-ready atmosphere. Efficient mini-splits provide comfortable climate control throughout the home, with capacity for one more unit if desired. Step outside through the newer French doors into a fully fenced backyard, ideal for pets, gardening, or simply enjoying the peaceful surroundings. Recent updates include 6 mini-splits, a new hot water heater (installed 11/25), a front roof that is 5–7 years old, and a rear roof just 5 years old with durable 50-year shingles. The third level boasts newly conditioned bonus spaces, offering flexible living or recreational options. Location is a true highlight. Situated minutes from the Sassafras River, a nearby marina, and popular restaurants including the Kitty Knight Inn and Restaurant, Fish Whistle, and Twinny’s. This property places waterfront dining and recreation right at your doorstep. You’re only one mile south of the Fredericktown boat ramp, making boating and water access effortless. Route 301 is an easy 10-minute drive for convenient travel north or south, and the home sits along the Chesapeake Scenic Byway—your gateway to charming waterfront towns such as Chesapeake City, Chestertown, and more. This remodeled farmhouse blends updated living with timeless country appeal and an unbeatable Eastern Shore location. Don’t miss the opportunity to make it yours.

3 Beds ⋅ 3 Baths

Welcome to this beautifully updated country farmhouse, where classic charm meets modern comfort in a serene rural setting. Thoughtfully renovated throughout, this inviting home offers a spacious first-floor primary suite, two additional bedrooms, and generous walk-in attic space—perfect for storage. The main level has been freshly painted and features new flooring, creating a bright, move-in-ready atmosphere. Efficient mini-splits provide comfortable climate control throughout the home, with capacity for one more unit if desired. Step outside through the newer French doors into a fully fenced backyard, ideal for pets, gardening, or simply enjoying the peaceful surroundings. Recent updates include 6 mini-splits, a new hot water heater (installed 11/25), a front roof that is 5–7 years old, and a rear roof just 5 years old with durable 50-year shingles. The third level boasts newly conditioned bonus spaces, offering flexible living or recreational options. Location is a true highlight. Situated minutes from the Sassafras River, a nearby marina, and popular restaurants including the Kitty Knight Inn and Restaurant, Fish Whistle, and Twinny’s. This property places waterfront dining and recreation right at your doorstep. You’re only one mile south of the Fredericktown boat ramp, making boating and water access effortless. Route 301 is an easy 10-minute drive for convenient travel north or south, and the home sits along the Chesapeake Scenic Byway—your gateway to charming waterfront towns such as Chesapeake City, Chestertown, and more. This remodeled farmhouse blends updated living with timeless country appeal and an unbeatable Eastern Shore location. Don’t miss the opportunity to make it yours.

13831 Augustine Herman Hwy, Galena

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

$487,000

SELLER-PAID 2-1 INTEREST RATE BUYDOWN AVAILABLE! Make homeownership more affordable with lower mortgage payments for the first two years! For example, based on an assumed 7.75% interest rate, buyers could enjoy a 5.75% rate in Year 1 (approximately $500/month savings), 6.75% in Year 2 (approximately $250/month savings), and 7.75% beginning in Year 3. That’s potentially $9,000 in savings over the first two years! Buyers may also have the opportunity to refinance if rates decrease, although refinancing is not guaranteed. Example only. Actual rates, payments, savings, and eligibility depend on loan terms and lender approval. Buyers must qualify at the full note rate, subject to lender requirements. Contact your lender for details. Welcome to 16 Howell Point Road in Betterton, Maryland, where small-town Eastern Shore charm meets comfortable living just a few blocks from beautiful Betterton Beach! This inviting 3-bedroom, 3-bath home offers plenty of space inside and out. The full walk-out basement is partially finished, providing additional living space with endless possibilities for a family room, home office, recreation area, guest space, or workshop. Step outside onto the back deck overlooking the fenced-in backyard, perfect for pets, entertaining, gardening, or simply relaxing at the end of the day. The large driveway provides plenty of parking, while the spacious backyard offers room to enjoy the outdoors. One of the home’s best features comes each evening—gorgeous sunsets stretching across the rolling hills and surrounding farmland, creating a peaceful Eastern Shore backdrop right from your own backyard. Located just blocks from Betterton Beach and the Chesapeake Bay, you’ll have easy access to swimming, boating, fishing, kayaking, and everything that makes this waterfront community such a special place to call home. Whether you’re searching for a full-time residence, weekend getaway, or Eastern Shore retreat, 16 Howell Point Road is ready to welcome you home!

3 Beds ⋅ 3 Baths

SELLER-PAID 2-1 INTEREST RATE BUYDOWN AVAILABLE! Make homeownership more affordable with lower mortgage payments for the first two years! For example, based on an assumed 7.75% interest rate, buyers could enjoy a 5.75% rate in Year 1 (approximately $500/month savings), 6.75% in Year 2 (approximately $250/month savings), and 7.75% beginning in Year 3. That’s potentially $9,000 in savings over the first two years! Buyers may also have the opportunity to refinance if rates decrease, although refinancing is not guaranteed. Example only. Actual rates, payments, savings, and eligibility depend on loan terms and lender approval. Buyers must qualify at the full note rate, subject to lender requirements. Contact your lender for details. Welcome to 16 Howell Point Road in Betterton, Maryland, where small-town Eastern Shore charm meets comfortable living just a few blocks from beautiful Betterton Beach! This inviting 3-bedroom, 3-bath home offers plenty of space inside and out. The full walk-out basement is partially finished, providing additional living space with endless possibilities for a family room, home office, recreation area, guest space, or workshop. Step outside onto the back deck overlooking the fenced-in backyard, perfect for pets, entertaining, gardening, or simply relaxing at the end of the day. The large driveway provides plenty of parking, while the spacious backyard offers room to enjoy the outdoors. One of the home’s best features comes each evening—gorgeous sunsets stretching across the rolling hills and surrounding farmland, creating a peaceful Eastern Shore backdrop right from your own backyard. Located just blocks from Betterton Beach and the Chesapeake Bay, you’ll have easy access to swimming, boating, fishing, kayaking, and everything that makes this waterfront community such a special place to call home. Whether you’re searching for a full-time residence, weekend getaway, or Eastern Shore retreat, 16 Howell Point Road is ready to welcome you home!

16 Howell Point Rd, Betterton

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

$259,000

Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own. The home provides a nice combination of living space, comfortable bedrooms, and the convenience of two full bathrooms. Whether you're a first-time buyer, looking to downsize, or simply searching for a home in the Chestertown area, this property is worth a look. Conveniently located near downtown Chestertown, local shopping, dining, and everyday amenities. Some listing photos have been digitally enhanced for presentation purposes. Certain furnishings and décor may have been virtually modified or added. No material structural features of the property have been altered

3 Beds ⋅ 2 Baths

Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own. The home provides a nice combination of living space, comfortable bedrooms, and the convenience of two full bathrooms. Whether you're a first-time buyer, looking to downsize, or simply searching for a home in the Chestertown area, this property is worth a look. Conveniently located near downtown Chestertown, local shopping, dining, and everyday amenities. Some listing photos have been digitally enhanced for presentation purposes. Certain furnishings and décor may have been virtually modified or added. No material structural features of the property have been altered

115 Chester Arms Dr, Chestertown

Listing courtesy of Samson Properties. Contact:

$359,000

This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its handcrafted touches. The living room features re-stored hardwood floors and a cozy gas fireplace, creating a warm cozy space. Natural light pours into the open and airy kitchen with newer painted cabinets, stenciled floors, shiplap walls, and a laundry/half bath just off kitchen. From the kitchen step straight into the private fenced courtyard, your own peaceful retreat. With a large brick patio, privacy plantings, and ample garden space to create your own haven. Upstairs you'll find two nice sized bedrooms, re-finished hardwood floors and a good size full bath with walk in shower. If you're looking for that quiet oasis in a downtown location, this is it!

2 Beds ⋅ 2 Baths

This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its handcrafted touches. The living room features re-stored hardwood floors and a cozy gas fireplace, creating a warm cozy space. Natural light pours into the open and airy kitchen with newer painted cabinets, stenciled floors, shiplap walls, and a laundry/half bath just off kitchen. From the kitchen step straight into the private fenced courtyard, your own peaceful retreat. With a large brick patio, privacy plantings, and ample garden space to create your own haven. Upstairs you'll find two nice sized bedrooms, re-finished hardwood floors and a good size full bath with walk in shower. If you're looking for that quiet oasis in a downtown location, this is it!

101 S College Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$281,000

Significant price correction! Package offering for two adjacent lots in historic Chestertown. The combined package is for over a quarter of an acre, zoned R-5, within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops, restaurants, waterfront activities, and all that historic Chestertown has to offer. Water and sewer hookups available. No property address has yet been assigned to the 9,381 sq ft lot; the 3,097 parcel is designated as 620 Cannon Street. Buyer to verify zoning, permitted uses, building requirements, and utility availability. Each lot is listed separately in separate listings.

Cannon Street, Chestertown

Listing courtesy of Taylor Properties. Contact:

$196,000

Major price reduction! Rare opportunity to own a cleared 9,381 sq. ft, nearly a quarter acre, lot within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops, restaurants, waterfront activities, and all that historic Chestertown has to offer. Water and sewer hookups available. The adjacent lot at the corner of Cannon and Lynchburg is also available for purchase. No property address has yet been assigned to this lot. Buyer to verify zoning, permitted uses, building requirements, and utility availability.

Cannon Street, Chestertown

Listing courtesy of Taylor Properties. Contact:

$730,000

Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A freshly sealed asphalt drive curves to a welcoming front entry, where a classic brick facade sets a warm, distinctive tone. A two-car attached garage provides direct entry and everyday convenience. * Inside, the open kitchen—complete with breakfast area—flows seamlessly into a spacious family room, perfect for everyday living. A separate dining room makes entertaining easy. The family room is an elegant space for gatherings, while a dedicated sunroom and screened-in porch invite you to enjoy the serene, park-like backyard in every season. The large deck offers an additional outdoor retreat with tranquil wooded views. * The generous primary suite features an en-suite bath, while two additional bedrooms makes for flexible bedroom accommodations for family, guests, or a quiet work-from-home office space. A convenient half bath and main-floor laundry round out the practical layout. A full basement offers abundant storage and endless potential for an artist’s studio, workshop, recreation room, or finished expansion. * With its pristine landscaping, mature plantings, and verdant views, this exceptional home is a rare find. And the location is second to none—just minutes from historic downtown Chestertown. Stroll tree-lined streets to discover specialty shops, art galleries, restaurants, and the Saturday Farmers Market at Fountain Park. Washington College, the nation’s tenth-oldest college, anchors the community with year-round cultural events, lectures, and performances. Outdoor enthusiasts will love the nearby Rail Trail, Sultana Lawrence Wetlands Preserve, marinas, and public boat launches providing easy access to the Chester River and Chesapeake Bay. First Friday celebrations, waterfront festivals, and a vibrant arts scene make Chestertown one of the Eastern Shore’s most beloved places to call home.

3 Beds ⋅ 3 Baths

Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A freshly sealed asphalt drive curves to a welcoming front entry, where a classic brick facade sets a warm, distinctive tone. A two-car attached garage provides direct entry and everyday convenience. * Inside, the open kitchen—complete with breakfast area—flows seamlessly into a spacious family room, perfect for everyday living. A separate dining room makes entertaining easy. The family room is an elegant space for gatherings, while a dedicated sunroom and screened-in porch invite you to enjoy the serene, park-like backyard in every season. The large deck offers an additional outdoor retreat with tranquil wooded views. * The generous primary suite features an en-suite bath, while two additional bedrooms makes for flexible bedroom accommodations for family, guests, or a quiet work-from-home office space. A convenient half bath and main-floor laundry round out the practical layout. A full basement offers abundant storage and endless potential for an artist’s studio, workshop, recreation room, or finished expansion. * With its pristine landscaping, mature plantings, and verdant views, this exceptional home is a rare find. And the location is second to none—just minutes from historic downtown Chestertown. Stroll tree-lined streets to discover specialty shops, art galleries, restaurants, and the Saturday Farmers Market at Fountain Park. Washington College, the nation’s tenth-oldest college, anchors the community with year-round cultural events, lectures, and performances. Outdoor enthusiasts will love the nearby Rail Trail, Sultana Lawrence Wetlands Preserve, marinas, and public boat launches providing easy access to the Chester River and Chesapeake Bay. First Friday celebrations, waterfront festivals, and a vibrant arts scene make Chestertown one of the Eastern Shore’s most beloved places to call home.

216 Birch Run Rd, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

$1,500,000

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 Hall. Opened in June 2022, Blue Heron has quickly developed a loyal following among residents and visitors, with waits for tables common during peak dining hours. The building was completely renovated inside and out in early 2022 and offers more than 4,000 square feet across two levels. The main level features an immaculate commercial kitchen, indoor and outdoor cold storage, dining and bar areas, and extensive indoor/outdoor service space. Furniture, fixtures and equipment are less than five years old, with a complete inventory available upon request. Indoor seating accommodates approximately 55 guests at tables plus 24 bar seats. Outdoor dining expands capacity with approximately 42 table seats and 26 additional seats at the tiki bar, bringing total seasonal seating capacity to approximately 147. More than 1,000 square feet on the second floor includes three inn rooms that are not currently being rented, providing an opportunity for a new owner to establish an additional lodging component and year-round revenue stream. An additional office and storage areas are also located upstairs. The property offers 24 on-site parking spaces, with additional parking currently available along Coleman Road and Route 20. Located just two blocks from Ferry Park Beach and within walking and biking distance of several Rock Hall marinas, Blue Heron is well positioned to serve both the local community and visitors to this popular Chesapeake Bay town. The restaurant currently operates approximately 27 hours per week, Wednesday through Sunday, and traditionally closes for a few weeks during the winter. Sale includes the real estate and operating business. Additional business information and FF&E inventory are available to qualified buyers upon execution of an NDA.

20658 Wilkins Ave, Rock Hall

Listing courtesy of TTR Sotheby's International Realty. Contact:

$85,000

Price correction! Here is your chance to get one of the last vacant lots in downtown Chestertown. And as an added bonus, the lot backs up to the Rail Trail for easy access to the Chester River waterfront and downtown Chestertown. Situated at the corner of Lynchburg and Cannon Streets, this 3,096 sq ft lot can be purchased alone, or along with the recently subdivided adjacent lot. Water and sewer hookups available. Buyer to confirm with the Town of Chestertown allowable uses and the use of the previous water/sewer allocation.

620 Cannon St, Chestertown

Listing courtesy of Taylor Properties. Contact:

$399,900

Welcome to 8630 Elm Road, where comfortable living meets the relaxed pace of Maryland’s Eastern Shore. Located in the water-oriented Tolchester Estates community, this refreshed five-bedroom, 2.5-bath home offers approximately 1,936 square feet of flexible living space on about 0.38 acres. Begin the day with a quiet moment on the furnished front porch, then enjoy a versatile interior with room to work from home, welcome overnight guests, and spend time together. The fifth bedroom can serve as a private home office, guest room, hobby room, or other flexible space separate from the main living area. Attractive ceiling fans throughout the home add comfort and style. The refreshed kitchen features bright white cabinetry, a French-door refrigerator, stainless-steel appliances, and a spacious adjoining dining area with room to gather and enjoy meals. The main living ar Start the day with a quiet moment on the furnished front porch, then enjoy a layout with room to work from home, welcome guests, and spend time together. The fifth bedroom can serve as a home office separate from the main living area, a guest room, or a hobby space. Attractive ceiling fans throughout the home add both comfort and style. The updated kitchen features bright white cabinetry, a French-door refrigerator, and stainless-steel appliances. A new white porcelain herringbone backsplash is scheduled for installation on October 8. The spacious kitchen and dining area offer room to gather and enjoy a meal. The main living area is anchored by a stylish electric fireplace with custom floating shelving, creating a warm focal point for the home. Adjustable fireplace settings add to the cozy atmosphere. Step outside to the expanded deck, unwind in the hot tub, or gather around the fire pit. Imagine sharing hot chocolate and s’mores on a crisp fall evening, or taking a quiet moment to enjoy the setting and watch for local wildlife. Boating enthusiasts will appreciate the nearby seasonal marina, with restaurants and a dive bar about three blocks away, and a public boat ramp approximately one mile away, providing convenient access to the area’s waterways. The expansive driveway offers parking for up to eight vehicles, with room for multiple cars, larger vehicles, and weekend guests. The partially finished one-car garage can become a game room, hobby area, home gym, or extra gathering space. Additional features include an approximately two-year-old water heater and a private well with a water-treatment and softening system, professionally serviced in 2025 with a new Clack neutralizer head installed. Furnishings throughout the home, including the porch furniture, are included. Though built in 2006, the home has been gently enjoyed primarily as a second home or vacation getaway and has received updates and improvements, including stainless-steel appliances, a built-in electric fireplace, and the newer water heater. This home could be a great fit if you’re: Looking for a second home or vacation getaway you can enjoy yourself and explore renting part-time when you’re away. Looking for an investment property with a history of income from both traditional and short-term rentals. Certain loan programs may consider rental income when evaluating an investment property; eligibility depends on lender guidelines. Looking for a primary residence with flexible living space and convenient access to the marina. Preferred Lender Credit: Eligible buyers may receive a lender credit when using the preferred lender. Financing programs and credits are subject to eligibility, underwriting, and lender approval. Whether you’re looking for a primary residence, a weekend retreat, or a home designed for entertaining, 8630 Elm Road offers space, versatility, thoughtful updates, and the Eastern Shore lifestyle in one inviting package. Ready to see it in person? Schedule your private showing today through the listing’s appointment link!

5 Beds ⋅ 3 Baths

Welcome to 8630 Elm Road, where comfortable living meets the relaxed pace of Maryland’s Eastern Shore. Located in the water-oriented Tolchester Estates community, this refreshed five-bedroom, 2.5-bath home offers approximately 1,936 square feet of flexible living space on about 0.38 acres. Begin the day with a quiet moment on the furnished front porch, then enjoy a versatile interior with room to work from home, welcome overnight guests, and spend time together. The fifth bedroom can serve as a private home office, guest room, hobby room, or other flexible space separate from the main living area. Attractive ceiling fans throughout the home add comfort and style. The refreshed kitchen features bright white cabinetry, a French-door refrigerator, stainless-steel appliances, and a spacious adjoining dining area with room to gather and enjoy meals. The main living ar Start the day with a quiet moment on the furnished front porch, then enjoy a layout with room to work from home, welcome guests, and spend time together. The fifth bedroom can serve as a home office separate from the main living area, a guest room, or a hobby space. Attractive ceiling fans throughout the home add both comfort and style. The updated kitchen features bright white cabinetry, a French-door refrigerator, and stainless-steel appliances. A new white porcelain herringbone backsplash is scheduled for installation on October 8. The spacious kitchen and dining area offer room to gather and enjoy a meal. The main living area is anchored by a stylish electric fireplace with custom floating shelving, creating a warm focal point for the home. Adjustable fireplace settings add to the cozy atmosphere. Step outside to the expanded deck, unwind in the hot tub, or gather around the fire pit. Imagine sharing hot chocolate and s’mores on a crisp fall evening, or taking a quiet moment to enjoy the setting and watch for local wildlife. Boating enthusiasts will appreciate the nearby seasonal marina, with restaurants and a dive bar about three blocks away, and a public boat ramp approximately one mile away, providing convenient access to the area’s waterways. The expansive driveway offers parking for up to eight vehicles, with room for multiple cars, larger vehicles, and weekend guests. The partially finished one-car garage can become a game room, hobby area, home gym, or extra gathering space. Additional features include an approximately two-year-old water heater and a private well with a water-treatment and softening system, professionally serviced in 2025 with a new Clack neutralizer head installed. Furnishings throughout the home, including the porch furniture, are included. Though built in 2006, the home has been gently enjoyed primarily as a second home or vacation getaway and has received updates and improvements, including stainless-steel appliances, a built-in electric fireplace, and the newer water heater. This home could be a great fit if you’re: Looking for a second home or vacation getaway you can enjoy yourself and explore renting part-time when you’re away. Looking for an investment property with a history of income from both traditional and short-term rentals. Certain loan programs may consider rental income when evaluating an investment property; eligibility depends on lender guidelines. Looking for a primary residence with flexible living space and convenient access to the marina. Preferred Lender Credit: Eligible buyers may receive a lender credit when using the preferred lender. Financing programs and credits are subject to eligibility, underwriting, and lender approval. Whether you’re looking for a primary residence, a weekend retreat, or a home designed for entertaining, 8630 Elm Road offers space, versatility, thoughtful updates, and the Eastern Shore lifestyle in one inviting package. Ready to see it in person? Schedule your private showing today through the listing’s appointment link!

8630 Elm Rd, Chestertown

Listing courtesy of Save 6, Incorporated. Contact:

$334,900

Adorable 3BR/2BA expanded Farm style home located on a spacious lot in the desirable neighborhood of the Town of Rock Hall. Make your way to the country style covered front porch and the door to your forever home. Step inside a home filled with original charm and character throughout offering an abundance of natural light, crown moldings, luxury flooring, and an open main floor plan. The main floor offers a large entry with a view of the living room, dining room, stunning kitchen, and a beautiful open wood staircase. The stunning kitchen boasts a vaulted ceiling, ample cabinets finished with crown moldings, stainless steel appliances (including an electric cooktop and lower wall oven), granite countertops, and a double stainless sink. Just off the entryway is a full bath with laundry. On the second floor are two sizable secondary bedrooms, a larger primary bedroom with access to one of the secondary bedrooms, and a full bath featuring a walk-in shower with a spa feature. From the kitchen's sliding doors, step onto a spacious wood deck overlooking the semi-fenced yard, which offers green space, numerous possibilities, and a detached garage. This move-in-ready home is ideal for any new homeowner and is located near shopping, restaurants and commuter routes.

3 Beds ⋅ 2 Baths

Adorable 3BR/2BA expanded Farm style home located on a spacious lot in the desirable neighborhood of the Town of Rock Hall. Make your way to the country style covered front porch and the door to your forever home. Step inside a home filled with original charm and character throughout offering an abundance of natural light, crown moldings, luxury flooring, and an open main floor plan. The main floor offers a large entry with a view of the living room, dining room, stunning kitchen, and a beautiful open wood staircase. The stunning kitchen boasts a vaulted ceiling, ample cabinets finished with crown moldings, stainless steel appliances (including an electric cooktop and lower wall oven), granite countertops, and a double stainless sink. Just off the entryway is a full bath with laundry. On the second floor are two sizable secondary bedrooms, a larger primary bedroom with access to one of the secondary bedrooms, and a full bath featuring a walk-in shower with a spa feature. From the kitchen's sliding doors, step onto a spacious wood deck overlooking the semi-fenced yard, which offers green space, numerous possibilities, and a detached garage. This move-in-ready home is ideal for any new homeowner and is located near shopping, restaurants and commuter routes.

5862 N Main St, Rock Hall

Listing courtesy of LPT Realty, LLC. Contact:

$585,000

Welcome to your dream home in Worton, MD! This stunning center hall Colonial-style property boasts 4 bedrooms, 2.5 bathrooms, and sits on over 6 acres of picturesque land. As you approach the home, you'll be greeted by a charming circular driveway and an oversized detached 2 car garage, perfect for storing all your vehicles and outdoor equipment. Inside, the home features beautiful hardwood floors throughout, adding warmth and character to the space. The kitchen is a chef's delight, with soapstone countertops, gas cooking and ample cabinet space for all your culinary needs. Cozy up by the fireplace; perfect for relaxing on chilly evenings. This property has a metal roof and owned solar panels, allowing for energy-efficient living and potential cost savings on utilities. With a shed for additional storage and plenty of space to roam on the expansive grounds, this property offers the perfect blend of comfort and tranquility and just a short drive to Chestertown. Don't miss your chance to make this idyllic retreat your own – schedule a showing today!

4 Beds ⋅ 3 Baths

Welcome to your dream home in Worton, MD! This stunning center hall Colonial-style property boasts 4 bedrooms, 2.5 bathrooms, and sits on over 6 acres of picturesque land. As you approach the home, you'll be greeted by a charming circular driveway and an oversized detached 2 car garage, perfect for storing all your vehicles and outdoor equipment. Inside, the home features beautiful hardwood floors throughout, adding warmth and character to the space. The kitchen is a chef's delight, with soapstone countertops, gas cooking and ample cabinet space for all your culinary needs. Cozy up by the fireplace; perfect for relaxing on chilly evenings. This property has a metal roof and owned solar panels, allowing for energy-efficient living and potential cost savings on utilities. With a shed for additional storage and plenty of space to roam on the expansive grounds, this property offers the perfect blend of comfort and tranquility and just a short drive to Chestertown. Don't miss your chance to make this idyllic retreat your own – schedule a showing today!

12118 Still Pond Creek Rd, Worton

Listing courtesy of Patterson-Schwartz-Hockessin. Contact:

$515,000

Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the kitchen and living rooms. Kitchen features stainless steel appliances, granite countertops and wood cabinets. Second floor has 5 bedrooms and 2 full baths. Partially finished full basement has another full bathroom and offers a range of possibilities for the next owner. This home has more room and storage than you could imagine. The Villages at Kennedyville is a quiet, local community. Less than 90 minutes to Philadelphia and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Close to Turners Creek State Park, Betterton Beach and the restaurants/marinas in Galena on the Sassafras River. Just a few minutes to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals and an award-winning weekly Farmer's Market. Seller will convey a brand new Carrier HVAC unit with the sale to replace the first floor one.

7 Beds ⋅ 5 Baths

Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the kitchen and living rooms. Kitchen features stainless steel appliances, granite countertops and wood cabinets. Second floor has 5 bedrooms and 2 full baths. Partially finished full basement has another full bathroom and offers a range of possibilities for the next owner. This home has more room and storage than you could imagine. The Villages at Kennedyville is a quiet, local community. Less than 90 minutes to Philadelphia and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Close to Turners Creek State Park, Betterton Beach and the restaurants/marinas in Galena on the Sassafras River. Just a few minutes to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals and an award-winning weekly Farmer's Market. Seller will convey a brand new Carrier HVAC unit with the sale to replace the first floor one.

11960 Flour Mill St, Kennedyville

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

$480,000

PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light. The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space to enjoy your morning coffee or unwind while overlooking the backyard. You'll also find a formal dining room for hosting special occasions, a welcoming living room, and a cozy family room that provides plenty of space for everyday living. Downstairs, the finished basement offers versatile additional living space ideal for a recreation room, home theater, fitness area, playroom, or home office. There is enough space to do all of it. The unfinished area has full laundry and ample storage. Upstairs, the expansive owner's suite serves as a private retreat, complete with a generous walk-in closet and an ensuite bathroom featuring a soaking tub. Two additional bedrooms each offer large closets and ample space for family, guests, or a home office. A full bathroom conveniently located off the second-floor sitting area completes the upper level. Step outside to your own private backyard oasis. The landscaped yard features a refreshing in-ground swimming pool with a new tile finish and a new filtration system, making it ready for years of enjoyment. A new deck with a privacy wall extends from the home, providing the perfect setting for outdoor dining, entertaining, or relaxing poolside. Additional highlights include a large storage shed and a newly installed rock bed surrounding the pool deck that enhances both beauty and low-maintenance landscaping. For added peace of mind, the home also features a roof that is only two years old. Combining spacious living areas, thoughtful updates, exceptional outdoor amenities, and a desirable location in historic Chestertown, this home truly has something for everyone. Don't miss the opportunity to make this exceptional property your next home!

3 Beds ⋅ 3 Baths

PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light. The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space to enjoy your morning coffee or unwind while overlooking the backyard. You'll also find a formal dining room for hosting special occasions, a welcoming living room, and a cozy family room that provides plenty of space for everyday living. Downstairs, the finished basement offers versatile additional living space ideal for a recreation room, home theater, fitness area, playroom, or home office. There is enough space to do all of it. The unfinished area has full laundry and ample storage. Upstairs, the expansive owner's suite serves as a private retreat, complete with a generous walk-in closet and an ensuite bathroom featuring a soaking tub. Two additional bedrooms each offer large closets and ample space for family, guests, or a home office. A full bathroom conveniently located off the second-floor sitting area completes the upper level. Step outside to your own private backyard oasis. The landscaped yard features a refreshing in-ground swimming pool with a new tile finish and a new filtration system, making it ready for years of enjoyment. A new deck with a privacy wall extends from the home, providing the perfect setting for outdoor dining, entertaining, or relaxing poolside. Additional highlights include a large storage shed and a newly installed rock bed surrounding the pool deck that enhances both beauty and low-maintenance landscaping. For added peace of mind, the home also features a roof that is only two years old. Combining spacious living areas, thoughtful updates, exceptional outdoor amenities, and a desirable location in historic Chestertown, this home truly has something for everyone. Don't miss the opportunity to make this exceptional property your next home!

129 Trafford Dr, Chestertown

Listing courtesy of Elevated Real Estate Solutions. Contact:

$725,000

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 your private dock, boat lift, and plenty of space for kayaks, paddleboards, and other water toys. The home features three bedrooms plus a walkout basement ready for your vision—ideal for creating additional living space, a recreation area, or guest accommodations. With easy access to points north and located less than 10 minutes from Middletown, Delaware, this property is perfectly suited as a weekend getaway or a comfortable downsized waterfront retreat.

3 Beds ⋅ 2 Baths

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 your private dock, boat lift, and plenty of space for kayaks, paddleboards, and other water toys. The home features three bedrooms plus a walkout basement ready for your vision—ideal for creating additional living space, a recreation area, or guest accommodations. With easy access to points north and located less than 10 minutes from Middletown, Delaware, this property is perfectly suited as a weekend getaway or a comfortable downsized waterfront retreat.

32745 Hunt Ln, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

$269,000

Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

3 Beds ⋅ 2 Baths

Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

10540 Tonopah Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$330,000

Adorable arts & craft style home with many upgrades and amenities. The original wood floors are warm and welcoming, wile the custom cabinetry and concrete countertops and sinks add an elegant modern touch. Two plus bedrooms and a custom built sleeping loft provide enough room for occasional guests. Fixed stairs to the attic offer room to expand. The Chesapeake Bay is a short walk to the end of the road where you can launch a kayak or just enjoy the water views. Just outside the quaint town of Rock Hall, this charming cottage would make a great vacation or retirement home.

2 Beds ⋅ 2 Baths

Adorable arts & craft style home with many upgrades and amenities. The original wood floors are warm and welcoming, wile the custom cabinetry and concrete countertops and sinks add an elegant modern touch. Two plus bedrooms and a custom built sleeping loft provide enough room for occasional guests. Fixed stairs to the attic offer room to expand. The Chesapeake Bay is a short walk to the end of the road where you can launch a kayak or just enjoy the water views. Just outside the quaint town of Rock Hall, this charming cottage would make a great vacation or retirement home.

21352 Allens Ln, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$699,000

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 vaulted ceilings and has access to a private pier and dock; it’s perfect for boating, fishing, crabbing, or just enjoying the outdoors. Located in Rock Hall, Maryland, known for hunting, fishing, and Chesapeake Bay boating, this property is being sold As-Is, offering a chance to remodel and complete your vision. Current owners originally built the house in 1986 as a cabin with a later add-on to the original structure. Rock Hall is a waterfront town located directly on the National Chesapeake Scenic Byway in Kent County. The boat pier will need extensive work and is non-operational. Property is being sold AS-IS with a Right-to-Inspect. Tremendous opportunity for a wooded, waterfront residence with some sweat equity.

4 Beds ⋅ 3 Baths

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 vaulted ceilings and has access to a private pier and dock; it’s perfect for boating, fishing, crabbing, or just enjoying the outdoors. Located in Rock Hall, Maryland, known for hunting, fishing, and Chesapeake Bay boating, this property is being sold As-Is, offering a chance to remodel and complete your vision. Current owners originally built the house in 1986 as a cabin with a later add-on to the original structure. Rock Hall is a waterfront town located directly on the National Chesapeake Scenic Byway in Kent County. The boat pier will need extensive work and is non-operational. Property is being sold AS-IS with a Right-to-Inspect. Tremendous opportunity for a wooded, waterfront residence with some sweat equity.

21610 Hidden Creek Dr, Rock Hall

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

201 N Lynchburg St Unit LOTS 4, 5, 6 & 7, Chestertown

$300,000

4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be sold with mls MDKE2006844

201 N Lynchburg St Unit LOTS 4, 5, 6 & 7, Chestertown

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

$500,000

A great opportunity for community mission driven organizations. The church and 5 additional parcels are all offered separately or together. Located in the heart of Chestertown, this charming church of a little over 3,500 square feet offers a unique opportunity for continued use as a place of worship, community gathering space, or potential conversion. The property features wheelchair accessibility, on-site parking, and a layout ideal for a variety of uses. With its peaceful setting and classic structure, this building is ready to serve its next purpose. Also available with mls MDKE2006846 additionally

201 N Lynchburg St, Chestertown

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

$259,900

*Open Every Tuesdy and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Priced at $259,900, this home also comes with a $5,000 builder incentive plus ½% ($1,299) through our lender partnership—making it possible to own for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations.

3 Beds ⋅ 2 Baths

*Open Every Tuesdy and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Priced at $259,900, this home also comes with a $5,000 builder incentive plus ½% ($1,299) through our lender partnership—making it possible to own for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations.

115 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

$1,595,000

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 appreciate the private dock, complete with a boat lift and Jet Ski lift and the location on the river. This charming four-bedroom home blends timeless character with everyday functionality. The thoughtfully designed floor plan features a first-floor primary suite, hardwood floors throughout, and spacious living areas ideal for both relaxing and entertaining. The detached garage includes a private apartment with an additional bedroom and an additional full bathroom, offering excellent space for guests or extended family. Including the garage apartment, this property has 5 bedrooms and 3 full baths, The expansive kitchen and living area open through sliding glass doors to a patio, screened porch, and beautifully landscaped lawn all overlooking the water, creating seamless indoor-outdoor living with broad water views. Mature trees provide shade, beauty, and privacy throughout the property. Conveniently located just minutes from Georgetown, you'll enjoy easy access to restaurants and a sought-after boating destination. Whether your passion is waterskiing, wakeboarding, paddleboarding, fishing, or peaceful kayaking, this location offers endless opportunities to enjoy life on the water. This is a property that truly should be experienced in person to appreciate its unique setting, exceptional amenities, and waterfront lifestyle.

4 Beds ⋅ 2 Baths

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 appreciate the private dock, complete with a boat lift and Jet Ski lift and the location on the river. This charming four-bedroom home blends timeless character with everyday functionality. The thoughtfully designed floor plan features a first-floor primary suite, hardwood floors throughout, and spacious living areas ideal for both relaxing and entertaining. The detached garage includes a private apartment with an additional bedroom and an additional full bathroom, offering excellent space for guests or extended family. Including the garage apartment, this property has 5 bedrooms and 3 full baths, The expansive kitchen and living area open through sliding glass doors to a patio, screened porch, and beautifully landscaped lawn all overlooking the water, creating seamless indoor-outdoor living with broad water views. Mature trees provide shade, beauty, and privacy throughout the property. Conveniently located just minutes from Georgetown, you'll enjoy easy access to restaurants and a sought-after boating destination. Whether your passion is waterskiing, wakeboarding, paddleboarding, fishing, or peaceful kayaking, this location offers endless opportunities to enjoy life on the water. This is a property that truly should be experienced in person to appreciate its unique setting, exceptional amenities, and waterfront lifestyle.

14046 Tockwogh Ln, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

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How much is your home worth?