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Waterfront living on Grays Inn Creek, just five minutes from Rock Hall. Situated on a private half-acre lot with protected western-facing views, this home offers beautiful sunsets, 3–4 feet MLW, and easy boating access to the Chester River, Chestertown, Kent Narrows, and Rock Hall. The home has seen numerous updates over the past six years, including new siding, roof, HVAC, LVP flooring, carpet, an updated kitchen and main-level bathroom, appliances, and improvements to the pier. Water views take center stage from the dining area, living room, and main bedrooms, while the manageable size and low-maintenance updates make this an easy waterfront property to enjoy. The property offers plenty of privacy and parking, along with a detached garage and carport. The protected setting on Grays Inn Creek combines peaceful waterfront living with convenient access to town and some of the best boating destinations on the Upper Eastern Shore. An affordable opportunity to own waterfront near Rock Hall without taking on a large property or extensive upkeep.

21728 Sunnyside Ave, Rock Hall

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

Selling Office: Unrepresented.

$625,000

Bayfront condo with exceptional views, located in the heart of Rock Hall! Beautiful open living space for entertaining, featuring a propane fireplace and bayfront balcony with awning. The eat-in kitchen features updated countertops and a Bosch electric range. The primary bedroom has its own bayfront balcony and an updated attached bathroom. Two additional bedrooms share a full bathroom. The third-floor bedroom has a fantastic view and could be used as an office, studio, or overflow space for guests . On the ground floor, the bayfront storage room is a great space to keep fishing poles, kayak, or pool floaties to use at the condo pool! One-car garage with additional outside parking, as well as communal overflow space for guests. Tilghman’s Landing condo is a beautiful waterfront condo association! Located in the heart of everything, yet tucked away from the hustle and bustle. Enjoy the pool in the summertime and never miss a sunset on the balcony. A sandy beach is located just outside the association, and the Rock Hall beach is just down the street. Short distance to ample restaurants, shops, and marinas.

Bayfront condo with exceptional views, located in the heart of Rock Hall! Beautiful open living space for entertaining, featuring a propane fireplace and bayfront balcony with awning. The eat-in kitchen features updated countertops and a Bosch electric range. The primary bedroom has its own bayfront balcony and an updated attached bathroom. Two additional bedrooms share a full bathroom. The third-floor bedroom has a fantastic view and could be used as an office, studio, or overflow space for guests . On the ground floor, the bayfront storage room is a great space to keep fishing poles, kayak, or pool floaties to use at the condo pool! One-car garage with additional outside parking, as well as communal overflow space for guests. Tilghman’s Landing condo is a beautiful waterfront condo association! Located in the heart of everything, yet tucked away from the hustle and bustle. Enjoy the pool in the summertime and never miss a sunset on the balcony. A sandy beach is located just outside the association, and the Rock Hall beach is just down the street. Short distance to ample restaurants, shops, and marinas.

20563 Rock Hall Ave Unit 16, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Gunther-McClary Real Estate.

$617,500

Spacious in-town home with coastal charm, just 1 block from the Rock Hall beach on the Chesapeake Bay! This home offers a luxe front porch, as well as a screened-in porch, perfect for meals and entertaining. The large family room boasts a gas fireplace, built-in shelving, wood ceilings, and a sunny balcony featuring a striped awning. The eat-in kitchen has updated appliances and ample room; it opens up to the front sitting room. Just around the corner is the light-filled formal dining room. Two first-floor bedrooms share a full bathroom. Two additional bedrooms upstairs share a full bathroom. This home offers the sought after first floor living option, with ample room for guests. There is a two-car garage with interior access and plenty of room for storage, hard to find in Rock Hall. The outside space has been lovingly landscaped, including a beautiful perennial pollinator garden running the length of the driveway. This property is move-in ready for the summer! A short distance to the Rock Hall beach, many dining options, ample marinas, and shops. Don’t miss this in-town gem! This home is move in ready. The sellers will consider including some contents.

4 Beds ⋅ 2 Baths

Spacious in-town home with coastal charm, just 1 block from the Rock Hall beach on the Chesapeake Bay! This home offers a luxe front porch, as well as a screened-in porch, perfect for meals and entertaining. The large family room boasts a gas fireplace, built-in shelving, wood ceilings, and a sunny balcony featuring a striped awning. The eat-in kitchen has updated appliances and ample room; it opens up to the front sitting room. Just around the corner is the light-filled formal dining room. Two first-floor bedrooms share a full bathroom. Two additional bedrooms upstairs share a full bathroom. This home offers the sought after first floor living option, with ample room for guests. There is a two-car garage with interior access and plenty of room for storage, hard to find in Rock Hall. The outside space has been lovingly landscaped, including a beautiful perennial pollinator garden running the length of the driveway. This property is move-in ready for the summer! A short distance to the Rock Hall beach, many dining options, ample marinas, and shops. Don’t miss this in-town gem! This home is move in ready. The sellers will consider including some contents.

20694 Mercer Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Rock Hall Properties Real Estate.

$615,000

The Pearce House has been a testament to fine Eastlake Victorian architecture since it was constructed by famous early Eastern Shore builder H.M. Stuart for Judge James Pearce who held the highest court in the State. The home boasts 6 fireplaces, ornate millwork all over, stained glass windows, soaring ceilings, massive pocket doors, spacious rooms, and surprisingly ample closet space. Homes aren't built like this anymore making adventuring the halls an absolute treat. Water views can be found from various windows of the home with specific angles highlighted seasonally. Outdoor living is celebrated with screened in porch flowing out back from the kitchen, covered front entry porch and second floor covered sleeping porch. The yard itself is a sanctuary with mature azaleas, magnolia, and gingko creating a calming setting. There is a driveway and your car can just stay there because this home is located just blocks walking from all of the dining, shopping, and culture that Chestertown has to offer. This home is part of the Maryland Historic Trust. Own a piece of American history less than two hours from DC, Baltimore, and Philadelphia while enjoying the walkable lifestyle of Chestertown's Historic District. **Interior professional photos are coming soon and are going to be really special**

The Pearce House has been a testament to fine Eastlake Victorian architecture since it was constructed by famous early Eastern Shore builder H.M. Stuart for Judge James Pearce who held the highest court in the State. The home boasts 6 fireplaces, ornate millwork all over, stained glass windows, soaring ceilings, massive pocket doors, spacious rooms, and surprisingly ample closet space. Homes aren't built like this anymore making adventuring the halls an absolute treat. Water views can be found from various windows of the home with specific angles highlighted seasonally. Outdoor living is celebrated with screened in porch flowing out back from the kitchen, covered front entry porch and second floor covered sleeping porch. The yard itself is a sanctuary with mature azaleas, magnolia, and gingko creating a calming setting. There is a driveway and your car can just stay there because this home is located just blocks walking from all of the dining, shopping, and culture that Chestertown has to offer. This home is part of the Maryland Historic Trust. Own a piece of American history less than two hours from DC, Baltimore, and Philadelphia while enjoying the walkable lifestyle of Chestertown's Historic District. **Interior professional photos are coming soon and are going to be really special**

103 Maple Ave, Chestertown

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

Privacy meets modern updates on two private acres in the sought-after Kinnaird’s Point community. This thoughtfully renovated home offers a peaceful setting with convenient access to the water, located just minutes from both Chestertown and Rock Hall. The property includes two community waterfront access points, featuring a private swim beach and boat launch along Still Pond Creek and Churn Creek. Inside, the bright, open single-level layout is centered around a fully remodeled kitchen with custom cabinetry, stone countertops, and a large island, flowing seamlessly into the living and dining areas. Outdoor spaces include a screened porch, composite deck, and stamped concrete patio, all designed to enjoy the home’s peaceful setting. The primary suite features a renovated bath, while additional bedrooms, updated bathrooms, and a dedicated office provide flexible living space. Major upgrades include a new HVAC system, new windows and doors, new siding, remodeled kitchen and bathrooms, a new water heater, spray-foam attic insulation, an encapsulated crawlspace, as well as full-house replumbing and an upgraded electrical system, offering a truly move-in ready, turnkey property. An oversized attached garage with a heated and cooled workspace and a fenced backyard add functionality and privacy. Tucked within a quiet, secluded neighborhood yet close to waterfront towns, marinas, and dining, this property delivers a well-updated Eastern Shore retreat with easy access to the water.

$602,500

Privacy meets modern updates on two private acres in the sought-after Kinnaird’s Point community. This thoughtfully renovated home offers a peaceful setting with convenient access to the water, located just minutes from both Chestertown and Rock Hall. The property includes two community waterfront access points, featuring a private swim beach and boat launch along Still Pond Creek and Churn Creek. Inside, the bright, open single-level layout is centered around a fully remodeled kitchen with custom cabinetry, stone countertops, and a large island, flowing seamlessly into the living and dining areas. Outdoor spaces include a screened porch, composite deck, and stamped concrete patio, all designed to enjoy the home’s peaceful setting. The primary suite features a renovated bath, while additional bedrooms, updated bathrooms, and a dedicated office provide flexible living space. Major upgrades include a new HVAC system, new windows and doors, new siding, remodeled kitchen and bathrooms, a new water heater, spray-foam attic insulation, an encapsulated crawlspace, as well as full-house replumbing and an upgraded electrical system, offering a truly move-in ready, turnkey property. An oversized attached garage with a heated and cooled workspace and a fenced backyard add functionality and privacy. Tucked within a quiet, secluded neighborhood yet close to waterfront towns, marinas, and dining, this property delivers a well-updated Eastern Shore retreat with easy access to the water.

24204 Drayton Landing Dr, Worton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Foraker Realty Co..

$575,000

Welcome to coastal charm at its finest. This beautifully updated 3-bedroom, 2-bath Cape Cod offers 1,680 square feet of thoughtfully designed living space in the heart of Rock Hall. Built with solid brick construction, this home seamlessly blends timeless character with modern upgrades. The main level features a stylishly updated kitchen with stainless steel appliances, warm hardwood floors, and a cozy living room centered around a wood-burning fireplace. A first-floor bedroom and full bath provide flexible living options, while the updated laundry room adds everyday convenience. Step outside to the screened-in porch—perfect for unwinding after a day on the water. Upstairs, two spacious bedrooms and a full bath are complemented by access to a private second-story deck, where you can take in serene water views of Rock Hall Harbor. Complete with your own hot tub, this outdoor space is designed for relaxation and entertaining. Ideally situated within walking distance to marinas, waterfront dining, shops, and all that Rock Hall has to offer, this home is the perfect full-time residence, weekend escape, or investment opportunity.

Welcome to coastal charm at its finest. This beautifully updated 3-bedroom, 2-bath Cape Cod offers 1,680 square feet of thoughtfully designed living space in the heart of Rock Hall. Built with solid brick construction, this home seamlessly blends timeless character with modern upgrades. The main level features a stylishly updated kitchen with stainless steel appliances, warm hardwood floors, and a cozy living room centered around a wood-burning fireplace. A first-floor bedroom and full bath provide flexible living options, while the updated laundry room adds everyday convenience. Step outside to the screened-in porch—perfect for unwinding after a day on the water. Upstairs, two spacious bedrooms and a full bath are complemented by access to a private second-story deck, where you can take in serene water views of Rock Hall Harbor. Complete with your own hot tub, this outdoor space is designed for relaxation and entertaining. Ideally situated within walking distance to marinas, waterfront dining, shops, and all that Rock Hall has to offer, this home is the perfect full-time residence, weekend escape, or investment opportunity.

20916 Bayside Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Rock Hall Properties Real Estate.

$567,000

Impeccably kept Kentmore Park home with a white picket fence. Over two acres with private rear yard for relaxation. Adorable brick outbuilding for storage, home office, man cave or she shed. Gazebo for al fresco dining, afternoon card games or just enjoying nature. Two additional sheds for storing just about anything. Habitat for many bird species in season. Owl, Heron and Eagle territory year round. This home mixes the old with the new. Character throughout this custom built home. Architectural details, crown and dentil molding. Large kitchen for casual dining and entertaining. Designer countertops and stainless appliances topped off with a Viking range and an antique coal range by AGA. Plenty of gathering space at the elongated island. Large windows bring the outside in to the kitchen. Owner suite is on the main floor. Second floor boasts a super large room and full bath for a guest/ family quarters. There is a beautiful livingroom with a fireplace and a family room with a fireplace and built in bookshelves. Excellent living spaces. The gracious dining room can host many a fine dining experience. The full size basement with indoor and outdoor access offers many possible uses from storage to crafts to games. A lovely sunny screen porch stretches across the back of the house with access to the kitchen and to the owners suite. A step from the porch takes you to the spa/ hot tub in it's own private setting. This home is being offered with an additional lot included. The lot affords this home access to the Kentmore Park Amenities. Beach, Piers, Boat ramp, and the Kentmore Park social association. This listing includes MLS listing # MDKE2005752, 0.11 acre lot on Anglewood Rd, Kentmore Park.

2 Beds ⋅ 3 Baths

Impeccably kept Kentmore Park home with a white picket fence. Over two acres with private rear yard for relaxation. Adorable brick outbuilding for storage, home office, man cave or she shed. Gazebo for al fresco dining, afternoon card games or just enjoying nature. Two additional sheds for storing just about anything. Habitat for many bird species in season. Owl, Heron and Eagle territory year round. This home mixes the old with the new. Character throughout this custom built home. Architectural details, crown and dentil molding. Large kitchen for casual dining and entertaining. Designer countertops and stainless appliances topped off with a Viking range and an antique coal range by AGA. Plenty of gathering space at the elongated island. Large windows bring the outside in to the kitchen. Owner suite is on the main floor. Second floor boasts a super large room and full bath for a guest/ family quarters. There is a beautiful livingroom with a fireplace and a family room with a fireplace and built in bookshelves. Excellent living spaces. The gracious dining room can host many a fine dining experience. The full size basement with indoor and outdoor access offers many possible uses from storage to crafts to games. A lovely sunny screen porch stretches across the back of the house with access to the kitchen and to the owners suite. A step from the porch takes you to the spa/ hot tub in it's own private setting. This home is being offered with an additional lot included. The lot affords this home access to the Kentmore Park Amenities. Beach, Piers, Boat ramp, and the Kentmore Park social association. This listing includes MLS listing # MDKE2005752, 0.11 acre lot on Anglewood Rd, Kentmore Park.

13983 Turners Point Rd, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Unrepresented.

$562,000

Custom-built waterfront gem nestled on the picturesque Chester River in Kent County. This stunning 3-bedroom, 2.5-bathroom home, constructed in 2006, spans a total of 4821 square feet and offers an open floor plan ideal for everyday living and entertaining indoors and out! Upgrades abound! Step inside to discover a home rich in upgrades and architectural detail. Soaring 9-foot and cathedral ceilings, dramatic two-story spaces, and gleaming hardwood floors create an airy, inviting atmosphere. The kitchen is enhanced with upgraded countertops and lighting, while a cozy wood-burning fireplace anchors the main living area. The main-level primary suite provides convenience and comfort, and a full unfinished basement with rough-in plumbing offers endless potential for future expansion. Additional features include a central vacuum system, and numerous thoughtful enhancements throughout. Set on a private 0.5-acre lot, the property truly shines with 75 feet of prime waterfront along the Chester River. With approximately 6 feet of mean low water depth, this is a boater’s dream—perfect for boating, kayaking, swimming, and fishing right from your own backyard. Ideally located, the home offers close proximity to historic Chestertown’s charm, dining, and waterfront amenities, while also being just a short drive to Middletown, Delaware—home to the vibrant Westown area and tax-free shopping.

Custom-built waterfront gem nestled on the picturesque Chester River in Kent County. This stunning 3-bedroom, 2.5-bathroom home, constructed in 2006, spans a total of 4821 square feet and offers an open floor plan ideal for everyday living and entertaining indoors and out! Upgrades abound! Step inside to discover a home rich in upgrades and architectural detail. Soaring 9-foot and cathedral ceilings, dramatic two-story spaces, and gleaming hardwood floors create an airy, inviting atmosphere. The kitchen is enhanced with upgraded countertops and lighting, while a cozy wood-burning fireplace anchors the main living area. The main-level primary suite provides convenience and comfort, and a full unfinished basement with rough-in plumbing offers endless potential for future expansion. Additional features include a central vacuum system, and numerous thoughtful enhancements throughout. Set on a private 0.5-acre lot, the property truly shines with 75 feet of prime waterfront along the Chester River. With approximately 6 feet of mean low water depth, this is a boater’s dream—perfect for boating, kayaking, swimming, and fishing right from your own backyard. Ideally located, the home offers close proximity to historic Chestertown’s charm, dining, and waterfront amenities, while also being just a short drive to Middletown, Delaware—home to the vibrant Westown area and tax-free shopping.

31667 W Edge Rd, Millington

Listing courtesy of Century 21 Gold Key Realty. Contact:

Selling Office: Gunther-McClary Real Estate.

$550,000

Nestled on a beautiful 4.26 acre lot in the peaceful countryside of Galena, MD, this charming ranch style home offers the perfect blend of comfort, space and outdoor living. Featuring 3 bedrooms and 2.5 baths with over 1500 square feet of living space, this property is ideal for those looking to enjoy a relaxed lifestyle with room to spread out. Inside, you’ll find a thoughtfully updated home with recent improvements throughout, including a remodeled kitchen (2022), remodeled primary bath (2024), and updated paint and flooring in the living room and primary bedroom (2025). The spacious living room flows into the kitchen and dining area, creating a warm and inviting space for everyday living and entertaining. Step outside and take in everything this property has to offer. Standing seam metal roof installed in 2021. A beautiful covered back porch/deck, added in 2021, overlooks the property and provides the perfect setting for morning coffee or evening gatherings. The large man-made pond adds a peaceful focal point to the land and attracts local wildlife, creating a true country retreat feel. The outdoor amenities continue with a fenced 16x33 fiberglass in-ground saltwater pool installed in 2022, complete with a surrounding concrete patio, perfect for summer entertaining. For those needing storage, workshop space, or hobby space, the property also features a large 20x40 pole barn shop with electric and concrete flooring, in addition to the attached 23x27 garage. Additional highlights include: 2 bedrooms + bonus room/3rd bedroom with mini-split HVAC 2.5 bathrooms Spacious laundry room Walk-in closet in the primary suite Covered and uncovered deck spaces totaling over 500 sq ft Crawl space encapsulation Septic recently serviced Surrounded by Kent County farmland and open skies, this property offers the kind of privacy, functionality, and lifestyle opportunities that are hard to find. Whether you’re looking for a peaceful homestead, hobby farm potential, or simply more room to enjoy life outdoors, this property delivers. Additional professional photos coming.

Nestled on a beautiful 4.26 acre lot in the peaceful countryside of Galena, MD, this charming ranch style home offers the perfect blend of comfort, space and outdoor living. Featuring 3 bedrooms and 2.5 baths with over 1500 square feet of living space, this property is ideal for those looking to enjoy a relaxed lifestyle with room to spread out. Inside, you’ll find a thoughtfully updated home with recent improvements throughout, including a remodeled kitchen (2022), remodeled primary bath (2024), and updated paint and flooring in the living room and primary bedroom (2025). The spacious living room flows into the kitchen and dining area, creating a warm and inviting space for everyday living and entertaining. Step outside and take in everything this property has to offer. Standing seam metal roof installed in 2021. A beautiful covered back porch/deck, added in 2021, overlooks the property and provides the perfect setting for morning coffee or evening gatherings. The large man-made pond adds a peaceful focal point to the land and attracts local wildlife, creating a true country retreat feel. The outdoor amenities continue with a fenced 16x33 fiberglass in-ground saltwater pool installed in 2022, complete with a surrounding concrete patio, perfect for summer entertaining. For those needing storage, workshop space, or hobby space, the property also features a large 20x40 pole barn shop with electric and concrete flooring, in addition to the attached 23x27 garage. Additional highlights include: 2 bedrooms + bonus room/3rd bedroom with mini-split HVAC 2.5 bathrooms Spacious laundry room Walk-in closet in the primary suite Covered and uncovered deck spaces totaling over 500 sq ft Crawl space encapsulation Septic recently serviced Surrounded by Kent County farmland and open skies, this property offers the kind of privacy, functionality, and lifestyle opportunities that are hard to find. Whether you’re looking for a peaceful homestead, hobby farm potential, or simply more room to enjoy life outdoors, this property delivers. Additional professional photos coming.

31531 Jim Davis Rd, Galena

Listing courtesy of Patterson-Schwartz Real Estate. Contact:

Selling Office: Foraker Realty Co..

$545,000

Seller says sell! Massive price reduction ! Below market for this pristine home well situated in chestertown historic district! A rare Water Street opportunity—see your boat from the front porch and enjoy walkable waterfront living in Chestertown. This thoughtfully rebuilt historic home offers 4 bedrooms, 3.5 baths, flexible guest spaces, and a water-view deck built to support a hot tub. Perfect as a primary residence or low-maintenance Chesapeake pied-à-terre for DC, Baltimore, and Philadelphia weekenders. Quality finishes include Andersen composite windows with plantation shutters, Heartland appliances, handcrafted cabinetry, and excellent storage. Walk to parks, dining, shops, arts, and the harbor. Vacant lot next door is separately owned.

Seller says sell! Massive price reduction ! Below market for this pristine home well situated in chestertown historic district! A rare Water Street opportunity—see your boat from the front porch and enjoy walkable waterfront living in Chestertown. This thoughtfully rebuilt historic home offers 4 bedrooms, 3.5 baths, flexible guest spaces, and a water-view deck built to support a hot tub. Perfect as a primary residence or low-maintenance Chesapeake pied-à-terre for DC, Baltimore, and Philadelphia weekenders. Quality finishes include Andersen composite windows with plantation shutters, Heartland appliances, handcrafted cabinetry, and excellent storage. Walk to parks, dining, shops, arts, and the harbor. Vacant lot next door is separately owned.

206 S Water St, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$541,500

Prime location in Downtown Chestertown’s Historic District offering approximately 1,785 square feet of practical office and workspace on three levels with 4 off-street parking spaces. The “RB” zoning also provides flexibility for live/work arrangements, and the property has rare building expansion potential to accommodate business growth.

110 S Queen St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Prime location in Downtown Chestertown’s Historic District offering approximately 1,785 square feet of practical living space on three levels with 4 off-street parking spaces. The “RB” zoning also provides flexibility for live/work arrangements, and the property has rare building expansion potential to accommodate family and/or business growth.

$541,500

Prime location in Downtown Chestertown’s Historic District offering approximately 1,785 square feet of practical living space on three levels with 4 off-street parking spaces. The “RB” zoning also provides flexibility for live/work arrangements, and the property has rare building expansion potential to accommodate family and/or business growth.

110 S Queen St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Welcome to 14504 John Peel Road, located in a desirable waterfront-oriented community in Galena offering private community dock access and the opportunity to enjoy the Eastern Shore lifestyle. Conveniently located just minutes from Route 301, this spacious 4-bedroom, 2.5-bath Colonial offers over 2,300 square feet of comfortable living space with plenty of room for everyone. The main level features a beautiful kitchen with cherry cabinetry and lvp flooring, a dining area or family room with an electric fireplace, and a convenient half bath. Enjoy additional living space in the screened-in porch, perfect for relaxing and taking in the peaceful surroundings. The front of the home offers two formal living rooms, providing flexible space for entertaining, a home office, or additional gathering areas. Upstairs you’ll find all four bedrooms and two full bathrooms, including a spacious primary suite with a Juliet balcony. The basement offers even more possibilities with a wood stove and additional space for storage, hobbies, or recreation. An attached two-car garage adds everyday convenience.

$540,000

Welcome to 14504 John Peel Road, located in a desirable waterfront-oriented community in Galena offering private community dock access and the opportunity to enjoy the Eastern Shore lifestyle. Conveniently located just minutes from Route 301, this spacious 4-bedroom, 2.5-bath Colonial offers over 2,300 square feet of comfortable living space with plenty of room for everyone. The main level features a beautiful kitchen with cherry cabinetry and lvp flooring, a dining area or family room with an electric fireplace, and a convenient half bath. Enjoy additional living space in the screened-in porch, perfect for relaxing and taking in the peaceful surroundings. The front of the home offers two formal living rooms, providing flexible space for entertaining, a home office, or additional gathering areas. Upstairs you’ll find all four bedrooms and two full bathrooms, including a spacious primary suite with a Juliet balcony. The basement offers even more possibilities with a wood stove and additional space for storage, hobbies, or recreation. An attached two-car garage adds everyday convenience.

14504 John Peel Rd, Galena

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

Selling Office: RE/MAX Associates - Newark.

$535,000

Welcome to 9816 Fairlee Road. Be Sure to Click the Virtual Tour!! This property has been meticulously cared for by the current owners and it shows. The property sits on 6.29 acres! If you want plenty of land without giving up on high end fixtures, this is the home for you. Pride of ownership shines through in this gem of a home. The paved driveway leads to a parking pad and a beautiful piece of property. This rancher gives you plenty of space both inside and out. Recently, there was an addition of a mudroom and a second owners suite. Both owners suites have their own bathroom and walk-in shower and one even has a jetted Jacuzzi tub to help you unwind after a long day. There is upgraded flooring through-out, whether it be hardwood or tile, every room feels polished and upscale. The living room includes a woodstove that was installed in 2025 along with a new chimney pipe. There is a creek directly behind your property, which means, water is just a short stroll away. Enjoy tons of natural light in the spacious kitchen where quartz countertops are partnered with a Stainless Steel Refrigerator, built-in microwave and stove. Soft-close cabinets and drawers add to the upscale feel. This home has three spacious bedrooms and three full baths. The un-finished lower level provides you with even more space for storage or it can be your very own blank canvas to finish and increase your living space. The laundry area is in the basement and the washer and dryer will stay with the home. The sliding glass door in the kitchen allows access to your deck and backyard. Enjoy the peace and quiet. Don't be surprised if you see ducks, turkey or deer, they have been known to enjoy the 6+ acres too! The water treatment system has been thoroughly maintained and will convey with the home. High Speed Talkie internet is available. New windows installed throughout most of the home in 2020. This is an Amazing Home! It is turn-key and ready to Welcome its New Owners.

Welcome to 9816 Fairlee Road. Be Sure to Click the Virtual Tour!! This property has been meticulously cared for by the current owners and it shows. The property sits on 6.29 acres! If you want plenty of land without giving up on high end fixtures, this is the home for you. Pride of ownership shines through in this gem of a home. The paved driveway leads to a parking pad and a beautiful piece of property. This rancher gives you plenty of space both inside and out. Recently, there was an addition of a mudroom and a second owners suite. Both owners suites have their own bathroom and walk-in shower and one even has a jetted Jacuzzi tub to help you unwind after a long day. There is upgraded flooring through-out, whether it be hardwood or tile, every room feels polished and upscale. The living room includes a woodstove that was installed in 2025 along with a new chimney pipe. There is a creek directly behind your property, which means, water is just a short stroll away. Enjoy tons of natural light in the spacious kitchen where quartz countertops are partnered with a Stainless Steel Refrigerator, built-in microwave and stove. Soft-close cabinets and drawers add to the upscale feel. This home has three spacious bedrooms and three full baths. The un-finished lower level provides you with even more space for storage or it can be your very own blank canvas to finish and increase your living space. The laundry area is in the basement and the washer and dryer will stay with the home. The sliding glass door in the kitchen allows access to your deck and backyard. Enjoy the peace and quiet. Don't be surprised if you see ducks, turkey or deer, they have been known to enjoy the 6+ acres too! The water treatment system has been thoroughly maintained and will convey with the home. High Speed Talkie internet is available. New windows installed throughout most of the home in 2020. This is an Amazing Home! It is turn-key and ready to Welcome its New Owners.

9816 Fairlee Rd, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

Recently updated "coastal" home located in a small community of 8 homes , three miles east of historic Chestertown. The house sits on high ground, less than a mile from a small Chester River boat landing where you can easily launch a kayak, Sunfish or small power boat. This comfortable home offers same floor living for much of the house, but also has a partly finished full basement with tv room. and full bath The kitchen has custom maple cabinets, leathered granite countertops, oversize farm sink and stainless-steel appliances. The large deck overlooks the peaceful farmland edged by a wooded hedgerow and the fenced yard. Chestertown, dating to the18th Century, is the County Seat of Kent County, with courthouse, churches, hospital. shopping and restaurants and is the home of Washington College. The $300 semi-annual fee is an estimate and is for road maintenance--- see deed restrictions

Recently updated "coastal" home located in a small community of 8 homes , three miles east of historic Chestertown. The house sits on high ground, less than a mile from a small Chester River boat landing where you can easily launch a kayak, Sunfish or small power boat. This comfortable home offers same floor living for much of the house, but also has a partly finished full basement with tv room. and full bath The kitchen has custom maple cabinets, leathered granite countertops, oversize farm sink and stainless-steel appliances. The large deck overlooks the peaceful farmland edged by a wooded hedgerow and the fenced yard. Chestertown, dating to the18th Century, is the County Seat of Kent County, with courthouse, churches, hospital. shopping and restaurants and is the home of Washington College. The $300 semi-annual fee is an estimate and is for road maintenance--- see deed restrictions

Preston Lane, Chestertown

Listing courtesy of Shoreline Realty. Contact:

Selling Office: Doug Ashley Realtors, LLC.

**All offers due on 7/4 by 5 pm. Set on a picturesque 2-acre lot, this exceptional property is surrounded by lush landscaping and mature trees, creating a private and tranquil retreat from the demands of everyday life. Scenic vistas and wooded surroundings provide a peaceful ambiance, offering the perfect balance of rural charm and modern convenience. Inside, a thoughtfully designed traditional floor plan seamlessly connects the home's living spaces. The gourmet kitchen is a chef's dream, featuring premium Viking stainless steel appliances, including a gas range, built-in microwave, and refrigerator. A spacious center island with a butcher block workstation provides abundant prep space, while upgraded countertops, imported deVOL fixtures, under-cabinet lighting, and elegant glass-front cabinetry add both style and functionality. The adjoining kitchen and dining area is ideal for entertaining, allowing for effortless flow and gathering. The home offers four generously sized bedrooms, each designed with comfort and relaxation in mind. The second-floor bathroom serves as a private spa retreat, complete with a jetted soaking tub and separate stall shower. An upper-level laundry room adds everyday convenience and efficiency. Outdoor amenities are equally impressive. A detached oversized garage provides abundant storage and parking and is uniquely equipped with a bathroom and walk-in cooler, offering exceptional versatility for hobbyists, entertainers, or business use. The expansive grounds provide endless opportunities for gardening, recreation, hosting gatherings, or simply enjoying the serenity of nature in complete privacy. Located outside the charming community of Worton, this property offers the best of both worlds—a peaceful rural setting with convenient access to local marinas, dining, community center with pool and recreational opportunities. Known for its welcoming atmosphere and proximity to outdoor adventures, Worton is an ideal destination for those seeking a relaxed lifestyle without compromising accessibility. Combining luxurious features, scenic surroundings, and a highly desirable location, this remarkable property presents a rare opportunity to experience refined country living. Discover a lifestyle defined by comfort, privacy, and timeless elegance in this truly exceptional home.

4 Beds ⋅ 2 Baths

**All offers due on 7/4 by 5 pm. Set on a picturesque 2-acre lot, this exceptional property is surrounded by lush landscaping and mature trees, creating a private and tranquil retreat from the demands of everyday life. Scenic vistas and wooded surroundings provide a peaceful ambiance, offering the perfect balance of rural charm and modern convenience. Inside, a thoughtfully designed traditional floor plan seamlessly connects the home's living spaces. The gourmet kitchen is a chef's dream, featuring premium Viking stainless steel appliances, including a gas range, built-in microwave, and refrigerator. A spacious center island with a butcher block workstation provides abundant prep space, while upgraded countertops, imported deVOL fixtures, under-cabinet lighting, and elegant glass-front cabinetry add both style and functionality. The adjoining kitchen and dining area is ideal for entertaining, allowing for effortless flow and gathering. The home offers four generously sized bedrooms, each designed with comfort and relaxation in mind. The second-floor bathroom serves as a private spa retreat, complete with a jetted soaking tub and separate stall shower. An upper-level laundry room adds everyday convenience and efficiency. Outdoor amenities are equally impressive. A detached oversized garage provides abundant storage and parking and is uniquely equipped with a bathroom and walk-in cooler, offering exceptional versatility for hobbyists, entertainers, or business use. The expansive grounds provide endless opportunities for gardening, recreation, hosting gatherings, or simply enjoying the serenity of nature in complete privacy. Located outside the charming community of Worton, this property offers the best of both worlds—a peaceful rural setting with convenient access to local marinas, dining, community center with pool and recreational opportunities. Known for its welcoming atmosphere and proximity to outdoor adventures, Worton is an ideal destination for those seeking a relaxed lifestyle without compromising accessibility. Combining luxurious features, scenic surroundings, and a highly desirable location, this remarkable property presents a rare opportunity to experience refined country living. Discover a lifestyle defined by comfort, privacy, and timeless elegance in this truly exceptional home.

11929 Colly Cove Ln, Worton

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

Selling Office: Real Broker, LLC - Chester.

Nestled in the desirable Crestview neighborhood, this beautifully maintained rancher built by respected local builder KRM Construction offers the perfect blend of quality craftsmanship, comfort, and modern convenience. Built in 2017, this 3 bedroom, 2 bathroom home features an inviting open layout with luxury plank hardwood flooring throughout the main living areas, granite countertops, abundant cabinet storage, and a cozy propane fireplace. The spacious primary suite includes a large walk-in closet and a luxurious en-suite bath complete with a soaking tub and separate shower. Enjoy relaxing mornings on the screened porch or unwind evenings around the fire pit on the paver patio just off the living room. Additional highlights include a 2-car attached garage, sprinkler system, hot water on demand, new propane furnace installed in 2026, and new dryer in 2025. Conveniently located close to all of Chestertown amenities, with a voluntary HOA of just $100/year. Showings begin 5/22 — this is one you won’t want to miss!

Nestled in the desirable Crestview neighborhood, this beautifully maintained rancher built by respected local builder KRM Construction offers the perfect blend of quality craftsmanship, comfort, and modern convenience. Built in 2017, this 3 bedroom, 2 bathroom home features an inviting open layout with luxury plank hardwood flooring throughout the main living areas, granite countertops, abundant cabinet storage, and a cozy propane fireplace. The spacious primary suite includes a large walk-in closet and a luxurious en-suite bath complete with a soaking tub and separate shower. Enjoy relaxing mornings on the screened porch or unwind evenings around the fire pit on the paver patio just off the living room. Additional highlights include a 2-car attached garage, sprinkler system, hot water on demand, new propane furnace installed in 2026, and new dryer in 2025. Conveniently located close to all of Chestertown amenities, with a voluntary HOA of just $100/year. Showings begin 5/22 — this is one you won’t want to miss!

1014 Twin Ct, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.

Nestled in the natural serene of Great Oak Estates, this beautiful 5 bedroom, 3.5 bathroom Nanticoke Home offers a flexible floor plan, updated kitchen, spacious backyard, and brand new Florida/Sun room, designed for both relaxation and entertaining. The heart of the home feautures a gourmet kitchen with granite counter tops, SS appliances, custom built ins, and connects to the family room with an amazing built in wood stove, warming the entire home. Sitting on a generous 2 acre lot (not reflected on tax record), and surrounded by lush farmland, this property offers you so much potential. Keep the extra lot as a natural buffer, or build a garage/workshop/granny annex, or just sell it on. You can't go wrong! Great Oak Estates offer direct access for its residents ($100 annually) to all the Marina amenities including: Outdoor pool, restaurant, 9 hole golf course, picnic and playground area by the water. And a beautiful sandy beach on the calm waters of Fairlee Creek.

5 Beds ⋅ 4 Baths

Nestled in the natural serene of Great Oak Estates, this beautiful 5 bedroom, 3.5 bathroom Nanticoke Home offers a flexible floor plan, updated kitchen, spacious backyard, and brand new Florida/Sun room, designed for both relaxation and entertaining. The heart of the home feautures a gourmet kitchen with granite counter tops, SS appliances, custom built ins, and connects to the family room with an amazing built in wood stove, warming the entire home. Sitting on a generous 2 acre lot (not reflected on tax record), and surrounded by lush farmland, this property offers you so much potential. Keep the extra lot as a natural buffer, or build a garage/workshop/granny annex, or just sell it on. You can't go wrong! Great Oak Estates offer direct access for its residents ($100 annually) to all the Marina amenities including: Outdoor pool, restaurant, 9 hole golf course, picnic and playground area by the water. And a beautiful sandy beach on the calm waters of Fairlee Creek.

22360 Great Oak Landing Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Compass Realty, Inc..

$515,000

Welcome to 591 Mill Lane in Galena, MD—your private country retreat set on 5.67 unrestricted acres of beautiful Eastern Shore landscape. This charming all-brick ranch style home offers 3 bedrooms and 2 full bathrooms, with over 2000 sq ft of finished living space, blending timeless character with comfortable, everyday living. Inside, you’ll find a spacious country kitchen, a separate dining area with a cozy fireplace, and a warm, inviting family room—perfect for gathering and relaxing. A bright sunroom adds additional living space to enjoy year-round, while main-level laundry provides convenience. The full, unfinished basement at almost 1800 sq ft —complete with heat, a large workbench, and ample storage—offers endless potential for a workshop, hobby space, or future finished living area. Step outside and discover what truly sets this property apart. The expansive 5.67-acre lot offers the space and freedom to create your ideal lifestyle—whether that’s gardening, homesteading, or simply enjoying the peace and privacy of country living. The property features a 28' x 35' pole barn, a detached oversized (28' x 22') 2-car garage with electric, and a greenhouse/shed, along with a variety of mature fruit and nut trees including cherry, pear, apple, black walnut, pecan, and hazelnut. Relax on the front porch or unwind on the rear patio while taking in the serene surroundings. Recent updates include improvements to the electrical and plumbing systems. Ready for your personal touch, this home offers an excellent opportunity to update and create a space tailored to your style. Conveniently located just minutes to US-301 and approximately 20 minutes to Middletown, DE, this property offers the perfect balance of privacy, space, and accessibility. If you’ve been looking for space, flexibility, and country charm—this is the one.

Welcome to 591 Mill Lane in Galena, MD—your private country retreat set on 5.67 unrestricted acres of beautiful Eastern Shore landscape. This charming all-brick ranch style home offers 3 bedrooms and 2 full bathrooms, with over 2000 sq ft of finished living space, blending timeless character with comfortable, everyday living. Inside, you’ll find a spacious country kitchen, a separate dining area with a cozy fireplace, and a warm, inviting family room—perfect for gathering and relaxing. A bright sunroom adds additional living space to enjoy year-round, while main-level laundry provides convenience. The full, unfinished basement at almost 1800 sq ft —complete with heat, a large workbench, and ample storage—offers endless potential for a workshop, hobby space, or future finished living area. Step outside and discover what truly sets this property apart. The expansive 5.67-acre lot offers the space and freedom to create your ideal lifestyle—whether that’s gardening, homesteading, or simply enjoying the peace and privacy of country living. The property features a 28' x 35' pole barn, a detached oversized (28' x 22') 2-car garage with electric, and a greenhouse/shed, along with a variety of mature fruit and nut trees including cherry, pear, apple, black walnut, pecan, and hazelnut. Relax on the front porch or unwind on the rear patio while taking in the serene surroundings. Recent updates include improvements to the electrical and plumbing systems. Ready for your personal touch, this home offers an excellent opportunity to update and create a space tailored to your style. Conveniently located just minutes to US-301 and approximately 20 minutes to Middletown, DE, this property offers the perfect balance of privacy, space, and accessibility. If you’ve been looking for space, flexibility, and country charm—this is the one.

591 Mill Ln, Galena

Listing courtesy of Compass. Contact:

Selling Office: Empower Real Estate, LLC.

$500,000

This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District. Located on a quiet side street just a block from Chestertown's dining, shopping, and galleries, this is the perfect blend of social and tranquil. This means that walking down to Evergrain or Modern Stone Age Kitchen for a croissant and cappuccino before a morning stroll along the waterfront promenade could become part of your morning routine. The thoughtful updates over the years have opened the floor plan and allowed for a modern layout. Many serious upgrades have occurred in the past year including the kitchen and electrical service. The wood burning stove, basement for storage, and garden building are amazing benefits. Invest wisely in an amazing home while improving your quality of life in this incredible community on the water less than 2 hours from Washington DC, Philadelphia, and Baltimore.

2 Beds ⋅ 3 Baths

This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District. Located on a quiet side street just a block from Chestertown's dining, shopping, and galleries, this is the perfect blend of social and tranquil. This means that walking down to Evergrain or Modern Stone Age Kitchen for a croissant and cappuccino before a morning stroll along the waterfront promenade could become part of your morning routine. The thoughtful updates over the years have opened the floor plan and allowed for a modern layout. Many serious upgrades have occurred in the past year including the kitchen and electrical service. The wood burning stove, basement for storage, and garden building are amazing benefits. Invest wisely in an amazing home while improving your quality of life in this incredible community on the water less than 2 hours from Washington DC, Philadelphia, and Baltimore.

101 S Mill St, Chestertown

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

Selling Office: Long & Foster Real Estate, Inc..

$495,000

Seller is motivated and can move quickly in 30 days! Welcome to 218 Camelot Drive, stunning colonial 3,932 total square feet of maintained living Situated on a beautifully landscaped corner lot in the established Coventry Farms community, this home features a fenced backyard with vinyl fencing—ideal for privacy, pets, and play. A brick paver patio with pergola and a creates multiple outdoor living zones perfect for entertaining, with direct access from the breakfast room. Inside, a light filled two story foyer welcomes you with elegant architectural details including crown molding, chair rail, wainscoting, turned stair railings, and hardwood floors throughout the main level. Neutral paint enhances the home’s timeless appeal. The gourmet kitchen is designed for both everyday living and entertaining, featuring stainless steel appliances (including a French door refrigerator), custom cabinetry, pantry, granite countertops, tile backsplash, and a center island with breakfast bar. The adjoining breakfast room or bonus space, framed by picture windows and a cathedral ceiling, is perfect for morning coffee or hosting holiday celebrations. The main level offers formal living and dining rooms, a convenient powder room, and a spacious family room highlighted by a floor to ceiling stone, wood burning fireplace with raised hearth and custom stone mantel—an inviting gathering space for family and friends. Upstairs, the primary suite is thoughtfully positioned for privacy and boasts double door entry, a walk-in closet plus an additional closet, and a luxurious ensuite bath with dual vanity, soaking tub, and stall shower. Three additional generously sized bedrooms and a full hall bath complete the upper level. The finished walk out lower level expands your living space with a large recreation area, a possible fifth bedroom, full bath with stall shower, a finished bonus room ideal for a fitness area or media room, and an oversized laundry, utility, and storage area with abundant space for seasonal and long-term storage. Conveniently located just minutes from shopping and local dining favorites, and a short drive to Historic Chestertown along the Chester River, you’ll enjoy easy access to charming boutiques, restaurants, galleries, Washington College, and rich cultural and historical attractions.

5 Beds ⋅ 4 Baths

Seller is motivated and can move quickly in 30 days! Welcome to 218 Camelot Drive, stunning colonial 3,932 total square feet of maintained living Situated on a beautifully landscaped corner lot in the established Coventry Farms community, this home features a fenced backyard with vinyl fencing—ideal for privacy, pets, and play. A brick paver patio with pergola and a creates multiple outdoor living zones perfect for entertaining, with direct access from the breakfast room. Inside, a light filled two story foyer welcomes you with elegant architectural details including crown molding, chair rail, wainscoting, turned stair railings, and hardwood floors throughout the main level. Neutral paint enhances the home’s timeless appeal. The gourmet kitchen is designed for both everyday living and entertaining, featuring stainless steel appliances (including a French door refrigerator), custom cabinetry, pantry, granite countertops, tile backsplash, and a center island with breakfast bar. The adjoining breakfast room or bonus space, framed by picture windows and a cathedral ceiling, is perfect for morning coffee or hosting holiday celebrations. The main level offers formal living and dining rooms, a convenient powder room, and a spacious family room highlighted by a floor to ceiling stone, wood burning fireplace with raised hearth and custom stone mantel—an inviting gathering space for family and friends. Upstairs, the primary suite is thoughtfully positioned for privacy and boasts double door entry, a walk-in closet plus an additional closet, and a luxurious ensuite bath with dual vanity, soaking tub, and stall shower. Three additional generously sized bedrooms and a full hall bath complete the upper level. The finished walk out lower level expands your living space with a large recreation area, a possible fifth bedroom, full bath with stall shower, a finished bonus room ideal for a fitness area or media room, and an oversized laundry, utility, and storage area with abundant space for seasonal and long-term storage. Conveniently located just minutes from shopping and local dining favorites, and a short drive to Historic Chestertown along the Chester River, you’ll enjoy easy access to charming boutiques, restaurants, galleries, Washington College, and rich cultural and historical attractions.

218 Camelot Dr, Chestertown

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Samson Properties.

$490,000

Welcome to this spacious 5-bedroom, 2.5 bath raised ranch located on picturesque Jim Davis Road in Galena, MD, offering peaceful country living on 2 acres with convenient access to surrounding areas. Enjoy a circular driveway and detached garage providing plenty of room for parking, hobbies, and guests. Step outside to your own private retreat featuring an inground pool, pool shed, deck, patio, and privacy fencing - perfect for summer entertaining and relaxation. The property also offers a play area and beautiful views of local farms, creating a serene and scenic setting. Inside, the home offers a flexible layout with extra living space in the finished basement, while all bedrooms are located above ground on the first floor. PREFER the opposite setup? The layout can easily be adjusted to fit your needs-whether you want more entertaining space, guest rooms, or a home office. For added peace of mind, the seller is providing a ONE YEAR HOME WARRANTY**** through American Home Shield. Galena is such an adorable little town with tons of charm & character. Now priced to SELL Conveniently located close to Delaware, Baltimore, and Pennsylvania, this home blends rural charm with commuter-friendly access. A unique opportunity offering space, privacy, and versaltility-schedule your private showing today!

5 Beds ⋅ 3 Baths

Welcome to this spacious 5-bedroom, 2.5 bath raised ranch located on picturesque Jim Davis Road in Galena, MD, offering peaceful country living on 2 acres with convenient access to surrounding areas. Enjoy a circular driveway and detached garage providing plenty of room for parking, hobbies, and guests. Step outside to your own private retreat featuring an inground pool, pool shed, deck, patio, and privacy fencing - perfect for summer entertaining and relaxation. The property also offers a play area and beautiful views of local farms, creating a serene and scenic setting. Inside, the home offers a flexible layout with extra living space in the finished basement, while all bedrooms are located above ground on the first floor. PREFER the opposite setup? The layout can easily be adjusted to fit your needs-whether you want more entertaining space, guest rooms, or a home office. For added peace of mind, the seller is providing a ONE YEAR HOME WARRANTY**** through American Home Shield. Galena is such an adorable little town with tons of charm & character. Now priced to SELL Conveniently located close to Delaware, Baltimore, and Pennsylvania, this home blends rural charm with commuter-friendly access. A unique opportunity offering space, privacy, and versaltility-schedule your private showing today!

31569 Jim Davis, Galena

Listing courtesy of Remax Vision. Contact:

Selling Office: RE/MAX Associates-Hockessin.

$490,000

*Days on Market Reporting Incorrectly- Property listed Oct 30, 2025* Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn. Step inside to discover wood floors, a private home office, and an inviting open-concept kitchen featuring luxury countertops and a sunroom bump-out with ample natural light—ideal for morning coffee, reading, or cozy dinners. Upstairs, the spacious primary suite offers a true retreat with a walk-in closet, en suite bathroom, and the convenience of an upstairs laundry room. The fully finished basement adds exceptional versatility, featuring its own private entrance, kitchenette, full bath with steam sauna, and open-concept living/bedroom area—perfect for guests, or entertaining. A dedicated workroom completes the lower level, ready for projects or hobbies. Outside, enjoy your fenced-in backyard oasis complete with a deck. This home has been meticulously cared for and thoughtfully updated, including: New roof, gutters, and gutter covers (2025) New HVAC system – furnace and A/C (2024) New 80-gallon water heater (2022) Fully renewed basement (2022) with new flooring, carpet, paint, and dual sump pumps Finished garage (2022) Ornamental Fence (2020) Furnishings Negotiable .

4 Beds ⋅ 4 Baths

*Days on Market Reporting Incorrectly- Property listed Oct 30, 2025* Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn. Step inside to discover wood floors, a private home office, and an inviting open-concept kitchen featuring luxury countertops and a sunroom bump-out with ample natural light—ideal for morning coffee, reading, or cozy dinners. Upstairs, the spacious primary suite offers a true retreat with a walk-in closet, en suite bathroom, and the convenience of an upstairs laundry room. The fully finished basement adds exceptional versatility, featuring its own private entrance, kitchenette, full bath with steam sauna, and open-concept living/bedroom area—perfect for guests, or entertaining. A dedicated workroom completes the lower level, ready for projects or hobbies. Outside, enjoy your fenced-in backyard oasis complete with a deck. This home has been meticulously cared for and thoughtfully updated, including: New roof, gutters, and gutter covers (2025) New HVAC system – furnace and A/C (2024) New 80-gallon water heater (2022) Fully renewed basement (2022) with new flooring, carpet, paint, and dual sump pumps Finished garage (2022) Ornamental Fence (2020) Furnishings Negotiable .

100 Adela Way, Chestertown

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: Keller Williams Gateway LLC.

$475,000

Welcome to 25428 Worton Lynch Road in Worton, Maryland! Situated on 1.28 acres, this charming 3-bedroom, 2.5-bath home offers comfortable living with thoughtful features throughout. The heart of the home is the kitchen, featuring granite countertops, LVP flooring, and ample cabinet space for cooking and entertaining. Just off the kitchen, the inviting living room boasts beautiful hardwood floors, a shiplap accent wall, and an electric fireplace that creates a warm and welcoming atmosphere. A convenient half bath is also located on the first floor for guests. The spacious first-floor primary suite provides a private retreat with a large walk-in closet, a hidden closet for additional storage, and an ensuite bathroom complete with a tiled shower. Upstairs, you'll find two additional bedrooms with carpeting and a full bathroom, offering comfortable space for family or guests. A full basement with a wood stove adds valuable storage, workshop potential, or future finishing possibilities. Outside, enjoy the peaceful setting from the rear deck overlooking the 1.28-acre property. Additional features include a shed with a concrete pad and a swing set that conveys with the sale. Offering the perfect blend of comfort, space, and country charm, this Worton property is ready to welcome its next owners home.

Welcome to 25428 Worton Lynch Road in Worton, Maryland! Situated on 1.28 acres, this charming 3-bedroom, 2.5-bath home offers comfortable living with thoughtful features throughout. The heart of the home is the kitchen, featuring granite countertops, LVP flooring, and ample cabinet space for cooking and entertaining. Just off the kitchen, the inviting living room boasts beautiful hardwood floors, a shiplap accent wall, and an electric fireplace that creates a warm and welcoming atmosphere. A convenient half bath is also located on the first floor for guests. The spacious first-floor primary suite provides a private retreat with a large walk-in closet, a hidden closet for additional storage, and an ensuite bathroom complete with a tiled shower. Upstairs, you'll find two additional bedrooms with carpeting and a full bathroom, offering comfortable space for family or guests. A full basement with a wood stove adds valuable storage, workshop potential, or future finishing possibilities. Outside, enjoy the peaceful setting from the rear deck overlooking the 1.28-acre property. Additional features include a shed with a concrete pad and a swing set that conveys with the sale. Offering the perfect blend of comfort, space, and country charm, this Worton property is ready to welcome its next owners home.

25428 Worton Lynch Rd, Worton

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

Selling Office: Century 21 Gold Key Realty.

$470,000

Spacious waterfront rancher with pole barn—priced below appraised value for a quick sale! Appraised at $534K, this motivated seller is offering a rare opportunity for instant equity on the upper Chester River. Conveniently located with easy access to Rt. 301, making commuting to Philadelphia, Middletown, or the Chesapeake Bay Bridge surprisingly convenient while still enjoying the perks of waterfront living. This well-maintained 3-bedroom, 2.5-bath rancher offers comfortable one-level living with beautiful river views throughout. The inviting living room features a stone propane fireplace, while the spacious primary suite includes a second gas fireplace, oversized bath with garden tub, walk-in shower, and private water closet. The kitchen was designed with both entertaining and everyday living in mind, featuring an island, double ovens, farmhouse sink, and river views right from the window. The dining area opens to a rear deck with retractable awning—perfect for relaxing evenings overlooking the water. One of the standout features is the impressive 1,200 sq. ft. pole barn connected by a breezeway. Complete with a second level and motorized lift, this space is ideal for contractors, hobbyists, boat storage, workshop space, car enthusiasts, or anyone needing serious storage and flexibility. Outside, enjoy kayaking and fishing right from your own property. The home is elevated well above the floodplain and may offer future options for water access improvements such as steps, a bulkhead, or small pier (buyer to confirm with county). Additional highlights include public water and sewer, a separate irrigation well, professionally landscaped grounds, regularly serviced HVAC, resealed driveways, and proactive maintenance throughout. Less than a mile to Food Lion and convenient to Chestertown, Middletown, and Bay Bridge travel routes. Freshened up for spring and ready for its next owner—add this waterfront opportunity to your watch list before it’s gone! All offers considered.

Spacious waterfront rancher with pole barn—priced below appraised value for a quick sale! Appraised at $534K, this motivated seller is offering a rare opportunity for instant equity on the upper Chester River. Conveniently located with easy access to Rt. 301, making commuting to Philadelphia, Middletown, or the Chesapeake Bay Bridge surprisingly convenient while still enjoying the perks of waterfront living. This well-maintained 3-bedroom, 2.5-bath rancher offers comfortable one-level living with beautiful river views throughout. The inviting living room features a stone propane fireplace, while the spacious primary suite includes a second gas fireplace, oversized bath with garden tub, walk-in shower, and private water closet. The kitchen was designed with both entertaining and everyday living in mind, featuring an island, double ovens, farmhouse sink, and river views right from the window. The dining area opens to a rear deck with retractable awning—perfect for relaxing evenings overlooking the water. One of the standout features is the impressive 1,200 sq. ft. pole barn connected by a breezeway. Complete with a second level and motorized lift, this space is ideal for contractors, hobbyists, boat storage, workshop space, car enthusiasts, or anyone needing serious storage and flexibility. Outside, enjoy kayaking and fishing right from your own property. The home is elevated well above the floodplain and may offer future options for water access improvements such as steps, a bulkhead, or small pier (buyer to confirm with county). Additional highlights include public water and sewer, a separate irrigation well, professionally landscaped grounds, regularly serviced HVAC, resealed driveways, and proactive maintenance throughout. Less than a mile to Food Lion and convenient to Chestertown, Middletown, and Bay Bridge travel routes. Freshened up for spring and ready for its next owner—add this waterfront opportunity to your watch list before it’s gone! All offers considered.

31729 W Edge Rd, Millington

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

Selling Office: Keller Williams Legacy.

$465,000

311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and family room with a gas fireplace. The home's design features an abundance of natural light due to its 9-foot ceilings and full-height glass walls on the first floor's rear. The sunroom and first floor primary suite access onto the rear deck with the view and privacy of mature trees. There is a primary bedroom suite on each level; and with there being three additional bedrooms, makes a total of five bedrooms or extra rooms for whatever the need may be. The home offers a garage as well as a full unfinished walk-out basement. The pictures prove the true beauty and spaciousness of this home. (room dimensions are approximate)

311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and family room with a gas fireplace. The home's design features an abundance of natural light due to its 9-foot ceilings and full-height glass walls on the first floor's rear. The sunroom and first floor primary suite access onto the rear deck with the view and privacy of mature trees. There is a primary bedroom suite on each level; and with there being three additional bedrooms, makes a total of five bedrooms or extra rooms for whatever the need may be. The home offers a garage as well as a full unfinished walk-out basement. The pictures prove the true beauty and spaciousness of this home. (room dimensions are approximate)

311 Devon Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Multiple offers received- Highest and Best due by 6/17 at noon! This property truly has a little something for everyone! Spacious 4-bedroom, 2-bath rancher situated on 1.94 private acres in the charming waterfront town of Betterton. Featuring a full walkout basement, attached 2-car garage, and a 30x40' pole building, there’s plenty of room for hobbies, storage, boats, workshops, or recreational toys. Step onto the welcoming screened front porch and into the cozy living room with a wood-burning fireplace. The recently remodeled kitchen features quartz countertops, new matte stainless appliances, double ovens, and plenty of space for cooking and gathering. The dining room, complete with a pellet stove, opens to the 12x20' composite back deck overlooking the peaceful wooded setting. The spacious primary suite offers a walk-in closet and private full bath. Two additional bedrooms and an updated full bath complete the main level. Downstairs, the walkout basement adds even more flexibility with a finished bedroom, rough-in for an additional bathroom, and a large open area ready for storage, recreation space, and possibilities. Oversized double doors provide easy access to the backyard. Home features a new roof and heat pump replaced within the past two years! Enjoy privacy surrounded by trees while still being within walking distance to Betterton Beach and the public boat ramp. Known as the “Jewel of the Chesapeake,” Betterton is home to one of the Chesapeake Bay’s best sandy beaches with calm waters, a pavilion, and a laid-back waterfront lifestyle. Conveniently located approximately 20 minutes to Chestertown, 30 minutes to Middletown, 1.5 hours to Philadelphia, and about 1 hour to the Bay Bridge. Add this one to your showing list today! Pics will be posted 6/20

$461,000

4 Beds ⋅ 2 Baths

Multiple offers received- Highest and Best due by 6/17 at noon! This property truly has a little something for everyone! Spacious 4-bedroom, 2-bath rancher situated on 1.94 private acres in the charming waterfront town of Betterton. Featuring a full walkout basement, attached 2-car garage, and a 30x40' pole building, there’s plenty of room for hobbies, storage, boats, workshops, or recreational toys. Step onto the welcoming screened front porch and into the cozy living room with a wood-burning fireplace. The recently remodeled kitchen features quartz countertops, new matte stainless appliances, double ovens, and plenty of space for cooking and gathering. The dining room, complete with a pellet stove, opens to the 12x20' composite back deck overlooking the peaceful wooded setting. The spacious primary suite offers a walk-in closet and private full bath. Two additional bedrooms and an updated full bath complete the main level. Downstairs, the walkout basement adds even more flexibility with a finished bedroom, rough-in for an additional bathroom, and a large open area ready for storage, recreation space, and possibilities. Oversized double doors provide easy access to the backyard. Home features a new roof and heat pump replaced within the past two years! Enjoy privacy surrounded by trees while still being within walking distance to Betterton Beach and the public boat ramp. Known as the “Jewel of the Chesapeake,” Betterton is home to one of the Chesapeake Bay’s best sandy beaches with calm waters, a pavilion, and a laid-back waterfront lifestyle. Conveniently located approximately 20 minutes to Chestertown, 30 minutes to Middletown, 1.5 hours to Philadelphia, and about 1 hour to the Bay Bridge. Add this one to your showing list today! Pics will be posted 6/20

121 1st Ave, Betterton

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

Selling Office: Integrity Real Estate.

$460,000

Open House Friday July 3rd 4-6pm! Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condominium offers an exceptional opportunity to enjoy life along the banks of the Chester River. Set within an architecturally significant 1800s building that reflects the timeless character of this remarkable town, the residence combines historic charm, modern comfort, and an enviable waterfront location. Filled with character and warmth, the home features beautiful hardwood floors, soaring ceilings, tall windows, built-ins, and a wonderful period gas fireplace that creates a welcoming focal point in the spacious living room. Two generously sized bedrooms and two beautifully appointed tiled bathrooms provide comfort and style, while an in-unit washer and dryer add everyday convenience. Generous room sizes and abundant natural light enhance the home's inviting atmosphere throughout. The heart of the home is the expansive kitchen and great room at the rear of the residence, overlooking the river. Designed for gathering, entertaining, and everyday living, this impressive space features gorgeous cabinetry, stainless steel appliances, gas cooking, abundant counter space, a farmhouse sink, sunny windows, and plenty of room for dining as well as additional living space. Whether hosting friends, enjoying a quiet morning coffee, or unwinding at the end of the day, it's a room you'll find yourself gravitating toward again and again. Just off the great room, the private balcony overlooks the Chester River and offers sweeping water views in a peaceful waterfront setting. Direct water access and a dedicated boat slip make it easy to enjoy the area's iconic Chester River and everything that life on the water has to offer. Chestertown is steeped in maritime tradition and widely admired for its extraordinary collection of Federal, Georgian, and Victorian architecture. One of the Eastern Shore's most desirable destinations, residents enjoy boutique shopping, fine dining, waterfront attractions, cultural events, and a thriving arts scene. Perfectly positioned along the Chester River, this residence is a historic treasure, a waterfront retreat, and an opportunity to experience the very best of life in one of the Eastern Shore's most cherished communities.

2 Beds ⋅ 2 Baths

Open House Friday July 3rd 4-6pm! Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condominium offers an exceptional opportunity to enjoy life along the banks of the Chester River. Set within an architecturally significant 1800s building that reflects the timeless character of this remarkable town, the residence combines historic charm, modern comfort, and an enviable waterfront location. Filled with character and warmth, the home features beautiful hardwood floors, soaring ceilings, tall windows, built-ins, and a wonderful period gas fireplace that creates a welcoming focal point in the spacious living room. Two generously sized bedrooms and two beautifully appointed tiled bathrooms provide comfort and style, while an in-unit washer and dryer add everyday convenience. Generous room sizes and abundant natural light enhance the home's inviting atmosphere throughout. The heart of the home is the expansive kitchen and great room at the rear of the residence, overlooking the river. Designed for gathering, entertaining, and everyday living, this impressive space features gorgeous cabinetry, stainless steel appliances, gas cooking, abundant counter space, a farmhouse sink, sunny windows, and plenty of room for dining as well as additional living space. Whether hosting friends, enjoying a quiet morning coffee, or unwinding at the end of the day, it's a room you'll find yourself gravitating toward again and again. Just off the great room, the private balcony overlooks the Chester River and offers sweeping water views in a peaceful waterfront setting. Direct water access and a dedicated boat slip make it easy to enjoy the area's iconic Chester River and everything that life on the water has to offer. Chestertown is steeped in maritime tradition and widely admired for its extraordinary collection of Federal, Georgian, and Victorian architecture. One of the Eastern Shore's most desirable destinations, residents enjoy boutique shopping, fine dining, waterfront attractions, cultural events, and a thriving arts scene. Perfectly positioned along the Chester River, this residence is a historic treasure, a waterfront retreat, and an opportunity to experience the very best of life in one of the Eastern Shore's most cherished communities.

105 N Water St Unit 2, Chestertown

Listing courtesy of Northrop Realty. Contact:

Rambling rancher on an established 3/4 acre garden in Country Club Estates with No HOA fees has extensive recent renovations: New architectural shingle Roof, New Heat pump, Stainless Kitchen appliances, New Bathroom fixtures, New Porch screening, New doors, New Ring video doorbell, ceiling lights and switches, Fresh paint and 6 New windows brighten a Basement Family room with 18” porcelain tile. A 40’ x 26’ block 2-car Garage with New insulated doors & openers, built-in shelving, jalousie windows, storage loft and 50% garage extension for Workshop as potential hobby space, home-based business or sporting gear cave. The Garage faces a private parking pad behind the home and a U-shaped driveway to a drive-through carport has the rear door entering a large Foyer convenient for bring in the groceries to the custom built Kitchen with a work-triangle layout. Finishing touches to the renovations are nearly complete, just choose the bedroom Carpeting and move into your New Home! Living Room: Walk along the slate flagstone path and pass through the New, classic Front Door into a spacious Living room featuring an elegant Fireplace and Hardwood floors that extend through a wide open Archway into the Dining room which opens to a comfortable screened Porch—the perfect spot to relax and enjoy the Garden view in this Prestigious neighborhood. Bedrooms: The main floor has a secluded Bedroom Wing with Hardwood floors and full Bathroom with 2 linen closets. A second Bathroom is conveniently close to Foyer and stairwell to Basement: The full Basement features an open Family room with brand-new windows that allow plenty of natural light inside. A side room equipped with a new sump pump well is a perfect blank canvas offering for an Office, Storage or a Rec room. Mechanical & Utillity Room: Separate Electric water heater from Oil boiler to provide comfortable hot water baseboard heat which is supplemented by a new HVAC system for Efficient heating and cooling. Enjoy Resort-like living in this Brick Ranch house only a chip shot away from the Chester River Yacht and Country Club with scenic river views while taking your neighborhood walks, And 5 minute drives along the Chester River, coming and going from your New Home to Historic Chestertown shopping and dining district, also well known for Live Arts, Festivals and home to Washington College.

$450,000